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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.
AuthorsAngel Josabad Alonso-Castro, Juan Ramón Zapata-Morales, Abigail Hernández-Munive, Nimsi Campos-Xolalpa, Salud Pérez-Gutiérrez, Cuauhtémoc Pérez-González
JournalBioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 23 Issue 10 Pg. 2529-37 (May 15 2015) ISSN: 1464-3391 [Electronic] England
PMID25863493 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2015 Elsevier Ltd. All rights reserved.
Chemical References
  • Analgesics
  • Anti-Inflammatory Agents, Non-Steroidal
  • Porphyrins
  • Naproxen
  • Carrageenan
  • Tetradecanoylphorbol Acetate
  • Indomethacin
Topics
  • Administration, Oral
  • Analgesics (chemical synthesis, pharmacology)
  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal (chemical synthesis, pharmacology)
  • Arthritis, Experimental (chemically induced, drug therapy, physiopathology)
  • Carrageenan
  • Disease Models, Animal
  • Edema (chemically induced, drug therapy, physiopathology)
  • Erythrocytes (drug effects)
  • Hemolysis (drug effects)
  • Indomethacin (pharmacology)
  • Male
  • Mice
  • Naproxen (pharmacology)
  • Nociception (drug effects)
  • Pain (drug therapy, physiopathology)
  • Pain Measurement
  • Porphyrins (chemical synthesis, pharmacology)
  • Rats
  • Rats, Wistar
  • Tetradecanoylphorbol Acetate

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