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Molecules 2013, 18(12), 15255-15275; https://doi.org/10.3390/molecules181215255

Synthesis and Structure-Activity Relationships of Novel Ecdysteroid Dioxolanes as MDR Modulators in Cancer

1
Department of Medical Microbiology and Immunobiology, University of Szeged, Dóm tér 9, Szeged 6720, Hungary
2
Unidade de Parasitologia e Microbiologia Médica, Institute of Hygiene and Tropical Medicine, Universidade Nova de Lisboa, Rua da Junqueira 100, Lisbon 1349-008, Portugal
3
Institute of Pharmacognosy, Faculty of Pharmacy, University of Szeged, Eötvös u. 6, Szeged 6720, Hungary
4
Ubichem Research Ltd., Illatos út 33, Budapest H-1097, Hungary
5
Center for Malaria and Other Tropical Diseases (CMDT), Institute of Hygiene and Tropical Medicine, Universidade Nova de Lisboa, Rua da Junqueira 100, Lisbon 1349-008, Portugal
6
Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szt. Gellért tér 4, Budapest H-1111, Hungary
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 31 October 2013 / Revised: 30 November 2013 / Accepted: 2 December 2013 / Published: 10 December 2013
(This article belongs to the Special Issue Bioactivity-focused Semi-synthesis in Drug Discovery)
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Abstract

Ecdysteroids, molting hormones of insects, can exert several mild, non-hormonal bioactivities in mammals, including humans. In a previous study, we have found a significant effect of certain derivatives on the ABCB1 transporter mediated multi-drug resistance of a transfected murine leukemia cell line. In this paper, we present a structure-activity relationship study focused on the apolar dioxolane derivatives of 20-hydroxyecdysone. Semi-synthesis and bioactivity of a total of 32 ecdysteroids, including 20 new compounds, is presented, supplemented with their complete 1H- and 13C-NMR signal assignment. View Full-Text
Keywords: ecdysteroids; 20-hydroxyecdysone; acetonide; dioxolane; stereochemistry; cancer; multi-drug resistance; P-glycoprotein; ABCB1 transporter; efflux pump ecdysteroids; 20-hydroxyecdysone; acetonide; dioxolane; stereochemistry; cancer; multi-drug resistance; P-glycoprotein; ABCB1 transporter; efflux pump
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Martins, A.; Csábi, J.; Balázs, A.; Kitka, D.; Amaral, L.; Molnár, J.; Simon, A.; Tóth, G.; Hunyadi, A. Synthesis and Structure-Activity Relationships of Novel Ecdysteroid Dioxolanes as MDR Modulators in Cancer. Molecules 2013, 18, 15255-15275.

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