{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,21]],"date-time":"2026-02-21T04:10:06Z","timestamp":1771647006211,"version":"3.50.1"},"reference-count":69,"publisher":"Oxford University Press (OUP)","issue":"8","license":[{"start":{"date-parts":[[2021,5,12]],"date-time":"2021-05-12T00:00:00Z","timestamp":1620777600000},"content-version":"vor","delay-in-days":4,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002261","name":"Russian Foundation for Basic Research","doi-asserted-by":"publisher","award":["19-29-04123"],"award-info":[{"award-number":["19-29-04123"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Koltzov Institute of Developmental Biology of the Russian Academy of Sciences","award":["0088-2021-0017"],"award-info":[{"award-number":["0088-2021-0017"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2021,9,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>Elevated plasma levels of hyaluronic acid (HA) is a disease marker in liver pathology and other inflammatory disorders. Inhibition of HA synthesis with coumarin 4-methylumbelliferone (4MU) has a beneficial effect in animal models of fibrosis, inflammation, cancer and metabolic syndrome. 4MU is an active compound of approved choleretic drug hymecromone with low bioavailability and a broad spectrum of action. New, more specific and efficient inhibitors of hyaluronan synthases (HAS) are required. We have tested several newly synthesized coumarin compounds and commercial chitin synthesis inhibitors to inhibit HA production in cell culture assay. Coumarin derivative compound VII (10\u2032-methyl-6\u2032-phenyl-3\u2032H-spiro[piperidine-4,2\u2032-pyrano[3,2-g]chromene]-4\u2032,8\u2032-dione) demonstrated inhibition of HA secretion by NIH3T3 cells with the half-maximal inhibitory concentration (IC50)\u00a0=\u00a01.69\u00a0\u00b1\u00a00.75\u00a0\u03bc\u039c superior to 4MU (IC50\u00a0=\u00a08.68\u00a0\u00b1\u00a01.6\u00a0\u03bc\u039c). Inhibitors of chitin synthesis, etoxazole, buprofezin, triflumuron, reduced HA deposition with IC50 of 4.21\u00a0\u00b1\u00a03.82 \u03bc\u039c, 1.24\u00a0\u00b1\u00a00.87 \u03bc\u039c and 1.48\u00a0\u00b1\u00a01.44 \u03bc\u039c, respectively. Etoxazole reduced HA production and prevented collagen fibre formation in the CCl4 liver fibrosis model in mice similar to 4MU. Bioinformatics analysis revealed homology between chitin synthases and HAS enzymes, particularly in the pore-forming domain, containing the proposed site for etoxazole binding.<\/jats:p>","DOI":"10.1093\/glycob\/cwab038","type":"journal-article","created":{"date-parts":[[2021,4,27]],"date-time":"2021-04-27T19:25:15Z","timestamp":1619551515000},"page":"959-974","source":"Crossref","is-referenced-by-count":11,"title":["Inhibition of hyaluronan secretion by novel coumarin compounds and chitin synthesis inhibitors"],"prefix":"10.1093","volume":"31","author":[{"given":"Alexandra A","family":"Tsitrina","sequence":"first","affiliation":[{"name":"Laboratory of problems of regeneration, Koltzov Institute of Developmental Biology of Russian Academy of Sciences, 119334 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Igor V","family":"Krasylov","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Taras Shevchenko National University of Kyiv, 01601 Kyiv, Ukraine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dmitry I","family":"Maltsev","sequence":"additional","affiliation":[{"name":"Laboratory of problems of regeneration, Koltzov Institute of Developmental Biology of Russian Academy of Sciences, 119334 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Irina N","family":"Andreichenko","sequence":"additional","affiliation":[{"name":"Center for Neurobiology and Brain Restoration and Center of Life Sciences, Skolkovo Institute of Science and Technology, Skolkovo, 143025 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Viktoria S","family":"Moskvina","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Taras Shevchenko National University of Kyiv, 01601 Kyiv, Ukraine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dmitry N","family":"Ivankov","sequence":"additional","affiliation":[{"name":"Center for Neurobiology and Brain Restoration and Center of Life Sciences, Skolkovo Institute of Science and Technology, Skolkovo, 143025 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elena V","family":"Bulgakova","sequence":"additional","affiliation":[{"name":"Laboratory of problems of regeneration, Koltzov Institute of Developmental Biology of Russian Academy of Sciences, 119334 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mikhail","family":"Nesterchuk","sequence":"additional","affiliation":[{"name":"Center for Neurobiology and Brain Restoration and Center of Life Sciences, Skolkovo Institute of Science and Technology, Skolkovo, 143025 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vera","family":"Shashkovskaya","sequence":"additional","affiliation":[{"name":"Center for Neurobiology and Brain Restoration and Center of Life Sciences, Skolkovo Institute of Science and Technology, Skolkovo, 143025 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nataliya O","family":"Dashenkova","sequence":"additional","affiliation":[{"name":"Laboratory of problems of regeneration, Koltzov Institute of Developmental Biology of Russian Academy of Sciences, 119334 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vladimir P","family":"Khilya","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Taras Shevchenko National University of Kyiv, 01601 Kyiv, Ukraine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Arsen","family":"Mikaelyan","sequence":"additional","affiliation":[{"name":"Laboratory of problems of regeneration, Koltzov Institute of Developmental Biology of Russian Academy of Sciences, 119334 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuri","family":"Kotelevtsev","sequence":"additional","affiliation":[{"name":"Center for Neurobiology and Brain 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