通过应变促进的叠氮化物-炔烃环加成反应开发新型类似卡铂的细胞质可追踪近红外荧光团缀合物。
Development of a novel carboplatin like cytoplasmic trackable near infrared fluorophore conjugate via strain-promoted azide alkyne cycloaddition.
机构信息
Centre for Synthesis & Chemical Biology, Department of Pharmaceutical & Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephens Green, Dublin 2, Ireland.
School of Chemistry, Chemistry Building, Trinity College Dublin, Dublin 2, Ireland.
出版信息
J Inorg Biochem. 2018 May;182:150-157. doi: 10.1016/j.jinorgbio.2018.02.010. Epub 2018 Feb 21.
The successful design and pre-clicked synthesis of a non-toxic and cytosol trackable carboplatin-like near infrared fluorophore conjugate via strain-promoted azide alkyne cycloaddition (SPAAC) is reported. Reaction of cis-[Pt(2-azidopropane-1,3-diamine)(cbdca)] (cbdca = cyclobutane-1,1-dicarboxylato) and a bicyclo[6.1.0]non-4-yne near-infrared (NIR) azadipyrromethene fluorophore gave the corresponding clicked Pt-Fluorophore conjugate. The X-ray crystal structure of cis-[Pt(2-azidopropane-1,3-diamine)(cbdca)] was determined featuring the azide on the bidentate 1,3-diaminopropane ligand. The Pt-fluorophore conjugate is the first example of a Pt conjugate clicked via strain-promoted azide alkyne cycloaddition (SPAAC) where the reactive azide handle is on the amine carrier ligand. The in vitro cytotoxicity and widefield fluorescence imaging of the Pt-Fluorophore conjugate in A2780P and A2780cisR cells are described.
通过应变促进的叠氮化物-炔烃环加成（SPAAC）反应，成功设计并预点击合成了一种无毒且可追踪细胞质的类卡铂近红外荧光团缀合物。顺式-[Pt（2-叠氮丙烷-1,3-二胺）（cbdca）]（cbdca=环丁烷-1,1-二羧酸）与双环[6.1.0]壬-4-炔近红外（NIR）氮杂二吡咯甲川荧光团反应得到相应的点击 Pt-荧光团缀合物。顺式-[Pt（2-叠氮丙烷-1,3-二胺）（cbdca）]的 X 射线晶体结构确定了双齿 1,3-二氨基丙烷配体上的叠氮化物。Pt-荧光团缀合物是通过应变促进的叠氮化物-炔烃环加成（SPAAC）点击的第一个 Pt 缀合物的例子，其中反应性叠氮化物处理在胺载体配体上。描述了 Pt-荧光团缀合物在 A2780P 和 A2780cisR 细胞中的体外细胞毒性和宽场荧光成像。
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