Synthesis, anti-leukemia activity, and molecular docking of novel 3,16-androstenedione derivatives.

Androstenedione Molecular Docking Simulation Phosphatidylinositol 3-Kinases / metabolism Signal Transduction
3,16-androstenedione derivatives Acute lymphoblastic leukemia Androsta-4,14-diene-3,16-dione Molecular docking Network pharmacology

Journal

Steroids
ISSN: 1878-5867
Titre abrégé: Steroids
Pays: United States
ID NLM: 0404536

Informations de publication

Date de publication:
11 2023
Historique:
received: 10 05 2023
revised: 30 07 2023
accepted: 02 08 2023
medline: 10 10 2023
pubmed: 8 8 2023
entrez: 7 8 2023
Statut: ppublish

Résumé

In this study, we synthesized androsta-4,14-diene-3,16-dione, 12β-hydroxyandrosta-4,14-diene-3,16-dione, and other 3,16-androstenedione derivatives from commercially available dehydroepiandrosterone as a starting material in 9-13 steps with high yields. The bioactivity of the obtained compounds was evaluated. Compounds 14a and 23a were shown to have high antitumor activity against acute lymphoblastic leukemia cell lines Nalm-6 and BALL-1, respectively. Network pharmacology analysis showed that the anti-leukemia activity of compounds 14a and 23a might be related to the JAK2, ABL1 protein, and PI3K/Akt signaling pathways. The molecular docking of compounds 14a and 23a identified possible active sites, with the lowest docking scores for PTGS2 and MAPK14, respectively. In addition, the absorption, distribution, metabolism, and excretion prediction results revealed the drug-likeness of the two compounds. Therefore, compounds 14a and 23a should be considered anti-leukemia candidates in future studies.

Identifiants

DOI: 10.1016/j.steroids.2023.109290 PMID: 37549776
pubmed: 37549776
pii: S0039-128X(23)00118-6
doi: 10.1016/j.steroids.2023.109290
pii:
doi:

Substances chimiques

Androstenedione 409J2J96VR
Phosphatidylinositol 3-Kinases EC 2.7.1.-

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

109290

Informations de copyright

Copyright © 2023 Elsevier Inc. All rights reserved.

Déclaration de conflit d'intérêts

Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Auteurs

Dongjie Chen (D)

Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming 650500, China.

Jiaying Huang (J)

Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.

Shanshan Xiao (S)

Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming 650500, China.

Guiguang Cheng (G)

Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming 650500, China.

Yaping Liu (Y)

Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming 650500, China.

Tianrui Zhao (T)

Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming 650500, China.

Caixia Chen (C)

Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming 650500, China.

Yongxin Yi (Y)

Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming 650500, China.

Yungui Peng (Y)

Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China. Electronic address: pyg@swu.edu.cn.

Jianxin Cao (J)

Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming 650500, China. Electronic address: jxcao321@hotmail.com.

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Classifications MeSH

questionsmedicales.fr › Hormones gonadiques › Hormones sexuelles stéroïdiennes › Congénères de la testostérone › Androstènedione › Synthesis, anti-leukemia activity, and...
questionsmedicales.fr › Sciences de l'information › Méthodologies informatiques › Simulation numérique › Simulation de docking moléculaire › Synthesis, anti-leukemia activity, and...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Protéines et peptides de signalisation intracellulaire › Phosphatidylinositol 3-kinases › Synthesis, anti-leukemia activity, and...
questionsmedicales.fr › Phénomènes physiologiques cellulaires › Transduction du signal › Synthesis, anti-leukemia activity, and...