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Synthesis, Characterization and Photodynamic Activity of Amino‐substituted Hypocrellin Derivatives ¶
Author(s) -
Tang YiJin,
Liu HongYan,
An JingYi,
Han Rei
Publication year - 2001
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1562/0031-8655(2001)0740201scapao2.0.co2
Subject(s) - chemistry , characterization (materials science) , stereochemistry , photodynamic therapy , combinatorial chemistry , organic chemistry , nanotechnology , materials science
Three new hypocrellin derivatives, amino‐ or amino acid–substituted on the side ring of hypocrellin B (HB), were synthesized by the reactions of HB with 3‐methoxypropylamine, 6‐aminohexanoic acid and γ‐amino‐ n ‐butyric acid, respectively. The structures of these compounds were characterized with proton nuclear magnetic resonance spectra, infrared spectra and mass spectra. The UV–visible absorption spectra, singlet oxygen–generating quantum yield and amphiphilicities of hypocrellin derivatives were measured and compared with HB, the parent compound. These derivatives showed strong absorption in the domain of the phototherapeutic window (600–900 nm) and improved amphiphilicity. HB and the derivatives were preliminarily tested for their photodynamic effects on human oral cavity epithelial carcinoma KB cell line in vitro. Two amino acid–substituted hypocrellins showed phototoxicity to the KB cell line. At an inhibitory dosage of 50% killing only 0.51 μmol L −1 compound 3 (or 0.88 μmol L −1 compound 2 ) and 0.5 J cm −2 irradiation were required. The hypocrellins exhibited some dark toxicity to the KB cell line. HB and amino acid–substituted hypocrellins showed lower dark toxicity to the KB cell line than amino‐substituted hypocrellins in the assessment of cell survival.