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| 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-α-d-mannopyranosyl trichloroacetimidates. De-esterification followed by regioselective dimannosylation of the unprotected monosaccharide derivatives with 2 equiv of tetra-O-benzoyl-α-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.
- 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-α-d-mannopyranosyl trichloroacetimidates. De-esterification followed by regioselective dimannosylation of the unprotected monosaccharide derivatives with 2 equiv of tetra-O-benzoyl-α-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. (en)
- Zabývali jsme se přípravou saponinů z několika lupanových triterpenů (lupeol, betulinová kyselina a betulin). Připojení cukru k sapogeninu jako hydrofilní transport-usnadňující funkční skupiny by mohlo zlepšit jejich schopnost vstupovat do cílových buněk pomocí interakce s manosovými receptory, zvýšit jejich rozpustnost a poskytnout tak vhodné lékové formy. Byly vyvinuty nové přístupy k syntéze derivatů saponinu lupeolu a 3-O-acetyl-betulinové kyseliny nesoucí manosu a 3,6-di-O-(α-D-mannopyranosyl)-α-D-mannopyranosu. Byla srovnávána protinádorová aktivita vybraných derivátu lupanu (odvozených od lupeolu, betulinu a kyseliny betulinové) na normálních lidských fibroblastech a některých lidských nádorových buněčných liniích. (cs)
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| Title
| - Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents
- Syntéza saponinů lupanového typu nesoucích manosyl a 3,6 rozvětvený trimanosylový zbytek a jejich využítí jako protinádorová léčiva (cs)
- Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents (en)
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| skos:prefLabel
| - Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents
- Syntéza saponinů lupanového typu nesoucích manosyl a 3,6 rozvětvený trimanosylový zbytek a jejich využítí jako protinádorová léčiva (cs)
- Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents (en)
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| skos:notation
| - RIV/61389030:_____/08:00322112!RIV09-AV0-61389030
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| http://linked.open...avai/riv/aktivita
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| http://linked.open...avai/riv/aktivity
| - Z(AV0Z50380511), Z(MSM6198959216)
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| http://linked.open...iv/cisloPeriodika
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| http://linked.open...vai/riv/dodaniDat
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| http://linked.open...aciTvurceVysledku
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| http://linked.open.../riv/druhVysledku
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| http://linked.open...iv/duvernostUdaju
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| http://linked.open...titaPredkladatele
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| http://linked.open...dnocenehoVysledku
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| http://linked.open...ai/riv/idVysledku
| - RIV/61389030:_____/08:00322112
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| http://linked.open...riv/jazykVysledku
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| http://linked.open.../riv/klicovaSlova
| - Saponin; Betulin; Lupeol; Betulinic acid (en)
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| http://linked.open.../riv/klicoveSlovo
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| http://linked.open...odStatuVydavatele
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| http://linked.open...ontrolniKodProRIV
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| http://linked.open...i/riv/nazevZdroje
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| http://linked.open...in/vavai/riv/obor
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| http://linked.open...ichTvurcuVysledku
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| http://linked.open...cetTvurcuVysledku
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| http://linked.open...UplatneniVysledku
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| http://linked.open...v/svazekPeriodika
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| http://linked.open...iv/tvurceVysledku
| - Strnad, Miroslav
- Swaczynová, Jana
- Cmoch, P.
- Pakulski, Z.
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| http://linked.open...ain/vavai/riv/wos
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| http://linked.open...n/vavai/riv/zamer
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| issn
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| number of pages
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