Molecules 2011, 16(8), 6902-6915; doi:10.3390/molecules16086902
Article

Analgesic and Anti-Inflammatory Activities of Salicylaldehyde 2-Chlorobenzoyl Hydrazone (H2LASSBio-466), Salicylaldehyde 4-Chlorobenzoyl Hydrazone (H2LASSBio-1064) and Their Zinc(II) Complexes

Walfrido Bispo Júnior 1 , Magna S. Alexandre-Moreira 1 , Marina A. Alves 2 , Anayive Perez-Rebolledo 3 , Gabrieli L. Parrilha 3 , Eduardo E. Castellano 4 , Oscar E. Piro 5 , Eliezer J. Barreiro 2 , Lídia Moreira Lima 2  and Heloisa Beraldo 3,* email
1 LaFI Laboratório de Farmacologia e Imunidade, Instituto de Ciências Biológicas e da Saúde, Universidade Federal de Alagoas, Maceió, AL, Brazil 2 LASSBio Laboratório de Avaliação e Síntese de Substâncias Bioativas (LASSBio, http://www.farmacia.ufrj.br/lassbio/), Faculdade de Farmácia, Universidade Federal do Rio de Janeiro, P. O. Box 68024, 21944-971, Rio de Janeiro, RJ, Brazil 3 Departamento de Química, Universidade Federal de Minas Gerais, 31270-901, Belo Horizonte, Brazil 4 Instituto de Física de São Carlos, Universidade de São Paulo, 13560-970, São Carlos, SP, Brazil 5 Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata and Instituto IFLP (CONICET – CCT La Plata), C.C. 67, 1900 La Plata, Argentina
* Author to whom correspondence should be addressed.
Received: 27 June 2011; in revised form: 2 August 2011 / Accepted: 11 August 2011 / Published: 15 August 2011
(This article belongs to the Section Medicinal Chemistry)
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Abstract: Salicylaldehyde 2-chlorobenzoyl hydrazone (H2LASSBio-466), salicylaldehyde 4-chlorobenzoyl hydrazone (H2LASSBio-1064) and their complexes [Zn(LASSBio-466)H2O]2 (1) and [Zn(HLASSBio-1064)Cl]2 (2) were evaluated in animal models of peripheral and central nociception, and acute inflammation. All studied compounds significantly inhibited acetic acid-induced writhing response. Upon coordination the anti-nociceptive activity was favored in the complex 1. H2LASSBio-466 inhibited only the first phase of the formalin test, while 1 was active in the second phase, like indomethacin, indicating its ability to inhibit nociception associated with the inflammatory response. Hence coordination to zinc(II) altered the pharmacological profile of H2LASSBio-466. H2LASSBio-1064 inhibited both phases but this effect was not improved by coordination. The studied compounds did not increase the latency of response in the hot plate model, indicating their lack of central anti-nociceptive activity. All compounds showed levels of inhibition of zymosan-induced peritonitis comparable or superior to indomethacin, indicating an expressive anti-inflammatory profile.
Keywords: acylhydrazones; zinc(II) complexes; analgesic activity; anti-inflammatory activity

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MDPI and ACS Style

Júnior, W.B.; Alexandre-Moreira, M.S.; Alves, M.A.; Perez-Rebolledo, A.; Parrilha, G.L.; Castellano, E.E.; Piro, O.E.; Barreiro, E.J.; Lima, L.M.; Beraldo, H. Analgesic and Anti-Inflammatory Activities of Salicylaldehyde 2-Chlorobenzoyl Hydrazone (H2LASSBio-466), Salicylaldehyde 4-Chlorobenzoyl Hydrazone (H2LASSBio-1064) and Their Zinc(II) Complexes. Molecules 2011, 16, 6902-6915.

AMA Style

Júnior WB, Alexandre-Moreira MS, Alves MA, Perez-Rebolledo A, Parrilha GL, Castellano EE, Piro OE, Barreiro EJ, Lima LM, Beraldo H. Analgesic and Anti-Inflammatory Activities of Salicylaldehyde 2-Chlorobenzoyl Hydrazone (H2LASSBio-466), Salicylaldehyde 4-Chlorobenzoyl Hydrazone (H2LASSBio-1064) and Their Zinc(II) Complexes. Molecules. 2011; 16(8):6902-6915.

Chicago/Turabian Style

Júnior, Walfrido Bispo; Alexandre-Moreira, Magna S.; Alves, Marina A.; Perez-Rebolledo, Anayive; Parrilha, Gabrieli L.; Castellano, Eduardo E.; Piro, Oscar E.; Barreiro, Eliezer J.; Lima, Lídia Moreira; Beraldo, Heloisa. 2011. "Analgesic and Anti-Inflammatory Activities of Salicylaldehyde 2-Chlorobenzoyl Hydrazone (H2LASSBio-466), Salicylaldehyde 4-Chlorobenzoyl Hydrazone (H2LASSBio-1064) and Their Zinc(II) Complexes." Molecules 16, no. 8: 6902-6915.

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