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Literature DB >> 12323033

Brominated hydroxyquinoline as a photolabile protecting group with sensitivity to multiphoton excitation.

Abstract

The synthesis and photochemistry of a new photolabile protecting group for carboxylic acids based on 8-bromo-7-hydroxyquinoline (BHQ) is described. BHQ possesses a greater single photon quantum efficiency than 4,5-dimethoxy-4-nitrobenzyl ester (DMNB) and 6-bromo-7-hydroxycoumarin-4-ylmethyl (Bhc), and it has sufficient sensitivity to multiphoton-induced photolysis for use in vivo. Its increased solubility and low fluorescence make it quite useful as a caging group for biological messengers. [structure: see text]

Entities: Chemical

Year: 2002 PMID： 12323033 DOI： 10.1021/ol026524g

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

21 in total

1. Improved synthesis of the two-photon caging group 3-nitro-2-ethyldibenzofuran and its application to a caged thymidine phosphoramidite.

Authors: Hrvoje Lusic; Rajendra Uprety; Alexander Deiters
Journal: Org Lett Date: 2010-03-05 Impact factor: 6.005

2. Light-triggered elimination of CO₂ and absorption of O₂ (artificial breathing reaction) in photolysis of 2-(4-nitrophenyl)-1H-indole derivatives.

Authors: Qianghua Lin; Manabu Abe
Journal: Photochem Photobiol Sci Date: 2021-02-26 Impact factor: 3.982

Brominated hydroxyquinoline as a photolabile protecting group with sensitivity to multiphoton excitation.

1. Improved synthesis of the two-photon caging group 3-nitro-2-ethyldibenzofuran and its application to a caged thymidine phosphoramidite.

2. Light-triggered elimination of CO₂ and absorption of O₂ (artificial breathing reaction) in photolysis of 2-(4-nitrophenyl)-1H-indole derivatives.

Review 3. Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy.

4. Spacer-Mediated Control of Coumarin Uncaging for Photocaged Thymidine.

5. Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.

6. Light-activated serotonin for exploring its action in biological systems.

7. Photoactivatable, biologically-relevant phenols with sensitivity toward 2-photon excitation.

8. Spatiotemporal control of embryonic gene expression using caged morpholinos.

9. Combinatorial discovery of two-photon photoremovable protecting groups.

10. Versatile synthesis and rational design of caged morpholinos.