Cited by 8Phytochemical Studies and BioactivitiesSteroid Chemistry and BiochemistryNatural product bioactivities and synthesis

In vitro adjuvant antitumor activity of various classes of semi-synthetic poststerone derivatives

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Savchenko, Rimma G., Nové, Márta, Spengler, Gabriella, Hunyadi, Attila, Parfenova, Lyudmila V.·2021·Bioorganic Chemistry

Abstract

Various classes of semi-synthetic analogs of poststerone, the product of oxidative cleavage of the C20-C22 bond in the side chain of the phytoecdysteroid 20-hydroxyecdysone, were synthesized. The analogs were obtained by reductive transformations using L-Selectride and H 2-Pd/C, by molecular abeo-rearrangements using the DAST reagent or ultrasonic treatment in the NaI-Zn-DMF system, and by acid-catalyzed reactions of poststerone derivatives with various aldehydes (o-FC 6 H 4 CHO, m-CF 3 C 6 H 4 CHO, CO 2 Me(CH 2)8 CHO). The products were tested on a mouse lymphoma cell line pair, L5178 and its ABCB1-transfected multi-drug resistant counterpart, L5178 MDR, for their in vitro activity alone and in combination with doxorubicin, and for the ability to inhibit the ABCB1 transporter. Among the tested compounds, new 2,3-dioxolane derivatives of the pregnane ecdysteroid were found to have a pronounced chemosensitizing activity towards doxorubicin and could be considered as promising candidates for further structure optimization for the development of effective chemosensitizing agents.

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Authors
Savchenko, R. G., Nové, M., Spengler, G., Hunyadi, A., & Parfenova, L. V.
Affiliations
  • University of Szeged (HU)
  • Institute of Catalysis and Petrochemistry (RU)
Corresponding author
  • Hunyadi, Attila
  • Parfenova, Lyudmila V.
Venue
Bioorganic Chemistry
Publisher
Elsevier BV
Published
2021-01
Volume
106
Pages
104485
ISSN
0045-2068 (ISSN-L)
OpenAlex
W3102002327
Cited by
8
References
39
Citations by year
2026: 2 · 2023: 1 · 2022: 3 · 2021: 2
FWCI
0.49
Type
journal article
Language
en
Open access
Locations
  • Bioorganic Chemistry (publishedVersion)
  • PubMed (publishedVersion)
  • SZTE Publicatio Repozitórium (University of Szeged) (acceptedVersion, other-oa)
Funders
  • National Research, Development and Innovation Office (K119770)
  • Ministry of Education and Science of the Russian Federation (2019-05-595-000-058)
  • Russian Foundation for Basic Research (20-03-00649, AAAA-A19-119022290012-3)
  • Russian Academy of Sciences
  • Nemzeti Kutatási Fejlesztési és Innovációs Hivatal
  • Emberi Eroforrások Minisztériuma (20391-3/2018/FEKUSTRAT)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical Studies and Bioactivities
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Natural product bioactivities and synthesis
Keywords
phytoecdysteroids, 20-hydroxyecdysone, chemosensitizers, multidrug resistance, doxorubicin, reductive transformation
MeSH terms
Antineoplastic Agents, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Ecdysterone, Humans, Structure-Activity Relationship, Tumor Cells, Cultured, Molecular Structure, Cell Proliferation

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