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Synthesis and Studies of Glucosamine Conjugated BF2‐Oxasmaragdyrin
ChemistrySelect ( IF 2.1 ) Pub Date : 2020-01-17 , DOI: 10.1002/slct.201903986
Kandala Laxman 1, 2, 3 , B. Pradeep K. Reddy 4 , Andrea Robinson 3 , Rohit Srivastava 4 , Mangalampalli Ravikanth 2
Affiliation  

A value addition to the existing NIR fluorescence imaging agents has been synthesized in the form of glucosamine conjugated BF2‐oxasmaragdyrin by treating mesop‐carboxyphenyl BF2‐oxasmaragdyrin with 6‐amine‐6‐deoxy‐1‐O‐Boc‐2‐N‐Boc‐β‐D‐glucosamine in the presence of HBTU. The glucosamine conjugated BF2‐oxasmaragdyrin was thoroughly characterized by HRMS, 1D, and 2D NMR spectroscopy. The photophysical studies revealed that the conjugates are highly stable, absorb in visible‐ far‐red region (400‐700 nm) and emits in far‐red region (715 nm) with moderate quantum yields. The electrochemical studies showed that the molecules are stable under redox conditions with one reversible reduction and three reversible oxidations. The glucosamine conjugated BF2‐oxasmaragdyrin was found to be highly biocompatible with good cellular uptake in L929 and MDA‐MB‐231 cells.

中文翻译:

葡糖胺共轭BF2-Oxasmaragdyrin的合成与研究

值除现有的NIR荧光成像剂已在葡糖胺偶联BF的形式被合成2 -oxasmaragdyrin通过处理内消旋- p -carboxyphenyl BF 2与6-胺-6-脱氧-1- -oxasmaragdyrin ö -Boc-2 -在HBTU存在的情况下-N - Boc - β -D-葡萄糖胺 氨基葡萄糖共轭BF 2-oxasmaragdyrin通过HRMS,1D和2D NMR光谱进行了全面表征。光物理研究表明,结合物具有很高的稳定性,在可见的远红色区域(400-700 nm)吸收,并在远红色区域(715 nm)发射,且量子产率适中。电化学研究表明该分子在氧化还原条件下稳定,具有一个可逆还原和三个可逆氧化。已发现,在L929和MDA-MB-231细胞中,氨基葡萄糖缀合的BF 2-奥沙玛拉汀具有高度的生物相容性并具有良好的细胞摄取。
更新日期:2020-01-17
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