Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities
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2007
Authors
Krstić, Natalija
Bjelaković, Mira

Žižak, Željko

Pavlović, Mirjana
Juranić, Zorica

Pavlović, Vladimir D.
Article (Published version)

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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 thiolactamsSource:
Steroids, 2007, 72, 5, 406-414Publisher:
- Elsevier
Funding / projects:
DOI: 10.1016/j.steroids.2007.02.005
ISSN: 0039-128X
PubMed: 17433824
WoS: 000246604100002
Scopus: 2-s2.0-34247205206
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IHTMTY - 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 . .