Analysis of the molecular association of rifampicin with hydroxypropyl-²-cyclodextrin

Authors

  • Denise Alves Ferreira Universidade Estadual Paulista Júlio de Mesquita Filho; Faculdade de Ciências Farmacêuticas; Departamento de Fármacos e Medicamentos
  • Antonio Gilberto Ferreira Universidade Federal de São Carlos; Departamento de Química; Laboratório de RMN
  • Lucinéia Vizzotto Universidade Federal de São Carlos; Departamento de Química; Laboratório de RMN
  • Alberto Federman Neto Universidade de São Paulo; Faculdade de Ciências Farmacêuticas de Ribeirão Preto; Laboratório de Química Farmacêutica
  • Anselmo Gomes de Oliveira Universidade Estadual Paulista Júlio de Mesquita Filho; Faculdade de Ciências Farmacêuticas; Departamento de Fármacos e Medicamentos

DOI:

https://doi.org/10.1590/S1516-93322004000100008

Keywords:

Rifampicin, Hydroxypropyl-ß-cyclodextrin, Inclusion complex, Molecular Modelling, Proton Nuclear Magnetic, Resonance

Abstract

Inclusion complexes of rifampicin (RP) were prepared with hydroxypropyl-²-cyclodextrin (HP²CD). The aqueous solubility of RP increased linearly with cyclodextrin concentration in all range of the solubility diagram. The data was analyzed using the framework of Higuchi and Connors. The stability constant (K) values for RP/HP²CD complex at pH 6.9 were 18 and 120-125 M-1 for ionic strength 0.01 and 0.18M, respectively. The analysis of the chemical shift data of ¹H and 15N for free RP and RP/HP²CD inclusion complex reveal that only peaks of the side chain related to the piperazine ring of RP change substantially, probably due to interaction of this region of RP molecule with the hydrophobic core of HP²CD. We also postulated the optimized structure of RP/HP²CD inclusion complex using molecular modelling study. We found that the postulated structure was in agreement with ¹H and 13C-NMR and 15N-NMR spectra.

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Published

2004-03-01

Issue

Vol. 40 No. 1 (2004)

Section

Original Papers

How to Cite

Analysis of the molecular association of rifampicin with hydroxypropyl-²-cyclodextrin. (2004). Revista Brasileira De Ciências Farmacêuticas, 40(1), 43-51. https://doi.org/10.1590/S1516-93322004000100008