{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T03:24:31Z","timestamp":1792121071591,"version":"4.4.0"},"reference-count":27,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2020,9,17]],"date-time":"2020-09-17T00:00:00Z","timestamp":1600300800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000054","name":"National Cancer Institute","doi-asserted-by":"publisher","award":["RO3\u2010CA143614\u201001"],"award-info":[{"award-number":["RO3\u2010CA143614\u201001"]}],"id":[{"id":"10.13039\/100000054","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chem Biol Drug Des"],"published-print":{"date-parts":[[2021,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Spiropyrans have been extensively investigated because of their thermo\u2010 and photochromic characteristics, but their biotherapeutic properties have not been explored much. We report anti\u2010proliferative properties of a novel 3,3\u2032\u2010azadimethylene dinaphthospiropyran <jats:bold>11<\/jats:bold>. Dibenzospiropyrans and dinaphthospiropyrans were synthesized by a simple and expedient method using acid\u2010catalyzed aldol condensation of salicylaldehyde and 2\u2010hydroxy\u20101\u2010naphthaldehyde, respectively, with cyclic ketones. Together with structural elucidation by 2D NMR and X\u2010ray crystallography studies, we provide a putative mechanism for their formation. Compound <jats:bold>11<\/jats:bold> showed solvatochromism and exhibited altered spectral characteristics depending on the pH. In acidic conditions, <jats:bold>11<\/jats:bold> remains in open form, whereas upon alkalinization it reverts back to closed form. Based on the in vitro anti\u2010proliferative activity in H441, HCT\u2010116, MiaPaCa\u20102, and Panc\u20101 cancer cell lines, <jats:bold>11<\/jats:bold> was submitted to further investigation. It reduced HCT116 colonosphere formation and demonstrated induction of caspase cascade, suggesting apoptosis. In vitro proliferation assays also suggested that HCl and trifluoroacetate salts of <jats:bold>11<\/jats:bold> are more effective. Treatment of mice carrying HCT\u2010116 xenografts with <jats:bold>11<\/jats:bold> (5\u00a0\u00b5g\/day, intraperitoneal for 3\u00a0weeks) suppressed tumor growth by 62%. Overall, the results reveal a new series of structurally complex, but relatively easy to synthesize molecules of which compound <jats:bold>11<\/jats:bold> represents a lead for anticancer development.<\/jats:p>","DOI":"10.1111\/cbdd.13785","type":"journal-article","created":{"date-parts":[[2020,9,18]],"date-time":"2020-09-18T00:55:28Z","timestamp":1600390528000},"page":"325-340","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Tumor suppressive activities of solvatochromic 3,3\u2032\u2010azadimethylene dinaphthospiropyran in colon cancer model"],"prefix":"10.1111","volume":"97","author":[{"given":"Pallavi","family":"Lagisetty","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Sciences University of Oklahoma Health Sciences Center Oklahoma City OK USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Venkateswararao","family":"Eeda","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Sciences University of Oklahoma Health Sciences Center Oklahoma City OK USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vivek R.","family":"Yadav","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Sciences University of Oklahoma Health Sciences Center Oklahoma City OK USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Susan L.","family":"Nimmo","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Oklahoma Norman OK USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dharmalingam","family":"Subramaniam","sequence":"additional","affiliation":[{"name":"Department of Molecular &amp; Integrative Physiology University of Kansas Medical Center Kansas City KS USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Douglas R.","family":"Powell","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Oklahoma Norman OK USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3611-9009","authenticated-orcid":false,"given":"Vibhudutta","family":"Awasthi","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Sciences University of Oklahoma Health Sciences Center Oklahoma City OK USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,9,17]]},"reference":[{"key":"e_1_2_5_2_1","first-page":"53711","volume-title":"Data collection: SMART software reference manual","author":"Bruker\u2010AXS","year":"1998"},{"key":"e_1_2_5_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/b606203b"},{"key":"e_1_2_5_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/JR9270001699"},{"key":"e_1_2_5_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/JR9280002077"},{"issue":"2","key":"e_1_2_5_6_1","first-page":"379","article-title":"Clonogenic assay with established human tumour xenografts: Correlation of in vitro to in vivo activity as a basis for anticancer drug discovery","volume":"67","author":"Fiebig H. 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