Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F08%3A00007661" target="_blank" >RIV/61989592:15310/08:00007661 - isvavai.cz</a>

Alternative codes found

RIV/61389030:_____/08:00322112

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents

Original language description

The saponins modified with mono- or trimannosyl residues can provide a convenient means of delivering drugs to certain human cells via interactions with mannose receptors. In the study reported therein, we developed a convenient approach for the synthesis of 3-O-mannoside and branched trimannoside derivatives of the saponin lupeol and of C-28 acyl esters of 3-O-acetyl-betulinic acid bearing the same mannosyl entities. Lupeol and 3-O-acetyl-betulinic acid were mannosylated with tetra-O-benzoyl- or tetra-O-acetyl-?-d-mannopyranosyl trichloroacetimidates. De-esterification followed by regioselective dimannosylation of the unprotected monosaccharide derivatives with 2 equiv of tetra-O-benzoyl-?-d-mannopyranosyl trichloroacetimidate selectively yielded O-3,O-6-linked trimannosides. The cytotoxic activity of selected lupane-type saponins (derivatives of lupeol, betulinic acid, and betulin) toward normal human fibroblasts and various cancer cell lines was also compared.

Czech name

Syntéza lupanových derivatů s mannosyly a trimannosyly a jejich protinádorové účinky

Czech description

Byly nasyntetizovány deriváty lupanu a betulinů s mannosylovými a trimannosylovými residuii a byly testovány jejich cytotoxické účinky na řadě nádorových a normálních lidských buněčných liniích.

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CE - Biochemistry

OECD FORD branch

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Project

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Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2008

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Carbohydrate Research

ISSN

0008-6215

e-ISSN

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Volume of the periodical

6

Issue of the periodical within the volume

343

Country of publishing house

GB - UNITED KINGDOM

Number of pages

9

Pages from-to

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UT code for WoS article

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EID of the result in the Scopus database

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