Synthesis 2017; 49(15): 3337-3346
DOI: 10.1055/s-0036-1590813
short review
© Georg Thieme Verlag Stuttgart · New York

Design and Synthesis of Two-Photon Responsive Chromophores for Near-Infrared Light-Induced Uncaging Reactions

a  Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan
,
Youhei Chitose
a  Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan
,
Satish Jakkampudi
a  Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan
,
Pham Thi Thu Thuy
a  Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan
,
Qianghua Lin
a  Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan
,
Bui Thi Van
a  Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan
,
Ayato Yamada
a  Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan
,
Ryoko Oyama
a  Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan
,
Miyu Sasaki
a  Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan
,
Claudine Katan*
b  Institut des Sciences Chimiques de Rennes, UMR6226, CNRS, Université de Rennes 1, Ecole Nationale Supérieure de Chimie de Rennes, INSA de Rennes�, 35042 Rennes, France   Email: [email protected]   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 16 May 2017

Accepted: 02 June 2017

Publication Date:
17 July 2017 (online)


Dedicated to Professor Herbert Mayr on the occasion of his 70th birthday

Abstract

Near-infrared two-photon (TP)-induced photorelease (uncaging) of bioactive molecules such as drugs has attracted considerable attention because of its ability to elucidate mechanistic aspects of biological processes. This short review summarizes recent developments in the design and synthesis of TP-responsive chromophores.

1 Introduction

2 Molecular Design of TP-Responsive Organic Chromophores for ‘Caging & Uncaging’

2.1 π-Conjugation

2.2 A Dipolar System

2.3 A Quadrupolar System

2.4 An Octupolar System

3 Recent Developments of TP Uncaging Reactions

3.1 4-Methoxy-7-nitroindolinyl Caged Auxins

3.2 Uncaging of GABA and Tryptophan Using TP-Induced Electron-Transfer Reactions

3.3 Effect of Position Isomery in Aminoquinoline-Derived Photolabile Protecting Groups (PPGs)

3.4 Cooperative Dyads for TP Uncaging

3.5 Caged Calcium with a Bis-styrylthiophene Backbone

3.6 Cloaked Caged Compounds

3.7 Three-Dimensional Control of DNA Hybridization by Orthogonal Two-Color TP Uncaging

3.8 TP-Induced Release of Diethyl Phosphate (DEP) and ATP

4 Our Contribution to TP Uncaging Reactions

5 Summary

 
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