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

Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils
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DOI:
10.1021/ja2065522
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发表时间:
2011-11-09
影响因子:
15
通讯作者:
Barbarella, Giovanna
Barbarella, Giovanna
中科院分区:
化学1区
文献类型:
--
作者:
Palama, Ilaria;Di Maria, Francesca;Barbarella, Giovanna

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为了寻找能够克服活细胞染色中现有有机染料限制的噻吩荧光团,我们合成了生物相容性二噻吩- s, s -二氧化物衍生物(dtos)。由活小鼠胚胎成纤维细胞和HeLa细胞自发摄取。经dtos处理后,细胞分泌纳米结构荧光原纤维,而细胞活力保持不变。新合成的噻吩荧光团与其他细胞渗透的行为比较表明,荧光原纤维的形成是DTTO染料所特有的。激光扫描共聚焦显微镜显示,荧光原纤维大多具有螺旋超分子结构。电泳分析和理论计算表明,dtto被前胶原多肽链的HyPro组分选择性识别,并通过形成多个h键结合。
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.