Core-Modified Coelenterazine Luciferin Analogues: Synthesis and Chemiluminescence Properties

被引:8
作者
Gagnot, Glwadys [1 ,2 ]
Hervin, Vincent [1 ]
Coutant, Eloi P. [1 ]
Goyard, Sophie [3 ]
Jacob, Yves [4 ]
Rose, Thierry [3 ]
Hibti, Fatima Ezzahra [5 ]
Quatela, Alessia [5 ]
Janin, Yves L. [1 ]
机构
[1] Inst Pasteur, Unite Chim & Biocatalyse, CNRS, UMR 3523, 28 Rue Dr Roux, F-75724 Paris 15, France
[2] Univ Paris, 12 Rue Ecole Med, F-75006 Paris, France
[3] Inst Pasteur, Ctr Innovat & Technol Res, 25 Rue Dr Roux, F-75724 Paris 15, France
[4] Inst Pasteur, Unite Genet Mol Virus ARN, CNRS, UMR 3569, 28 Rue Dr Roux, F-75724 Paris 15, France
[5] HORIBA FRANCE SAS, 14 Blvd Thomas Gobert,Passage Jobin Yvon CS45002, F-91120 Palaiseau, France
关键词
bioluminescence; chemiluminescence; homogeneous catalysis; luciferin; synthesis design; RED-SHIFTED BIOLUMINESCENCE; SINGLET-EXCITED-STATE; HIGH QUANTUM YIELD; IN-VITRO; LUMINESCENCE; PROTEIN; DERIVATIVES; MECHANISM; VARIANTS; AEQUORIN;
D O I
10.1002/chem.202004311
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this work on the design and studies of luciferins related to the blue-hued coelenterazine, the synthesis of heterocyclic analogues susceptible to produce a photon, possibly at a different wavelength, is undertaken. Here, the synthesis of O-acetylated derivatives of imidazo[1,2-b]pyridazin-3(5 H)-one, imidazo[2,1-f][1,2,4]triazin-7(1 H)-one, imidazo[1,2-a]pyridin-3-ol, imidazo[1,2-a]quinoxalin-1(5 H)-one, benzo[f]imidazo[1,2-a]quinoxalin-3(11 H)-one, imidazo[1 ',2 ':1,6]pyrazino[2,3-c]quinolin-3(11 H)-one, and 5,11-dihydro-3 H-chromeno[4,3-e]imidazo[1,2-a]pyrazin-3-one is described thanks to extensive use of the Buchwald-Hartwig N-arylation reaction. The acidic hydrolysis of these derivatives then gave solutions of the corresponding luciferin analogues, which were studied. Not too unexpectedly, even if these were "dressed" with substituents found in actual substrates of the nanoKAZ/NanoLuc luciferase, no bioluminescence was observed with these compounds. However, in a phosphate buffer, all produced a light signal, by chemiluminescence, with extensive variations in their respective intensity and this could be increased by adding a quaternary ammonium salt in the buffer. This aspect was actually instrumental to determine the emission spectra of many of these luciferin analogues.
引用
收藏
页码:2112 / 2123
页数:12
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