A fungal metabolite with antimuscarinic and anticancer activities
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Migrastatin

Item No. 32885

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(5S)-5-[(2R,3Z,5R,6S,7S,8E,12E)-6-hydroxy-7-methoxy-3,5-dimethyl-14-oxooxacyclotetradeca-3,8,12-trien-2-yl]-4-oxohexyl]-2,6-piperidinedione
CAS Number
314245-65-3
Synonyms
  • (+)-Migrastatin
Molecular Formula
C27H39NO7
Formula Weight
489.6
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleMethanol: soluble
SMILES
O=C(NC(C1)=O)CC1CCCC([C@H]([C@]2([H])/C(C)=C\[C@H]([C@@H]([C@H](/C=C/CC/C=C/C(O2)=O)OC)O)C)C)=O
InChi Code
InChI=1S/C27H39NO7/c1-17-14-18(2)27(35-25(32)13-8-6-5-7-12-22(34-4)26(17)33)19(3)21(29)11-9-10-20-15-23(30)28-24(31)16-20/h7-8,12-14,17,19-20,22,26-27,33H,5-6,9-11,15-16H2,1-4H3,(H,28,30,31)/b12-7+,13-8+,18-14-/t17-,19-,22+,26+,27+/m1/s1
InChi Key
OGYMUMAKGYYNHV-IJMHZYIBSA-N
Origin
Bacterium/Streptomyces sp. MK929-43F1
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $835

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    Product Description

    Migrastatin is a bacterial metabolite that has been found in Streptomyces with antimuscarinic and anticancer activities.1,2 It binds to M1-5 muscarinic acetylcholine receptors (Kis = >200, 200, 31, 43, and >200 µM, respectively) and inhibits calcium mobilization induced by carbamoylcholine (carbachol; Item No. 14486) in SK-N-SH cells (IC50 = 28 µM), as well as in primary rat bladder smooth muscle cells.1 Migrastatin inhibits the migration of EC17 esophageal cancer cells in a wound healing assay (IC50 = 10 µg/ml) and 4T1 mouse mammary carcinoma cells in a chamber cell migration assay (IC50 = 29 µM).2 It enhances cytotoxicity induced by vinblastine (Item No. 11762) in vincristine-resistant P388/VCR cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nakae, K., Nishimura, Y., Ohba, S., et al. Migrastatin acts as a muscarinic acetylcholine receptor antagonist. J. Antibiot. (Tokyo) 59(11), 685-692 (2006).

    2. Reymond, S., and Cossy, J. Migrastatin and analogues: New anti-metastatic agents. C. R. Chim. 11(11-12), 1447-1462 (2008).

    3. Takemoto, Y., Tashiro, E., and Imoto, M. Suppression of multidrug resistance by migrastatin. J. Antibiot. (Tokyo) 59(7), 435-438 (2006).