Synthesis and in vitro investigation of potential antiproliferative monosaccharide-d-secoestrone bioconjugates.
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 IC50value in the low micromolar range against A2780 cell line.
Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Brigitta
B
Bodnár
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Erzsébet
E
Mernyák
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Johanna
J
Szabó
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
János
J
Wölfling
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Gyula
G
Schneider
Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.
István
I
Zupkó
Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary. Electronic address: kupihar.zoltan@med.u-szeged.hu.
Zoltán
Z
Kupihár
Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary. Electronic address: kovacs.lajos@med.u-szeged.hu.
Lajos
L
Kovács
D000480:Alkynes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001386:Azides / Q000737:chemistry; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D061565:Cycloaddition Reaction; D004970:Estrone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005947:Glucose / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D061986:MCF-7 Cells; D009005:Monosaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009369:Neoplasms / Q000188:drug therapy; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000480:Alkynes; D000970:Antineoplastic Agents; D001386:Azides; C000614206:D-secoestrone; D006001:Glycoconjugates; D009005:Monosaccharides; D010091:Oximes; D004970:Estrone; D005947:Glucose
Bioconjugate; CuAAC; Monosaccharide; Oxime; d-Secoestrone