Bimodal chemiluminescence of 8-chlorostyryl-6-phenylethynylimidazopyrazinone: Large bathochromic shift caused by a styryl group at 8-position

被引：12

作者：

Nakamura, H ^{[1
]}

Wu, C ^{[1
]}

Takeuchi, D ^{[1
]}

Murai, A ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 060, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 3-4期

关键词：

D O I：

10.1016/S0040-4039(97)10547-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3,7-Dihydro-8-chlorostyryl-6-phenylethynyl-2-imidazo[1,2-a]pyrazin-3-one (5a) prepared from 2-amino-3,5-diphenylethynylpyrazine by condensation with methylglyoxal showed bimodal luminescence in DMSO, i.e., orange-colored luminescence under acidic to neutral conditions and yellow-colored luminescence under basic conditions. The large bathochromic shift of chemiluminescence caused by a styryl group at the 8 position was established by synthesizing 3,7-dihydro-8-styryl-6-phenylethynyl-2-imidazo[1,2-a]pyrazin-3-one (5b). (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：301 / 304

页数：4

共 9 条

[1] [Anonymous], 1988, CHEMILUMINESCENCE PR
[2] Nakamura H, 1996, SYNLETT, P1015
[3] Efficient bioluminescence of bisdeoxycoelenterazine with the luciferase of a deep-sea shrimp Oplophorus
Nakamura, H
Wu, C
Murai, A
Inouye, S
Shimomura, O
[J]. TETRAHEDRON LETTERS, 1997, 38 (36) : 6405 - 6406
[4] NAKAMURA H, 1995, SYNLETT, P1277
[5] NAKAMURA H, 1997, ELECT C HETEROCYCLIC
[6] Shining the light: The mechanism of the bioluminescence reaction of calcium-binding photoproteins
Ohmiya, Y
Hirano, T
[J]. CHEMISTRY & BIOLOGY, 1996, 3 (05): : 337 - 347
[7] LIGHT-EMITTING PROPERTIES OF RECOMBINANT SEMISYNTHETIC AEQUORINS AND RECOMBINANT FLUORESCEIN-CONJUGATED AEQUORIN FOR MEASURING CELLULAR CALCIUM
SHIMOMURA, O
MUSICKI, B
KISHI, Y
INOUYE, S
[J]. CELL CALCIUM, 1993, 14 (05) : 373 - 378
[8] CAUSE OF SPECTRAL VARIATION IN THE LUMINESCENCE OF SEMISYNTHETIC AEQUORINS
SHIMOMURA, O
[J]. BIOCHEMICAL JOURNAL, 1995, 306 : 537 - 543
[9] RECOMBINANT AEQUORIN AND RECOMBINANT SEMISYNTHETIC AEQUORINS - CELLULAR CA-2+ ION INDICATORS
SHIMOMURA, O
INOUYE, S
MUSICKI, B
KISHI, Y
[J]. BIOCHEMICAL JOURNAL, 1990, 270 (02) : 309 - 312

← 1 →