title: Synthesis and pharmacological screening of novel meso-substituted porphyrin analogs.
abstract: A novel series of mesotetrakis[aryl]-21H,23H-porphyrin derivatives 2a-j was synthesized from the condensation of aldehyde derivatives 1a-j with pyrrole in the presence of p-toluenesulfonic acid. The synthesized porphyrins were considered as a model to study the free radical-induced damage of biological membranes and the protective effects of these porphyrins. It was found that these compounds effectively inhibit the free radical-induced oxidative hemolysis of red blood cells. Compounds 2c and 2d which bear a sulfur atom, a nitro group, and a chlorine atom exhibited markedly higher antihemolysis activity than the other analogous. Compounds 2a, 2c, 2d, and 2j showed the highest protection activity against DNA damage induced by the bleomycin-iron complex. Compounds 2d, 2f, 2i, and 2j were proved to exhibit antioxidative activity.
authors.affiliation: Faculty of Science, Department of Chemistry, Mansoura University, Mansoura 35516, Egypt. afadda50@yahoo.com
authors.forename: Ahmed A
authors.initials: AA
authors.lastname: Fadda
authors.forename: Rasha E
authors.initials: RE
authors.lastname: El-Mekawy
authors.forename: Ahmed I
authors.initials: AI
authors.lastname: El-Shafei
authors.forename: Harold
authors.initials: H
authors.lastname: Freeman
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001761:Bleomycin / Q000494:pharmacology; D045744:Cell Line, Tumor; D002522:Chlorocebus aethiops; D004249:DNA Damage / Q000187:drug effects*; D005609:Free Radicals / Q000378:metabolism; D006461:Hemolysis / Q000187:drug effects*; D006801:Humans; D010084:Oxidation-Reduction / Q000187:drug effects; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D013329:Structure-Activity Relationship; D014709:Vero Cells
chemical_list: D000970:Antineoplastic Agents; D000975:Antioxidants; D005609:Free Radicals; D011166:Porphyrins; D001761:Bleomycin