Photobiological properties of positively charged methylene violet analogs

作     者：Houghtaling, MA Perera, R Owen, KE Wagner, S Kuhn, RJ Morrison, H 

作者机构：Purdue Univ Dept Chem W Lafayette IN 47907 USA Purdue Univ Dept Sci Biol W Lafayette IN 47907 USA Amer Res Cross Biomed Serv Jerome H Holland Lab Med Sci Rockville MD USA 

出 版 物：《PHOTOCHEMISTRY AND PHOTOBIOLOGY》 (光化学与光生物学)

年 卷 期：2000年第71卷第1期

页      面：20-28页

核心收录：

学科分类：0710[理学-生物学] 071010[理学-生物化学与分子生物学] 07[理学] 

基　　金：NCI NIH HHS [5T32 CA09634] Funding Source: Medline NIGMS NIH HHS [GM 56279] Funding Source: Medline 

主　　题：抗病毒药/化学 抗病毒药/药理学 细胞死亡/药物作用 DNA/化学 甲基化 分子结构 酚噻嗪类/化学 酚噻嗪类/药理学 光生物学 光化学 Sindbis病毒/药物作用 光谱分析 

摘      要：O-Methyl methylene violet (OMeMV), O-methyl bromomethylene violet (OMeBrMV) and O-methyl iodomethylene violet (OMeIMV) have been prepared in order to test their potential utility as anti-viral and anti-tumor phototoxic dyes. Rates of photosensitized toxicity of KB cells with 633 mn irradiation are (x10(-19) photon(-1)): 2.4, 2.2, 1.9 and 0.17 for OMeIMV, OMeBrMV, methylene violet (MV) and OMeMV, respectively. Rates of photosensitized inactivation of Sindbis virus in phosphate-buffered saline with 633 nn irradiation are (x10(-18) photon(-1)): 3.3, 1.8, 0.99, 0.15 for MV, OMeIMV, OMeBrMV and OMeMV, respectively, Quantum efficiencies for singlet oxygen formation were determined as OMeIMV, 0.64;OMeBrMV, 0.40;OMeMV, 0.054, Titration of the dyes with double-stranded (ds)DNA resulted in bathochromic shifts and hypochromic effects in the visible absorption spectra, Association constants for interaction of the methylated dyes with dsDNA of similar to 1 x 10(5) M-1 were determined by Scatchard analysis of equilibrium dialysis and UV absorption titration data. Photolysis of the halogenated dyes with DNA under argon led to covalent bond formation with the nucleic acid;there was no evidence of covalent binding in the dark.