{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T07:40:53Z","timestamp":1792654853366,"version":"4.5.0"},"reference-count":51,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T00:00:00Z","timestamp":1792627200000},"content-version":"vor","delay-in-days":21,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T00:00:00Z","timestamp":1790812800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp;amp; Biodiversity"],"published-print":{"date-parts":[[2026,10]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    The aim of this work was to examine the influence of introduction of heteroaromatic motifs like pyridyl and imidazole rings into alendronic acid molecule on its biological properties. For this purpose, a series of heterocyclic N\u2010substituted alendronate derivatives were synthesized via a two\u2010step, one\u2010pot procedure. This procedure involves the condensation of alendronate and heteroaromatic aldehydes in the presence of triethylamine, which leads to the formation of appropriate Schiff bases, followed by the in situ reduction of the resulting imines with sodium borohydride. The study investigated the ability of the obtained bisphosphonates to bind to hydroxyapatite (HAP), as well as their antiproliferative effect against RAW 264.7 mouse macrophages, MCF\u20107 human breast cancer and MCF\u201010A normal breast epithelial cells. Among the tested derivatives, the 2\u2010imidazole derivative (\n                    <jats:bold>4f<\/jats:bold>\n                    ) and its\n                    <jats:italic>N<\/jats:italic>\n                    \u2010methylated analog (\n                    <jats:bold>4g<\/jats:bold>\n                    ) showed the best activity against both RAW 264.7 macrophages and MCF\u20107 cells, with an IC\n                    <jats:sub>50<\/jats:sub>\n                    value of 19.4 and 76.1\u00a0\u00b5M and of 26.4 and 107.9\u00a0\u00b5M, respectively. Furthermore, all synthesized derivatives were non\u2010cytotoxic toward MCF\u201010A normal cells under the tested experimental conditions. The 4(5)\u2010imidazole (\n                    <jats:bold>4e<\/jats:bold>\n                    ) derivative showed the highest affinity to HAP.\n                  <\/jats:p>","DOI":"10.1002\/cbdv.71865","type":"journal-article","created":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T07:15:34Z","timestamp":1792653334000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of a Series of Heterocyclic N\u2010Substituted Derivatives of Alendronic Acid and Their Preliminary Biological Evaluation"],"prefix":"10.1002","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6167-5923","authenticated-orcid":false,"given":"Anna","family":"Nasulewicz\u2010Goldeman","sequence":"first","affiliation":[{"name":"Department of Experimental Oncology Hirszfeld Institute of Immunology and Experimental Therapy Polish Academy of Sciences  Wroc\u0142aw Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9995-3260","authenticated-orcid":false,"given":"Tomasz M.","family":"Goszczy\u0144ski","sequence":"additional","affiliation":[{"name":"Department of Experimental Oncology Hirszfeld Institute of Immunology and Experimental Therapy Polish Academy of Sciences  Wroc\u0142aw Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4980-6606","authenticated-orcid":false,"given":"Joanna","family":"Wietrzyk","sequence":"additional","affiliation":[{"name":"Department of Experimental Oncology Hirszfeld Institute of Immunology and Experimental Therapy Polish Academy of Sciences  Wroc\u0142aw Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5856-8609","authenticated-orcid":false,"given":"Waldemar","family":"Goldeman","sequence":"additional","affiliation":[{"name":"Department of Organic and Medicinal Chemistry Faculty of Chemistry Wroc\u0142aw University of Science and Technology  Wroc\u0142aw Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,10,22]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1002\/cmdc.201700769","article-title":"Interactions Between Clinically Used Bisphosphonates and Bone Mineral: From Coordination Chemistry to Biomedical Applications and Beyond","volume":"13","author":"Ga\u0142\u0119zowska J.","year":"2018","journal-title":"ChemMedChem"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201000016"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/ml5004603"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/14651858.CD004956.pub3"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.2147\/TCRM.S58367"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1177\/2040622310374783"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1093\/rheumatology\/ket236"},{"key":"e_1_2_9_9_1","first-page":"441","article-title":"Bisphosphonates. 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