Inclusion complexes of propiconazole nitrate with substituted β-cyclodextrins: the synthesis and in silico and in vitro assessment of their antifungal properties

B. Minea; N. Marangoci; D. Peptanariu; I. Rosca; V. Nastasa; A. Corciova; C. Varganici; A. Nicolescu; A. Fifere; A. Neamtu; M. Mares; M. Barboiu; M. Pinteala

doi:10.1039/C5NJ01811K

Inclusion complexes of propiconazole nitrate with substituted β-cyclodextrins: the synthesis and in silico and in vitro assessment of their antifungal properties†

B. Minea,^ab N. Marangoci,^a D. Peptanariu,^a I. Rosca,^a V. Nastasa,^c A. Corciova,^b C. Varganici,^a A. Nicolescu,^a A. Fifere,^a A. Neamtu,^b M. Mares,^c M. Barboiu*^d and M. Pinteala*^a

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* Corresponding authors

^a Centre of Advanced Research in Bionanoconjugates and Biopolymers (IntelCentru) “Petru Poni” Institute of Macromolecular Chemistry, 41A Grigore Ghica Voda Alley, 700487 Iasi, Romania
E-mail: pinteala@icmpp.ro

^b “Gr. T. Popa” University of Medicine and Pharmacy, 16 University Street, 700115 Iasi, Romania

^c Laboratory of Antimicrobial Chemotherapy, “Ion Ionescu de la Brad” University, 8 Sadoveanu Alley, 700489 Iasi, Romania

^d Adaptative Supramolecular Nanosystems Group, Institut Européen des Membranes, ENSCM/UMII/UMR-CNRS 5635, 34095 Montpellier Cedex 5, France
E-mail: mihail-dumitru.barboiu@univmontp2.fr

Abstract

Inclusion complexes of protonated propiconazole nitrate (PCZH-NO₃) with three substituted cyclodextrin (CD) derivatives, namely, sulfobutylether-β-CD (SBE7-β-CD), sulfated-β-CD (β-CD-SNa) and monochlorotriazinyl-β-CD (MCT-β-CD), were investigated as new antifungal systems and compared with a previously published complex of PCZH-NO₃ with unsubstituted β-CD. The inclusion complexes were prepared by the freeze-drying method and were characterized by ¹H-NMR, 2D Roesy NMR and DSC. This study demonstrates the coexistence of two types of PCZH-NO₃ inclusion into the CD cavity. The complexes with SBE7-β-CD had the highest association constant values and the inclusion efficiency was close to 100%. Comparative in silico docking and molecular dynamics simulations were performed. The antifungal activity was assessed on Candida spp. and was similar for all four inclusion complexes. The cytotoxicity assessed on normal human dermal fibroblasts (NHDF) was significantly higher for the complex with β-CD than that of the complexes of substituted CDs.

New Journal of Chemistry

Inclusion complexes of propiconazole nitrate with substituted β-cyclodextrins: the synthesis and in silico and in vitro assessment of their antifungal properties†

Abstract

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Inclusion complexes of propiconazole nitrate with substituted β-cyclodextrins: the synthesis and in silico and in vitro assessment of their antifungal properties

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