Inclusion complex of a new propiconazole derivative with β-cyclodextrin: NMR, ESI-MS and preliminary pharmacological studies

Results in Pharma Sciences
Narcisa MarangociBogdan C Simionescu

Abstract

A novel inclusion complex of the propiconazole nitrate (NO3PCZ) with β-cyclodextrin (β-CD) was prepared by treatment of propiconazole (PCZ) with an acidic nitrating agent. The formation of NO3PCZ and its inclusion complex with β-CD has been studied by NMR, ESI-MS, TGA, DSC methods. Using the undecoupled signal in the HMBC correlation spectra, almost identical coupling constants of CH from trizolic ring of PCZ and NO3PCZ compounds ((1)J(HC)3=207 Hz, (1)J(CH)5=214 Hz, for PCZ; (1)J(HC)3=208 Hz and (1)J(CH)5=215 Hz, for NO3PCZ) were determined, confirming that the geometry of the heterocyclic skeleton is identical in both the forms. The 1:1 stoichiometry of the complex was determined by ESI-MS and was confirmed using Scott's equation in DMSO and Higuchi and Connors equation in water. The solubility curve obtained for NO3PCZ in presence of β-CD in distilled water was constructed, resulting in a solubility diagram of AL type. Solubility of NO3PCZ in water was determined by DLS studies. The results showed that NO3PCZ was encapsulated within the β-CD cavity with a binding constant of 330 M-1 in DMSO and 975 M-1 in water. Preliminary pharmacological studies showed higher antifungal activities for NO3PCZ and its inclusion complex, compa...Continue Reading

Citations

Feb 1, 2013·Beilstein Journal of Organic Chemistry·Adrian FifereMariana Pinteala
Sep 17, 2014·European Journal of Clinical Microbiology & Infectious Diseases : Official Publication of the European Society of Clinical Microbiology·B MineaM Mares
Jul 8, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ananiy KohutAndriy Voronov
Jan 17, 2014·Journal of Inclusion Phenomena and Macrocyclic Chemistry·Joanna BiernackaAleksander P Mazurek
Dec 20, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Munkhtugs DavaatserenMi-Jung Choi
Nov 13, 2020·Life Sciences·Eloísa Portugal Barros Silva Soares de SouzaAdriano Antunes de Souza Araújo
Jun 16, 2021·Physical Chemistry Chemical Physics : PCCP·Jordan M RabusEduardo Carrascosa

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