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Synthesis of N-acetyl Glucosamine Analogs as Inhibitors for Hyaluronan Biosynthesis.

ABSTRACT: Elevated hyaluronan expression is a hallmark of many types of cancer. Therefore, inhibition of hyaluronan biosynthesis can potentially slow the growth of tumor cells. Herein, we explore a chain termination strategy to reduce hyaluronan synthesis by tumor cells. Several analogs of glucosamine were prepared, which contained modifications at the C-3 positions. These analogs can possibly cap the nonreducing end of a growing hyaluronan chain, thus lowering the amount of hyaluronan synthesized. Upon incubation with pancreatic cancer cells, a fluorine-containing glucosamine analog was found to exhibit significant inhibitory activities of hyaluronan synthesis. Furthermore, it drastically reduced the proliferation of cancer cells.

SUBMITTER: Wasonga G

PROVIDER: S-EPMC4834982 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Synthesis of <i>N</i>-acetyl Glucosamine Analogs as Inhibitors for Hyaluronan Biosynthesis.

Wasonga Gilbert G Tatara Yota Y Kakizaki Ikuko I Huang Xuefei X

Journal of carbohydrate chemistry 20130902 5-6

Elevated hyaluronan expression is a hallmark of many types of cancer. Therefore, inhibition of hyaluronan biosynthesis can potentially slow the growth of tumor cells. Herein, we explore a chain termination strategy to reduce hyaluronan synthesis by tumor cells. Several analogs of glucosamine were prepared, which contained modifications at the C-3 positions. These analogs can possibly cap the nonreducing end of a growing hyaluronan chain, thus lowering the amount of hyaluronan synthesized. Upon i ...[more]

PMID: 27099411

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