Biolocalisation and photochemical properties of two novel macrocyclic photosensitisers: a spectroscopic study.
Biolocalisation and photochemical properties of novel macrocyclic photosensitisers, guanidiniocarbonyl-substituted tetraphenylporphyrin (1) and sugar-substituted sapphyrin (2) were investigated by spectroscopic methods. Both photosensitisers absorb in far visible region and showed good tumour localisation. Photosensitiser 2 demonstrated significantly larger absolute and relative to normal tissue (T/N) amount in tumour (330 microg g(-1) wet tissue, T/N=19.0) than photosensitiser 1 did (13 microg g(-1) wet tissue, T/N=2.1). According to iodometric and uric acid assays, compound 1 produced large amount of 1O2 (phidelta=0.60-0.68), while compound 2 showed non-significant 1O2 production (phidelta=0.04). The electronic spectroscopic study confirms that only photosensitiser 1 is able to mediate photooxidation of model compounds (BSA, poly(Trp), Tyr, Trp, and GMP) after light irradiation. Pour photochemical activity of compound 2 was explained by its self-aggregation. Raman spectroscopic study indicated that monomerised photosensitiser 2 effectively damaged BSA and calf thymus DNA after light excitation at the conditions of high excess of these macromolecules.
Synytsya
Alla
A
Department of Analytical Chemistry, Institute of Chemical Technology in Prague, Technická 5, 166 28 Prague 6, Czech Republic. alla.syntsya@vscht.cz
Král
Vladimír
V
Blechová
Miroslava
M
Volka
Karel
K
D000042:Absorption; D000818:Animals; D002241:Carbohydrates / Q000737:chemistry; D004247:DNA / Q000737:chemistry / Q000378:metabolism / Q000528:radiation effects; D005260:Female; D006147:Guanine / Q000737:chemistry; D051379:Mice; D015394:Molecular Structure; D009369:Neoplasms / Q000378:metabolism / Q000473:pathology; D010100:Oxygen / Q000378:metabolism; D010777:Photochemistry; D017319:Photosensitizing Agents / Q000008:administration & dosage / Q000737:chemistry* / Q000493:pharmacokinetics*; D011166:Porphyrins / Q000008:administration & dosage / Q000737:chemistry* / Q000493:pharmacokinetics*; D012710:Serum Albumin, Bovine / Q000737:chemistry / Q000378:metabolism; D012996:Solutions / Q000737:chemistry; D013057:Spectrum Analysis; D013059:Spectrum Analysis, Raman
D002241:Carbohydrates; D017319:Photosensitizing Agents; D011166:Porphyrins; D012996:Solutions; C440448:sapphyrin; C409084:tetraphenylporphyrin; D012710:Serum Albumin, Bovine; D006147:Guanine; D004247:DNA; D010100:Oxygen