دورية أكاديمية
أعرض في EDS

Conjugates of 17-substituted testosterone and epitestosterone with pyropheophorbide a differing in the length of linkers.

التفاصيل البيبلوغرافية
العنوان: Conjugates of 17-substituted testosterone and epitestosterone with pyropheophorbide a differing in the length of linkers.
المؤلفون: Zolottsev VA; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia., Ponomarev GV; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia., Taratynova MO; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia., Morozevich GE; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia., Novikov RA; Engelhardt Institute of Molecular Biology RAS, Moscow, Russia., Timofeev VP; Engelhardt Institute of Molecular Biology RAS, Moscow, Russia. Electronic address: tim@eimb.ru., Solyev PN; Engelhardt Institute of Molecular Biology RAS, Moscow, Russia., Zavialova MG; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia., Zazulina OV; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia., Tkachev YV; Engelhardt Institute of Molecular Biology RAS, Moscow, Russia., Misharin AY; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia.
المصدر: Steroids [Steroids] 2018 Oct; Vol. 138, pp. 82-90. Date of Electronic Publication: 2018 Jul 07.
نوع المنشور: Journal Article; Research Support, Non-U.S. Gov't
اللغة: English
بيانات الدورية: Publisher: Elsevier Country of Publication: United States NLM ID: 0404536 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1878-5867 (Electronic) Linking ISSN: 0039128X NLM ISO Abbreviation: Steroids Subsets: MEDLINE
أسماء مطبوعة: Publication: New York Ny : Elsevier
Original Publication: San Francisco.
مواضيع طبية MeSH: Antineoplastic Agents/*chemistry , Chlorophyll/*analogs & derivatives , Epitestosterone/*chemistry , Testosterone/*chemistry, Antineoplastic Agents/pharmacology ; Cell Line, Tumor ; Cell Proliferation/drug effects ; Cell Survival ; Chlorophyll/chemistry ; Humans ; Male ; PC-3 Cells ; Prostatic Neoplasms/metabolism ; Structure-Activity Relationship
مستخلص: Conjugates of 17α-substituted testosterone (1 and 2) and 17β-substituted epitestosterone (3 and 4) with pyropheophorbide a were synthesized. The scheme consisted of synthesis of 17α-hydroxy-3-oxopregn-4-en-21-oic and 17β-hydroxy-3-oxopregn-4-en-21-oic acids, and their coupling with pyropheophorbide a by means of either ethylene diamine, or 1,5-diamino pentane linkers. Mutual influence of steroidal and macrocyclic fragments in conjugates molecules was dependent on configuration of C17 and length of linker, that was established by analysis of 1 H NMR spectra and molecular models of conjugates. Studies of interaction of conjugates with prostate carcinoma cells revealed that their uptake and internalization were independent on the androgen receptor activity, but dependent on the structure of conjugates, decreasing in the following row: 3 > 4 ≥ 1 > 2. Conjugates significantly decreased the LNCaP and PC-3 cells growth at 96 h incubation. Epitestosterone derivatives 3 and 4 also showed superior anti-proliferative activity versus testosterone ones. Conformationally more rigid conjugates 1 and 3, comprising short linkers, were more active than those with long linkers; conjugate 3 was the most potent.
(Copyright © 2018. Published by Elsevier Inc.)
فهرسة مساهمة: Keywords: Chemical synthesis; Interaction with prostate carcinoma cells; Molecular models; Steroid conjugates; Structure-activity relationships; Tetrapyrrolic macrocycles
المشرفين على المادة: 0 (Antineoplastic Agents)
1406-65-1 (Chlorophyll)
24533-72-0 (pyropheophorbide a)
3XMK78S47O (Testosterone)
481-30-1 (Epitestosterone)
تواريخ الأحداث: Date Created: 20180724 Date Completed: 20190219 Latest Revision: 20190320
رمز التحديث: 20221213
DOI: 10.1016/j.steroids.2018.06.011
PMID: 30033342
قاعدة البيانات: MEDLINE
الوصف
تدمد:1878-5867
DOI:10.1016/j.steroids.2018.06.011