CA2592991A1 - Nanoparticles for protein drug delivery - Google Patents

Nanoparticles for protein drug delivery Download PDF

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Publication number
CA2592991A1
CA2592991A1 CA002592991A CA2592991A CA2592991A1 CA 2592991 A1 CA2592991 A1 CA 2592991A1 CA 002592991 A CA002592991 A CA 002592991A CA 2592991 A CA2592991 A CA 2592991A CA 2592991 A1 CA2592991 A1 CA 2592991A1
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CA
Canada
Prior art keywords
dose
nanoparticles
component
bioactive agent
insulin
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Granted
Application number
CA002592991A
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French (fr)
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CA2592991C (en
Inventor
Hosheng Tu
Hsing-Wen Sung
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NANOMEGA MEDICAL Corp
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Nanomega Medical Corporation
Hosheng Tu
Hsing-Wen Sung
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Priority claimed from US11/029,082 external-priority patent/US7265090B2/en
Application filed by Nanomega Medical Corporation, Hosheng Tu, Hsing-Wen Sung filed Critical Nanomega Medical Corporation
Publication of CA2592991A1 publication Critical patent/CA2592991A1/en
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Publication of CA2592991C publication Critical patent/CA2592991C/en
Expired - Fee Related legal-status Critical Current
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51Nanocapsules; Nanoparticles
    • A61K9/5107Excipients; Inactive ingredients
    • A61K9/513Organic macromolecular compounds; Dendrimers
    • A61K9/5146Organic macromolecular compounds; Dendrimers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyamines, polyanhydrides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/13Amines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/473Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7008Compounds having an amino group directly attached to a carbon atom of the saccharide radical, e.g. D-galactosamine, ranimustine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/726Glycosaminoglycans, i.e. mucopolysaccharides
    • A61K31/727Heparin; Heparan
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • A61K38/16Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22Hormones
    • A61K38/28Insulins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/61Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0019Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51Nanocapsules; Nanoparticles
    • A61K9/5107Excipients; Inactive ingredients
    • A61K9/513Organic macromolecular compounds; Dendrimers
    • A61K9/5161Polysaccharides, e.g. alginate, chitosan, cellulose derivatives; Cyclodextrin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51Nanocapsules; Nanoparticles
    • A61K9/5192Processes
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00Nanotechnology
    • Y10S977/70Nanostructure
    • Y10S977/773Nanoparticle, i.e. structure having three dimensions of 100 nm or less

Abstract

The invention discloses the nanoparticles composed of chitosan, poly-.gamma.-glutamic acid, and at least one bioactive agent characterized with a positive surface charge and their enhanced permeability for paracellular drug delivery.

Claims (44)

1. A dose of nanoparticles to a patient characterized by enhancing intestinal paracellular transport or brain blood paracellular transport, each nanoparticle comprising a first component of at least one bioactive agent, a second component that is negatively charged, and a third component of low molecular weight chitosan, wherein said first and second components occupy a center core and said third component dominates on a surface of said nanoparticle.
2. The dose of claim 1, wherein said second component is .gamma.-PGA.
3. The dose of claim 2, wherein a weight ratio of said chitosan to .gamma.-PGA
in nanoparticles is 0.75 to 0.167 or higher.
4. The dose of claim 1, wherein said first component is insulin.
5. The dose of claim 1, wherein said first component is insulin and said second component is .gamma.-PGA, wherein a weight ratio of the three components is about 0.083:0.167:0.75.
6. The dose of claim 1, wherein said first component is insulin, wherein an insulin loading capacity is at least 8 w/w% of the nanoparticles.
7. The dose of claim 1, wherein said first component is insulin, wherein an insulin loading capacity is at least 14 w/w% of the nanoparticles.
8. The dose of claim 1, wherein a zeta potential of the nanoparticles is between about 15 and 40 mV.
9. The dose of claim 1, wherein a zeta potential of the nanoparticles is between about 25 to 40 mV.
10. The dose of claim 1, wherein said second component is heparin or alginate.
11. The dose of claim 1, wherein the at least one bioactive agent is an antagonist for Alzheimer's disease.
12. The dose of claim 1, wherein the at least one bioactive agent is for treating Alzheimer's disease selected from a group consisting of memantine hydrochloride, donepezil hydrochloride, rivastigmine tartrate, galantamine hydrochloride, and tacrine hydrochloride.
13. The dose of claim 1, wherein the at least one bioactive agent is insulin or insulin analog.
14. The dose of claim 1, wherein the at least one bioactive agent is selected from a group consisting of proteins, peptides, nucleosides, nucleotides, antiviral agents, antineoplastic agents, antibiotics, and anti-inflammatory drugs.
15. The dose of claim 1, wherein the at least one bioactive agent is an antagonist for Parkison's disease.
16. The dose of claim 1, wherein the at least one bioactive agent is selected from a group consisting of epidermal growth factor (EGF), insulin-like growth factor (IGF), transforming growth factor (TGF), nerve growth factor (NGF), platelet-derived growth factor (PDGF), bone morphogenic protein (BMP), and fibroblast growth factor.
17. The dose of claim 1, wherein the at least one bioactive agent is selected from a group consisting ofoxytocin, vasopressin, adrenocorticotrophic hormone, prolactin, luliberin or luteinising hormone releasing hormone, growth hormone, growth hormone releasing factor, somatostatin, glucagon, interferon, gastrin, tetragastrin, pentagastrin, urogastroine, secretin, calcitonin, enkephalins, endorphins, angiotensins, renin, bradykinin, bacitracins, polymixins, colistins, tyrocidin, gramicidines, monoclonal antibodies and soluble vaccines.
18. The dose of claim 1, wherein the at least one bioactive agent comprises stem cells.
19. The dose of claim 1, wherein said nanoparticles are further encapsulated in a gelcap capsule.
20. The dose of claim 19, wherein a surface of said gelcap capsule comprises glycerin.
21. The dose of claim 20, wherein a surface of said gelcap capsule is hydrophilic.
22. The dose of claim 1, wherein the third component is crosslinked.
23. The dose of claim 22, wherein the third component is crosslinked at a degree of crosslinking less than 50%.
24. The dose of claim 22, wherein the third component is crosslinked with a crosslinking agent selected from a group consisting of genipin, its derivatives, analog, stereoisomers and mixtures thereof.
25. The dose of claim 1, wherein the low molecule weight chitosan has a molecular weight of 80 kDa or less.
26. The dose of claim 1, wherein the low molecule weight chitosan is further grafted with a polymer having a chemical formula as:

where R is >= 12
27. The dose of claim 1, wherein the low molecular weight chitosan has a molecular weight of less than about 40 kDa.
28. The dose of claim 1, wherein the nanoparticles have a mean particle size between about 100 and 300 nanometers.
29. The dose of claim 1, wherein the nanoparticles are formed via a simple and mild ionic-gelation method.
30. A method of enhancing intestinal paracellular transport or brain blood paracellular transport comprising administering a dose of nanoparticles, wherein each nanoparticle comprises a first component of at least one bioactive agent, a second component that is negatively charged, and a third component of low molecular weight chitosan, wherein said third component dominates on a surface of said nanoparticle.
31. The method of claim 30, wherein the step of administering said dose of nanoparticles is via oral administration for enhancing the intestinal paracellular transport.
32. The method of claim 30, wherein the step of administering said dose of nanoparticles is via blood vessel administration for enhancing the brain blood paracellular transport.
33. An oral dose of nanoparticles that enhance intestinal paracellular transport or blood brain paracellular transport comprising .gamma.-PGA and low molecular weight chitosan, wherein said chitosan dominates on a surface of said nanoparticles.
34. The oral dose of claim 33, wherein a weight ratio of said chitosan to .gamma.-PGA is 0.75 to 0.167 or higher.
35. The oral dose of claim 33, wherein said nanoparticles further comprise at least one bioactive agent.
36. The oral dose of claim 35, wherein the bioactive agent is an Alzheimer antagonist.
37. The oral dose of claim 35, wherein the bioactive agent is selected from a group consisting of proteins, peptides, nucleosides, nucleotides, antiviral agents, antineoplastic agents, antibiotics, and anti-inflammatory drugs.
38. The oral dose of claim 33, wherein said .gamma.-PGA is characterized with a negative charge.
39. The oral dose of claim 33, wherein the surface of said nanoparticles is characterized with a positive surface charge.
40. The oral dose of claim 33, wherein a zeta potential of the nanoparticles is between about 15 and 40 mV.
41. The oral dose of claim 33, wherein a zeta potential of the nanoparticles is between about 25 to 40 mV.
42. The oral dose of claim 33, wherein said nanoparticles are further encapsulated in a gelcap capsule.
43. The oral dose of claim 42, wherein a surface of said gelcap capsule comprises glycerin.
44. The oral dose of claim 42, wherein a surface of said gelcap capsule is hydrophilic.
CA2592991A 2005-01-04 2005-12-27 Nanoparticles for protein drug delivery Expired - Fee Related CA2592991C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US11/029,082 US7265090B2 (en) 2004-10-05 2005-01-04 Nanoparticles for paracellular drug delivery
US11/029,082 2005-01-04
US11/284,734 US7282194B2 (en) 2004-10-05 2005-11-21 Nanoparticles for protein drug delivery
US11/284,734 2005-11-21
PCT/US2005/047125 WO2006073950A2 (en) 2005-01-04 2005-12-27 Nanoparticles for protein drug delivery

Publications (2)

Publication Number Publication Date
CA2592991A1 true CA2592991A1 (en) 2006-07-13
CA2592991C CA2592991C (en) 2012-09-11

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US (4) US7282194B2 (en)
EP (1) EP1833470A4 (en)
JP (2) JP5384831B2 (en)
CN (1) CN101360486B (en)
AU (1) AU2005322940B2 (en)
BR (1) BRPI0518093A (en)
CA (1) CA2592991C (en)
HK (1) HK1122508A1 (en)
WO (1) WO2006073950A2 (en)

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