{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T11:09:33Z","timestamp":1785409773143,"version":"3.56.0"},"reference-count":61,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2026,5,16]],"date-time":"2026-05-16T00:00:00Z","timestamp":1778889600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100005643","name":"University of Lodz","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100005643","id-type":"DOI","asserted-by":"crossref"}]},{"id":[{"id":"https:\/\/ror.org\/05cq64r17","id-type":"ROR","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Miconazole is a commonly used imidazole antifungal drug with a broad spectrum of activity against Candida strains and other microorganisms. However, its poor solubility and low bioavailability have limited its use to topical infections. To overcome this limitation through the use of cocrystalization techniques, the present work focuses on the relatively less explored class of heterocyclic carboxylic acid coformers, containing two nitrogen atoms in the ring, aimed at developing alternative multicomponent forms of miconazole. Five new forms of miconazole were subjected to in-depth structural analysis, including an evaluation of the effect of hydrate formation. Furthermore, layered motifs in the supramolecular crystal architectures were subjected to qualitative and quantitative surface analysis using CSD-Particle. All new forms of miconazole were also characterized by FT-IR spectroscopy and thermogravimetric analysis. Water solubility was identified as the most important physicochemical property, and significant improvements were obtained for four of the five salts studied. Notably, the newly synthesized miconazole salts with heterocyclic (di)carboxylic acids exhibited high antifungal activity. The tested compounds effectively inhibited the growth of C. albicans and C. parapsilosis at concentrations several times lower than the parent drug and also showed activity against the important C. auris strain. Therefore, the obtained salts may constitute attractive alternatives to currently used antifungal therapies.<\/jats:p>","DOI":"10.3390\/molecules31101686","type":"journal-article","created":{"date-parts":[[2026,5,18]],"date-time":"2026-05-18T08:56:27Z","timestamp":1779094587000},"page":"1686","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["New Miconazole Salts with Heterocyclic Carboxylic Acids with Improved Water Solubility and Enhanced Antifungal Activity"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3287-1049","authenticated-orcid":false,"given":"Anna","family":"Ben","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, University of Lodz, Pomorska 163\/165, 90-236 Lodz, Poland"},{"name":"Doctoral School of Exact and Natural Sciences, University of Lodz, Narutowicza 68, 90-136 Lodz, Poland"},{"name":"Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Poznan, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7939-2953","authenticated-orcid":false,"given":"Aleksandra","family":"Felczak","sequence":"additional","affiliation":[{"name":"Department of Industrial Microbiology and Biotechnology, Faculty of Biology and Environmental Protection, University of Lodz, Banacha 12\/16, 90-237 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3167-4871","authenticated-orcid":false,"given":"Micha\u0142","family":"Gacki","sequence":"additional","affiliation":[{"name":"Institute of General and Ecological Chemistry, Lodz University of Technology, \u017beromskiego 114, 90-924 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6395-570X","authenticated-orcid":false,"given":"Katarzyna","family":"Lisowska","sequence":"additional","affiliation":[{"name":"Department of Industrial Microbiology and Biotechnology, Faculty of Biology and Environmental Protection, University of Lodz, Banacha 12\/16, 90-237 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2282-9816","authenticated-orcid":false,"given":"Mateusz Rafa\u0142","family":"Go\u0142dyn","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Poznan, Poland"},{"name":"Center for Advanced Technologies, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 10, 61-614 Poznan, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"El\u017cbieta","family":"Bartoszak-Adamska","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Poznan, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3546-920X","authenticated-orcid":false,"given":"Lilianna","family":"Ch\u0119ci\u0144ska","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Lodz, Pomorska 163\/165, 90-236 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,5,16]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1111\/j.1439-0507.1971.tb03028.x","article-title":"Topical Treatment of Nail and Skin Infections with Miconazole, A New Broad-Spectrum Antimycotic","volume":"14","author":"Botter","year":"1971","journal-title":"Mycoses"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"406","DOI":"10.2165\/00003495-197509060-00002","article-title":"Miconazole: A Review of its Antifungal Activity and Therapeutic Efficacy","volume":"9","author":"Sawyer","year":"1975","journal-title":"Drugs"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"552","DOI":"10.1111\/myc.12620","article-title":"New Insights on the Antibacterial Efficacy of Miconazole in vitro","volume":"60","author":"Nenoff","year":"2017","journal-title":"Mycoses"},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Hu, M., and Li, X. 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