Ecteinascidin 770

Ecteinascidin 770 (ET-770) is a 1, 2, 3, 4-tetrahydroisoquinoline alkaloid with potent anti-cancer activities; inhibits U373MG cells with an IC50 of 4.83 nM.

Product information

CAS Number: 114899-80-8

Molecular Weight: 770.85

Formula: C40H42N4O10S

Synonym:

Ecteinascidine 770

Et-770

Chemical Name: [(1R, 2R, 3R, 11S, 12R, 14R, 26R)-12-cyano-5, 6'-dihydroxy-6, 7'-dimethoxy-7, 21, 30-trimethyl-27-oxospiro[17, 19, 28-trioxa-24-thia-13, 30-diazaheptacyclo[12.9.6.13, 11.02, 13.04, 9.015, 23.016, 20]triaconta-4(9), 5, 7, 15, 20, 22-hexaene-26, 1'-3, 4-dihydro-2H-isoquinoline]-22-yl] acetate

Smiles: CN1[C@H]2[C@@H]3[C@@H]4SC[C@]5(NCCC6=CC(O)=C(C=C56)OC)C(=O)OC[C@@H](C5C4=C(OC(C)=O)C(C)=C4OCOC4=5)N3[C@@H](C#N)[C@@H]1CC1=CC(C)=C(OC)C(O)=C12

InChiKey: BGFXHQYUWCGGLL-QWIBJBKUSA-N

InChi: InChI=1S/C40H42N4O10S/c1-17-9-21-10-23-24(13-41)44-25-14-51-39(48)40(22-12-27(49-5)26(46)11-20(22)7-8-42-40)15-55-38(32(44)31(43(23)4)28(21)33(47)34(17)50-6)30-29(25)37-36(52-16-53-37)18(2)35(30)54-19(3)45/h9,11-12,23-25,31-32,38,42,46-47H,7-8,10,14-16H2,1-6H3/t23-,24-,25-,31+,32+,38+,40+/m0/s1

Technical Data

Appearance: Solid Power

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

Solubility: Soluble in DMSO

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: ≥360 days 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

How to use

In Vitro:

Ecteinascidin 770 induces apoptosis of U373MG cells. The IC50 concentration of ecteinascidin 770 for killing U373MG glioblastoma cells in culture by using the MTT assay is 4.83 nM by a 72 hour-treatment. The IC50 values against human cell lines HCT116, QG56, and DU145 are 0.6, 2.4, and 0.81 nM, respectively. ET-770 is shown to enhance anoikis response of human lung cancer H23 cells in a dose-dependent manner. Ecteinascidin 770 sensitizes the cells by activating the p53 protein, which in turn down-regulates anti-apoptotic myeloid cell leukemia sequence-1 (MCL1) and up-regulates BCL2-associated X protein (BAX) proteins. However, B-cell lymphoma-2 (BCL2) proteins are not significantly affected by Ecteinascidin 770. The anoikis sensitization of ET-770 is observed in H460 lung cancer cells.

References:

1. Tabunoki H, et al. Molecular network profiling of U373MG human glioblastoma cells following induction of apoptosis by novel marine-derived anti-cancer 1,2,3,4-tetrahydroisoquinoline alkaloids. Cancer Cell Int. 2012 Apr 11;12(1):14.
2. Saktrakulkla P, et al. Chemistry of ecteinascidins. Part 3: preparation of 2'-N-acyl derivatives of ecteinascidin 770 and evaluation of cytotoxicity. Bioorg Med Chem. 2011 Aug 1;19(15):4421-36.
3. Powan P, et al. Ecteinascidin 770, a tetrahydroisoquinoline alkaloid, sensitizes human lung cancer cells to anoikis. Anticancer Res. 2013 Feb;33(2):505-12.

Products are for research use only. Not for human use.