The synthesis, distribution, and anti-hepatic cancer activity of YSL
(I) HCl/CH3OH; (II) DCC/HOBt/NMM with corresponding carboxyl component; (III) HCl/CH3CO2C2H5 (6mol/L); (IV) NaOH/H2O/CH3OH; (V) 3H2 and 10% Pd/C. YSL was prepared stepwise from C terminal to N terminal with the side chain un-protective amino acids, Boc-Leu-OMe, Boc-Ser-OH, and Boc-Tyr-OH, as the sta...
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Published in | Bioorganic & medicinal chemistry Vol. 12; no. 18; pp. 4989 - 4994 |
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Main Authors | , , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Oxford
Elsevier Ltd
15.09.2004
Elsevier Science |
Subjects | |
Online Access | Get full text |
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Summary: | (I) HCl/CH3OH; (II) DCC/HOBt/NMM with corresponding carboxyl component; (III) HCl/CH3CO2C2H5 (6mol/L); (IV) NaOH/H2O/CH3OH; (V) 3H2 and 10% Pd/C.
YSL was prepared stepwise from C terminal to N terminal with the side chain un-protective amino acids, Boc-Leu-OMe, Boc-Ser-OH, and Boc-Tyr-OH, as the starting materials in 39.5% total yield (31.2g/per batch). With the side chain un-protective Boc-(3,5-dibromo)-Tyr-OH and HCl·Ser-Leu-OMe as the starting materials (3,5-3H-Tyr)-Ser-Leu-OH was obtained in 29% yield. The determination of radioactive quantity in the urine and feces indicated that even after the administration for 130h only 8.4% (5.35% in urine and 3.05% in feces) of total radioactive quantity from the metabolite of [3,5-3H-Tyr]-Ser-Leu-OH were monitored. The distribution study revealed the relative accumulation level of the individual tissue was arranged in the sequence of spleen>liver>kidney>lung>heart>muscle>brain. Selecting hepatic cancer as the target YSL significantly increased the survival time of H22 tumor cells implanted mice. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0968-0896 1464-3391 |
DOI: | 10.1016/j.bmc.2004.06.030 |