{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,8]],"date-time":"2026-07-08T18:43:28Z","timestamp":1783536208060,"version":"3.55.0"},"reference-count":73,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2024,12,2]],"date-time":"2024-12-02T00:00:00Z","timestamp":1733097600000},"content-version":"am","delay-in-days":701,"URL":"http:\/\/www.elsevier.com\/open-access\/userlicense\/1.0\/"},{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"funder":[{"DOI":"10.13039\/501100000038","name":"Natural Sciences and Engineering Research Council of Canada","doi-asserted-by":"publisher","award":["RGPIN-2016-05867"],"award-info":[{"award-number":["RGPIN-2016-05867"]}],"id":[{"id":"10.13039\/501100000038","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001655","name":"Deutscher Akademischer Austauschdienst","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001655","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000054","name":"National Cancer Institute","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000054","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004489","name":"Mitacs","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004489","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100010221","name":"Higher Education Commision, Pakistan","doi-asserted-by":"publisher","award":["20\u201315846\/NRPU\/R&D\/HEC\/2021"],"award-info":[{"award-number":["20\u201315846\/NRPU\/R&D\/HEC\/2021"]}],"id":[{"id":"10.13039\/501100010221","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100016714","name":"University of Sharjah","doi-asserted-by":"publisher","award":["2201110159"],"award-info":[{"award-number":["2201110159"]}],"id":[{"id":"10.13039\/100016714","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["European Journal of Medicinal Chemistry"],"published-print":{"date-parts":[[2023,1]]},"DOI":"10.1016\/j.ejmech.2022.114958","type":"journal-article","created":{"date-parts":[[2022,11,26]],"date-time":"2022-11-26T09:29:22Z","timestamp":1669454962000},"page":"114958","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":14,"special_numbering":"C","title":["Design and synthesis of new adamantyl derivatives as promising antiproliferative agents"],"prefix":"10.1016","volume":"246","author":[{"given":"Afnan I.","family":"Shahin","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Seyed-Omar","family":"Zaraei","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bilal O.","family":"AlKubaisi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Saif","family":"Ullah","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hanan S.","family":"Anbar","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Randa","family":"El-Gamal","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Varsha","family":"Menon","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohammed S.","family":"Abdel-Maksoud","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chang-Hyun","family":"Oh","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raafat","family":"El-Awady","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nicolly Espindola","family":"Gelsleichter","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Julie","family":"Pelletier","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jean","family":"S\u00e9vigny","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jamshed","family":"Iqbal","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Taleb H.","family":"Al-Tel","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8587-0520","authenticated-orcid":false,"given":"Mohammed I.","family":"El-Gamal","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.ejmech.2022.114958_bib1","series-title":"Cancer, in: Fact Sheets","year":"2022"},{"key":"10.1016\/j.ejmech.2022.114958_bib2","series-title":"Advances in Cancer Research","first-page":"1","article-title":"Chapter 1 the function, proteolytic processing, and histopathology of met in cancer","author":"Hanna","year":"2009"},{"key":"10.1016\/j.ejmech.2022.114958_bib3","doi-asserted-by":"crossref","first-page":"437","DOI":"10.1007\/s11302-012-9309-4","article-title":"Cellular function and molecular structure of ecto-nucleotidases","volume":"8","author":"Zimmermann","year":"2012","journal-title":"Purinergic Signal."},{"key":"10.1016\/j.ejmech.2022.114958_bib4","doi-asserted-by":"crossref","first-page":"11402","DOI":"10.1039\/C6OB02236G","article-title":"New one-pot synthesis of N-fused isoquinoline derivatives by palladium-catalyzed C\u2013H arylation: potent inhibitors of nucleotide pyrophosphatase-1 and -3","volume":"14","author":"Ausekle","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib5","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.pharmthera.2005.01.003","article-title":"The 5\u2032-nucleotidases as regulators of nucleotide and drug metabolism","volume":"107","author":"Hunsucker","year":"2005","journal-title":"Pharmacol. Ther."},{"key":"10.1016\/j.ejmech.2022.114958_bib6","doi-asserted-by":"crossref","first-page":"224","DOI":"10.1016\/j.clineuro.2010.11.018","article-title":"The expression of ecto-nucleotide pyrophosphatase\/phosphodiesterase 1 (E-NPP1) is correlated with astrocytic tumor grade","volume":"113","author":"Aerts","year":"2011","journal-title":"Clin. Neurol. Neurosurg."},{"key":"10.1016\/j.ejmech.2022.114958_bib7","doi-asserted-by":"crossref","first-page":"929","DOI":"10.1038\/cdd.2014.12","article-title":"Stem cell characteristics in glioblastoma are maintained by the ecto-nucleotidase E-NPP1","volume":"21","author":"Bageritz","year":"2014","journal-title":"Cell Death Differ."},{"key":"10.1016\/j.ejmech.2022.114958_bib8","first-page":"134","article-title":"Dysregulated ENPP1 increases the malignancy of human lung cancer by inducing epithelial-mesenchymal transition phenotypes and stem cell features","volume":"9","author":"Hu","year":"2019","journal-title":"Am. J. Cancer Res."},{"key":"10.1016\/j.ejmech.2022.114958_bib9","doi-asserted-by":"crossref","first-page":"7318","DOI":"10.1038\/ncomms8318","article-title":"Loss of microRNA-27b contributes to breast cancer stem cell generation by activating ENPP1","volume":"6","author":"Takahashi","year":"2015","journal-title":"Nat. Commun."},{"key":"10.1016\/j.ejmech.2022.114958_bib10","doi-asserted-by":"crossref","first-page":"9254","DOI":"10.1021\/acs.jmedchem.9b01213","article-title":"Development of an ENPP1 fluorescence probe for inhibitor screening, cellular imaging, and prognostic assessment of malignant breast cancer","volume":"62","author":"Kawaguchi","year":"2019","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib11","first-page":"763","article-title":"Expression and localization of ecto-nucleotide pyrophosphatase\/phosphodiesterase I-3 (E-NPP3\/CD203c\/PD-I\u03b2\/B10\/gp130RB13-6) in human colon carcinoma","volume":"12","author":"Yano","year":"2003","journal-title":"Int. J. Mol. Med."},{"key":"10.1016\/j.ejmech.2022.114958_bib12","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1038\/nrd2467","article-title":"Carbonic anhydrases: novel therapeutic applications for inhibitors and activators","volume":"7","author":"Supuran","year":"2008","journal-title":"Nat. Rev. Drug Discov."},{"key":"10.1016\/j.ejmech.2022.114958_bib13","doi-asserted-by":"crossref","first-page":"759","DOI":"10.3109\/14756366.2012.672983","article-title":"Structure-based drug discovery of carbonic anhydrase inhibitors","volume":"27","author":"Supuran","year":"2012","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib14","doi-asserted-by":"crossref","first-page":"4389","DOI":"10.1016\/j.bmcl.2014.08.015","article-title":"Discovery of a new family of carbonic anhydrases in the malaria pathogen Plasmodium falciparum\u2014the \u03b7-carbonic anhydrases","volume":"24","author":"Del Prete","year":"2014","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2022.114958_bib15","doi-asserted-by":"crossref","first-page":"3467","DOI":"10.1016\/j.bmcl.2010.05.009","article-title":"Carbonic anhydrase inhibitors","volume":"20","author":"Supuran","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2022.114958_bib16","doi-asserted-by":"crossref","first-page":"591","DOI":"10.1517\/17460441.2015.1038235","article-title":"Designing carbonic anhydrase inhibitors for the treatment of breast cancer","volume":"10","author":"Supuran","year":"2015","journal-title":"Expet Opin. Drug Discov."},{"key":"10.1016\/j.ejmech.2022.114958_bib17","doi-asserted-by":"crossref","first-page":"1896","DOI":"10.1021\/jm101541x","article-title":"Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis","volume":"54","author":"Pacchiano","year":"2011","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib18","doi-asserted-by":"crossref","first-page":"3505","DOI":"10.1158\/0008-5472.CAN-07-6151","article-title":"Estrogen receptor regulation of carbonic anhydrase XII through a distal enhancer in breast cancer","volume":"68","author":"Barnett","year":"2008","journal-title":"Cancer Res."},{"key":"10.1016\/j.ejmech.2022.114958_bib19","doi-asserted-by":"crossref","first-page":"5210","DOI":"10.1038\/onc.2012.550","article-title":"Targeting carbonic anhydrase IX depletes breast cancer stem cells within the hypoxic niche","volume":"32","author":"Lock","year":"2013","journal-title":"Oncogene"},{"key":"10.1016\/j.ejmech.2022.114958_bib20","doi-asserted-by":"crossref","first-page":"2220","DOI":"10.1073\/pnas.040554897","article-title":"Carbonic anhydrase inhibitor suppresses invasion of renal cancer cells in vitro","volume":"97","author":"Parkkila","year":"2000","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"10.1016\/j.ejmech.2022.114958_bib21","doi-asserted-by":"crossref","first-page":"510","DOI":"10.1016\/j.juro.2008.04.024","article-title":"Serum carbonic anhydrase 9 level is associated with postoperative recurrence of conventional renal cell cancer","volume":"180","author":"Li","year":"2008","journal-title":"J. Urol."},{"key":"10.1016\/j.ejmech.2022.114958_bib22","doi-asserted-by":"crossref","first-page":"837","DOI":"10.1046\/j.1365-2036.2003.01738.x","article-title":"Expression of carbonic anhydrase IX in human pancreatic cancer","volume":"18","author":"Juh\u00e1sz","year":"2003","journal-title":"Aliment. Pharmacol. Ther."},{"key":"10.1016\/j.ejmech.2022.114958_bib23","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1136\/gut.2004.047340","article-title":"Expression of carbonic anhydrase 9 at the invasion front of gastric cancers","volume":"54","author":"Chen","year":"2005","journal-title":"Gut"},{"key":"10.1016\/j.ejmech.2022.114958_bib24","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1007\/s00428-011-1105-y","article-title":"Overexpression of carbonic anhydrase IX (CAIX) is an independent unfavorable prognostic marker in endometrioid ovarian cancer","volume":"459","author":"Choschzick","year":"2011","journal-title":"Virchows Arch."},{"key":"10.1016\/j.ejmech.2022.114958_bib25","doi-asserted-by":"crossref","first-page":"1760","DOI":"10.1158\/1055-9965.EPI-07-0080","article-title":"Carbonic anhydrase IX is highly expressed in hereditary nonpolyposis colorectal cancer, cancer epidemiology","volume":"16","author":"Niemel\u00e4","year":"2007","journal-title":"Biomarkers & Prevention"},{"key":"10.1016\/j.ejmech.2022.114958_bib26","first-page":"8924","article-title":"Carbonic anhydrase 9 as an endogenous marker for hypoxic cells in cervical cancer","volume":"61","author":"Olive","year":"2001","journal-title":"Cancer Res."},{"key":"10.1016\/j.ejmech.2022.114958_bib27","doi-asserted-by":"crossref","first-page":"3288","DOI":"10.2174\/138161210793429788","article-title":"Modulation of carbonic anhydrase 9 (CA9) in human brain cancer","volume":"16","author":"Said","year":"2010","journal-title":"Curr. Pharmaceut. Des."},{"key":"10.1016\/j.ejmech.2022.114958_bib28","doi-asserted-by":"crossref","first-page":"302","DOI":"10.1007\/s00432-005-0068-2","article-title":"Tumor-associated carbonic anhydrases are linked to metastases in primary cervical cancer","volume":"132","author":"Kim","year":"2006","journal-title":"J. Cancer Res. Clin. Oncol."},{"key":"10.1016\/j.ejmech.2022.114958_bib29","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1016\/j.ejmech.2014.06.064","article-title":"Synthesis, in vitro antiproliferative activity, and in silico studies of fused tricyclic coumarin sulfonate derivatives","volume":"84","author":"El-Gamal","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib30","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1002\/bkcs.10651","article-title":"A new series of cycloalkane-fused coumarin sulfonates: synthesis and in vitro antiproliferative screening","volume":"37","author":"El-Gamal","year":"2016","journal-title":"Bull. Kor. Chem. Soc."},{"key":"10.1016\/j.ejmech.2022.114958_bib31","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2019.07.063","article-title":"Synthesis, biological evaluation, and docking studies of new raloxifene sulfonate or sulfamate derivatives as inhibitors of nucleotide pyrophosphatase\/phosphodiesterase","volume":"181","author":"El-Gamal","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib32","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/j.jinorgbio.2016.06.008","article-title":"Sulfonated Schiff base Sn(IV) complexes as potential anticancer agents","volume":"162","author":"Hazra","year":"2016","journal-title":"J. Inorg. Biochem."},{"key":"10.1016\/j.ejmech.2022.114958_bib33","doi-asserted-by":"crossref","first-page":"4681","DOI":"10.1016\/j.bmcl.2012.05.083","article-title":"Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines","volume":"22","author":"Winum","year":"2012","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2022.114958_bib34","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1016\/j.ejmech.2019.06.052","article-title":"Sulfamates in drug design and discovery: pre-clinical and clinical investigations","volume":"179","author":"Zaraei","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib35","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1586\/era.10.201","article-title":"Irosustat: a first-generation steroid sulfatase inhibitor in breast cancer","volume":"11","author":"Palmieri","year":"2011","journal-title":"Expert Rev. Anticancer Ther."},{"key":"10.1016\/j.ejmech.2022.114958_bib36","doi-asserted-by":"crossref","DOI":"10.1371\/journal.pone.0080305","article-title":"STX140, but not paclitaxel, inhibits mammary tumour initiation and progression in C3(1)\/SV40 T\/t-Antigen transgenic mice","volume":"8","author":"Meyer-Losic","year":"2013","journal-title":"PLoS One"},{"key":"10.1016\/j.ejmech.2022.114958_bib37","doi-asserted-by":"crossref","first-page":"26249","DOI":"10.3390\/ijms161125953","article-title":"Betulinyl sulfamates as anticancer agents and radiosensitizers in human breast cancer cells","volume":"16","author":"Bache","year":"2015","journal-title":"Int. J. Mol. Sci."},{"key":"10.1016\/j.ejmech.2022.114958_bib38","doi-asserted-by":"crossref","first-page":"2762","DOI":"10.1016\/j.bmc.2016.04.040","article-title":"Design, synthesis, and biological evaluation of new arylamide derivatives possessing sulfonate or sulfamate moieties as steroid sulfatase enzyme inhibitors","volume":"24","author":"El-Gamal","year":"2016","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib39","doi-asserted-by":"crossref","first-page":"2741","DOI":"10.1016\/j.bmc.2019.04.031","article-title":"Synthesis, biological evaluation, and molecular docking study of sulfonate derivatives as nucleotide pyrophosphatase\/phosphodiesterase (NPP) inhibitors","volume":"27","author":"Semreen","year":"2019","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib40","doi-asserted-by":"crossref","DOI":"10.1016\/j.bioorg.2020.103677","article-title":"Antiproliferative activity of cycloalkanecarboxamide derivatives possessing sulfonate or sulfamate moiety","volume":"97","author":"El-Gamal","year":"2020","journal-title":"Bioorg. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib41","doi-asserted-by":"crossref","DOI":"10.1016\/j.bmc.2020.115406","article-title":"A new series of aryl sulfamate derivatives: design, synthesis, and biological evaluation","volume":"28","author":"El-Gamal","year":"2020","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib42","doi-asserted-by":"crossref","DOI":"10.1016\/j.bioorg.2020.104305","article-title":"Evaluation of sulfonate and sulfamate derivatives possessing benzofuran or benzothiophene nucleus as inhibitors of nucleotide pyrophosphatases\/phosphodiesterases and anticancer agents","volume":"104","author":"Anbar","year":"2020","journal-title":"Bioorg. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib43","doi-asserted-by":"crossref","first-page":"3889","DOI":"10.1016\/j.bmc.2019.07.026","article-title":"Sulfonate and sulfamate derivatives possessing benzofuran or benzothiophene nucleus as potent carbonic anhydrase II\/IX\/XII inhibitors","volume":"27","author":"Zaraei","year":"2019","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib44","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1016\/j.ejmech.2016.01.045","article-title":"Novel 4-anilinoquinazoline derivatives featuring an 1-adamantyl moiety as potent EGFR inhibitors with enhanced activity against NSCLC cell lines","volume":"110","author":"Yu","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib45","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2022.114434","article-title":"Design and synthesis of new quinoline derivatives as selective C-RAF kinase inhibitors with potent anticancer activity","volume":"238","author":"Zaraei","year":"2022","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib46","doi-asserted-by":"crossref","first-page":"5794","DOI":"10.1039\/C6GC01318J","article-title":"Direct cycle between co-product and reactant: an approach to improve the atom economy and its application in the synthesis and protection of primary amines","volume":"18","author":"Guan","year":"2016","journal-title":"Green Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib47","volume":"vol. 7","author":"Baird","year":"2018"},{"key":"10.1016\/j.ejmech.2022.114958_bib48","first-page":"184","article-title":"Extracellular cGAMP is a cancer cell-produced immunotransmitter involved in radiation-induced anti-cancer immunity","volume":"1","author":"Carozza","year":"2020","journal-title":"Nat. Can. (Que.)"},{"key":"10.1016\/j.ejmech.2022.114958_bib49","doi-asserted-by":"crossref","first-page":"879","DOI":"10.1158\/2159-8290.CD-14-0341","article-title":"Targeting cancer-derived adenosine:new therapeutic approaches","volume":"4","author":"Young","year":"2014","journal-title":"Cancer Discov."},{"key":"10.1016\/j.ejmech.2022.114958_bib50","doi-asserted-by":"crossref","first-page":"1187","DOI":"10.1039\/D1MD00117E","article-title":"Discovery of potent nucleotide pyrophosphatase\/phosphodiesterase3 (NPP3) inhibitors with ancillary carbonic anhydrase inhibition for cancer (immuno)therapy","volume":"12","author":"Lee","year":"2021","journal-title":"RSC Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib51","doi-asserted-by":"crossref","first-page":"350","DOI":"10.1136\/jclinpath-2020-207073","article-title":"Carbonic anhydrase IX: a regulator of pH and participant in carcinogenesis","volume":"74","author":"Aldera","year":"2021","journal-title":"J. Clin. Pathol."},{"key":"10.1016\/j.ejmech.2022.114958_bib52","doi-asserted-by":"crossref","first-page":"685","DOI":"10.2174\/138161208783877893","article-title":"Cancer-associated carbonic anhydrases and their inhibition","volume":"14","author":"Pastorek","year":"2008","journal-title":"Curr. Pharmaceut. Des."},{"key":"10.1016\/j.ejmech.2022.114958_bib53","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1016\/S0002-9440(10)65569-1","article-title":"Immunohistochemical study of colorectal tumors for expression of a novel transmembrane carbonic anhydrase, MN\/CA IX, with potential value as a marker of cell proliferation","volume":"153","author":"Saarnio","year":"1998","journal-title":"Am. J. Pathol."},{"key":"10.1016\/j.ejmech.2022.114958_bib54","first-page":"7992","article-title":"Expression of hypoxia-inducible carbonic anhydrase-9 relates to angiogenic pathways and independently to poor outcome in non-small cell lung cancer","volume":"61","author":"Giatromanolaki","year":"2001","journal-title":"Cancer Res."},{"key":"10.1016\/j.ejmech.2022.114958_bib55","first-page":"6394","article-title":"Carbonic anhydrase (CA IX) expression, a potential new intrinsic marker of hypoxia: correlations with tumor oxygen measurements and prognosis in locally advanced carcinoma of the cervix","volume":"61","author":"Loncaster","year":"2001","journal-title":"Cancer Res."},{"key":"10.1016\/j.ejmech.2022.114958_bib56","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1038\/sj.bjc.6600936","article-title":"Diagnostic, prognostic and therapeutic implications of carbonic anhydrases in cancer","volume":"89","author":"Potter","year":"2003","journal-title":"Br. J. Cancer"},{"key":"10.1016\/j.ejmech.2022.114958_bib57","doi-asserted-by":"crossref","first-page":"3364","DOI":"10.1158\/0008-5472.CAN-10-4261","article-title":"Targeting tumor hypoxia: suppression of breast tumor growth and metastasis by novel carbonic anhydrase IX inhibitors","volume":"71","author":"Lou","year":"2011","journal-title":"Cancer Res."},{"key":"10.1016\/j.ejmech.2022.114958_bib58","doi-asserted-by":"crossref","first-page":"435","DOI":"10.1111\/cas.13163","article-title":"Crucial role of carbonic anhydrase IX in tumorigenicity of xenotransplanted adult T-cell leukemia-derived cells","volume":"108","author":"Nasu","year":"2017","journal-title":"Cancer Sci."},{"key":"10.1016\/j.ejmech.2022.114958_bib59","doi-asserted-by":"crossref","first-page":"889","DOI":"10.1107\/S2059798320010505","article-title":"Crystal structures of human ENPP1 in apo and bound forms","volume":"76","author":"Dennis","year":"2020","journal-title":"Acta Crystallogr. D Struct. Biol."},{"key":"10.1016\/j.ejmech.2022.114958_bib60","doi-asserted-by":"crossref","first-page":"3580","DOI":"10.1021\/acs.jmedchem.7b00032","volume":"60","author":"Desroy","year":"2017","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib61","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1016\/j.bbagen.2016.12.019","article-title":"The promiscuous ectonucleotidase NPP1: molecular insights into substrate binding and hydrolysis","volume":"1861","author":"Namasivayam","year":"2017","journal-title":"Biochim. Biophys. Acta"},{"key":"10.1016\/j.ejmech.2022.114958_bib62","doi-asserted-by":"crossref","first-page":"2481","DOI":"10.1111\/febs.14489","article-title":"Structural basis for nucleotide recognition by the ectoenzyme CD203c","volume":"285","author":"Gorelik","year":"2018","journal-title":"FEBS J."},{"key":"10.1016\/j.ejmech.2022.114958_bib63","doi-asserted-by":"crossref","first-page":"992","DOI":"10.1107\/S1744309109036665","article-title":"High-resolution structure of human carbonic anhydrase II complexed with acetazolamide reveals insights into inhibitor drug design","volume":"65","author":"Sippel","year":"2009","journal-title":"Acta Crystallogr., Sect. F: Struct. Biol. Cryst. Commun."},{"key":"10.1016\/j.ejmech.2022.114958_bib64","doi-asserted-by":"crossref","first-page":"9004","DOI":"10.1021\/acs.jmedchem.5b01343","article-title":"Efficient expression and crystallization system of cancer-associated carbonic anhydrase isoform IX","volume":"58","author":"Leitans","year":"2015","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib65","doi-asserted-by":"crossref","first-page":"6937","DOI":"10.1016\/j.bmc.2013.09.029","article-title":"Benzenesulfonamides with pyrimidine moiety as inhibitors of human carbonic anhydrases I, II, VI, VII, XII, and XIII","volume":"21","author":"\u010capkauskait\u0117","year":"2013","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib66","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1080\/14756366.2018.1530225","article-title":"Design, synthesis, in vitro anticancer evaluation, kinase inhibitory effects, and pharmacokinetic profile of new 1,3,4-triarylpyrazole derivatives possessing terminal sulfonamide moiety","volume":"34","author":"Abdel-Maksoud","year":"2019","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib67","doi-asserted-by":"crossref","first-page":"75","DOI":"10.2174\/1871520616666160620074534","article-title":"Synthesis, in vitro antiproliferative and antiinflammatory activities, and kinase inhibitory effects of new 1,3,4-triarylpyrazole derivatives","volume":"17","author":"El-Gamal","year":"2017","journal-title":"Anti Cancer Agents Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib68","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1111\/j.1432-1033.1994.tb20068.x","article-title":"Biochemical characterization of human PC-1, an enzyme possessing alkaline phosphodiesterase I and nucleotide pyrophosphatase activities","volume":"226","author":"Belli","year":"1994","journal-title":"Eur. J. Biochem."},{"key":"10.1016\/j.ejmech.2022.114958_bib69","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1006\/geno.1995.0036","article-title":"Molecular cloning and chromosomal assignment of the human brain-type phosphodiesterase I\/nucleotide pyrophosphatase gene (PDNP2)","volume":"30","author":"Kawagoe","year":"1995","journal-title":"Genomics"},{"key":"10.1016\/j.ejmech.2022.114958_bib70","doi-asserted-by":"crossref","first-page":"8485","DOI":"10.1021\/jm100597c","article-title":"Diadenosine 5\u2032,5\u2032\u2032-(boranated)polyphosphonate analogues as selective nucleotide pyrophosphatase\/phosphodiesterase inhibitors","volume":"53","author":"Eliahu","year":"2010","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib71","doi-asserted-by":"crossref","first-page":"140","DOI":"10.1016\/j.ejmech.2014.03.023","article-title":"New aminobenzenesulfonamide\u2013thiourea conjugates: synthesis and carbonic anhydrase inhibition and docking studies","volume":"78","author":"Zaib","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2022.114958_bib73","year":"2017"},{"key":"10.1016\/j.ejmech.2022.114958_bib74","series-title":"Discovery Studio Modeling Environment","year":"2016"}],"container-title":["European Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523422008601?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523422008601?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,1]],"date-time":"2025-10-01T14:47:31Z","timestamp":1759330051000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0223523422008601"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1]]},"references-count":73,"alternative-id":["S0223523422008601"],"URL":"https:\/\/doi.org\/10.1016\/j.ejmech.2022.114958","relation":{},"ISSN":["0223-5234"],"issn-type":[{"value":"0223-5234","type":"print"}],"subject":[],"published":{"date-parts":[[2023,1]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Design and synthesis of new adamantyl derivatives as promising antiproliferative agents","name":"articletitle","label":"Article Title"},{"value":"European Journal of Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.ejmech.2022.114958","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2022 Elsevier Masson SAS. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"114958"}}