CA2339054A1 - E-isomeric fullerene derivatives - Google Patents

E-isomeric fullerene derivatives Download PDF

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CA2339054A1
CA2339054A1 CA002339054A CA2339054A CA2339054A1 CA 2339054 A1 CA2339054 A1 CA 2339054A1 CA 002339054 A CA002339054 A CA 002339054A CA 2339054 A CA2339054 A CA 2339054A CA 2339054 A1 CA2339054 A1 CA 2339054A1
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alkyl
aryl
amino
ether
alkylaryl
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CA2339054C (en
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Long Y. Chiang
Vijayaraj Anantharaj
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2604/00—Fullerenes, e.g. C60 buckminsterfullerene or C70
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/70—Nanostructure
    • Y10S977/734—Fullerenes, i.e. graphene-based structures, such as nanohorns, nanococoons, nanoscrolls or fullerene-like structures, e.g. WS2 or MoS2 chalcogenide nanotubes, planar C3N4, etc.
    • Y10S977/735—Carbon buckyball
    • Y10S977/737—Carbon buckyball having a modified surface
    • Y10S977/74—Modified with atoms or molecules bonded to the surface
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/70—Nanostructure
    • Y10S977/773—Nanoparticle, i.e. structure having three dimensions of 100 nm or less
    • Y10S977/775—Nanosized powder or flake, e.g. nanosized catalyst
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/902—Specified use of nanostructure
    • Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
    • Y10S977/915—Therapeutic or pharmaceutical composition
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/902—Specified use of nanostructure
    • Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
    • Y10S977/926—Topical chemical, e.g. cosmetic or sunscreen
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/902—Specified use of nanostructure
    • Y10S977/932—Specified use of nanostructure for electronic or optoelectronic application
    • Y10S977/949—Radiation emitter using nanostructure
    • Y10S977/95—Electromagnetic energy
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/902—Specified use of nanostructure
    • Y10S977/932—Specified use of nanostructure for electronic or optoelectronic application
    • Y10S977/953—Detector using nanostructure
    • Y10S977/954—Of radiant energy

Abstract

An E-isomeric fulleropyrrolidine compound of formula (I):

(see formula I) is disclosed. Also disclosed is a method for preparing and polymers prepared from such a compound.

Claims (60)

1. A compound of formula (I):

wherein F f is F(-K)m(-Y-Z)q in which F is a fullerene core; each K, independently, is -OH, -SH, -NH2, -NHOH, -SO3H, -OSO3H, -CO2H, -CONH2, -CONHNH2, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2-NH3+, -O-PO(O-)-O-CH2CH2-N+(CH3)3, -glycoside, -OCH3, -OCH2(CHOH)4-CH2OH, -OCH2(CHOH)2-CH2OH, -NH-CH2-CO2H, -[CH(CO2H)-CH2]1-100-OH, -[CH(CO2R a)-CH2]1-100-OH, -[C(CH3)(CO2H)-CH2]1-100-OH, -[C(CH3)(CO2 R a)-CH2]1-100-OH, -N(OH)2, -NH3+, -N+H2R2, -N+HR a R b, or -N+R a R b R c; each Y is -A-B-, in which A is -O-, -NH-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -O-CO-NH-, -NH-CO-NH-, -CO-NH-, or-NH-CO-; and B is -R a-O-[Si(CH3)2-O-]1-100, C1-2000 alkyl, C6-40 aryl, C7-2000 alkylaryl, C7-2000 arylalkyl, (C1-30 alkyl ether)1-100, (C6-40 aryl ether)1-100,(C7-2000 alkylaryl ether)1-100, (C7-2000 arylalkyl ether)1-100, (C1-30 alkyl thioether)1-100, (C6-40 aryl thioether)1-100, (C7-2000 alkylaryl thioether)1-100, (C7-2000 arylalkyl thioether)1-100, (C2-50 alkyl ester)1-100, (C7-2000 aryl ester)1-100, (C8-2000 alkylaryl ester)1-100, (C8-2000 arylalkyl ester)1-100, -R a-CO-O-(C1-30 alkyl ether)1-100, -R a-CO-O-(C6-40 aryl ether)1-100, -R a-CO-O-(C7-2000 alkylaryl ether)1-100, -R a-CO-O-(C7-2000 arylalkyl ether)1-100, (C4-50 alkyl urethane)1-100, (C14-60 aryl urethane)1-100, (C10-2000 alkylaryl urethane)1-100, (C10-2000 arylalkyl urethane)1-100, (C5-50 alkyl urea)1-100, (C14-60 aryl urea)1-100, (C10-2000 alkylaryl urea)1-100, (C10-2000 arylalkyl urea)1-100, (C2-50 alkyl amide)1-100, (C7-60 aryl amide)1-100, (C8-2000 alkylaryl amide)1-100, (C8-2000 arylalkyl amide)1-100, (C3-30 alkyl anhydride)1-100, (C8-50 aryl anhydride)1-100, (C9-2000 alkylaryl anhydride)1-100, (C9-2000 arylalkyl anhydride)1-100, (C2-30 alkyl carbonate)1-100, (C7-50 aryl carbonate)1-100, (C8-2000 alkylaryl carbonate)1-100, (C8-2000 arylalkyl carbonate)1-100, -R a-O-CO-NH-(R b or Ar-R
b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether, or C7-2000 arylalkyl ether)1-100, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether, or C7-2000 arylalkyl ether)1-100-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100-R c-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether, or C7-2000 arylalkyl ether)1-100, -R b-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, alkylaryl ether, or C7-2000 arylalkyl ether)1-100-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100-R c-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-NH-(C2-50 alkyl amide, C7-60 aryl amide, C8-2000 alkylaryl amide, or C8-2000 arylalkyl amide)1-100, -R a-NH-CO-NH-(R b Or Ar-R b-Ar)-NH-CO-NH-(C2-50 alkyl amide, C7-60 aryl amide, C8-2000 alkylaryl amide, or C8-2000 arylalkyl amide)1-100, or a bond;
each Z, independently, is -G-D, wherein G is -R a-, -R a-Ar-, -Ar-R a-, or -Ar-; and D is -H, -OH, -SH, -NH2, -NHOH, -SO3H, -OSO3H, -CO2H, -CONH2, -CONHNH2, -CH(NH2)-CO2H, -NH-CH2-CO2H, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2NH3+, -O-PO(O-)-O-CH2CH2-N+(CH3)3, -glycoside, -oligosaccharide, -CO-glycoside, -CO-oligosaccharide, -OCH3, -OCH2(CHOH)4-CH2OH, -OCH2(CHOH)2-CH2OH, -CO-OCH2(CHOH)4-CH2OH, -C6H3(OH)2, -N(CH2CO2H)2, -CO-N(CH2CO2H)2, -CO-NH-C(CH2CH2CO2H)3, -CO-NH-C(CH2CH2OH)3, -[CH2-CH(CO2R a)]1-100-H, -NH3+, -N+H2R a, -N+HR a R b, or -N+R a R b R c, each of R
a, R b, and R c, independently, being C1-20 alkyl and Ar being aryl; q is 0-30; and m is 0-30;
provided that the sum of q and m is 0-30;
each of R1 and R4, independently, is =O or C1-20 hydrocarbon; and each of R2 and R5, independently, is C1-20 hydrocarbon; wherein R1 and R2, or R4 and R5 can join together to form C6-40 aryl which is optionally substituted with halide, -OH, -NHNH2, -NH2OH, -NH-CH2-CO2H, -CH2-CH2-D, -CH2-B-Z, -CO-CH2-D, -CO-B-Z, -O-B-Z, or -NH-B-Z;
each of B, D, and Z having been defined above;
each of R3 and R6, independently, is -H, -CH2-D, -B-Z, -G-E, -G-CO-E, or a side chain of an amino acid; each of B, D, and Z having been defined above, and E
being E1, E2, or E3, in which E1 is Y1, Y2-amino, (Y1 ,Y2-alkyl)-amino, Y1, Y2-ethylenediamino, (dihydroxymethyl)alkylamino, (X1,X3-aryl)amino, or X1,X3-aryloxy; E2 is Y1, Y2-alkoxy, (Y1, Y2-amino)alkoxy, (Y1, Y2, Y3-aryl)oxy, (dihydroxyalkyl)-aryloxy, (Y1,Y2,Y3-alkyl)amino, (Y1,Y2,Y3-aryl)amino, dihydroxyalkylamino, Y1,Y2,Y3-alkoxy, (trihydroxyalkyl)alkoxy, (trihydroxyalkyl)alkylamino, (dicarboxyalkyl)amino, (Y1,Y2,Y3-alkyl)thio, (X1,X3-aryl)thio, (Y1,Y2-alkyl)thio, (dihydroxyalkyl)thio, Y1,Y2-dioxoalkyl, or tri-(Y1,Y2,Y3-methylaminocarboxyethyl)methylamino; and E3 is ((glycosidyl)oxoheteroaryl)amino, ((glycosidyl)oxoaryl)amino, (X1,X2,X3-heteroaryl)amino, (X1-diarylketone)amino, (X,X1-oxoaryl)amino, (X,X1-dioxoaryl)amino, (Y1-alkyl,Y2-alkyldioxoheteroaryl)amino, (Y1-alkyl,Y2-alkyldioxoaryl)amino, (di(Y1,Y2-methyl)dioxoheteroaryl)amino, (di(Y1,Y2-methyl)dioxoaryl)amino, ((glycosidyl)heteroaryl)amino, ((glycosidyl)aryl)amino, ((carboxylacetylalkyl)oxo-heteroaryl)amino, ((carboxylacetylalkyl)oxoaryl)amino, ((isopropylaminohydroxy-alkoxy)aryl)amino, (X1,X2,X3-alkylaryl)amino, (X1,X2,X3-heteroaryl)oxy, (isopropylaminohydroxyalkyl)aryloxy, (X1,X2,X3-oxoheteroaryl)oxy, (X1,X2,X3-oxoaryl)oxy, (X1,Y1-oxoheteroaryl)oxy, (X1-diarylketone)oxy, (X,X1-oxoaryl)oxy, (X1,X2-dioxoaryl)oxy, (Y1,Y2,di-aminodihydroxy)alkyl, (X1,X2-heteroaryl)thio, ((tricarboxylalkyl)ethylene-diamino)alkoxy, (X1,X2-oxoaryl)thio, (X1,X2-dioxoaryl)thio, (glycosidylheteroaryl)thio, (glycosidylaryl)thio, Y1-alkyl(thiocarbonyl)thio, Y1,Y2,-alkyl(thiocarbonyl)thio, Y1,Y2,Y3-alkyl(thiocarbonyl)thio, (Y1,Y2-aminothiocarbonyl)thio, (pyranosyl)thio, cysteinyl, tyrosinyl, (phenylalainyl)amino, (dicarboxyalkyl)thio, (aminoaryl)1-100amino, (pyranosyl)amino, (Y1-aminoaryl)1-100amino, (amino(sulfoaryl))1-100amino, peptidyl, thymidinyl, uridinyl, guanosinyl, adenosinyl, cholesteryl, or biotinylalkoxy; wherein X is halide; each of X1, X2, and X3, independently, is -Y1, -O-Y1, -S-Y1, -NH-Y1, -CO-O-Y1, -O-CO-Y1, -CO-NH-Y1, -CO-NY1Y2, -NH-CO-Y1, -SO2-Y1, -CHY1Y2, or -NY1Y2; and each of Y1, Y2, and Y3, independently, is -Z
or -B-Z;
each of x and y, independently, is 0 or 1; and s is 1-6;

provided that when x is 0, R1 is =O; that when y is 0, R4 is =O; that when x is 1, R1 and R2 join together to form C6-40 aryl; and that when y is 1, R4 and R5 join together to form C6-40 aryl; and or a salt thereof.
2. The compound of claim 1, wherein at least one of x and y is 1.
3. The compound of claim 2, wherein R1 and R2, or R4 and R5 can join together to form a benzene ring.
4. The compound of claim 3, wherein F is C60, C61, C62, C63, C64, C65, C70, C76, C78, C82, C84, or C92, or La@C n, Ho@C n, Gd@C n, or Er@C n, in which n is 60, 74, or 82.
5. The compound of claim 3, wherein the sum of q and m is 0-20.
6. The compound of claim 3, wherein each K, independently, is -SH, -NHOH, -SO3H, -OSO3H, -CONH2, -CONHNH2, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2NH3+, -glycoside, -O-CH2-(CHOH)4-CH2OH, -O-CH2-(CHOH)2-CHOH, -N+HR a R b, or N+HR a R b R c.
7. The compound of claim 3, wherein D is -SH, -NHOH, -SO3H, -OSO3H, -CONH2, -CONHNH2, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2NH3+, -glycoside, -oligosaccharide, -CO-glycoside, -CO-oligosaccharide, -(CHOH)4-CH2OH, -O-CH2-(CHOH)2-CHOH, -N+HR a R b, or N+HR a R b R c.
8. The compound of claim 3, wherein only one of x and y is 1.
9. The compound of claim 8, wherein x is 1, y is 0, and R1 and R2 join together to form a benzene ring.
10. The compound of claim 9, wherein R3 is -H, -B-Z, -G-E, or -G-CO-E.
11. The compound of claim 9, wherein R6 is -G-E, -G-CO-E, or a side chain of an amino acid.
12. The compound of claim 13, wherein R6 is a side chain of alanine, aspartic acid, cysteine, glutamic acid, phenylalanine, halophenylalanine, hydroxyphenylalanine, glycine, histidine, isoleucine, lysine, leucine, methionine, asparagine, glytamine, arginine, serine, theronine, valine, tryptophan, tyrosine, 2-aminobutyric acid, halophenylalanine, cyclohexylalanine, citrulline, homocitrulline, homoserine, norleucine, norvaline, or ornithine.
13. The compound of claim 12, wherein R3 is -H, -B-Z, -G-E, or -Cr-CO-E.
14. The compound of claim 13, wherein F is C60, and the sum of q and m is 0-20.
15. The compound of claim 14, said compound is the E-isomer of 1-dimethyl-3-hydroxyphenylmethyl-fulleropyrrolidine-1,3-dicarboxylic acid, 1-dimethyl-3-(3,4-dihydroxyphenyl)methyl-fulleropyrrolidine-1,3-dicarboxylic acid, 1-isobutyl-3-(o-hydroxyphenyl)-fulleropyrrolidine-1-carboxylic acid, 1-methyl-3-ethyl-3'-(o-hydroxyphenyl)-fulleropyrrolidine-1-carboxylic acid, or 1-methyl-3-(2,3,4-trihydroxyphenyl)-fulleropyrrolidine-1-carboxylic acid.
16. The compound of claim 1, wherein both x and y are 0.
17. The compound of claim 16, wherein F is C60, C61, C62, C63, C64, C65, C70, C76, C78, C82, C84, or C92, or La@C n, Ho@C n, Gd@C n, or Er@C n, in which n is 60, 74, or 82.
18. The compound of claim 16, wherein the sum of q and m is 0-20.
19. The compound of claim 16, wherein each K, independently, is -SH, -NHOH, -SO3H, -OSO3H, -CONH2, -CONHNH2, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2NH3+, -glycoside, -O-CH2-(CHOH)4-CH2OH, -O-CH2-(CHOH)2-CHOH, -N+HR a R b, or N+HR a R b R c.

PO(OH)2, -O-PO(O-)-O-CH2CH2NH3+, -glycoside, -O-CH2-(CHOH)4-CH2OH, -O-CH2-(CHOH)2-CHOH, -N+HR a R b, or N+HR a R b R c.
20. The compound of claim 16, wherein D is -SH, -NHOH, -SO3H, -OSO3H, -CONH2, -CONHNH2, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2NH3+, -glycoside, -oligosaccharide, -CO-glycoside, -CO-oligosaccharide, -O-CH2-(CHOH)4-CH2OH, -O-CH2-(CHOH)2-CHOH, -N+HR a R b, or N+HR a R b R c.
21. The compound of claim 16, wherein each of R3 and R6, independently, is -B-Z, -G-E, -G-CO-E, or a side chain of alanine, aspartic acid, cysteine, glutamic acid, phenylalanine, halophenylalanine, hydroxyphenylalanine, glycine, histidine, isoleucine, lysine, leucine, methionine, asparagine, glytamine, arginine, serine, theronine, valine, tryptophan, tyrosine, 2-aminobutyric acid, halophenylalanine, cyclohexylalanine, citrulline, homocitrulline, homoserine, norleucine, norvaline, or ornithine.
22. The compound of claim 21, wherein F is C60, and the sum of q and m is 0-20.
23. The compound of claim 22, said compound is the E-isomer of 1,3-dimethyl-fulleropyrrolidine-1,3-dicarboxylic acid, fulleropyrrolidine-1,3-di(3-propanoic acid)-1,3-dicarboxylic acid, 1-methyl-3-thiomethyl-fulleropyrrolidine-1,3-dicarboxylic acid, or 1-methyl-3-hydroxymethyl-fulleropyrrolidine-1,3-dicarboxylic acid.
24. A method for preparing a compound of formula (I):

wherein F f is F(-K)m(-Y-Z)q in which F is a fullerene core; each K, independently, is -OH, -SH, -NH2, -NHOH, -SO3H, -OSO3H, -CO2H, -CONH2, -CONHNH2, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2-NH3+, -O-PO(O-)-O-CH2CH2-N+(CH3)3, -glycoside, -OCH3, -OCH2(CHOH)4-CH2OH, -OCH2(CHOH)2-CH2OH, -NH-CH2-CO2H, -[CH(CO2H)-CH2]1-100-OH, -[CH(CO2R a)-CH2]1-100-OH, -[C(CH3)(CO2H)-CH2]1-100-OH, -[C(CH3)(CO2 R4)-CH2]1-100-OH, -N(OH)2, -NH3+, -N+H2R a, -N+HR a R b, or -N+R a R b R c; each Y is -A-B-, in which A is -O-, -NH-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -O-CO-NH-, -NH-CO-NH-, -CO-NH-, or-NH-CO-; and B is -R a-O-[Si(CH3)2-O-]1-100, C1-2000 alkyl, C6-40 aryl, C7-2000 alkylaryl, C7-2000 arylalkyl, (C1-30 alkyl ether)1-100, (C6-40 aryl ether)1-100, (C7-2000 alkylaryl ether)1-100, (C7-2000 arylalkyl ether)1-100, (C1-30 alkyl thioether)1-100, (C6-40 aryl thioether)1-100, (C7-2000 alkylaryl thioether)1-100, (C7-2000 arylalkyl thioether)1-100, (C2-50 alkyl ester)1-100, (C7-2000 aryl ester)1-100, (C8-2000 alkylaryl ester)1-100, (C8-2000 arylalkyl ester)1-100, -R a-CO-O-(C1-30 alkyl ether)1-100, -R a-CO-O-(C6-40 aryl ether)1-100, -R a-CO-O-(C7-2000 alkylaryl ether)1-100, -R a-CO-O-(C7-2000 arylalkyl ether)1-100, (C4-50 alkyl urethane)1-100, (C14-60 aryl urethane)1-100, (C10-2000 alkylaryl urethane)1-100, (C10-2000 arylalkyl urethane)1-100, (C5-50 alkyl urea)1-100, (C14-60 aryl urea)1-100, (C10-2000 alkylaryl urea)1-100, (C10-2000 arylalkyl urea)1-100, (C2-50 alkyl amide)1-100, (C7-60 aryl amide)1-100, (C8-2000 alkylaryl amide)1-100, (C8-2000 arylalkyl amide)1-100, (C3-30 alkyl anhydride)1-100, (C8-50 aryl anhydride)1-100, (C9-2000 alkylaryl anhydride)1-100, (C9-2000 arylalkyl anhydride)1-100, (C2-30 alkyl carbonate)1-100, (C7-50 aryl carbonate)1-100, (C8-2000 alkylaryl carbonate)1-100, (C8-2000 arylalkyl carbonate)1-100, -R a-O-CO-NH-(R b or Ar-R
b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether, or C7-2000 arylalkyl ether)1-100, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether, or C7-2000 arylalkyl ether)1-100-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100-R c-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether, or C7-2000 arylalkyl ether)1-100, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, alkylaryl ether, or C7-2000 arylalkyl ether)1-100-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100-R c-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-NH-(C2-50 alkyl amide, C7-60 aryl amide, C8-2000 alkylaryl amide, or C8-2000 arylalkyl amide)1-100, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-NH-(C2-50 alkyl amide, C7-60 aryl amide, C8-2000 alkylaryl amide, or C8-2000 arylalkyl amide)1-100, or a bond;
each Z, independently, is -G-D, wherein G is -R a-, -R a-Ar-, -Ar-R a-, or -Ar-; and D is -H, -OH, -SH, -NH2, -NHOH, -SO3H, -OSO3H, -CO2H, -CONH2, -CONHNH2, -CH(NH2)-CO2H, -NH-CH2-CO2H, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2NH3+, -O-PO(O-)-O-CH2CH2-N+(CH3)3, -glycoside, -oligosaccharide, -CO-glycoside, -CO-oligosaccharide, -OCH3, -OCH2(CHOH)4-CH2OH, -OCH2(CHOH)2-CH2OH, -CO-OCH2(CHOH)4-CH2OH, -C6H3(OH)2, -N(CH2CO2H)2, -CO-N(CH2CO2H)2, -CO-NH-C(CH2CH2CO2H)3, -CO-NH-C(CH2CH2OH)3, -[CH2-CH(CO2R a)]1-100-H, -NH3+, -N+H2R a , -N+HR a R b, or -N+R a R b R c, each of R a, R b, and R c, independently, being C1-20 alkyl and Ar being aryl; q is 0-30; and m is 0-30;
provided that the sum of q and m is 0-30;
each of R1 and R4, independently, is =O or C1-20 hydrocarbon; and each of R2 and R5, independently, is C1-20 hydrocarbon; wherein R1 and R2, or R4 and R5 can join together to form C6-40 aryl which is optionally substituted with halide, -OH, -NHNH2, -NH2OH, -NH-CH2-CO2H, -CH2-CH2-D, -CH2-B-Z, -CO-CH2-D, -CO-B-Z, -O-B-Z, or -NH-B-Z; each of B, D, and Z having been defined above;
each of R3 and R6, independently, is -H, -CH2-D, -B-Z, -G-E, -G-CO-E or a side chain of an amino acid; each of B, D, and Z having been defined above, and E
being E1, E2, or E3, in which E1 is Y1,Y2-amino, (Y1,Y2-alkyl)-amino, Y1,Y2-ethylenediamino, (dihydroxymethyl)alkylamino, (X1,X3-aryl)amino, or X1,X3-aryloxy; E2 is Y1,Y2-alkoxy, (Y1,Y2-amino)alkoxy, (Y1,Y2,Y3-aryl)oxy, (dihydroxyalkyl)-aryloxy, (Y1,Y2,Y3-alkyl)amino, (Y1,Y2,Y3-aryl)amino, dihydroxyalkylamino, Y1,Y2,Y3-alkoxy, (trihydroxyalkyl)alkoxy, (trihydroxyalkyl)alkylamino, (dicarboxyalkyl)amino, (Y1,Y2,Y3-alkyl)thio, (X1,X3-aryl)thio, (Y1,Y2-alkyl)thio, (dihydroxyalkyl)thio, Y1,Y2-dioxoalkyl, or tri-(Y1,Y2,Y3-methylaminocarboxyethyl)methylamino; and E3 is ((glycosidyl)oxoheteroaryl)amino, ((glycosidyl)oxoaryl)amino, (X1,X2,X3-heteroaryl)amino, (X1-diarylketone)amino, (X,X1-oxoaryl)amino, (X,X1-dioxoaryl)amino, (Y1-alkyl,Y2-alkyldioxoheteroaryl)amino, (Y1-alkyl,Y2-alkyldioxoaryl)amino, (di(Y1,Y2-methyl)dioxoheteroaryl)amino, (di(Y1,Y2-methyl)dioxoaryl)amino, ((glycosidyl)heteroaryl)amino, ((glycosidyl)aryl)amino, ((carboxylacetylalkyl)oxo-heteroaryl)amino, ((carboxylacetylalkyl)oxoaryl)amino, ((isopropylaminohydroxy-alkoxy)aryl)amino, (X1,X2,X3-alkylaryl)amino, (X1,X2,X3-heteroaryl)oxy, (isopropylaminohydroxyalkyl)aryloxy, (X1,X2,X3-oxoheteroaryl)oxy, (X1,X2,X3-oxoaryl)oxy, (X1,Y1-oxoheteroaryl)oxy, (X1-diarylketone)oxy, (X,X1-oxoaryl)oxy, (X1,X2-dioxoaryl)oxy, (Y1,Y2,di-aminodihydroxy)alkyl, (X1,X2-heteroaryl)thio, ((tricarboxylalkyl)ethylene-diamino)alkoxy, (X1,X2-oxoaryl)thio, (X1,X2-dioxoaryl)thio, (glycosidylheteroaryl)thio, (glycosidylaryl)thio, Y1-alkyl(thiocarbonyl)thio, Y1,Y2,-alkyl(thiocarbonyl)thio, Y1,Y2,Y3-alkyl(thiocarbonyl)thio, (Y1,Y2-aminothiocarbonyl)thio, (pyranosyl)thio, cysteinyl, tyrosinyl, (phenylalainyl)amino, (dicarboxyalkyl)thio, (aminoaryl)1-1000amino, (pyranosyl)amino, (Y1-aminoaryl)1-100amino, (amino(sulfoaryl))1-100amino, peptidyl, thymidinyl, uridinyl, guanosinyl, adenosinyl, cholesteryl, or biotinylalkoxy; wherein X is halide; each of X1, X2, and X3, independently, is -Y1, -O-Y1, -S-Y1, -NH-Y1, -CO-O-Y1, -O-CO-Y1, -CO-NH-Y1, -CO-NY1Y2, -NH-CO-Y1, -SO2-Y1, -CHY1Y2, or -NYC1Y2; and each of Y1, Y2, and Y3, independently, is -2 or -B-Z;
each of x and y, independently, is 0 or 1; and s is 1-6;

provided that when x is 0, R1 is =O; that when y is 0, R4 is =O; that when x is 1, R1 and R2 join together to form C6-40 aryl; and that when y is 1, R4 and R5 join together to form C6-40 aryl; and or a salt thereof;
the method comprising:
reacting a compound of formula (II) wherein M is a Cu, Mn, Fe, Co, Ni, Ru, Rh, Os, Zn, Cr, Ti, or Zr ion;
with a fullerene compound F f of the formula F(-K)m(-Y-Z)q wherein the sum of q and m is 0 to form a compound of formula (III) removing M from the compound of formula (III) to form a compound of formula (I) wherein the sum of q and m is 0; and optionally treating the compound of formula (I) wherein the sum of q and m is 0 with a nitrating or sulfating agent to form a nitrofullerene or cyclosulfated fullerene, and contacting the nitrofullerene or cyclosulfated fullerene with a nucleophilic agent to form a compound of formula (I) wherein the sum of q and m is greater than 0.
25. The method of claim 24, wherein only one of x and y is 0.
26. The method of claim 25, wherein x is l, y is 0, and R1 and R2 join together to form a benzene ring.
27. The method of claim 24, wherein both x and y are 0.
28. The method of claim 24, wherein M is a Cu ion.
29. The method of claim 24, wherein the compound of formula (II) is prepared by reacting a compound of formula (IV) with a metal salt MX, wherein M has been defined above, and X is an anion.
30. The method of claim 29, wherein X is halide, sulfate, nitrate, or acetate.
31. The method of claim 29, wherein the compound of formula (IV) is prepared by reacting a compound of formula (V) with a compound of formula (VI)
32. The method of claim 31, wherein each of R3 and R6, independently, is -H, -B-Z, -G-E, -G-CO-E, or a side chain of an amino acid, wherein B, E, G, and Z have been defined above.
33. A compound of formula (VII):

wherein F f is F(-K)m(-Y-Z)q in which F is a fullerene core; each K, independently, is -OH, -SH, -NH2, -NHOH, -SO3H, -OSO3H, -CO2H, -CONH2, -CONHNH2, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2-NH3+, -O-PO(O-)-O-CH2CH2-N+(CH3)3, -glycoside, -OCH3, -OCH2(CHOH)4-CH2OH, -OCH2(CHOH)2-CH2OH, -NH-CH2-CO2H, -[CH(CO2H)-CH2]1-100-OH, -(CH(CO2R a)-CH2]1-100-OH, -[C(CH3)(CO2H)-CH2]1-100-OH, -[C(CH3)(CO2R a)-CH2]1-100-OH, -N(OH)2, -NH3+, -N+H2R a, -N+HR a R b, or -N+R a R b R c; each Y is -A-B-, in which A is -O-, -NH-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -O-CO-NH-, -NH-CO-NH-, -CO-NH-, or -NH-CO-; and B is -R a-O-[Si(CH3)2-O-]1-100, C1-2000 alkyl, C6-40 aryl, C7-2000 alkylaryl, C7-2000 arylalkyl, (C1-30 alkyl ether)1-100, (C6-40 aryl ether)1-100, (C7-2000 alkylaryl ether)1-100, (C7-2000 arylalkyl ether)1-100, (C1-30 alkyl thioether)1-100, (C6-40 aryl thioether)1-100, (C7-2000 alkylaryl thioether)1-100, (C7-2000 arylalkyl thioether)1-100, (C2-50 alkyl ester)1-100, (C7-2000 aryl ester)1-100, (C8-2000 alkylaryl ester)1-100, (C8-2000 arylalkyl ester)1-100, -R a-CO-O-(C1-30 alkyl ether)1-100, -R a-CO-O-(C6-40 aryl ether)1-100, -R a-CO-O-(C7-2000 alkylaryl ether)1-100, -R a-CO-O-(C7-2000 arylalkyl ether)1-100, (C4-50 alkyl urethane)1-100, (C14-60 aryl urethane)1-100, (C10-2000 alkylaryl urethane)1-100, (C10-2000 arylalkyl urethane)1-100, (C5-50 alkyl urea)1-100, (C14-60 aryl urea)1-100, (C10-2000 alkylaryl urea)1-100, (C10-2000 arylalkyl urea)1-100, (C2-50 alkyl amide)1-100, (C7-60 aryl amide)1-100, (C8-2000 alkylaryl amide)1-100, (C8-2000 arylalkyl amide)1-100, (C3-30 alkyl anhydride)1-100, (C8-50 aryl anhydride)1-100, (C9-2000 alkylaryl anhydride)1-100, (C9-2000 arylalkyl anhydride)1-100, (C2-30 alkyl carbonate)1-100, (C7-50 aryl carbonate)1-100, (C8-2000 alkylaryl carbonate)1-100, (C8-2000 arylalkyl carbonate)1-100, -R a-O-CO-NH-(R b or Ar-R
b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether or C7-2000 arylalkyl ether)1-100, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether, or C7-2000 arylalkyl ether)1-100-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100-R c-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether, or C7-2000 arylalkyl ether)1-100,-R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, alkylaryl ether, or C7-2000 arylalkyl ether)1-100-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100-R c-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-NH-(C2-50 alkyl amide, C7-60 aryl amide, C8-2000 alkylaryl amide, or C8-2000 arylalkyl amide)1-100, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-NH-(C2-50 alkyl amide, C7-60 aryl amide, C8-2000 alkylaryl amide, or C8-2000 arylalkyl amide)1-100, or a bond; each Z, independently, is -G-D, wherein G is -R a-, -R a-Ar-, -Ar-R a-, or -Ar-; and D
is -H, -OH, -SH, -NH2, -NHOH, -SO3H, -OSO3H, -CO2H, -CONH2, -CONHNH2, -CH(NH2)-CO2H, -NH-CH2-CO2H, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2NH3+, -O-PO(O-)-O-CH2CH2-N+(CH3)3, -glycoside, -oligosaccharide, -CO-glycoside, -CO-oligosaccharide, -OCH3, -OCH2(CHOH)4-CH2OH, -OCH2(CHOH)2-CH2OH, -CO-OCH2(CHOH)4-CH2OH, -C6H3(OH)2, -N(CH2CO2H)2, -CO-N(CH2CO2H)2, -CO-NH-C(CH2CH2CO2H)3, -CO-NH-C(CH2CH2OH)3, -[CH2-CH(CO2R a)]1-100-H, -NH3+, -N+H2R a , -N+HR a R b, or -N+R a R b R c, each of R a, R b, and R c, independently, being C1-20 alkyl and Ar being aryl; q is 0-30; and m is 0-30; provided that the sum of q and m is 0-30;
each of R1 and R4, independently, is =O or C1-20 hydrocarbon; and each of R2 and R5, independently, is C1-20 hydrocarbon; wherein R1 and R2, or R4 and R5 can join together to form C6-40 aryl which is optionally substituted with halide, -OH, -NHNH2, -NH2OH, -NH-CH2-CO2H, -CH2-CH2-D, -CH2-B-Z, -CO-CH2-D, -CO-B-Z, -O-B-Z, or -NH-B-Z; each of B, D, and Z having been defined above;
each of R3 and R6, independently, is -H, -CH2-D, -B-Z, -G-E, -G-CO-E or a side chain of an amino acid; each of B, D, and Z having been defined above, and E
being E1, E2, or E3, in which E1 is Y1,Y2-amino, (Y1,Y2-alkyl)-amino, Y1,Y2-ethylenediamino, (dihydroxymethyl)alkylamino, (X1,X3-aryl)amino, or X1,X3-aryloxy; E2 is Y1,Y2-alkoxy, (Y1,Y2-amino)alkoxy, (Y1,Y2,Y3-aryl)oxy, (dihydroxyalkyl)-aryloxy, (Y1,Y2,Y3-alkyl)amino, (Y1,Y2,Y3-aryl)amino, dihydroxyalkylamino, Y1,Y2,Y3-alkoxy, (trihydroxyalkyl)alkoxy, (trihydroxyalkyl)alkylamino, (dicarboxyalkyl)amino, (Y1,Y2,Y3-alkyl)thio, (X1,X3-aryl)thio, (Y1,Y2-alkyl)thio, (dihydroxyalkyl)thio, Y1,Y2-dioxoalkyl, or tri-(Y1,Y2,Y3-methylaminocarboxyethyl)methylamino; and E3 is ((glycosidyl)oxoheteroaryl)amino, ((glycosidyl)oxoaryl)amino, (X1,X2,X3-heteroaryl)amino, (X1-diarylketone)amino, (X,X1-oxoaryl)amino, (X,X1-dioxoaryl)amino, (Y1-alkyl,Y2-alkyldioxoheteroaryl)amino, (Y1-alkyl,Y2-alkyldioxoaryl)amino, (di(Y1,Y2-methyl)dioxoheteroaryl)amino, (di(Y1,Y2-methyl)dioxoaryl)amino, ((glycosidyl)heteroaryl)amino, ((glycosidyl)aryl)amino, ((carboxylacetylalkyl)oxo-heteroaryl)amino, ((carboxylacetylalkyl)oxoaryl)amino, ((isopropylaminohydroxy-alkoxy)aryl)amino, (X1,X2,X3-alkylaryl)amino, (X1,X2,X3-heteroaryl)oxy, (isopropylaminohydroxyalkyl)aryloxy, (X1,X2,X3-oxoheteroaryl)oxy, (X1,X2,X3-oxoaryl)oxy, (X1,Y1-oxoheteroaryl)oxy, (X1-diarylketone)oxy, (X,X1-oxoaryl)oxy, (X1,X2-dioxoaryl)oxy, (Y1,Y2,di-aminodihydroxy)alkyl, (X1,X2-heteroaryl)thio, ((tricarboxylalkyl)ethylene-diamino)alkoxy, (X1,X2-oxoaryl)thio, (X1,X2-dioxoaryl)thio, (glycosidylheteroaryl)thio, (glycosidylaryl)thio, Y1-alkyl(thiocarbonyl)thio, Y1,Y2,-alkyl(thiocarbonyl)thio, Y1,Y2,Y3-alkyl(thiocarbonyl)thio, (Y1,Y2-aminothiocarbonyl)thio, (pyranosyl)thio, cysteinyl, tyrosinyl, (phenylalainyl)amino, (dicarboxyalkyl)thio, (aminoaryl)1-100amino, (pyranosyl)amino, (Y1-aminoaryl)1-100amino, (amino(sulfoaryl))1-100amino, peptidyl, thymidinyl, uridinyl, guanosinyl, adenosinyl, cholesteryl, or biotinylalkoxy; wherein X is halide; each of X1, X2, and X3, independently, is -Y1, -O-Y1, -S-Y1, -NH-Y1, -CO-O-Y1, -O-CO-Y1, -CO-NH-Y1, -CO-NY1Y2, -NH-CO-Y1, -SO2-Y1, -CHY1Y2, or -NY1Y2; and each of Y1, Y2, and Y3, independently, is -Z
or -B-Z; B
and Z having been defined above;
R7 is -R d or -O-R e; wherein R d is -OH, -OM, -NHNH2, -NHOH, -NH-CH2-CO2H, -O-B-Z, -NH-B-Z, -E, -O-G-E, -NH-G-E, -O-G-CO-E, or -NH-G-CO-E; M being Cu, Mn, Fe, Co, Ni, Ru, Rh, Os, Zn, Cr, Ti, or Zr ion; and R e is -H, -CH2-CH2-D, -CH2-B-Z, -CH2-G-E, -CH2-G-CO-E, -CO-CH2-D, -CO-B-Z, -CO-G-E, or -CO-G-CO-E; each of B, D, E, G, and Z having been defined above;
R8 is R e;
R9 is -O- or a bond;
R10 is -R d or -R e; each of which having been defined above;
each of x and y, independently, is 0 or 1; and p is 1-30;
provided that when x is 0, R1 is =O, and R7 is -R d; that when y is 0, R4 is =O, and R9 is a bond, and R10 is -R d; that when x is 1, R1 and R2 join together to form C6-40 aryl, and R7 is -O-R c; and that when y is 1, R4 and R5 join together to form C6-40 aryl, R9 is -O-, and R10 is -R e; and further provided that when p is greater than 1, x is 0;
or a salt thereof.
34. The compound of claim 33, wherein F is C6o, C61, C62, C63, C64, C65, C70, C76, C78, C82, C84, or C92, or La@C n, Ho@C n, Gd@C n, or Er@C n, in which n is 60, 74, or 82.
35. The compound of claim 33, wherein the sum of q and m is 0-20.
36. The compound of claim 33, wherein p is 2-10.
37. The compound of claim 33, wherein each of R3 and R6, independently, is -H, -B-Z, -G-E, -G-CO-E or a side chain of an amino acid.
38. The compound of claim 33, wherein R d is -OH, -NHNH2, -E, -O-G-E, -NH-G-E, -O-G-CO-E, or -NH-G-CO-E.
39. The compound of claim 33, wherein R e is -H, -CH2-G-E, -CH2-G-CO-E, -CO-G-E, or -CO-G-CO-E.
40. The compound of claim 33, wherein both x and y are 0.
41. The compound of claim 40, wherein R d is -OH, -NHNH2, -E, -O-G-E, -NH-G-E, -O-G-CO-E, or -NH-G-CO-E.
42. The compound of claim 41, wherein R d is -H, -CH2-G-E, -CH2-G-CO-E, -CO-G-E, or -CO-G-CO-E.
43. The compound of claim 42, wherein p is 2-10.
44. The compound of claim 43, said compound is oligo(1,3-dimethyl-fulleropyrrolidine-1,3-dicarboxylic N amide).
45. A compound of formula (VIII):

wherein F f is F(-K)m(-Y-Z)q in which F is a fullerene core; each K, independently, is -OH, -SH, -NH2, -NHOH, -SO3H, -OSO3H, -CO2H, -CONH2, -CONHNH2, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2-NH3+, -O-PO(O-)-O-CH2CH2-N+(CH3)3, -glycoside, -OCH3, -OCH2(CHOH)4-CH2OH, -OCH2(CHOH)2-CH2OH, -NH-CH2-CO2H, -[CH(CO2H)-CH2]1-100-OH, -[CH(CO2R a)-CH2]1-100-OH, -[C(CH3)(CO2H)-CH2]1-100-OH, -[C(CH3)(CO2 R a)-CH2]1-100-OH, -N(OH)2, -NH3+, -N+H2R a, -N+HR a R b, or -N+R a R b R c; each Y is -A-B-, in which A is -O-, -NH-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -O-CO-NH-, -NH-CO-NH-, -CO-NH-, or-NH-CO-; and B is -R a-O-[Si(CH3)2-O-]1-100, C1-2000 alkyl, C6-40 aryl, C7-2000 alkylaryl, C7-2000 arylalkyl, (C1-30 alkyl ether)1-100, (C6-40 aryl ether)1-100, (C7-2000alkylaryl ether)1-100, (C7-2000 arylalkyl ether)1-100, (C1-30 alkyl thioether)1-100, (C6-40 aryl thioether)1-100, (C7-2000 alkylaryl thioether)1-100, (C7-2000 arylalkyl thioether)1-100, (C2-50 alkyl ester)1-100, (C7-2000 aryl ester)1-100, (C8-2000 alkylaryl ester)1-100, (C8-2000 arylalkyl ester)1-100, -R a-CO-O-(C1-30 alkyl ether)1-100, -R a-CO-O-(C6-40 aryl ether)1-100, -R a-CO-O-(C7-2000 alkylaryl ether)1-100, -R a-CO-O-(C7-2000 arylalkyl ether)1-100, (C4-50 alkyl urethane)1-100, (C14-60 aryl urethane)1-100, (C10-2000 alkylaryl urethane)1-100, (C10-2000 arylalkyl urethane)1-1001-100, (C5-50 alkyl urea)1-100, (C14-60 aryl urea)1-100, (C10-2000 alkylaryl urea)1-100, (C10-2000 arylalkyl urea)1-100, (C2-50 alkyl amide)1-100, (C7-60 aryl amide)1-100, (C8-2000 alkylaryl amide)1-100, (C8-2000 arylalkyl amide)1-100, (C3-30 alkyl anhydride)1-100, (C8-50 aryl anhydride)1-100, (C9-2000 alkylaryl anhydride)1-100, (C9-2000 arylalkyl anhydride)1-100, (C2-30 alkyl carbonate)1-100, (C7-50 aryl carbonate)1-100, (C8-2000 alkylaryl carbonate)1-100, (C8-2000 arylalkyl carbonate)1-100, -R a-O-CO-NH-(R b or Ar-R
b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether, or C7-2000 arylalkyl ether)1-100, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether, or C7-2000 arylalkyl ether)1-100-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100-R c-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, C7-2000 alkylaryl ether, or C7-2000 arylalkyl ether)1-100, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C1-30 alkyl ether, C6-40 aryl ether, alkylaryl ether, or C7-2000 arylalkyl ether)1-100-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-(C2-50 alkyl ester, C7-60 aryl ester, C8-2000 alkylaryl ester, or C8-2000 arylalkyl ester)1-100-R c-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-O-, -R a-O-CO-NH-(R b or Ar-R b-Ar)-NH-CO-NH-(C2-50 alkyl amide, C7-60 aryl amide, C8-2000 alkylaryl amide, or C8-2000 arylalkyl amide)1-100, -R a-NH-CO-NH-(R b or Ar-R b-Ar)-NH-CO-NH-(C2-50 alkyl amide, C7-60 aryl amide, C8-2000 alkylaryl amide, or C8-2000 arylalkyl amide)1-100, or a bond; each Z, independently, is -G-D, wherein G is -R a-, -R a-Ar-, -Ar-R a-, or -Ar-; and D
is -H, -OH, -SH, -NH2, -NHOH, -SO3H, -OSO3H, -CO2H, -CONH2, -CONHNH2, -CH(NH2)-CO2H, -NH-CH2-CO2H, -P(OH)3, -PO(OH)2, -O-PO(OH)2, -O-PO(OH)-O-PO(OH)2, -O-PO(O-)-O-CH2CH2NH3+, -O-PO(O-)-O-CH2CH2-N+(CH3)3, -glycoside, -oligosaccharide, -CO-glycoside, -CO-oligosaccharide, -OCH3, -OCH2(CHOH)4-CH2OH, -OCH2(CHOH)2-CH2OH, -CO-OCH2(CHOH)4-CH2OH, -C6H3(OH)2, -N(CH2CO2H)2, -CO-N(CH2CO2H)2, -CO-NH-C(CH2CH2CO2H)3, -CO-NH-C(CH2CH2OH)3, -[CH2-CH(CO2R a)]1-100-H, -NH3+, -N+H2R a, -N+HR a R b, or -N+R a R b R c, each of R a, R b, and R c, independently, being C1-20 alkyl and Ar being aryl; q is 0-30; and m is 0-30; provided that the sum of q and m is 0-30;
each of R1 and R4, independently, is =O or C1-20 hydrocarbon; and each of R2 and R5, independently, is C1-20 hydrocarbon; wherein R1 and R2, or R4 and R5 can join together to form C6-40 aryl which is optionally substituted with halide, -OH, -NHNH2, -NH2OH, -NH-CH2-CO2H, -CH2-CH2-D, -CH2-B-Z-CO-CH2-D, -CO-B-Z, -O-B-Z, or -NH-B-Z; each of B, D, and Z having been defined above;

each of R3 and R6, independently, is -H, -CH2-D, -B-Z, -G-E, -G-CO-E or a side chain of an amino acid; each of B, D. and Z having been defined above, and E
being E1, E2, or E3, in which E1 is Y1,Y2-amino, (Y1,Y2-alkyl)-amino, Y1,Y2-ethylenediamino, (dihydroxymethyl)alkylamino, (X1,X3-aryl)amino, or X1,X3-aryloxy; E2 is Y1,Y2-alkoxy, (Y1,Y2-amino)alkoxy, (Y1,Y2,Y3-aryl)oxy, (dihydroxyalkyl)-aryloxy, (Y1,Y2,Y3-alkyl)amino, (Y1,Y2,Y3-aryl)amino, dihydroxyalkylamino, Y1,Y2,Y3-alkoxy, (trihydroxyalkyl)alkoxy, (trihydroxyalkyl)alkylamino, (dicarboxyalkyl)amino, (Y1,Y2,Y3-alkyl)thio, (X1,X3-aryl)thio, (Y1,Y2-alkyl)thio, (dihydroxyalkyl)thio, Y1,Y2-dioxoalkyl, or tri-(Y1,Y2,Y3-methylaminocarboxyethyl)methylamino; and E3 is ((glycosidyl)oxoheteroaryl)amino, ((glycosidyl)oxoaryl)amino, (X1,X2,X;-heteroaryl)amino, (X1-diarylketone)amino, (X,X1-oxoaryl)amino, (X,X1-dioxoaryl)amino, (Y1-alkyl,Y2-alkyldioxoheteroaryl)amino, (Y1-alkyl,Y2-alkyldioxoaryl)amino, (di(Y1,Y2-methyl)dioxoheteroaryl)amino, (di(Y1,Y2-methyl)dioxoaryl)amino, ((glycosidyl)heteroaryl)amino, ((glycosidyl)aryl)amino, ((carboxylacetylalkyl)oxo-heteroaryl)amino, ((carboxylacetylalkyl)oxoaryl)amino, ((isopropylaminohydroxy-alkoxy)aryl)amino, (X1,X2,X3-alkylaryl)amino, (X1,X2,X3-heteroaryl)oxy, (isopropylaminohydroxyalkyl)aryloxy, (X1,X2,X3-oxoheteroaryl)oxy, (X1,X2,X3-oxoaryl)oxy, (X1,Y1-oxoheteroaryl)oxy, (X1-diarylketone)oxy, (X,X1-oxoaryl)oxy, (X1,X2-dioxoaryl)oxy, (Y1,Y2,di-aminodihydroxy)alkyl, (X1,X2-heteroaryl)thio, ((tricarboxylalkyl)ethylene-diamino)alkoxy, (X1,X2-oxoaryl)thio, (X1,X2-dioxoaryl)thio, (glycosidylheteroaryl)thio, (glycosidylaryl)thio, Y1-alkyl(thiocarbonyl)thio, Y1,Y2,-alkyl(thiocarbonyl)thio, Y1,Y2,Y3-alkyl(thiocarbonyl)thio, (Y1,Y2-aminothiocarbonyl)thio, (pyranosyl)thio, cysteinyl, tyrosinyl, (phenylalainyl)amino, (dicarboxyalkyl)thio, (aminoaryl)1-100 amino, (pyranosyl)amino, (Y1-aminoaryl)1-100 amino, (amino(sulfoaryl))1-100 amino, peptidyl, thymidinyl, uridinyl, guanosinyl, adenosinyl, cholesteryl, or biotinylalkoxy; wherein X is halide; each of X1, X2, and X3, independently, is -Y1, -O-Y1, -S-Y1, -NH-Y1, -CO-O-Y1, -O-CO-Y1, -CO-NH-Y1, -CO-NY1Y2, -NH-CO-Y1, -SO2-Y1, -CHY1Y2, or -NY1Y2; and each of Y1, Y2, and Y3, independently, is -Z
or -B-Z; B
and Z having been defined above;

R7 is -R d or -O-R e; wherein R d is -OH, -OM, -NHNH2, -NHOH, -NH-CH2-CO2H, -O-B-Z, -NH-B-Z, -E, -O-G-E, -NH-G-E, -O-G-CO-E, or -NH-G-CO-E; M being Cu, Mn, Fe, Co, Ni, Ru, Rh, Os, Zn, Cr, Ti, or Zr ion; and R e is -H, -CH2-CH2-D, -CH2-B-Z, -CH2-G-E, -CH2-G-CO-E, -CO-CH2-D, -CO-B-Z, -CO-G-E, or -CO-G-CO-E; each of B, D, E, G, and Z having been defined above;

R5 is R e, which has the same meaning as set forth above;

R9 is -O-R f- or -R g-; wherein R f is -CO-B-G-O-, -CO-B-G-NH-, -CO-B-G-CO-O-, or -CO-B-G-CO-NH-; and R g is -NH-, -O-, -O-B-G-O-, -NH-B-G-O-, -NH-B-G-NH-, -O-CO-B-G-CO-O-, or -NH-CO-B-G-CO-NH-; B and G having been defined above;

R10 is -H;

each of x and y, independently, is 0 or 1; and r is 1-100;

provided that when x is 0, R1 is =O, and R7 is -R d; that when y is 0, R4 is =O, and R9 is -R8, and R10 is -H; that when x is 1, R1 and R2 join together to form C6-40 aryl, and R7 is -O-R e; and that when y is 1, R4 and R5 join together to form C6-40 aryl, R9 is -O-R f, and R10 is -H; and further provided that when r is greater than 1, x is 0;
or a salt thereof.
46. The compound of claim 45, wherein F is C60, C61, C62, C63, C64, C65, C70, C76, C78, C82, C84, or C92, or La@C n, Ho@C n, Gd@C n, or Er@C n, in which n is 60, 74, or 82.
47. The compound of claim 45, wherein the sum of q and m is 0-20.
48. The compound of claim 45, wherein r is 2-30.
49. The compound of claim 45, wherein each of R3 and R6, independently, is -H, -B-Z, -G-E, -G-CO-E, or a side chain of an amino acid.
50. The compound of claim 45, wherein R d is -OH, -NHNH2, -E, -O-G-E, -NH-G-E, -O-G-CO-E, or -NH-G-CO-E.
51. The compound of claim 45, wherein R e is -H, -CH2-G-E, -CH2-G-CO-E, -CO-G-E, or -CO-G-CO-E.
52. The compound of claim 45, wherein R f is -CO-B-G-NH- or -CO-B-G-CO-NH-.
53. The compound of claim 45, wherein R g is -O-B-G-O-, -NH-B-G-O-, -NH-B-G-NH-, -O-CO-B-G-CO-O-, or -NH-CO-B-G-CO-NH-.
54. The compound of claim 45, wherein both x and y are 0.
55. The compound of claim 54, wherein each of R3 and R6, independently, is -H, -B-Z, -G-E, -G-CO-E, or a side chain of an amino acid.
56. The compound of claim 55, wherein R d is -OH, -MHNH2, -E, -O-G-E, -NH-G-E, -O-G-CO-E, or -NH-G-CO-E.
57. The compound of claim 56, wherein R e is -H, -CH2-G-E, -CH2-G-CO-E, -CO-G-E, or -CO-G-CO-E.
58. The compound of claim 57, wherein R f is -CO-B-G-NH- or -CO-B-G-CO-NH-.
59. The compound of claim 58, wherein R8 is -O-B-G-O-, -NH-B-G-O-, -NH-B-G-NH-, -O-CO-B-G-CO-O-, or -NH-CO-B-G-CO-NH-.
60. The compound of claim 59, wherein r is 2-30.
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