Yıl: 2015 Cilt: 39 Sayı: 1 Sayfa Aralığı: 179 - 193 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer

Öz:
Abstract: Alnustone-like compounds are promising inhibitors for estrogen receptor alpha (ER-alpha), which is a novel cancer therapeutic target. Therefore, 10 alnustone-like compounds with substituents at the phenyl rings were synthesized by condensation of 4-phenyl-2-butanones and cinnamaldehydes via in situ enamination. The compounds displayed either protective activity or inhibited cell growth and proliferation of human breast cancer cells. Molecular docking studies indicated that the synthesized compounds interact with ER-alpha efficiently. In this work, the protective and inhibitive roles of the synthesized compounds were related to their functional groups and to their binding mode of action on ER-alpha protein. The compounds are potential drug candidates as ER-alpha antagonists.
Anahtar Kelime:

Konular: Mühendislik, Kimya
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • Claeson, P.; Tuchinda, P.; Reutrakul, V. J. Indian Chem. Soc. 1994, 71, 509–521.
  • Suga, T.; Asakawa, Y.; Iwata, N.; Chem. Ind. (London) 1971, 27, 766.
  • Suga, T.; Iwata, N.; Asakawa, Y. Bull. Chem. Soc. Jpn. 1972, 45, 2058–2060.
  • Sakakibara, M.; Mori, K.; Matsui, M. Agr. Biol. Chem. 1972, 36, 1825–1827.
  • Vig, O. P.; Ahuja, V. D.; Sehgal, V. K.; Vig, A. K. Ind. J. Chem. 1975, 13, 1129–1130.
  • Kato, N.; Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1984, 32, 3323–3326.
  • Vig, O. P.; Bari, S. S.; Sattar, M. A.; Sharma, S.; Mahajan, N. J. Indian Chem. Soc. 1989, 66, 98–100.
  • Goksu, S.; Celik, H.; Se ̧cen, H. Turk. J. Chem. 2003, 27, 31–34. Burmaoglu, S.; Celik, H.; Goksu, S.; Mara ̧s, A.; Altunda ̧s R.; Se ̧cen, H. Synth. Commun. 2009, 39, 1549–1562.
  • Baranovsky, A.; Schmitt, B.; Fowler, D. J.; Scheneider, B. Synth. Commun. 2003, 33, 1019–1045.
  • Hikino, H.; Kiso, Y.; Kato, N.; Hamada, Y.; Shioiri, T.; Aiyama, R.; Itokawa, H.; Kiuchi, F.; Sankawa, U. J. Ethnopharmacol. 1985, 14, 31–39.
  • Claeson, P.; Panthong, A.; Tuchinda, P.; Reutrakul, V.; Kanjanapothi, D.; Taylor, W. C. Santisuk, T. Planta Med. 1993, 59, 451–454.
  • Huang, W.; Dai, X.; Liu, Y.; Zhang, C.; Zhang, M.; Wang, Z. J. Plant Resour. Environ. 2006, 15, 37–40.
  • Huang, W.; Zhang, C.; Zhang, M.; Wang, Z. J. Chin. Chem. Soc. 2007, 54, 1553–1556.
  • Suksamrarn, A.; Ponglikitmongkol, M.; Wongkrajang, K.; Chindaduang, A.; Kittidanairak, S.; Jankam, A.; Yingy- ongnarongkul, B. E.; Kittipanumat, N.; Chokchaisiri, R.; Khetkam, P.; et al. Bioorg. Med. Chem. 2008, 16, 6891–6902.
  • Grienke, U.; Schmidtke, M.; Kirchmair, J.; Pfarr, K.; Wutzler, P.; Durrwald, R.; Wolber, G.; Liedl, K. R.; Stuppner, H.; Rollinger, J. M. J. Med. Chem. 2010, 53, 778–786.
  • Li, Y.; Yang, L.; Wang, C.; Chou, G.; Wang, Z. Shang Hai Zhong Yi Yao Da Xue Xue Bao 2010, 24, 72–75.
  • Surveillance, Epidemiology, and End Results Program. National Cancer Institute. http://seer.cancer.gov/statfacts/html/breast.html (accessed 03.03.14).
  • Ali, S.; Coombes, R. C. J. Mammary Gland Biol. Neoplasia 2000, 5, 271–281.
  • Higa, G. M.; Fell, R. G. Int. J. Breast Cancer 2013, 2013, Article ID:284036, http://dx.doi.org/10.1155/2013/284036.
  • Williams, C.; Lin, C. Y. Ecancermedicalscience 2013, 7, 370.
  • Martin, M. B.; Angeloni, S. V.; Garcia-Morales, P.; Sholler, P. F.; Castro-Galache, M. D.; Ferragut, J. A.; Saceda,
APA Küçükoğlu K, Seçinti-Klopf H, Ozgur A, Seçen H, TUTAR Y (2015). Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer. , 179 - 193.
Chicago Küçükoğlu Kaan,Seçinti-Klopf Hatice,Ozgur Aykut,Seçen Hasan,TUTAR YUSUF Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer. (2015): 179 - 193.
MLA Küçükoğlu Kaan,Seçinti-Klopf Hatice,Ozgur Aykut,Seçen Hasan,TUTAR YUSUF Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer. , 2015, ss.179 - 193.
AMA Küçükoğlu K,Seçinti-Klopf H,Ozgur A,Seçen H,TUTAR Y Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer. . 2015; 179 - 193.
Vancouver Küçükoğlu K,Seçinti-Klopf H,Ozgur A,Seçen H,TUTAR Y Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer. . 2015; 179 - 193.
IEEE Küçükoğlu K,Seçinti-Klopf H,Ozgur A,Seçen H,TUTAR Y "Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer." , ss.179 - 193, 2015.
ISNAD Küçükoğlu, Kaan vd. "Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer". (2015), 179-193.
APA Küçükoğlu K, Seçinti-Klopf H, Ozgur A, Seçen H, TUTAR Y (2015). Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer. Turkish Journal of Chemistry, 39(1), 179 - 193.
Chicago Küçükoğlu Kaan,Seçinti-Klopf Hatice,Ozgur Aykut,Seçen Hasan,TUTAR YUSUF Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer. Turkish Journal of Chemistry 39, no.1 (2015): 179 - 193.
MLA Küçükoğlu Kaan,Seçinti-Klopf Hatice,Ozgur Aykut,Seçen Hasan,TUTAR YUSUF Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer. Turkish Journal of Chemistry, vol.39, no.1, 2015, ss.179 - 193.
AMA Küçükoğlu K,Seçinti-Klopf H,Ozgur A,Seçen H,TUTAR Y Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer. Turkish Journal of Chemistry. 2015; 39(1): 179 - 193.
Vancouver Küçükoğlu K,Seçinti-Klopf H,Ozgur A,Seçen H,TUTAR Y Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer. Turkish Journal of Chemistry. 2015; 39(1): 179 - 193.
IEEE Küçükoğlu K,Seçinti-Klopf H,Ozgur A,Seçen H,TUTAR Y "Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer." Turkish Journal of Chemistry, 39, ss.179 - 193, 2015.
ISNAD Küçükoğlu, Kaan vd. "Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer". Turkish Journal of Chemistry 39/1 (2015), 179-193.