Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils

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• 作者：Ilaria Palam脿 ; Francesca Di Maria ; Ilenia Viola ; Eduardo Fabiano ; Giuseppe Gigli ; Cristian Bettini ; Giovanna Barbarella
• 刊名：Journal of the American Chemical Society
• 出版年：2011
• 出版时间：November 9, 2011
• 年：2011
• 卷：133
• 期：44
• 页码：17777-17785
• 全文大小：1209K
• 年卷期：v.133,no.44(November 9, 2011)
• ISSN：1520-5126

文摘

In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives (DTTOs) that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.