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

Manabu Abe; Youhei Chitose; Satish Jakkampudi; Pham Thi Thu Thuy; Qianghua Lin; Bui Thi Van; Ayato Yamada; Ryoko Oyama; Miyu Sasaki; Claudine Katan

doi:10.1055/s-0036-1590813

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(15): 3337-3346
DOI: 10.1055/s-0036-1590813

short review

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

Manabu Abe *

^aDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan

,

Youhei Chitose

^aDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan

,

Satish Jakkampudi

^aDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan

,

Pham Thi Thu Thuy

^aDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan

,

Qianghua Lin

^aDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan

,

Bui Thi Van

^aDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan

,

Ayato Yamada

^aDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan

,

Ryoko Oyama

^aDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan

,

Miyu Sasaki

^aDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan

,

Claudine Katan*

^bInstitut 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: mabe@hiroshima-u.ac.jp eMail: claudine.katan@univ-rennes1.fr

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Abstract

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

Key words

caging reactions - uncaging reactions - photolabile protecting groups - two-photon absorption - time-dependent density functional theory

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Referenzen

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