具有阳离子侧链的水溶性N-杂卟啉的酸碱性质及与DNA的结合

Acid-base properties and DNA-binding of water soluble N-confused porphyrins with cationic side-arms.

作者信息

Ikawa Yoshiya, Moriyama Shoji, Harada Hiroyuki, Furuta Hiroyuki

机构信息

Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan.

出版信息

Org Biomol Chem. 2008 Nov 21;6(22):4157-66. doi: 10.1039/b810171j. Epub 2008 Sep 16.

DOI:10.1039/b810171j

PMID:18972046

Abstract

Water soluble N-confused porphyrins, 5,10,15,20-tetrakis(alpha-pyridinio-p-tolyl)-2-aza-21-carbaporphyrin (pPyNCP) and its N-methyl derivative, 2-N-methyl-5,10,15,20-tetrakis(alpha-pyridinio-p-tolyl)-2-aza-21-carbaporphyrin (NMe-pPyNCP), have been synthesized by introducing cationic side-arms at the meso-positions of N-confused porphyrin. Their acid-base properties (pK(1-4)) and DNA-binding ability in aqueous solutions were elucidated in comparison with the corresponding porphyrin derivative. Photophysical behaviors of pPyNCP were largely influenced by buffer compositions and DNA structures, whereas NMe-pPyNCP is considerably robust against these factors. In addition, significant enhancement of the fluorescence was observed with NMe-pPyNCP by the addition of DNA. The unique properties of pPyNCP and NMe-pPyNCP stem from the confused pyrrole rings in the macrocycle.

摘要

水溶性 N-杂卟啉、5,10,15,20-四（α-吡啶鎓对甲苯基）-2-氮杂-21-碳杂卟啉（pPyNCP）及其 N-甲基衍生物 2-N-甲基-5,10,15,20-四（α-吡啶鎓对甲苯基）-2-氮杂-21-碳杂卟啉（NMe-pPyNCP）已通过在 N-杂卟啉的中位引入阳离子侧链合成。与相应的卟啉衍生物相比，阐明了它们在水溶液中的酸碱性质（pK(1-4)）和 DNA 结合能力。pPyNCP 的光物理行为在很大程度上受缓冲液组成和 DNA 结构的影响，而 NMe-pPyNCP 对这些因素相当稳健。此外，通过添加 DNA 观察到 NMe-pPyNCP 的荧光显著增强。pPyNCP 和 NMe-pPyNCP 的独特性质源于大环中混乱的吡咯环。