title: Synthesis, antinociceptive and anti-inflammatory effects of porphyrins.
abstract: Porphyrins are natural compounds with several biological activities. We report the synthesis and the evaluation of the anti-inflammatory and antinociceptive effects of 4 porphyrins: 5,10,15,20-tetraphenylporphyrin (TPP), 5,10,15,20-tetra(4'-fluorophenyl)porphyrin (TpFPP), 5,10,15,20-tetra(4'-chlorophenyl)porphyrin (TpClPP), and 5,10,15,20-tetra(4'-bromophenyl)porphyrin (TpBrPP). The in vitro anti-inflammatory effects were evaluated on heat-induced hemolysis. The antinociceptive effects were evaluated using the hot plate and formalin tests. The in vivo anti-inflammatory assays were tested on the acute and chronic TPA (12-O-tetradecanoylphorbol 13-acetate) method to induce ear edema. The anti-arthritic effects were evaluated using carrageenan kaolin induced arthritis (CKIA). All porphyrins inhibited hemolysis with similar potency than naproxen (NPX). In the antinociceptive tests, all porphyrins tested at 200mg/kg showed similar effects compared to 100mg/kg NPX. In the in vivo anti-inflammatory acute assay, only three porphyrins (TPP, TpFPP and TpBrPP) decreased inflammation with similar activity than 2mg/ear indomethacin (IND). Further anti-inflammatory experiments were carried out with TPP, TpFPP and TpBrPP. In the in vivo anti-inflammatory chronic assay, porphyrins decreased inflammation with similar activity than 8mg/kg IND. Porphyrins tested at 200mg/kg showed anti-arthritic effects. The antinociceptive, anti-inflammatory and arthritic activities of porphyrins suggest that these compounds might be a good alternative for the treatment of inflammatory diseases.
authors: Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana-Xochimilco, Mexico.
authors: Angel Josabad
authors: AJ
authors: Alonso-Castro
authors: Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana-Xochimilco, Mexico.
authors: Juan Ramón
authors: JR
authors: Zapata-Morales
authors: Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana-Xochimilco, Mexico.
authors: Abigail
authors: A
authors: Hernández-Munive
authors: Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana-Xochimilco, Mexico.
authors: Nimsi
authors: N
authors: Campos-Xolalpa
authors: Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana-Xochimilco, Mexico.
authors: Salud
authors: S
authors: Pérez-Gutiérrez
authors: Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana-Xochimilco, Mexico. Electronic address: cperezg@correo.xoc.uam.mx.
authors: Cuauhtémoc
authors: C
authors: Pérez-González
mesh_terms: D000284:Administration, Oral; D000700:Analgesics / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology; D001169:Arthritis, Experimental / Q000139:chemically induced / Q000188:drug therapy* / Q000503:physiopathology; D002351:Carrageenan; D004195:Disease Models, Animal; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy* / Q000503:physiopathology; D004912:Erythrocytes / Q000187:drug effects; D006461:Hemolysis / Q000187:drug effects; D007213:Indomethacin / Q000494:pharmacology; D008297:Male; D051379:Mice; D009288:Naproxen / Q000494:pharmacology; D059225:Nociception / Q000187:drug effects; D010146:Pain / Q000188:drug therapy* / Q000503:physiopathology; D010147:Pain Measurement; D011166:Porphyrins / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D017208:Rats, Wistar; D013755:Tetradecanoylphorbol Acetate
chemical_list: D000700:Analgesics; D000894:Anti-Inflammatory Agents, Non-Steroidal; D011166:Porphyrins; D009288:Naproxen; D002351:Carrageenan; D013755:Tetradecanoylphorbol Acetate; D007213:Indomethacin
keywords: Antinociceptive; Inflammation; Porphyrins; Synthesis; TPA