Synthesis and biological activities of phthalocyanine-estradiol conjugates.
Phthalocyanine-based photosensitizers, coupled via a 17alpha-ethynyl group to estradiol using Pd(II) as a catalyst, were synthesized and evaluated for their estrogen receptor binding affinity and in vitro photocytotoxicity. The highest receptor binding affinities (RBA=8-13) were observed with lipophilic conjugates coupled via a relative long spacer group while the sulfonated analogues showed little binding affinities (RBA <2). The highest photocytotoxicity was observed with the sulfonated conjugates, the nature of the spacer group did not have a pronounced effect.
Khan
Ehtsham H
EH
Department of Chemistry, A.M.U. Aligarh (U.P.) India.
Ali
Hasrat
H
Tian
Hongjian
H
Rousseau
Jacques
J
Tessier
Guillame
G
Shafiullah
van Lier
Johan E
JE
D002384:Catalysis; D002470:Cell Survival / Q000187:drug effects; D004958:Estradiol / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D007202:Indicators and Reagents; D007211:Indoles / Q000737:chemistry* / Q000494:pharmacology*; D054833:Isoindoles; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D011960:Receptors, Estrogen / Q000187:drug effects / Q000378:metabolism; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014407:Tumor Cells, Cultured
D007202:Indicators and Reagents; D007211:Indoles; D054833:Isoindoles; D017319:Photosensitizing Agents; D011960:Receptors, Estrogen; D004958:Estradiol; D010165:Palladium; C013647:phthalocyanine