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

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

1,2,†,* , 3,†
, 4
, 1
, 5
, 1
, 6
, 6
 and 3,*
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.
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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