The rhodafluor family.: An initial study of potential ratiometric fluorescent sensors for Zn2+
The rhodafluor family.: An initial study of potential ratiometric fluorescent sensors for Zn2+
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DOI：
10.1021/ic026048q
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发表时间：
2002-12-16
影响因子：
4.6
通讯作者：
Lippard, SJ
中科院分区：
文献类型：
--
作者：
Burdette, SC;Lippard, SJ
一类新的比率Zn 2+传感器，采用混合荧光素和罗丹明荧光团已被设计，和两个成员的罗丹明或家庭的传感器，RF 1和RF 2。已经合成了。RF 1的制备（9-（邻羧基苯基）-2-氯-6-[双（2-吡啶基甲基）氨基]-3-氧杂蒽酮（Rhodoryl-1），采用常规的合成方法，Escherichia coli的RF 1的合成试图增强对Zn 2+的亲和性，但没有成功，因此采用钯催化的芳基胺化反应来制备RF 2（1-[9 '-（o-羧基苯基）-6'-氨基-2 '-氯-3'-氧杂蒽酮]-4，10-（二乙基）-7-（2-吡啶基甲基）-1，4，7，10-四氮杂环十二烷，Rhodoryl-2），合成RF 2的关键步骤是将三保护的四氮杂大环（cyclen）偶联到3-溴茴香胺上，RF 2结合Zn 2+的解离常数为13.5 μ M，伴随着类似的量子产率增加到50%，虽然只有小的吸收波长的偏移被观察到，因为质子化的氨基氮原子的大环阻止未络合的传感器采用所需的内消旋体。强度加倍使得探针在我们先前的紧密结合（
A new class of ratiometric Zn2+ sensors that employ a hybrid fluorescein and rhodamine fluorophore has been designed, and two members of the rhodafluor family of sensors, RF1 and RF2. have been synthesized. The preparation of RF1 (9-(o-carboxyphenyl)-2-chloro-6-[bis(2-pyridylmethyl)amino]-3-xanthanone, Rhodafluor-1), uses conventional synthetic methods, Elaboration of the RF1 synthesis in an effort to enhance the Zn2+, affinity was unsuccessful, so palladium-catalyzed aryl amination was applied to prepare RF2 (1-[9'-(o-carboxyphenyl)-6'-amino2'-chloro-3'-xanthanone]-4,10-(diethyl)-7-(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane, Rhodafluor-2), The key step in the synthesis of RF2 is coupling of a triprotected tetraazamacrocycle (cyclen) to 3-bromoanisidine, RF2 binds Zn2+ with a dissociation constant of 13.5 muM accompanied by an similar to50% increase in quantum yield, Although only small shifts in absorption wavelength were observed, because protonation of the amino nitrogen atoms of the macrocycle prevents the uncomplexed sensor from adopting the desired mesomer. the intensity doubling makes the probe of value for immediate application in situations where our previous tight binding (