Synthesis and photophysical properties of thioglycosylated chlorins, isobacteriochlorins, and bacteriochlorins for bioimaging and diagnostics.
Synthesis and photophysical properties of thioglycosylated chlorins, isobacteriochlorins, and bacteriochlorins for bioimaging and diagnostics.
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DOI：
10.1021/bc100356z
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发表时间：
2010-11-17
影响因子：
4.7
通讯作者：
Drain, Charles Michael
中科院分区：
文献类型：
--
作者：
Singh, Sunaina;Aggarwal, Amit;Thompson, Sebastian;Tome, Joao P. C.;Zhu, Xianchun;Samaroo, Diana;Vinodu, Mikki;Gao, Ruomei;Drain, Charles Michael
报道了三种非水解巯基卟啉类化合物的合成及其物理性质。从内消旋全氟苯基卟啉开始，可以在2 - 3个步骤中制备不可水解的巯基糖基化卟啉（PGlc4）、二氢卟酚（CGlc4）、异菌二氢卟酚（IGlc4）和菌二氢卟酚（BGlc4）。将广泛的靶向剂附加到全氟苯基部分上的能力、化学稳定性和微调发色团的生物物理性质的能力使其成为用于开发生物化学标签、诊断或作为光动力治疗剂的合适平台。与磷酸盐缓冲盐水中的卟啉相比，CGlc4在650 nm附近具有显著更大的红光吸收和6倍的荧光量子产率增加;而IGlc4具有宽的Q带和12倍的荧光量子产率增加。BGlc 4具有与PGlc 4相似的荧光量子产率（<10%），但BGlc 4的最低能量吸收/发射峰显著红移至接近730 nm，具有几乎50倍的更大吸光度，这可以允许该缀合物成为有效的PDT试剂。可以在nM浓度下观察到CGlc4、IGlc4和BGlc4衍生物摄取到细胞如人乳腺癌细胞MDA-MB-231和K：Molv NIH 3T3小鼠成纤维细胞中。在这些条件下的光漂白是最小的。
The facile synthesis and photophysical properties of three non-hydrolysable thioglycosylated porphyrinoids are reported. Starting from meso perfluorophenylporphyrin, the non-hydrolysable thioglycosylated porphyrin (PGlc4), chlorin (CGlc4), isobacteriochlorin (IGlc4), and bacteriochlorin (BGlc4) can be made in 2–3 steps. The ability to append a wide range of targeting agents onto the perfluorophenyl moieties, the chemical stability, and the ability to fine-tune the photophysical properties of the chromophores make this a suitable platform for development of biochemical tags, diagnostics, or as photodynamic therapeutic agents. Compared to the porphyrin in phosphate buffered saline, CGlc4 has a markedly greater absorbance of red light near 650 nm and a 6-fold increase in fluorescence quantum yield; whereas IGlc4 has broad Q bands and a 12-fold increase in fluorescence quantum yield. BGlc4 has a similar fluorescence quantum yield to PGlc4, (<10%) but the lowest energy absorption/emission peaks of BGlc4 are considerably red shifted to near 730 nm with a nearly 50-fold greater absorbance, which may allow this conjugate to be an effective PDT agent. The uptake of CGlc4, IGlc4, and BGlc4 derivatives into cells such as human breast cancer cells MDA-MB-231 and K:Molv NIH 3T3 mouse fibroblast cells can be observed at nM concentrations. Photobleaching under these conditions is minimal.
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影响因子：
7.3
作者：
Huang, Ying-Ying;Mroz, Pawel;Zhiyentayev, Timur;Sharma, Sulbha K.;Balasubramanian, Thiagarajan;Ruzie, Christian;Krayer, Michael;Fan, Dazhong;Borbas, K. Eszter;Yang, Eunkyung;Kee, Hooi Ling;Kirmaier, Christine;Diers, James R.;Bocian, David F.;Holten, Dewey;Lindsey, Jonathan S.;Hamblin, Michael R.
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影响因子：
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影响因子：
2.1
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Boisbrun, Michel;Vanderesse, Regis;Frochot, Celine
通讯作者：
Frochot, Celine
影响因子：
2.1
作者：
Fox, Simon;Boyle, Ross W.
通讯作者：
Boyle, Ross W.