{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T10:41:49Z","timestamp":1785408109097,"version":"3.56.0"},"reference-count":63,"publisher":"International Union of Crystallography (IUCr)","issue":"2","license":[{"start":{"date-parts":[[2024,3,1]],"date-time":"2024-03-01T00:00:00Z","timestamp":1709251200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2024,3,1]],"date-time":"2024-03-01T00:00:00Z","timestamp":1709251200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/100016270","name":"Global Challenges Research Fund","doi-asserted-by":"crossref","award":["MR\/P027989\/1"],"award-info":[{"award-number":["MR\/P027989\/1"]}],"id":[{"id":"10.13039\/100016270","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["IUCrJ","IUCr J","Int Union Crystallogr J","Int Union Cryst J"],"accepted":{"date-parts":[[2024,2,13]]},"published-print":{"date-parts":[[2024,3,1]]},"abstract":"<jats:p>\n                    Leishmaniasis is a neglected parasitic tropical disease with numerous clinical manifestations. One of the causative agents of cutaneous leishmaniasis (CL) is\n                    <jats:italic>Leishmania tropica<\/jats:italic>\n                    (\n                    <jats:italic>L. tropica<\/jats:italic>\n                    ) known for causing ulcerative lesions on the skin. The adverse effects of the recommended available drugs, such as amphotericin B and pentavalent antimonial, and the emergence of drug resistance in parasites, mean the search for new safe and effective anti-leishmanial agents is crucial. Miltefosine (MIL) was the first recommended oral medication, but its use is now limited because of the rapid emergence of resistance. Pharmaceutical cocrystallization is an effective method to improve the physicochemical and biological properties of active pharmaceutical ingredients (APIs). Herein, we describe the cocrystallization of coumarin-3-carboxylic acid (\n                    <jats:bold>CU<\/jats:bold>\n                    ,\n                    <jats:bold>1a<\/jats:bold>\n                    ; 2-oxobenzopyrane-3-carboxylic acid, C\n                    <jats:sub>10<\/jats:sub>\n                    H\n                    <jats:sub>6<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    ) with five coformers [2-amino-3-bromopyridine (\n                    <jats:bold>1b<\/jats:bold>\n                    ), 2-amino-5-(trifluoromethyl)-pyridine (\n                    <jats:bold>1c<\/jats:bold>\n                    ), 2-amino-6-methylpyridine (\n                    <jats:bold>1d<\/jats:bold>\n                    ),\n                    <jats:italic>p<\/jats:italic>\n                    -aminobenzoic acid (\n                    <jats:bold>1e<\/jats:bold>\n                    ) and amitrole (\n                    <jats:bold>1f<\/jats:bold>\n                    )] in a 1:1 stoichiometric ratio via the neat grinding method. The cocrystals\n                    <jats:bold>2<\/jats:bold>\n                    \u2013\n                    <jats:bold>6<\/jats:bold>\n                    obtained were characterized via single-crystal X-ray diffraction, powder X-ray diffraction, differential scanning calorimetry and thermogravimetric analysis, as well as Fourier transform infrared spectroscopy. Non-covalent interactions, such as van der Waals, hydrogen bonding, C\u2014H...\u03c0 and \u03c0...\u03c0 interactions contribute significantly towards the packing of a crystal structure and alter the physicochemical and biological activity of\n                    <jats:bold>CU<\/jats:bold>\n                    . In this research, newly synthesized cocrystals were evaluated for their anti-leishmanial activity against the MIL-resistant\n                    <jats:italic>L. tropica<\/jats:italic>\n                    and cytotoxicity against the 3T3 (normal fibroblast) cell line. Among the non-cytotoxic cocrystals synthesized (\n                    <jats:bold>2<\/jats:bold>\n                    \u2013\n                    <jats:bold>6<\/jats:bold>\n                    ),\n                    <jats:bold>CU<\/jats:bold>\n                    :\n                    <jats:bold>1b<\/jats:bold>\n                    (\n                    <jats:bold>2<\/jats:bold>\n                    , IC\n                    <jats:sub>50<\/jats:sub>\n                    = 61.83 \u00b1 0.59\u2005\u00b5\n                    <jats:italic>M<\/jats:italic>\n                    ),\n                    <jats:bold>CU<\/jats:bold>\n                    :\n                    <jats:bold>1c<\/jats:bold>\n                    (\n                    <jats:bold>3<\/jats:bold>\n                    , 125.7 \u00b1 1.15\u2005\u00b5\n                    <jats:italic>M<\/jats:italic>\n                    ) and\n                    <jats:bold>CU<\/jats:bold>\n                    :\n                    <jats:bold>1d<\/jats:bold>\n                    (\n                    <jats:bold>4<\/jats:bold>\n                    , 48.71 \u00b1 0.75\u2005\u00b5\n                    <jats:italic>M<\/jats:italic>\n                    ) appeared to be potent anti-leishmanial agents and showed several-fold more anti-leishmanial potential than the tested standard drug (MIL, IC\n                    <jats:sub>50<\/jats:sub>\n                    = 169.55 \u00b1 0.078\u2005\u00b5\n                    <jats:italic>M<\/jats:italic>\n                    ). The results indicate that cocrystals\n                    <jats:bold>2<\/jats:bold>\n                    \u2013\n                    <jats:bold>4<\/jats:bold>\n                    are promising anti-leishmanial agents which require further exploration.\n                  <\/jats:p>","DOI":"10.1107\/s2052252524001416","type":"journal-article","created":{"date-parts":[[2024,2,28]],"date-time":"2024-02-28T04:58:15Z","timestamp":1709096295000},"page":"224-236","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":4,"title":["Cocrystals of a coumarin derivative: an efficient approach towards anti-leishmanial cocrystals against MIL-resistant\n                    <i>Leishmania tropica<\/i>"],"prefix":"10.1107","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8834-7791","authenticated-orcid":true,"given":"Muhammad","family":"Shahbaz","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05bbbc791","id-type":"ROR","asserted-by":"publisher"}],"department":["H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7069-2618","authenticated-orcid":true,"given":"Saba","family":"Farooq","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05bbbc791","id-type":"ROR","asserted-by":"publisher"}],"department":["Dr Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"M. Iqbal","family":"Choudhary","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05bbbc791","id-type":"ROR","asserted-by":"publisher"}],"department":["H.E.J. 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