Study on expression of luminescence function of short life-excited molecules in bioluminescence

短寿命激发分子生物发光中发光函数表达的研究

• 批准号: 14560082
• 负责人: TERANISHI Katsunori
• 金额: $ 2.3万
• 依托单位: Mie University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2002
• 资助国家: 日本
• 起止时间: 2002 至 2003
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-14560082/
• 关键词: Bioluminescence; Chemiluminescence; Luminescence Efficiency; 発光

In providing chemiluminescent probes that have high chemiluminescence intensity and high specificity to superoxide anions, novel chemiluminescent probes involving cyclodextrins covalently bound to6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one with fluorescein were synthesized and characterized. Using the hypoxanthine-xanthine oxidase system for the generation of the superoxide anions, these novel chemiluminescent probes showed higher superoxide-induced chemiluminescence intensity than that of 6-[4-[2-[N-(5-fluoresceinyl)thioureido]-ethoxy]phenyl]-2-methylimidazo[1,2-a]pyrazin-3(7H)-one(FCLA). When tested at a probe concentration of 1.0mM, compound, in which 6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one and fluorescein are covalently attached on the secondary and primary hydroxyl faces of γ-cyclodextrin, respectively, showed green-luminescence intensity that was 26 times that of FCLA, which was also the highest luminescence intensity in this present study. At probe concentrations of less than 1.0mM, the ratio of the superoxide-dependent chemiluminescence intensity to the background chemiluminescence intensity for the compound was higher than that of FCLA. These high superoxide-induced chemiluminescence intensity and superoxide-specificity n low probe concentrations indicates that the compound can be more effective than FCLA towards the measurement of superoxide anions.

为了提供高化学发光强度和对超氧阴离子高特异性的化学发光探针，合成了一种新型荧光素与6-（4-甲氧基苯基）咪唑[1,2-a]吡嗪-3(7H)- 1共价结合的环糊精化学发光探针。利用次黄嘌呤-黄嘌呤氧化酶体系生成超氧阴离子，这些新型化学发光探针比6-[4-[2-[N-（5-荧光素基）硫脲基]-乙氧基]苯基]-2-甲基咪唑[1,2-a]吡嗪-3(7H)- 1 （FCLA）具有更高的超氧诱导化学发光强度。当探针浓度为1.0mM时，6-（4-甲氧基苯基）咪唑[1,2-a]吡嗪-3(7H)- 1和荧光素分别共价附着在γ-环糊精的仲、仲羟基面上的化合物显示出绿色发光强度，是FCLA的26倍，也是本研究中最高的发光强度。在探针浓度小于1.0mM时，化合物的超氧化物依赖化学发光强度与背景化学发光强度之比高于FCLA。这些高超氧化物诱导的化学发光强度和低探针浓度下的超氧化物特异性表明该化合物可以比FCLA更有效地测量超氧化物阴离子。

项目成果

Katsunori Teranishi: "Cyclodextrin-bound 6-(4-Methoxyphenyl)imidazo[1,2-a] pyrazin-3(7H)-ones with fluorescein as green-chemiluminescent probes for superoxide anions"Anal.Biochem. 325. 185-195 (2004)

Katsunori Teranishi：“环糊精结合的 6-(4-甲氧基苯基)咪唑并[1,2-a]吡嗪-3(7H)-酮与荧光素作为超氧阴离子的绿色化学发光探针”Anal.Biochem。

K.Teranishi: "Enhanced chemiluminescence of 6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one by attachment of cyclomaltooligosaccharide (cyclodextrin). Attachment of cyclomaltononaose (γ-cyclodextrin)"Carbohydr. Res. 228. 987-993 (2003)

K.Teranishi：“通过连接环麦芽低聚糖（环糊精）增强 6-（4-甲氧基苯基）咪唑并[1,2-a]吡嗪-3（7H）-酮的化学发光。连接环麦芽酮糖（γ-环糊精）”碳水化合物。决议228。987-993（2003）

Katsunori Teranishi: "Regioselective silylation of C-2 hydroxyl group of α-cyclodextrin dependent on reaction temperature"Tetrahedron Lett.. 43. 2393-2398 (2002)

Katsunori Teranishi：“α-环糊精的 C-2 羟基的区域选择性硅烷化取决于反应温度”Tetrahedron Lett.. 43. 2393-2398 (2002)

Miyuki Narita: "Selective Fluorescent Molecular Sensing Based on 2A, 2D-Disulfonyl Dibenzosulforan-Diphenyl-Capped β-Cyclodextrin for Phenolic Guests""Anal. Sci.. 18. 711-713 (2002)

Miyuki Narita：“基于 2A, 2D-二磺酰基二苯并硫醚-二苯基封端 β-环糊精对酚类客体的选择性荧光分子传感”《Anal. Sci.. 18. 711-713 (2002)》

Katsunori Teranishi: "Cyclodextrin-bound 6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one as chemiluminescent probe for superoxide anions"ITE Letters on Batteries, New Technologies & Medicine. 4. 16-20 (2003)

Katsunori Teranishi：“环糊精结合的 6-(4-甲氧基苯基)咪唑并[1,2-a]吡嗪-3(7H)-one 作为超氧阴离子的化学发光探针”ITE Letters on Batteries, New Technologies