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Swainsonine

Swainsonine is an indolizidine alkaloid isolated from the fungus metharhizium anisopliae. It is an antineoplastic immunomodulator. Swainsonine restores the capacities of immunodeficient mice such that the growth and metastasis of implanted tumors are inhibited. The anti-metastatic effect may be the result of the stimulation of lymphocyte proliferation and augmentation of natural killer cell reactivity of the immune system. Swainsonine has been found to induce apoptosis in esophageal squamous cell carcinoma and human lung cancer cells as well as C6 glioma cells. In addition to its anti-proliferative effect on tumor cells, swainsonine has been found to potentiate cytotoxic effects of chemotherapeutic drugs such as paclitaxel and cisplatin.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18974295

Cas No.

72741-87-8

Formula

C8H15NO3

Formula Wt.

173.20

Chemical Name

(1S,2R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triol

IUPAC Name

(1S,2R,8R,8aR)-Octahydro-1,2,8-indolizinetriol

Synonym

SwainMoia; (1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol;      D-Swainsonine; 8A,B-INDOLIZIDINE-1,2A,8B-TRIOL;SWAINSONINE;Tridolgosir; SwainMoia;    (1S,2R,8R,8aR)-octahydro-1,2,8-indolizinetriol; 

Solubility

10 mg/ml in water, 5 mg/ml in methanol

Appearance

Beige lyophilized powder

Mohla S, Humphries MJ, White SL, et al. Swainsonine: a new antineoplastic immunomodulator. J Natl Med Assoc. 1989, 81(10):1049-56. PMID: 2509720 PMCID: PMC2571577.

Kino T, Inamura N, Nakahara K, et al. Studies of an immunomodulator, swainsonine. II. Effect of swainsonine
on mouse immunodeficient system and experimental murine tumor. J Antibiot (Tokyo). 1985, 38(7):936-40. PMID: 3928564.

Dennis JW. Effects of swainsonine and polyinosinic:polycytidylic acid on murine tumor cell growth and metastasis. Cancer Res. 1986, ;46(10):5131-6. PMID: 3093060.

White SL , Schweitzer K, Humphries MJ, Olden K. Stimulation of DNA synthesis in murine lymphocytes by the drug swainsonine: immunomodulatory properties. Biochem Biophys Res Commun. 1988, 150(2):615-25. PMID: 3124836.

Humphries MJ , Matsumoto K, White SL, et. al. Augmentation of murine natural killer cell activity by swainsonine, a new antimetastatic immunomodulator. Cancer Res. 198, 48(6):1410-5. PMID: 3125963

Li Z , Huang Y, Dong F, et al. Swainsonine promotes apoptosis in human oesophageal squamous cell carcinoma cells in vitro and in vivo through activation of mitochondrial pathway. J Biosci. 2012, 37(6):1005-16. PMID: 23151791

Li Z , Xu X, Huang Y, et al. Swainsonine activates mitochondria-mediated apoptotic pathway in human lung cancer A549 cells and retards the growth of lung cancer xenografts. Int J Biol Sci. 2012, 8(3):394-405. doi: 10.7150/ijbs.3882. Epub 2012 Feb 24. PMID: 22393311 PMCID: PMC3291856 DOI: 10.7150/ijbs.3882

Sun JY , Yang H, Miao S, et al. Suppressive effects of swainsonine on C6 glioma cell in vitro and in vivo. Phytomedicine. 2009, 16(11):1070-4. doi: 10.1016/j.phymed.2009.02.012. Epub 2009 May 8. PMID: 19427771 DOI: 10.1016/j.phymed.2009.02.012.

You N , Liu W, Wang T, et al. Swainsonine inhibits growth and potentiates the cytotoxic effect of paclitaxel in hepatocellular carcinoma in vitro and in vivo. Oncol Rep. 2012, 28(6):2091-100. doi: 10.3892/or.2012.2035. Epub 2012 Sep 17. PMID: 22993037 DOI: 10.3892/or.2012.2035

Santos FM , Latorre AO, Hueza IM, et al. Increased antitumor efficacy by the combined administration of swainsonine and cisplatin in vivo. Phytomedicine. 2011, 18(12):1096-101. doi: 10.1016/j.phymed.2011.06.005. Epub 2011 Jul 16. PMID: 21763115 DOI: 10.1016/j.phymed.2011.06.005.

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