WO2012040204A3 - Cytosolic fluorescent ion indicators - Google Patents

Cytosolic fluorescent ion indicators Download PDF

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Publication number
WO2012040204A3
WO2012040204A3 PCT/US2011/052353 US2011052353W WO2012040204A3 WO 2012040204 A3 WO2012040204 A3 WO 2012040204A3 US 2011052353 W US2011052353 W US 2011052353W WO 2012040204 A3 WO2012040204 A3 WO 2012040204A3
Authority
WO
WIPO (PCT)
Prior art keywords
crown
fluorophore
families
indicator
attaching
Prior art date
Application number
PCT/US2011/052353
Other languages
French (fr)
Other versions
WO2012040204A2 (en
Inventor
Akwasi Minta
Pedro Rogelio Escamilla
Original Assignee
Asante Research, Llc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Asante Research, Llc filed Critical Asante Research, Llc
Priority to EP11827351.5A priority Critical patent/EP2619199A4/en
Priority to CN201180055664.2A priority patent/CN103687857B/en
Publication of WO2012040204A2 publication Critical patent/WO2012040204A2/en
Publication of WO2012040204A3 publication Critical patent/WO2012040204A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/90—Xanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Abstract

Novel fluorophores for fluorescent ion indicators incorporate water-solubilizing functional groups. These fluorophores enable visible-wavelength analysis of ion concentrations with chelators that are insoluble or poorly soluble in water. A green version of the fluorophore comprises a putative fluorescein with carboxylate appendages. An orange version of the fluorophore comprises a putative rhodamine, also with carboxylate appendages. Attaching the fluorophore to a 12-crown-4, a 15-crown-5, a 18-crown-6, a 21-crown-7, or a 24-crown-8 produces lithium, sodium, potassium, rubidium, and cesium indicator families, respectively. Attaching the fluorophore to diaza [1,1,1], [1,1,2], [1,2,2], [2,2,2], [2,2,3], [2,3,3], or [3,3,3] cryptands produces more selective lithium, sodium, potassium, rubidium, and cesium indicator families, respectively. Attaching the fluorophore to BAPTA, APTRA, or half- BAPTA or their analogs produces new calcium, magnesium, and other metal ions indicator families that strongly resist leakage from the cell.
PCT/US2011/052353 2010-09-20 2011-09-20 Cytosolic fluorescent ion indicators WO2012040204A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP11827351.5A EP2619199A4 (en) 2010-09-20 2011-09-20 Cytosolic fluorescent ion indicators
CN201180055664.2A CN103687857B (en) 2010-09-20 2011-09-20 The fluoride ions indicator of kytoplasm

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US38469510P 2010-09-20 2010-09-20
US61/384,695 2010-09-20

Publications (2)

Publication Number Publication Date
WO2012040204A2 WO2012040204A2 (en) 2012-03-29
WO2012040204A3 true WO2012040204A3 (en) 2014-04-17

Family

ID=45874320

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2011/052353 WO2012040204A2 (en) 2010-09-20 2011-09-20 Cytosolic fluorescent ion indicators

Country Status (3)

Country Link
EP (1) EP2619199A4 (en)
CN (1) CN103687857B (en)
WO (1) WO2012040204A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014085568A2 (en) * 2012-11-27 2014-06-05 Saint Louis University Hbv rnase h purification and enzyme inhbitors
US10590155B2 (en) 2016-07-15 2020-03-17 Arizona Board Of Regents On Behalf Of Arizona State University Mitochondria-targeting fluorescent potassium+ sensor and method of making the same
US20210072222A1 (en) * 2019-09-05 2021-03-11 University Of Massachusetts Compositions and methods for visualization of extracellular activity
CN112939997B (en) * 2021-02-03 2022-09-20 山西大学 Spiropyran-crown ether derivative SP-CE and synthetic method and application thereof
CN115215878B (en) * 2022-07-08 2024-03-01 中国科学院理化技术研究所 Fluorescent probe for detecting millimole free calcium ions and synthesis method thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5049673A (en) * 1987-10-30 1991-09-17 The Regents Of The University Of California Fluorescent indicator dyes for calcium working at long wavelengths
US20060030054A1 (en) * 2002-07-08 2006-02-09 Tetsuo Nagano Fluorescent probe
US20070141658A1 (en) * 2005-10-27 2007-06-21 The Regents Of The University Of California Fluorogenic probes for reactive oxygen species
WO2008151303A1 (en) * 2007-06-05 2008-12-11 Invitrogen Corporation Long wavelength fluorogenic intercellular ion indicators
US20100047821A1 (en) * 2000-12-20 2010-02-25 Life Technologies Corporation Crown ether derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20070053293A (en) * 2004-09-22 2007-05-23 도쿠리쓰교세이호징 가가쿠 기주쓰 신코 기코 Water-soluble fluorescent material and method for producing same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5049673A (en) * 1987-10-30 1991-09-17 The Regents Of The University Of California Fluorescent indicator dyes for calcium working at long wavelengths
US20100047821A1 (en) * 2000-12-20 2010-02-25 Life Technologies Corporation Crown ether derivatives
US20060030054A1 (en) * 2002-07-08 2006-02-09 Tetsuo Nagano Fluorescent probe
US20070141658A1 (en) * 2005-10-27 2007-06-21 The Regents Of The University Of California Fluorogenic probes for reactive oxygen species
WO2008151303A1 (en) * 2007-06-05 2008-12-11 Invitrogen Corporation Long wavelength fluorogenic intercellular ion indicators

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP2619199A4 *

Also Published As

Publication number Publication date
CN103687857B (en) 2016-11-09
CN103687857A (en) 2014-03-26
EP2619199A2 (en) 2013-07-31
WO2012040204A2 (en) 2012-03-29
EP2619199A4 (en) 2015-08-12

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