Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore
Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore
复制标题
邻乙酰氨基对 3-羟基苯基取代的二氧杂环丁烷发光体 pH 依赖性发光的影响
DOI：
10.1021/acs.orglett.8b03913
复制
发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Nobuki Kato and Tsunehiko Higuchi
中科院分区：
文献类型：
--
作者：
Yosuke Hisamatsu;Takehiro Fukiage;Kojiro Honma;Andrii G. Balia;Naoki Umezawa;Nobuki Kato and Tsunehiko Higuchi
Schaap及其同事报道了一种开创性的化学发光分子，3-(2 ' -spiroadamantane)-4-甲氧基-4-（3″-羟基）苯基-1,2-二氧乙烷（AMPD），不需要酶激活，但不适合在生理条件下使用。为了克服这一限制，我们开发了一种新的AMPD衍生物，该衍生物在羟基的理论位置上含有乙酰氨基基团作为分子内氢键位点，以降低pkvalue。该化合物在生理相关的pH范围内对AMPD表现出优异的化学发光响应。
A pioneering chemiluminescent molecule reported by Schaap and co-workers, 3-(2′-spiroadamantane)-4-methoxy-4-(3″-hydroxy)phenyl-1,2-dioxetane (AMPD), does not require enzymatic activation but is unsuitable for use under physiological conditions. To overcome this limitation, we have developed a new AMPD derivative that contains an acetamido group at theorthoposition of the hydroxy group as an intramolecular hydrogen-bonding site in order to lower the pKavalue. This compound exhibits a superior chemiluminescence response to AMPD in the physiologically relevant pH range.