{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T23:17:00Z","timestamp":1788477420852,"version":"build-2803163510"},"reference-count":50,"publisher":"American Chemical Society (ACS)","issue":"9","license":[{"start":{"date-parts":[[2017,9,8]],"date-time":"2017-09-08T00:00:00Z","timestamp":1504828800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100000054","name":"National Cancer Institute","doi-asserted-by":"publisher","award":["ZIA BC 011232"],"award-info":[{"award-number":["ZIA BC 011232"]}],"id":[{"id":"10.13039\/100000054","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100007496","name":"Biomedical Laboratory Research and Development, VA Office of Research and Development","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007496","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2017,9,30]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Glycoamino acid analogues of the Thomsen\u2013Friedenreich antigen disaccharide, where the 4\u2032 and 4\u2033 hydroxyl groups were substituted with fluorine or hydrogen, were synthesized and incorporated into the asialylated antiproliferative factor (as-APF), a biologically active form of APF, a glycopeptide found in the urine of patients with interstitial cystitis. Various strategies were employed to incorporate the fluorine atom at the 4-positions of either the galactose or N-acetylgalactosamine unit of the disaccharide antigen, based on stereochemistry and reactivity. These glycopeptides were evaluated in antiproliferative assays on both primary normal bladder epithelial cells and T24 bladder carcinoma cells. Unlike many previously published substitutions to APF, mono-4\u2032-fluorination of the GalNAc residue did not affect the activity, whereas fluoro-derivatives of the galactose 4\u2033-position or both 4\u2032 and 4\u2033 hydroxyls showed a reduced potency relative to the monosubstituted GalNAc derivative. A fourth compound where the 4\u2033 position of galactose was deoxygenated showed a lower potency than the parent and monosubstituted compounds. These results suggest that specific substitutions in the sugar moieties in the APF can be tolerated, and the glycomimetic design of APF analogues can include fluorine in the GalNAc sugar of the disaccharide.<\/jats:p>","DOI":"10.1021\/acsomega.7b01018","type":"journal-article","created":{"date-parts":[[2017,9,8]],"date-time":"2017-09-08T09:28:00Z","timestamp":1504862880000},"page":"5618-5632","source":"Crossref","is-referenced-by-count":8,"title":["Glycoamino Acid Analogues of the Thomsen\u2013Friedenreich\nTumor-Associated Carbohydrate Antigen: Synthesis and Evaluation of\nNovel Antiproliferative Factor Glycopeptides"],"prefix":"10.1021","volume":"2","author":[{"given":"Maqbool A.","family":"Siddiqui","sequence":"first","affiliation":[{"name":"National Cancer Institute at Frederick , , , ,","place":["Frederick, Maryland, United States, 21702"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shailesh","family":"Ambre","sequence":"additional","affiliation":[{"name":"National Cancer Institute at Frederick , , , ,","place":["Frederick, Maryland, United States, 21702"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Susan K.","family":"Keay","sequence":"additional","affiliation":[{"name":"Medical Service, Veterans Administration Maryland Health Care System , , ,","place":["Baltimore, Maryland, United States, 21201"]},{"name":"Baltimore Research and Education Foundation , , ,","place":["Baltimore, Maryland, United States, 21201"]},{"name":"University of Maryland School of Medicine , , , ,","place":["Baltimore, Maryland, United States, 21201"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jeffrey M.","family":"Rhyne","sequence":"additional","affiliation":[{"name":"University of Maryland School of Medicine , , , ,","place":["Baltimore, Maryland, United States, 21201"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chen-Ou","family":"Zhang","sequence":"additional","affiliation":[{"name":"University of Maryland School of Medicine , , , ,","place":["Baltimore, Maryland, United States, 21201"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9906-0799","authenticated-orcid":true,"suffix":"Jr.","given":"Joseph J.","family":"Barchi","sequence":"additional","affiliation":[{"name":"National Cancer Institute at Frederick , , , ,","place":["Frederick, Maryland, United States, 21702"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2017,9,8]]},"reference":[{"key":"2026090318122191200_cit1","article-title":"Structural Basis\nof Glycan Diversity","volume-title":"Essentials of Glycobiology","author":"Bertozzi","year":"2009","edition":"2"},{"key":"2026090318122191200_cit2","article-title":"Biological Roles\nof Glycans","volume-title":"Essentials of Glycobiology","author":"Varki","year":"2009","edition":"2"},{"key":"2026090318122191200_cit3","article-title":"Glycosylation Changes\nin Cancer","volume-title":"Essentials of Glycobiology","author":"Varki","year":"2009","edition":"2"},{"key":"2026090318122191200_cit4","doi-asserted-by":"publisher","first-page":"1303","DOI":"10.1016\/0161-5890(85)90050-1","article-title":"Tn Epitopes, Immunoreactive with Ordinary Anti-Tn Antibodies,\non Normal, Desialylated Human Erythrocytes and on Thomsen-Friedenreich\nAntigen Isolated Therefrom","volume":"22","author":"Springer","year":"1985","journal-title":"Mol. 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