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Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities

Authorized Users Only
2007
Authors
Krstić, Natalija
Bjelaković, Mira
Žižak, Željko
Pavlović, Mirjana
Juranić, Zorica
Pavlović, Vladimir D.
Article (Published version)
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Abstract
The antiproliferative activity of previously synthesized (Z)-cholest-4-en-6-one oxime (1), (E)-cholest-4-en-6-one oxime (2), 7-aza-B-homocholest-4-en-6-one (3) and 6-aza-B-homocholest-4-en-7-one (4) and newly synthesized 6-thioxo-7-aza-B-homocholest-4-ene (5) and 6-aza-7-thioxo-B-homocholest-4-ene (6) was tested for their possible effects against two human tumor cell lines, cervical carcinoma (HeLa) and chronic myelogenous leukemia (K-562). Compounds 1-6, exerted a dose-dependent antiproliferative effect toward cell lines used in experimental design, showing high selectivity in their action for tumor cells in comparison to normal immunocompetent cells (non-stimulated PBMC and PHA-stimulated PBMC). Compounds 2, 3 and 4 exhibited a very high but selective antitumor activity, by inducing apoptosis in sensitive, for that purpose targeted tumor cell line (HeLa cells). Low toxic effect upon both non-stimulated, and PHA stimulated PBMCs from control, healthy volunteers, has been detected for ...compounds 1, 2, 3 and 4. The possible reasons for profound differences in the effects of this spectrum of steroidal compounds between tumor cell lines and normal stimulated and non-stimulated PBMCs are discussed. The molecular mechanisms for apoptotic events in HeLa cell line are suggested. The guidelines for further research are underlined.

Keywords:
Antiproliferative activity / Steroidal lactams / Steroidal oximes / Steroidal thiolactams
Source:
Steroids, 2007, 72, 5, 406-414
Publisher:
  • Elsevier
Funding / projects:
  • Sinteza različitih korisnih proizvoda iz steroidnih molekula (RS-142033)

DOI: 10.1016/j.steroids.2007.02.005

ISSN: 0039-128X

PubMed: 17433824

WoS: 000246604100002

Scopus: 2-s2.0-34247205206
[ Google Scholar ]
59
58
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/363
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Krstić, Natalija
AU  - Bjelaković, Mira
AU  - Žižak, Željko
AU  - Pavlović, Mirjana
AU  - Juranić, Zorica
AU  - Pavlović, Vladimir D.
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/363
AB  - The antiproliferative activity of previously synthesized (Z)-cholest-4-en-6-one oxime (1), (E)-cholest-4-en-6-one oxime (2), 7-aza-B-homocholest-4-en-6-one (3) and 6-aza-B-homocholest-4-en-7-one (4) and newly synthesized 6-thioxo-7-aza-B-homocholest-4-ene (5) and 6-aza-7-thioxo-B-homocholest-4-ene (6) was tested for their possible effects against two human tumor cell lines, cervical carcinoma (HeLa) and chronic myelogenous leukemia (K-562). Compounds 1-6, exerted a dose-dependent antiproliferative effect toward cell lines used in experimental design, showing high selectivity in their action for tumor cells in comparison to normal immunocompetent cells (non-stimulated PBMC and PHA-stimulated PBMC). Compounds 2, 3 and 4 exhibited a very high but selective antitumor activity, by inducing apoptosis in sensitive, for that purpose targeted tumor cell line (HeLa cells). Low toxic effect upon both non-stimulated, and PHA stimulated PBMCs from control, healthy volunteers, has been detected for compounds 1, 2, 3 and 4. The possible reasons for profound differences in the effects of this spectrum of steroidal compounds between tumor cell lines and normal stimulated and non-stimulated PBMCs are discussed. The molecular mechanisms for apoptotic events in HeLa cell line are suggested. The guidelines for further research are underlined.
PB  - Elsevier
T2  - Steroids
T1  - Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities
VL  - 72
IS  - 5
SP  - 406
EP  - 414
DO  - 10.1016/j.steroids.2007.02.005
ER  - 
@article{
author = "Krstić, Natalija and Bjelaković, Mira and Žižak, Željko and Pavlović, Mirjana and Juranić, Zorica and Pavlović, Vladimir D.",
year = "2007",
abstract = "The antiproliferative activity of previously synthesized (Z)-cholest-4-en-6-one oxime (1), (E)-cholest-4-en-6-one oxime (2), 7-aza-B-homocholest-4-en-6-one (3) and 6-aza-B-homocholest-4-en-7-one (4) and newly synthesized 6-thioxo-7-aza-B-homocholest-4-ene (5) and 6-aza-7-thioxo-B-homocholest-4-ene (6) was tested for their possible effects against two human tumor cell lines, cervical carcinoma (HeLa) and chronic myelogenous leukemia (K-562). Compounds 1-6, exerted a dose-dependent antiproliferative effect toward cell lines used in experimental design, showing high selectivity in their action for tumor cells in comparison to normal immunocompetent cells (non-stimulated PBMC and PHA-stimulated PBMC). Compounds 2, 3 and 4 exhibited a very high but selective antitumor activity, by inducing apoptosis in sensitive, for that purpose targeted tumor cell line (HeLa cells). Low toxic effect upon both non-stimulated, and PHA stimulated PBMCs from control, healthy volunteers, has been detected for compounds 1, 2, 3 and 4. The possible reasons for profound differences in the effects of this spectrum of steroidal compounds between tumor cell lines and normal stimulated and non-stimulated PBMCs are discussed. The molecular mechanisms for apoptotic events in HeLa cell line are suggested. The guidelines for further research are underlined.",
publisher = "Elsevier",
journal = "Steroids",
title = "Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities",
volume = "72",
number = "5",
pages = "406-414",
doi = "10.1016/j.steroids.2007.02.005"
}
Krstić, N., Bjelaković, M., Žižak, Ž., Pavlović, M., Juranić, Z.,& Pavlović, V. D.. (2007). Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities. in Steroids
Elsevier., 72(5), 406-414.
https://doi.org/10.1016/j.steroids.2007.02.005
Krstić N, Bjelaković M, Žižak Ž, Pavlović M, Juranić Z, Pavlović VD. Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities. in Steroids. 2007;72(5):406-414.
doi:10.1016/j.steroids.2007.02.005 .
Krstić, Natalija, Bjelaković, Mira, Žižak, Željko, Pavlović, Mirjana, Juranić, Zorica, Pavlović, Vladimir D., "Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities" in Steroids, 72, no. 5 (2007):406-414,
https://doi.org/10.1016/j.steroids.2007.02.005 . .

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