Antiproliferative potential of sarcophine and its semisynthetic sulfur-containing derivatives against human mammary carcinoma cell lines
详细信息 查看全文
- 作者：Jamal M. Arif (1) (4)
Swapnali S. Sawant (2)
Khalid A. El Sayed (2)
Muhammad Kunhi (1)
Manogaran P. Subramanian (1)
Yunus M. Siddiqui (1)
Diaa T. A. Youssef (3)
Khalid Al-Hussain (1)
Mohammed N. Al-Ahdal (1)
Fahad Al-Khodairy (1) - 关键词：Sarcophine ; Apoptosis ; Antiproliferation ; MCF ; 7 ; MDA ; MB ; 231
- 刊名：Journal of Natural Medicines
- 出版年：2007
- 出版时间：April 2007
- 年：2007
- 卷：61
- 期：2
- 页码：154-158
- 全文大小：189KB
- 参考文献：1. El Sayed KA, Hamann MT, Waddling CA, Jensen C, Lee SK, Dunstan CA, Pezzuto JM (1998) Structurally novel bioconversion products of the marine natural product sarcophine effectively inhibit JB6 cell transformation. J Org Chem 63(21):7449-455 CrossRef
2. Sawant SS, Sylvester PW, Avery MA, Desai P, Youssef DTA, El Sayed KA (2004) Bioactive rearranged and halogenated semisynthetic derivatives of the marine natural product sarcophine. J Nat Prod 67(12):2017-023 CrossRef
3. Sawant SS, Sylvester PW, Arant ME, Mayer AMS, Youssef DTA, El Sayed KA (2006) Anticancer and anti-inflammatory sulfur-containing semisynthetic derivatives of sarcophine. Chem Pharm Bull 54(8):1119-123 CrossRef
4. Sharghi H, Ali Nasseri M, Niknam K (2001) Phenol-containing macrocyclic diamides as new catalysts in the highly regioselective conversion of epoxides to beta-hydroxy thiocyanates. J Org Chem 66(22):7287-293 CrossRef
5. Tamami B, Mahdavi H (2002) Synthesis of thiocyanohydrins from epoxides using quaternized amino functionalized cross-linked polyacrylamide as a new solid–liquid phase-transfer catalyst. Tetrahedron Lett 43(35):6225-228 CrossRef
6. Yadav JS, Reddy BVS, Reddy CS (2004) Selectfluor: a novel and efficient reagent for the synthesis of β-hydroxy thiocyanates. Tetrahedron Lett 45(6):1291-293 CrossRef
7. Jesberger M, Davis TP, Barner L (2003) Applications of Lawesson’s reagent in organic and organometallic syntheses. Synthesis 13:1929-958 CrossRef
8. Shabana R, Osman FH, Atrees SS (1994) Organophosphorus compounds. XV. The reaction of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson’s reagent) with aromatic dihydroxy compounds. Simple new route to 1,3,2-dioxaphospholane 2-sulfide. Tetrahedron 50(23):6975-988 CrossRef
9. Nishio T (1989) A novel transformation of alcohols to thiols. Chem Commun 4:205-06
10. El-Barbary AA (1984) Reaction of esters, ortho esters, acetals, thioacetals and epoxides with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson reagent). Monatsh Chem 115(6-):769-77 CrossRef
11. Arif JM, Kunhi M, Siddiqui YM, El Sayed KA, Orabi KY, Al-Hazzani A, Al-Ahdal MN, Al-Khodairy FM (2004) Role of intermediary biomarkers in determining the anticancer efficacy of marine compounds. Med Chem Res 13(6-):553-62 CrossRef
12. Arif JM, Kunhi M, Siddiqui YM, El Sayed KA, Orabi KY, Al-Hazzani A, Al-Ahdal MN, Al-Khodairy FM (2004) Differential modulation of benzo[a]pyrene-derived DNA adducts in MCF-7 cells by marine compounds. Int J Cancer Prev 1:259-68
13. Satyanarayana C, Deevi Dhanavanthri S, Rajagopalan R, Srinivas N, Rajagopal S (2004) DRF 3188 a novel semi-synthetic analog of andrographolide: cellular response to MCF 7 breast cancer cells. BMC Cancer 4:26-3 CrossRef
14. Kuo P-L, Hsu Y-L, Lin T-C, Lin L-T, Chang J-K, Lin C-C (2005) Casuarinin from the bark of Terminalia arjuna induces apoptosis and cell cycle arrest in human breast adenocarcinoma MCF-7 cells. Planta Med 71(3):237-43 CrossRef
15. Tabruyn SP, Nguyen N-Q-N, Cornet AM, Martial JA, Struman I (2005) The antiangiogenic factor, 16-kDa human prolactin, induces endothelial cell cycle arrest by acting at both the G0-G1 and the G2-M phases. Mol Endocrinol 19(7):1932-942 CrossRef
16. Varshochi R, Halim F, Sunters A, Alao JP, Madureira PA, Hart SM, Ali S, Vigushin DM, Coombes RC, Lam EWF (2005) ICI182,780 induces p21Waf1 gene transcription through releasing histone deacetylase 1 and estrogen receptor alpha from Sp1 sites to induce cell cycle arrest in MCF-7 breast cancer cell line. J Biol Chem 280(5):3185-196 CrossRef
17. El-Deiry WS, Harper JW, O’Connor PM, Velculescu VE, Canman CE, Jackman J, Pietenpol JA, Burrell M, Hill DE, Wang Y et al (1994) WAF1/CIP1 is induced in p53-mediated G1 arrest and apoptosis. Cancer Res 54(5):1169-174
18. Bernstein J, Shmeuli U, Zadock E, Kashman Y, Neeman I (1974) Sarcophine, a new epoxy cembranolide from marine origin. Tetrahedron 30(16):2817-824 CrossRef
19. Krishan A (1975) Rapid flow cytofluorometric analysis of mammalian cell cycle by propidium iodide staining. J Cell Biol 66(1):188-93 CrossRef - 作者单位：Jamal M. Arif (1) (4)
Swapnali S. Sawant (2)
Khalid A. El Sayed (2)
Muhammad Kunhi (1)
Manogaran P. Subramanian (1)
Yunus M. Siddiqui (1)
Diaa T. A. Youssef (3)
Khalid Al-Hussain (1)
Mohammed N. Al-Ahdal (1)
Fahad Al-Khodairy (1)
1. Biological and Medical Research, King Faisal Specialist Hospital and Research Center, MBC #03-81, P.O. Box 3354, Riyadh, 11211, Saudi Arabia
4. Department of Biotechnology, Integral University, Lucknow, 226026, India
2. Department of Basic Pharmaceutical Sciences, College of Pharmacy, University of Louisiana at Monroe, 700 University Avenue, Monroe, LA, 71209, USA
3. Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia, 41522, Egypt - ISSN：1861-0293
文摘
The marine-derived cembranoid sarcophine (1) and its sulfur-containing semisynthetic derivatives (2-strong class="a-plus-plus">6) were evaluated for anticancer potential using cell cycle progression markers. No effect on MCF-7 cell viability or apoptosis was seen with these derivatives at concentrations of up to 100?μM after 72?h of incubation. At 100?μM, sarcophine and its derivatives 2-strong class="a-plus-plus">5 arrested the MCF-7 cells in G0/G1 phase, with concomitant decrease in the cell populations at S and G2+M phases. MDA-MB-231 cells were not responsive to any of the derivatives. Our preliminary results suggest that the sulfur-containing derivatives of sarcophine, especially 2 and 3, show potent and cell-specific antiproliferative activity.