Abstract
The syntheses of monosaccharide-d-secoestrone conjugates are reported. They were prepared from 3-(prop-2-inyloxy)-d-secoestrone alcohol or oxime and monosaccharide azides via Cu(I)-catalyzed azide-alkyne cycloaddition reactions (CuAAC). The antiproliferative activities of the conjugates were investigated in vitro against a panel of human adherent cancer cell lines (HeLa, A2780 and MCF-7) by means of MTT assays. The protected d-glucose-containing d-secoestrone oxime bioconjugate (24b) proved to be the most effective with an IC50 value in the low micromolar range against A2780 cell line.
Keywords:
Bioconjugate; CuAAC; Monosaccharide; Oxime; d-Secoestrone.
Copyright © 2017 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkynes / chemistry
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry*
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Antineoplastic Agents / pharmacology*
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Azides / chemistry
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Cycloaddition Reaction
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Estrone / analogs & derivatives*
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Estrone / chemical synthesis
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Estrone / chemistry
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Estrone / pharmacology
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Glucose / chemical synthesis
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Glucose / chemistry*
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Glucose / pharmacology*
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Glycoconjugates / chemical synthesis
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Glycoconjugates / chemistry*
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Glycoconjugates / pharmacology*
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HeLa Cells
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Humans
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MCF-7 Cells
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Monosaccharides / chemical synthesis
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Monosaccharides / chemistry
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Monosaccharides / pharmacology
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Neoplasms / drug therapy
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Oximes / chemical synthesis
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Oximes / chemistry
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Oximes / pharmacology
Substances
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Alkynes
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Antineoplastic Agents
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Azides
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D-secoestrone
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Glycoconjugates
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Monosaccharides
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Oximes
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Estrone
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Glucose