Cellular uptake and photocytotoxicity of glycoconjugated chlorins in HeLa cells
Cellular uptake and photocytotoxicity of glycoconjugated chlorins in HeLa cells
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DOI：
10.1016/j.jphotobiol.2004.09.003
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发表时间：
2005-01-14
影响因子：
5.4
通讯作者：
Yano, S
中科院分区：
文献类型：
--
作者：
Hirohara, S;Obata, M;Yano, S
用惠特洛克法经二亚胺还原合成了8个5，10，15，20-四[3-或4-(β-D-糖基黄烷氧基)苯基]氯，并用反相薄层层析(RP-TLC)对其进行了纯化。用氢核磁共振波谱、电子喷雾电离飞行时间质谱仪(ESI-TOF MS)和紫外-可见光谱(UV-Vis)对化合物进行了表征。电喷雾飞行时间质谱仪可以检测到糖共轭氯与其对应的卟啉(即5，10，15，20-四[3-或4-(beta-D-glycopyranosyloxy)phenyl]porphyrin).])之间的2H分子量差异HeLa细胞对这8种氯素的摄取进行了评估。所有糖结合的氯素显示出比四苯基卟啉四磺酸(TPPS)更高的细胞摄取率，而5，10，15，20-tetrakis[3-(beta-D-xylopyranosyloxy)phenyl]chlorin的摄取率是TPPS的50倍。在2×10~(-7)M(5，10，15，20-tetrakis[3-(beta-D-glucopyranosyloxy)phenyl]chlorin，5，10，15，20-tetrakis[3-(beta-D-xylopyranosyloxy)phenyl]chlorin/dm(3))浓度下，测定了TPP和TPP对HeLa细胞的光细胞毒作用。这些光敏剂在黑暗中没有细胞毒性，但它们的光细胞毒性按5，10，15，20-tetrakis[3-(beta-D-glucopyranosyloxy)phenyl]chlorin>；5，10，15，20-tetrakis[3-(beta-D-xylopyranosyloxy)phenyl]chlorin>；TPPS的顺序递减。结果表明，光细胞毒性不是简单地与细胞摄取有关。(C)2004爱思唯尔B.V.保留所有权利。
Eight 5,10,15,20-tetrakis[3- or 4-(beta-D-glycopyranosyloxy)phenyl]chlorins were synthesized by means of the Whitlock method with diimide reduction and purified by reversed-phase thin layer chromatography (RP-TLC). All compounds were characterized by H-1 NMR spectroscopy, electron-spray ionization time-of-flight mass spectrometry (ESI-TOF MS), and UV-Vis spectroscopy. ESI-TOF MS could detect the 2H difference in molecular weight between a glycoconjugated chlorin and its corresponding porphyrin (i.e., 5,10,15,20-tetrakis[3- or 4-(beta-D-glycopyranosyloxy)phenyl]porphyrin). The cellular uptake of the eight chlorins was evaluated in HeLa cells. All glycoconjugated chlorins showed higher cellular uptake than tetraphenylporphyrin tetrasulfonic acid (TPPS), and 5,10,15,20-tetrakis[3-(beta-D-xylopyranosyloxy)phenyl]chlorin showed 50-fold higher uptake than TPPS. The photocytotoxicity of 5,10,15,20-tetrakis[3-(beta-D-glucopyranosyloxy)phenyl]chlorin, 5,10,15,20-tetrakis[3-(beta-D-xylopyranosyloxy)phenyl]chlorin and TPPS towards HeLa cells was examined at the concentration of 2 x 10(-7) M (mol/dm(3)). These photosensitizers had no cytotoxicity in the dark, but their photocytotoxicity decreased in the order of 5,10,15,20-tetrakis[3-(beta-D-glucopyranosyloxy)phenyl]chlorin > 5,10,15,20-tetrakis[3-(beta-D-xylopyranosyloxy)phenyl]chlorin > TPPS. The results indicate that the photocytotoxicity is not related simply to cellular uptake. (C) 2004 Elsevier B.V. All rights reserved.