Visible light-induced nitric oxide release from a novel nitrobenzene derivative cross-conjugated with a coumarin fluorophore

被引:22
作者
Kitamura, Kai [1 ]
Ieda, Naoya [1 ]
Hishikawa, Kazuhiro [1 ]
Suzuki, Takayoshi [2 ]
Miyata, Naoki [1 ]
Fukuhara, Kiyoshi [3 ]
Nakagawa, Hidehiko [1 ]
机构
[1] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan
[2] Kyoto Prefectural Univ Med, Kita Ku, Kyoto 4038334, Japan
[3] Showa Univ, Sch Pharm, Shinagawa Ku, Tokyo 1428555, Japan
基金
日本科学技术振兴机构;
关键词
Nitric oxide; NO donor; Visible light-control; Caged compound; Cross-conjugation; PHOTOLABILE PROTECTING GROUPS;
D O I
10.1016/j.bmcl.2014.10.075
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Nitric oxide (NO) is a well-known free-radical molecule which is endogenously biosynthesised and shows various functions in mammals. To investigate NO functions, photocontrollable NO donors, compounds which release NO in response to light, are expected to be potentially useful. However, most of the conventional NO donors require harmful ultra-violet light for NO release. In this study, two dimethylnitrobenzene derivatives conjugated with coumarins were designed, synthesized and evaluated as photocontrollable NO donors. The optical properties and efficiency of photo-induced NO release were dependent upon the nature of the conjugation system. One of these compounds, Bhc-DNB (1), showed spatiotemporally well-controlled NO release in cultured cells upon exposure to light in the less-cytotoxic visible wavelength range (400-430 nm). (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5660 / 5662
页数:3
相关论文
共 22 条
[1]   o-Nitrobenzyl photolabile protecting groups with red-shifted absorption:: Syntheses and uncaging cross-sections for one- and two-photon excitation [J].
Aujard, Isabelle ;
Benbrahim, Chouaha ;
Gouget, Marine ;
Ruel, Odile ;
Baudin, Jean-Bernard ;
Neveu, Pierre ;
Jullien, Ludovic .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (26) :6865-6879
[2]   Nitric Oxide and Schizophrenia: Present Knowledge and Emerging Concepts of Therapy [J].
Bernstein, Hans-Gert ;
Keilhoff, Gerburg ;
Steiner, Johann ;
Dobrowolny, Henrik ;
Bogerts, Bernhard .
CNS & NEUROLOGICAL DISORDERS-DRUG TARGETS, 2011, 10 (07) :792-807
[3]   Synthesis and photochemical behavior of coumarin-caged cholesterol [J].
Bourbon, Pauline ;
Peng, Qian ;
Ferraudi, Guillermo ;
Stauffacher, Cynthia ;
Wiest, Olaf ;
Helquist, Paul .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (07) :2162-2165
[4]   S-Nitrosylation of Drp1 Mediates β-Amyloid-Related Mitochondrial Fission and Neuronal Injury [J].
Cho, Dong-Hyung ;
Nakamura, Tomohiro ;
Fang, Jianguo ;
Cieplak, Piotr ;
Godzik, Adam ;
Gu, Zezong ;
Lipton, Stuart A. .
SCIENCE, 2009, 324 (5923) :102-105
[5]  
COBBS CS, 1995, CANCER RES, V55, P727
[6]   Photochemical generation of nitric oxide from 6-nitrobenzo[a]pyrene [J].
Fukuhara, K ;
Kurihara, M ;
Miyata, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (36) :8662-8666
[7]   Bhc-cNMPs as either water-soluble or membrane-permeant photoreleasable cyclic nucleotides for both one- and two-photon excitation [J].
Furuta, T ;
Takeuchi, H ;
Isozaki, M ;
Takahashi, Y ;
Kanehara, M ;
Sugimoto, M ;
Watanabe, T ;
Noguchi, K ;
Dore, TM ;
Kurahashi, T ;
Iwamura, M ;
Tsien, RY .
CHEMBIOCHEM, 2004, 5 (08) :1119-1128
[8]   Brominated 7-hydroxycoumarin-4-ylmethyls: Photolabile protecting groups with biologically useful cross-sections for two photon photolysis [J].
Furuta, T ;
Wang, SSH ;
Dantzker, JL ;
Dore, TM ;
Bybee, WJ ;
Callaway, EM ;
Denk, W ;
Tsien, RY .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (04) :1193-1200
[9]   Photolabile protecting groups for nucleosides: Synthesis and photodeprotection rates [J].
Hasan, A ;
Stengele, KP ;
Giegrich, H ;
Cornwell, P ;
Isham, KR ;
Sachleben, RA ;
Pfleiderer, W ;
Foote, RS .
TETRAHEDRON, 1997, 53 (12) :4247-4264
[10]   Multiple bond-conjugated photoinduced nitric oxide releaser working with two-photon excitation [J].
Hishikawa, Kazuhiro ;
Nakagawa, Hidehiko ;
Furuta, Toshiaki ;
Fukuhara, Kiyoshi ;
Tsumoto, Hiroki ;
Suzuki, Takayoshi ;
Miyata, Naoki .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (01) :302-305