Photodynamic properties of dipeptide-modified hypocrellin B derivatives: the role of tyrosine and tryptophan groups.
Three long-wavelength absorbing dipeptide-modified hypocrellin B (HB) derivatives, Gly-HB, Tyr-HB, and Trp-HB, were prepared for application in photodynamic therapy (PDT). Their abilities to produce free radicals and singlet oxygen were compared in detail with EPR technique, and their binding interactions with calf thymus DNA (CT DNA) were studied by absorption spectra and DNA melting temperature measurements. Tyr-HB and Trp-HB distinguish themselves from Gly-HB and HB remarkably by their significantly improved efficiencies to generate semiquinone anion radicals, superoxide anion radicals, and hydroxyl radicals, as well as their affinity to CT DNA, as the result of the electron-donating properties and intercalating abilities of tyrosine and tryptophan groups. Tyr-HB and Trp-HB show remarkably enhanced photodamage capabilities on CT DNA than their parent HB in aerobic conditions. Moreover, they possess moderate photodamage abilities on CT DNA even in anaerobic conditions, indicating the role of Type I mechanism in their photodynamic behaviors.
Zeng
Zhanghua
Z
Laboratory of Organic Optoelectronic Functional Materials and Molecular Engineering, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100080, People's Republic of China.
Qiao
Rui
R
Zhou
Jiahong
J
Xia
Shengqin
S
Zhang
Yan
Y
Liu
Yanyan
Y
Chen
Jinrong
J
Wang
Xuesong
X
Zhang
Baowen
B
D000838:Anions / Q000737:chemistry / Q000528:radiation effects; D004247:DNA / Q000737:chemistry / Q000528:radiation effects; D004578:Electron Spin Resonance Spectroscopy / Q000379:methods; D005609:Free Radicals / Q000737:chemistry / Q000528:radiation effects; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry / Q000528:radiation effects; D010569:Perylene / Q000031:analogs & derivatives* / Q000737:chemistry / Q000528:radiation effects; D010777:Photochemistry; D010778:Photochemotherapy; D011789:Quantum Theory; D011809:Quinones / Q000737:chemistry* / Q000528:radiation effects; D012680:Sensitivity and Specificity; D014364:Tryptophan / Q000737:chemistry* / Q000528:radiation effects; D014443:Tyrosine / Q000737:chemistry* / Q000528:radiation effects; D014466:Ultraviolet Rays
D000838:Anions; D005609:Free Radicals; D011809:Quinones; D014443:Tyrosine; D010569:Perylene; D014364:Tryptophan; D004247:DNA; C427203:calf thymus DNA; D010100:Oxygen; C064522:hypocrellin B