title: Anti-inflammatory effect of (E)-4-(3,7-dimethylocta-2,6-dienylamino)phenol, a new derivative of 4-nerolidylcatechol.
abstract: OBJECTIVE
  We have investigated the anti-inflammatory and antinociceptive effects of (E)-4-(3,7-dimethylocta-2,6-dienylamino)phenol (LQFM-015), which was designed through molecular simplification strategy from 4-nerolidylcatechol.
  
  
  METHODS
  The possible anti-inflammatory and antinociceptive effects were assayed on carrageenan-induced paw oedema and pleurisy, acetic acid-induced abdominal writhing and formalin tests in mice.
  
  
  RESULTS
  LQFM-015 reduced the activity of PLA₂ enzyme in vitro by 18%. Docking studies into the catalytic site of PLA₂ were used to identify the binding mode of the LQFM-015. LQFM-015 showed a moderate antinociceptive effect, since this compound reduced the number of writhings by approximately up to 40% in the acetic acid-induced pain model; this antinociceptive activity also emerged in the second phase of the formalin-induced pain model (58% of inhibition). The anti-inflammatory action of LQFM-015 was confirmed in acute inflammation models, in which it reduced the formation of oedema to 52.78 ± 8.6 and 46.64 ± 5.2 at the second and third hour of carrageenan-induced paw oedema, respectively. Also in the carrageenan-induced pleurisy model, LQFM-015 reduced the migration of leucocytes by 26.0% and decrease myeloperoxidase activity by 50%. LQFM-015 showed different concentrations to inhibit 50% of isoenzyme cyclooxygenase activity (IC50); COX-1 IC50 = 36 μM) and COX-2 IC50 = 28 μM.
  
  
  CONCLUSIONS
  LQFM-015 demonstrated inhibition of both PLA₂ and COX enzymes; thus, the moderate antinociceptive effect of this compound could be attributed to its anti-inflammatory activity.
authors.affiliation: Department of Physiological Sciences, Institute of Biological Sciences, Federal University of Goiás, Goiânia, Brazil.
authors.forename: Roberta Campos
authors.initials: RC
authors.lastname: Lino
authors.forename: Fabiula Ines
authors.initials: FI
authors.lastname: Martins
authors.forename: Iziara Ferreira
authors.initials: IF
authors.lastname: Florentino
authors.forename: Marcus Vinicius Mariano
authors.initials: MV
authors.lastname: Nascimento
authors.forename: Pablinny Moreira
authors.initials: PM
authors.lastname: Galdino
authors.forename: Carolina H
authors.initials: CH
authors.lastname: Andrade
authors.forename: Kênnia Rocha
authors.initials: KR
authors.lastname: Rezende
authors.forename: Ricardo
authors.initials: R
authors.lastname: Menegatti
authors.forename: Elson Alves
authors.initials: EA
authors.lastname: Costa
mesh_terms: D015746:Abdominal Pain / Q000201:enzymology / Q000517:prevention & control; D000700:Analgesics / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use*; D020134:Catalytic Domain; D002396:Catechols / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use*; D002465:Cell Movement / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D004487:Edema / Q000201:enzymology / Q000276:immunology / Q000517:prevention & control; D004791:Enzyme Inhibitors / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use*; D008214:Lymphocytes / Q000187:drug effects / Q000201:enzymology / Q000276:immunology; D008297:Male; D051379:Mice; D008968:Molecular Conformation; D062105:Molecular Docking Simulation; D010088:Oxidoreductases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D064801:Phospholipase A2 Inhibitors; D054467:Phospholipases A2 / Q000737:chemistry; D010998:Pleurisy / Q000201:enzymology / Q000276:immunology / Q000517:prevention & control; D013237:Stereoisomerism
chemical_list: C581041:(E)-4-(3,7-dimethylocta-2,6-dienylamino)phenol; C110583:4-nerolidylcatechol; D000700:Analgesics; D000894:Anti-Inflammatory Agents, Non-Steroidal; D002396:Catechols; D004791:Enzyme Inhibitors; D064801:Phospholipase A2 Inhibitors; D010088:Oxidoreductases; D054467:Phospholipases A2