Lateritin

Lateritin is An Acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor and a platelet aggregation inhibitor isolated from the mycelial cake of Gibberella lateritium; bassiatin is the (3S, 6R) isomer.

Product information

CAS Number: 65454-13-9

Molecular Weight: 261.32

Formula: C15H19NO3

Chemical Name: 3-benzyl-6-isopropyl-4-methylmorpholine-2, 5-dione

Smiles: CC(C)C1OC(=O)C(CC2C=CC=CC=2)N(C)C1=O

InChiKey: YOKBTBNVNCFOBF-UHFFFAOYSA-N

InChi: InChI=1S/C15H19NO3/c1-10(2)13-14(17)16(3)12(15(18)19-13)9-11-7-5-4-6-8-11/h4-8,10,12-13H,9H2,1-3H3

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: To be determined

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

References:

1. Hughes AB, Sleebs MM. Total synthesis of bassiatin and its stereoisomers: novel divergent behavior of substrates in Mitsunobu cyclizations. J Org Chem. 2005 Apr 15;70(8):3079-88. PubMed PMID: 15822967.
2. h H, Kim T, Oh GS, Pae HO, Hong KH, Chai KY, Kwon TO, Chung HT, Lee HS. (3R,6R)-4-methyl-6-(1-methylethyl)-3-phenylmethyl-perhydro-1,4-oxazine-2,5-dione: an apoptosis-inducer from the fruiting bodies of Isaria japonica. Planta Med. 2002 Apr;68(4):345-8. PubMed PMID: 11988860.
3. Meng L, Feng B, Tao H, Yang T, Meng Y, Zhu W, Huang C. A novel antioestrogen agent (3R,6R)-bassiatin inhibits cell proliferation and cell cycle progression by repressing cyclin D1 expression in 17β-oestradiol-treated MCF-7 cells. Cell Biol Int. 2011 Jun;35(6):599-605. doi: 10.1042/CBI20100765. PubMed PMID: 21241249.
4. Jow GM, Chou CJ, Chen BF, Tsai JH. Beauvericin induces cytotoxic effects in human acute lymphoblastic leukemia cells through cytochrome c release, caspase 3 activation: the causative role of calcium. Cancer Lett. 2004 Dec 28;216(2):165-73. PubMed PMID: 15533592.
5. Meng L, Tao H, Dong G, Yang T, Zhang W, Zhu W, Huang C. ERK1/2 and Akt pathway activated during (3R,6R)-bassiatin(1)-induced apoptosis in MCF-7 cells. Cell Biol Int. 2012 Apr 1;36(4):345-8. doi: 10.1042/CBI20110388. PubMed PMID: 22150072.
6. Tang CY, Chen YW, Jow GM, Chou CJ, Jeng CJ. Beauvericin activates Ca2+-activated Cl- currents and induces cell deaths in Xenopus oocytes via influx of extracellular Ca2+. Chem Res Toxicol. 2005 May;18(5):825-33. PubMed PMID: 15892576.

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