Central C-C Bonding Increases Optical and Chemical Stability of NIR Fluorophores.
Central C-C Bonding Increases Optical and Chemical Stability of NIR Fluorophores.
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DOI：
10.1039/c4ra11225c
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发表时间：
2014-01-01
期刊：
影响因子：
3.9
通讯作者：
Henary M
中科院分区：
文献类型：
--
作者：
Hyun H;Owens EA;Narayana L;Wada H;Gravier J;Bao K;Frangioni JV;Choi HS;Henary M
功能性近红外（NIR）荧光团在生物成像领域的最新进展中发挥了重要作用。然而，近红外荧光团在生物和生理环境中的光学和物理化学稳定性仍然是一个挑战。特别是七甲基胺核心的中位碳上的醚键在暴露于血清蛋白或其他富含胺的生物分子时是脆弱的。为了解决这种结构限制，通过Suzuki偶联将刚性碳-碳键安装在醚连接的近红外荧光团的框架上。替换为ZW800-1C和ZW800-3C的荧光团在各种溶剂和100%温血清环境（> - 99%,24 h）中表现出增强的光学和化学稳定性。C-C偶联ZW800化合物的生物分布和清除率与先前开发的氧取代ZW800化合物几乎相同。当与小分子配体偶联时，ZW800-1C在温血清中保持相同的稳定形态（>98%,24 h），而ZW800-1A在孵育4 h后迅速水解（34%,24 h）。
Functional near-infrared (NIR) fluorophores have played a major role in the recent advances in bioimaging. However, the optical and physicochemical stabilities of NIR fluorophores in the biological and physiological environment are still a challenge. Especially, the ether linkage on the meso carbon of heptamethine core is fragile when exposed to serum proteins or other amine-rich biomolecules. To solve such a structural limitation, a rigid carbon-carbon bond was installed onto the framework of ether-linked NIR fluorophores through the Suzuki coupling. The robust fluorophores replaced as ZW800-1C and ZW800-3C displayed enhanced optical and chemical stability in various solvents and a 100% warm serum environment (> 99%, 24 h). The biodistribution and clearance of C-C coupled ZW800 compounds were almost identical to the previously developed oxygen-substituted ZW800 compounds. When conjugated with a small molecule ligand, ZW800-1C maintained the identical stable form in warm serum (>98%, 24 h), while ZW800-1A hydrolyzed quickly after 4 h incubation (34%, 24 h).