Cellular Uptake and Photocytotoxicity of Glycoconjugated Porphyrins in HeLa Cells¶

IF 2.6 4区生物学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Photochemistry and Photobiology Pub Date : 2004-01-01 DOI:10.1562/2004-03-07-RA-103.1

S. Hirohara, M. Obata, Atsuhiro Saito, S. Ogata, C. Ohtsuki, S. Higashida, S. Ogura, I. Okura, Yuko Sugai, Y. Mikata, M. Tanihara, S. Yano

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引用次数: 8

Abstract

Abstract Thirty-two glycoconjugated porphyrins were synthesized by a modification of Lindsey method in the presence of Zn(OAc)2·2H2O as a template. The Zn2+ ion template strategy improved the yield about three-fold in the case of meta-substituted tetraphenylporphyrins. In addition, free-base porphyrins were obtained almost quantitatively by demetalation with 4 M HCl. Sixteen deacetylated glycoconjugated porphyrins were tested as candidate photodynamic therapy (PDT) drugs using HeLa cells. Most of the deacetylated glycoconjugated porphyrins showed higher cellular uptake than tetraphenylporphyrin tetrasulfonic acid (TPPS), and 5,10,15,20-tetrakis[4-(β-d-arabinopyranosyloxy)phenyl]porphyrin (p-5d) in particular showed 18.5-fold higher uptake than TPPS. The photocytotoxicity of 5,10,15,20-tetrakis[4-(β-d-glucopyranosyloxy)phenyl]porphyrin (p-5a), p-5d and TPPS was examined with HeLa cells, using a light dose of 16 J/cm2. These photosensitizers had no cytotoxicity in the dark, but their photocytotoxicity increased in the order of TPPS < p-5a < p-5d. These results suggest p-5d is a good candidate for a PDT drug.

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HeLa细胞中糖缀合卟啉的细胞摄取和光细胞毒性

摘要以Zn(OAc)2·2H2O为模板剂，采用Lindsey法合成了32种糖缀合卟啉。Zn2+离子模板策略使间取代四苯基卟啉的产率提高了约3倍。另外，用4 m3盐酸脱金属，得到的游离基卟啉几乎是定量的。16种去乙酰化糖缀合卟啉作为HeLa细胞光动力治疗(PDT)候选药物进行了测试。大多数去乙酰化糖缀合卟啉的细胞摄取高于四苯基卟啉四磺酸(TPPS)，特别是5、10、15、20-四基[4-(β-d-阿拉伯吡喃氧基)苯基]卟啉(p-5d)的细胞摄取比TPPS高18.5倍。采用16 J/cm2的光剂量，用HeLa细胞检测5、10、15、20-四[4-(β-d-葡萄糖氨基氧基)苯基]卟啉(p-5a)、p-5d和TPPS的光毒性。这些光敏剂在黑暗中没有细胞毒性，但其光细胞毒性从TPPS < p-5a < p-5d的顺序依次增大。这些结果表明p-5d是PDT药物的良好候选者。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Photochemistry and Photobiology 生物-生化与分子生物学

CiteScore

6.70

自引率

12.10%

发文量

171

审稿时长

2.7 months

期刊介绍： Photochemistry and Photobiology publishes original research articles and reviews on current topics in photoscience. Topics span from the primary interaction of light with molecules, cells, and tissue to the subsequent biological responses, representing disciplinary and interdisciplinary research in the fields of chemistry, physics, biology, and medicine. Photochemistry and Photobiology is the official journal of the American Society for Photobiology.