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Inclusion complexes of 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin with 2-hydroxypropyl-(-cyclodextrin: solubility and antimicrobial activity
Hadziabdic, Jasmina; Spirtovic-Halilovic, Selma; Osmanovic, Amar; Zahirovic, Lejla; Elezovic, Amar.
  • Hadziabdic, Jasmina; University of Sarajevo. Faculty of Pharmacy. Department of Pharmaceutical Technology. Sarajevo. BA
  • Spirtovic-Halilovic, Selma; University of Sarajevo. Faculty of Pharmacy. Department of Pharmaceutical Chemistry. Sarajevo. BA
  • Osmanovic, Amar; University of Sarajevo. Faculty of Pharmacy. Department of Pharmaceutical Chemistry. Sarajevo. BA
  • Zahirovic, Lejla; KJP Veterinary Station Ltd. Sarajevo. Microbiological-chemical laboratory for testing and examination of food. Sarajevo. BA
  • Elezovic, Amar; Agency for Drugs and Medical Devices. Control Laboratory Sarajevo. Sarajevo. BA
Braz. J. Pharm. Sci. (Online) ; 58: e20013, 2022. tab, graf
Article in English | LILACS | ID: biblio-1394062
ABSTRACT
The aim of the present study is to improve the solubility and antimicrobial activity of 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin by formulating its inclusion complexes with 2-hydroxypropyl-ß-cyclodextrin in solution and in solid state. The phase solubility study was used to investigate the interactions between 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin and 2-hydroxypropyl-ß-cyclodextrin and to estimate the molar ratio between them. The structural characterization of binary systems (prepared by physical mixing, kneading and solvent evaporation methods) was analysed using the FTIR-ATM spectroscopy. The antimicrobial activity of 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin and inclusion complexes prepared by solvent evaporation method was tested by the diffusion and dilution methods on various strains of microorganisms. The results of phase solubility studies showed that 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin formed the inclusion complexes with 2-hydroxypropyl-ß-cyclodextrin of AP type. The solubility of 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin was increased 64.05-fold with 50% w/w of 2-hydroxypropyl-ß-cyclodextrin at 37 oC. The inclusion complexes in solid state, prepared by the solvent evaporation method, showed higher solubility in purified water and in phosphate buffer solutions in comparison with 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin alone. The inclusion complexes prepared by solvent evaporation method showed higher activity on Bacillus subtilis and Staphylococcus aureus compared to uncomplexed 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin due to improved aqueous solubility, thus increasing the amount of available 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin that crosses the bacterial membrane.
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Full text: Available Index: LILACS (Americas) Main subject: Solubility / Cyclodextrins / Anti-Infective Agents Language: English Journal: Braz. J. Pharm. Sci. (Online) Journal subject: Farmacologia / Terapˆutica / Toxicologia Year: 2022 Type: Article Affiliation country: Bosnia and Herzegovina Institution/Affiliation country: Agency for Drugs and Medical Devices/BA / KJP Veterinary Station Ltd. Sarajevo/BA / University of Sarajevo/BA

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Full text: Available Index: LILACS (Americas) Main subject: Solubility / Cyclodextrins / Anti-Infective Agents Language: English Journal: Braz. J. Pharm. Sci. (Online) Journal subject: Farmacologia / Terapˆutica / Toxicologia Year: 2022 Type: Article Affiliation country: Bosnia and Herzegovina Institution/Affiliation country: Agency for Drugs and Medical Devices/BA / KJP Veterinary Station Ltd. Sarajevo/BA / University of Sarajevo/BA