Synthesis and characterization of 8-aminoquinoline photocages for biological applications

被引：3

作者：

Kontra, Bence ^{[1
,2
]}

Bogdan, Dora ^{[1
]}

Alaghehmand, Behta ^{[1
]}

Csomos, Attila ^{[3
,4
]}

Dunkel, Petra ^{[1
]}

机构：

[1] Semmelweis Univ, Dept Organ Chem, Hogyes Endre Utca 7, H-1092 Budapest, Hungary

[2] Brain Vis Ctr, Dept Chem, Liliom Utca 43-45, H-1094 Budapest, Hungary

[3] Femtonics Ltd, Dept Chem, Tu Zolto Utca 59, H-1094 Budapest, Hungary

[4] ELTE Hevesy Gyorgy PhD Sch Chem, Pazmany Peter Stny 1-A, H-1117 Budapest, Hungary

来源：

TETRAHEDRON LETTERS | 2023年 / 124卷

关键词：

Photoremovable protecting groups; Photocages; Quinolines; Buchwald-Hartwig coupling; Nitrogen heterocycles; PHOTOREMOVABLE PROTECTING GROUPS; CAGED COMPOUNDS; 2-PHOTON; SENSITIVITY; CHEMISTRY; DESIGN; PHOTOLYSIS; RELEASE;

D O I：

10.1016/j.tetlet.2023.154587

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Inspired by the 8-dimethylaminoquinoline (8-DMAQ) caging chromophore, photocleavable 8-aminoqui-noline derivatives were prepared with the aim of furnishing a robust synthetic pathway for novel cage scaffolds. The four-step versatile process allows a facile introduction of various amino-substituents and its overall yield is feasible for scale-up. The novel photocages showed high photolysis efficiency and low fluorescence, comparable to literature reference compounds (as 8-DMAQ-OAc, BHQ-OAc and CyHQ-OAc), demonstrating the utility of the probes for uncaging applications. Several derivatives allow further functionalizations on the side chain, therefore could serve as building blocks for the design of more complex photoresponsive systems.& COPY; 2023 The Author(s). Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

引用

页数：5

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