TY - JOUR AU - Bodnár, Brigitta AU - Mernyák, Erzsébet AU - Szabó, Johanna AU - Wölfling, János AU - Schneider, Gyula AU - Zupkó, István AU - Kupihár, Zoltán AU - Kovács, Lajos TI - Synthesis and in vitro investigation of potential antiproliferative monosaccharide-D-secoestrone bioconjugates JF - BIOORGANIC & MEDICINAL CHEMISTRY LETTERS J2 - BIOORG MED CHEM LETT VL - 27 PY - 2017 IS - 9 SP - 1938 EP - 1942 PG - 5 SN - 0960-894X DO - 10.1016/j.bmcl.2017.03.029 UR - https://m2.mtmt.hu/api/publication/3201077 ID - 3201077 N1 - Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :3 Export Date: 11 February 2020 CODEN: BMCLE Correspondence Address: Kupihár, Z.; Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Hungary; email: kupihar.zoltan@med.u-szeged.hu Chemicals/CAS: azide, 12596-60-0, 14343-69-2; estrone, 53-16-7; glucose, 50-99-7, 84778-64-3; Alkynes; Antineoplastic Agents; Azides; D-secoestrone; Estrone; Glucose; Glycoconjugates; Monosaccharides; Oximes Funding details: Hungarian Scientific Research Fund Funding details: K109293, K113150 Funding details: European Social Fund, ESF, A/2-11/1-2012-0001 Funding details: A-11/1/KONV-2012-0047, T?MOP-4.2.2 Funding text 1: The authors thank the Hungarian Scientific Research Fund ? Hungary (OTKA K113150 and K109293), the New Hungary Development Plan (T?MOP-4.2.2.A-11/1/KONV-2012-0047) for financial support. This research was also supported by the European Union and the State of Hungary, co-financed by the European Social Fund ? Belgium and Hungary (T?MOP-4.2.4.A/2-11/1-2012-0001 ?National Excellence Program?). Funding Agency and Grant Number: Hungarian Scientific Research Fund HungaryOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [OTKA K113150, K109293]; New Hungary Development Plan [TAMOP-4.2.2.A-11/1/KONV-2012-0047]; European UnionEuropean Union (EU); State of Hungary; European Social Fund - Belgium and Hungary [TAMOP-4.2.4.A/2-11/1-2012-0001] Funding text: The authors thank the Hungarian Scientific Research Fund Hungary (OTKA K113150 and K109293), the New Hungary Development Plan (TAMOP-4.2.2.A-11/1/KONV-2012-0047) for financial support. This research was also supported by the European Union and the State of Hungary, co-financed by the European Social Fund - Belgium and Hungary (TAMOP-4.2.4.A/2-11/1-2012-0001 'National Excellence Program'). Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :3 Export Date: 29 August 2020 CODEN: BMCLE Correspondence Address: Kupihár, Z.; Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Hungary; email: kupihar.zoltan@med.u-szeged.hu Chemicals/CAS: azide, 12596-60-0, 14343-69-2; estrone, 53-16-7; glucose, 50-99-7, 84778-64-3; Alkynes; Antineoplastic Agents; Azides; D-secoestrone; Estrone; Glucose; Glycoconjugates; Monosaccharides; Oximes Funding details: European Social Fund, ESF, T?MOP-4.2.4, A/2-11/1-2012-0001 Funding details: Hungarian Scientific Research Fund, OTKA Funding details: European Commission, EC Funding details: Hungarian Scientific Research Fund, OTKA, K109293, K113150 Funding details: -2012-0047 Funding text 1: The authors thank the Hungarian Scientific Research Fund ? Hungary (OTKA K113150 and K109293), the New Hungary Development Plan (T?MOP-4.2.2.A-11/1/KONV-2012-0047) for financial support. This research was also supported by the European Union and the State of Hungary, co-financed by the European Social Fund ? Belgium and Hungary (T?MOP-4.2.4.A/2-11/1-2012-0001 ?National Excellence Program?). Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :4 Export Date: 10 January 2021 CODEN: BMCLE Correspondence Address: Kupihár, Z.; Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Hungary; email: kupihar.zoltan@med.u-szeged.hu Chemicals/CAS: azide, 12596-60-0, 14343-69-2; estrone, 53-16-7; glucose, 50-99-7, 84778-64-3; Alkynes; Antineoplastic Agents; Azides; D-secoestrone; Estrone; Glucose; Glycoconjugates; Monosaccharides; Oximes Funding details: European Social Fund, ESF, T?MOP-4.2.4, A/2-11/1-2012-0001 Funding details: Hungarian Scientific Research Fund, OTKA Funding details: European Commission, EC Funding details: Hungarian Scientific Research Fund, OTKA, K109293, K113150 Funding details: -2012-0047 Funding text 1: The authors thank the Hungarian Scientific Research Fund ? Hungary (OTKA K113150 and K109293), the New Hungary Development Plan (T?MOP-4.2.2.A-11/1/KONV-2012-0047) for financial support. This research was also supported by the European Union and the State of Hungary, co-financed by the European Social Fund ? Belgium and Hungary (T?MOP-4.2.4.A/2-11/1-2012-0001 ?National Excellence Program?). AB - 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. © 2017 Elsevier Ltd LA - English DB - MTMT ER -