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Host–guest complexation of a nitroheterocyclic compound with cyclodextrins: a spectrofluorimetric and molecular modeling study

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Abstract

Nitroheterocyclic compounds (NC) were candidate drugs proposed for Chagas disease chemotherapy. In this study, we investigated the complexation of hydroxymethylnitrofurazone (NFOH), a potential antichagasic compound, with α-cyclodextrin (α-CD), β-cyclodextrin (β-CD), Hydroxypropyl-β-cyclodextrin (HP-β-CD), Dimethyl-β-cyclodextrin (DM-β-CD) and γ-cyclodextrin (γ-CD) by fluorescence spectroscopy and molecular modeling studies. Hildebrand–Benesi equation was used to calculate the formation constants of NFOH with cyclodextrins based on the fluorescence differences in the CDs solution. The complexing capacity of NFOH with different CDs was compared through the results of association constant according to the following order: DM-β-CD > β-CD > α-CD > HP-β-CD > γ-CD. Molecular modeling studies give support for the experimental assignments, in favor of the formation of an inclusion complex between cyclodextrins with NFOH. This is an important study to investigate the effects of different kinds of cyclodextrins on the inclusion complex formation with NFOH and to better characterize a potential formulations to be used as therapeutic options for the oral treatment of Chagas disease.

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Acknowledgments

We are grateful to FAPESP (05/03045-9), FAPEMIG and CNPq, Brazilian agencies for funding this work and CENAPAD-SP for the computational facilities. RG (08/01222-9) and NFSM (06/00121-9) are recipients of fellowships from Fapesp.

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Authors and Affiliations

  1. Universidade Estadual Paulista Júlio de Mesquita Filho, Campus Sorocaba, Av. Três de Março, 511, 18087-180, Sorocaba, São Paulo, Brazil

    Renato Grillo & Leonardo Fernandes Fraceto

  2. Departamento de Bioquímica, Instituto de Biologia, Unicamp, Cidade Universitária Zeferino Vaz, s/n, Campinas, SP, Brazil

    Nathalie F. S. de Melo, Daniele R. de Araújo & Leonardo Fernandes Fraceto

  3. Universidade Federal do ABC, Santo André, SP, Brazil

    Daniele R. de Araújo

  4. Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil

    Gustavo H. G. Trossini

  5. Universidade Federal de Lavras, Campus Universitário da UFLA, Lavras, MG, Brazil

    Elaine F. F. da Cunha & Teodorico de Castro Ramalho

Authors
  1. Renato Grillo
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  2. Nathalie F. S. de Melo
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  3. Daniele R. de Araújo
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  4. Gustavo H. G. Trossini
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  5. Elaine F. F. da Cunha
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  6. Teodorico de Castro Ramalho
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  7. Leonardo Fernandes Fraceto
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Correspondence to Leonardo Fernandes Fraceto.

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Grillo, R., de Melo, N.F.S., de Araújo, D.R. et al. Host–guest complexation of a nitroheterocyclic compound with cyclodextrins: a spectrofluorimetric and molecular modeling study. J Incl Phenom Macrocycl Chem 66, 417–421 (2010). https://doi.org/10.1007/s10847-009-9632-8

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  • DOI: https://doi.org/10.1007/s10847-009-9632-8

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