Chemi- and bioluminescence of coelenterazine analogues possessing an adamantylmethyl group

被引:22
作者
Hirano, T
Negishi, R
Yamaguchi, M
Chen, FQ
Ohmiya, Y
Tsuji, FI
Ohashi, M
机构
[1] SHIZUOKA UNIV, FAC EDUC, DEPT BIOCHEM, SHIZUOKA 422, JAPAN
[2] UNIV CALIF SAN DIEGO, SCRIPPS INST OCEANOG, DIV MARINE BIOL RES, LA JOLLA, CA 92093 USA
关键词
D O I
10.1016/S0040-4020(97)00812-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Coelenterazine analogues possessing the adamantylmethyl group at the C2 or C8 position were prepared to study their effects on chemi-and bioluminescence. Stability of the excited state coelenteramide analogues was significantly affected by the substitutions, resulting in a neutral amide emission of chemiluminescence in diglyme-acetate buffer and in a blue-shifted emission of bioluminescence in Tris-HCl buffer. Substitution of the adamantylmethyl group in the C8 position caused bioluminescence intensity to double. The 8-adamantylmethyl group may serve to orient the coelenterazine skeleton in a suitable position in the active site for efficient bioluminescence activity. Results with semi-synthetic AQs containing 8-adamantylmethyl analogues, and those of semi-synthetic AQs containing 2-benzyl and 2-methyl analogues, indicate that apoAQ and apoAQ C145,152,180S have the ability to recognize the C2 and C8 side-chains in coelenterazine during AQ regeneration. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:12903 / 12916
页数:14
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