WO2007050810A3 - Fluorogenic probes for reactive oxygen species - Google Patents
Fluorogenic probes for reactive oxygen species Download PDFInfo
- Publication number
- WO2007050810A3 WO2007050810A3 PCT/US2006/041883 US2006041883W WO2007050810A3 WO 2007050810 A3 WO2007050810 A3 WO 2007050810A3 US 2006041883 W US2006041883 W US 2006041883W WO 2007050810 A3 WO2007050810 A3 WO 2007050810A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- probes
- oxygen species
- reactive oxygen
- pxl
- pfl
- Prior art date
Links
- 239000003642 reactive oxygen metabolite Substances 0.000 title abstract 5
- 239000000523 sample Substances 0.000 title abstract 5
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 abstract 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 abstract 1
- 230000001413 cellular effect Effects 0.000 abstract 1
- 239000003086 colorant Substances 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 230000005284 excitation Effects 0.000 abstract 1
- 210000004295 hippocampal neuron Anatomy 0.000 abstract 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- 238000000386 microscopy Methods 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 230000007170 pathology Effects 0.000 abstract 1
- 230000035699 permeability Effects 0.000 abstract 1
- 230000035479 physiological effects, processes and functions Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The present invention provides a novel class of fluorogenic probes for reactive oxygen species. Exemplary probes of the invention utilize a boronate deprotection mechanism to provide high selectivity and optical dynamic range for detecting H2O2 in aqueous solution over similar reactive oxygen species (ROS) including superoxide, nitric oxide, tert-butyl hydroperoxide, and hydroxyl radical; Peroxyresorufin-1 (PRl), Peroxyfluor- 1 (PFl), and Peroxyxanthone-1 (PXl) are first-generation probes that respond to H2O2 by an increase in red, green, and blue fluorescence, respectively. The boronate dyes are cell- permeable and can detect micromolar changes in H2O2 concentrations in living cells, including hippocampal neurons, using confocal and two-photon microscopy. The unique combination of ROS selectivity, membrane permeability, and a range of available excitation/emission colors establishes the potential value of PRl, PFl, PXl, and related probes for interrogating the physiology and pathology of cellular H2O2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06826796A EP1948824A4 (en) | 2005-10-27 | 2006-10-27 | Fluorogenic probes for reactive oxygen species |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73108505P | 2005-10-27 | 2005-10-27 | |
| US60/731,085 | 2005-10-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2007050810A2 WO2007050810A2 (en) | 2007-05-03 |
| WO2007050810A3 true WO2007050810A3 (en) | 2009-04-30 |
Family
ID=37968572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2006/041883 WO2007050810A2 (en) | 2005-10-27 | 2006-10-27 | Fluorogenic probes for reactive oxygen species |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP1948824A4 (en) |
| WO (1) | WO2007050810A2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009152102A2 (en) * | 2008-06-10 | 2009-12-17 | The Regents Of The University Of California | Pro-fluorescent probes |
| WO2012027274A2 (en) | 2010-08-23 | 2012-03-01 | The Regents Of The University Of California | Compositions and methods for imaging |
| ES2678211T3 (en) | 2012-03-27 | 2018-08-09 | Ventana Medical Systems, Inc. | Signaling conjugates and use procedures |
| US20140248218A1 (en) * | 2013-02-08 | 2014-09-04 | The Regents Of The University Of California | Ros-sensitive fluorescent probes |
| US10877051B2 (en) * | 2014-01-31 | 2020-12-29 | The University Of Hong Kong | Bistrifilate-based fluorogenic probes for detection of superoxide anion radical |
| CN106632436B (en) * | 2016-10-11 | 2018-05-04 | 济南大学 | A kind of preparation and application of hydrogen peroxide fluorescent probe compounds |
| EP3831820A1 (en) * | 2019-12-05 | 2021-06-09 | ETH Zurich | Compounds and methods for amine oxidase imaging |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050214807A1 (en) * | 2003-11-19 | 2005-09-29 | Iain Johnson | Environmental sensitive fluorogenic compounds and their application for singlet oxygen and protein detection |
-
2006
- 2006-10-27 EP EP06826796A patent/EP1948824A4/en not_active Withdrawn
- 2006-10-27 WO PCT/US2006/041883 patent/WO2007050810A2/en active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050214807A1 (en) * | 2003-11-19 | 2005-09-29 | Iain Johnson | Environmental sensitive fluorogenic compounds and their application for singlet oxygen and protein detection |
Non-Patent Citations (1)
| Title |
|---|
| See also references of EP1948824A4 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007050810A2 (en) | 2007-05-03 |
| EP1948824A2 (en) | 2008-07-30 |
| EP1948824A4 (en) | 2011-02-16 |
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| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
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