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Phthaloyl amino acids as anti-inflammatory and immunomodulatory prototypes

2013; Springer Science+Business Media; Volume: 23; Issue: 4 Linguagem: Inglês

10.1007/s00044-013-0730-1

1554-8120

Ana Cristina Lima Leite, Fábio Fernandes Barbosa, Marcos Veríssimo de Oliveira Cardoso, Diogo Rodrigo Magalhães Moreira, Lucas Cunha Duarte Coêlho, Elany Barbosa da Silva, Gevânio Bezerra de Oliveira Filho, Valdênia Maria Oliveira de Souza, Valéria Rêgo Alves Pereira, Luiza Campos Reis, Paulo Michel Pinheiro Ferreira, Cláudia Pessoa, Almir Gonçalves Wanderley, Fernanda Virgínia Barreto Mota, Teresinha G. da Silva,

Pharmacological Effects of Natural Compounds

A series of phthalimide analogs were synthesized by derivatization of phthalic anhydride, a highly toxic substance, using a "one pot" condensation reaction to α-amino acids. All phthaloyl amino acid derivatives presented anti-oral inflammatory activity, but compounds 2e and 2g were found to possess the best activities comparable to thalidomide. Most of the compounds effectively suppressed nitric oxide production in murine cells stimulated with lipopolysaccharide. N-phthaloyl amino acids did not exhibit any significant cytotoxicity in vitro when tested against tumor cells as well as a spleen cell culture of BALB/c mice. Compounds 2a, 2g, and 2h were able to inhibit TNF-α and IL-1β production by macrophages. At the same concentration, thalidomide did not exhibit significant inhibitory activity. [The pharmacological evaluation of eight N-phthaloyl amino acids 2a–h, including their anti-inflammatory and cytotoxic effects and nitric oxide, TNF-α, and IL-1β production, is described.]