Study of Bioactive Amino Esters with Cardiolipin
Monolayer in Langmuir Films
Renato S. Gonçalves,1 Pedro H.B. Aoki,1 Rosineide C. Simas,2 Marcos N. Eberlin,2
Alvicler Magalhães,3 Carlos, J.L. Constantino,1 Eduardo, R.P. Gonzáles1
1
Departamento de Física, Química e Biologia, Faculdade de Ciências e Tecnologia,
UNESP, C.P. 467, Presidente Prudente, 19060-900, SP, Brasil.
2
ThoMSon Mass Spectrometry Laboratory, Institute of Chemistry, State University of
Campinas, Campinas, São Paulo, Brazil.
3
Laboratório de Inorgânica, Institute of Chemistry, State University of Campinas,
Campinas, São Paulo, Brazil.
The use of biological phospholipids as mimetic systems has been increased in last years.
These systems can to serve as support to observed specific interactions between
membrane-models and determinate drugs. Local anesthetic, for instance, cold
interactive with membrane proteins or membrane lipids, or both to cause the inhibition
of pharmacologically-relevant channel, receptors and enzymes. [1] In this work,
potentially bioactive N-(aminoalkyl)lactamic amino acids and esters were synthesized
by SNAr reactions of aromatic acids with N-(3-aminopropyl)lactams followed by
esterification with tertiary amino alcohols. [2] Langmuir films technique was used to
investigate the possibility of interaction between cardiolipin (CLP-negative
phospholipid) and a N-(aminoalkyl)lactamic amino esters (S1). Langmuir films of CLP
in the presence of co-spread S1 were investigated through surface pressure versus mean
molecular area (π–A) isotherms. The results showed that for concentrations of S1 below
20 mol%, the drug is expelled to water subphase for high values of surface pressure
(condensed phase). For concentration above this value, the S1 keeps bound to CLP
floating monolayer. All the synthesized products have been characterized by NMR, FTIR and Mass Spectrometry.
Keywords: Amino acid, Amino Ester, SNAr, Langmuir films,
[1] B. Suwalsky, C. Schneider, F. Villena, Blood Cells Mol Dis. 29, 14 (2002)
[2] R. S. Gonçalves, P. V. Abdeunur, V. C. Santos, R. C. Simas, M. N. Eberlin, A.
Magalhães, E. P. R. González, Amino Acids J. (2010). DOI: 10.1007/s00726-0100634-z
[email protected], C.P. 467, Presidente Prudente, SP, 19060-900, Brazil