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MedKoo Cat#: 463972 | Name: Migrastatin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Migrastatin is a bacterial metabolite that has been found in Streptomyces with antimuscarinic and anticancer activities. It binds to M1-5 muscarinic acetylcholine receptors and inhibits calcium mobilization induced by carbamoylcholine in SK-N-SH cells, as well as in primary rat bladder smooth muscle cells. Migrastatin inhibits the migration of EC17 esophageal cancer cells in a wound healing assay and 4T1 mouse mammary carcinoma cells in a chamber cell migration assay. It enhances cytotoxicity induced by vinblastine in vincristine-resistant P388/VCR cells.

Chemical Structure

Migrastatin
Migrastatin
CAS#314245-65-3

Theoretical Analysis

MedKoo Cat#: 463972

Name: Migrastatin

CAS#: 314245-65-3

Chemical Formula: C27H39NO7

Exact Mass: 489.2727

Molecular Weight: 489.61

Elemental Analysis: C, 66.24; H, 8.03; N, 2.86; O, 22.87

Price and Availability

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1mg USD 1,150.00 2 Weeks
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Synonym
Migrastatin; (+)-Migrastatin; (+) Migrastatin;
IUPAC/Chemical Name
4-((S)-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)piperidine-2,6-dione
InChi Key
OGYMUMAKGYYNHV-IJMHZYIBSA-N
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
SMILES Code
O=C1NC(CC(CCCC([C@@H](C)[C@@]2(/C(C)=C\[C@@H](C)[C@H](O)[C@@H](OC)/C=C/CC/C=C/C(O2)=O)[H])=O)C1)=O
Appearance
Solid powder
Purity
>90% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Migrastatin binds to M1-5 muscarinic acetylcholine receptors.
In vitro activity:
Migrastatin inhibited intracellular calcium mobilization induced by carbachol in neuroblastoma SK-N-SH cells without affecting Ca2+ mobilization and cAMP accumulation induced by ligands of other receptors. Functionally, migrastatin inhibited Ca2+ mobilization induced by carbachol in primary cultures of smooth muscle cells of rat bladder. This study reveals that migrastatin acts as a muscarinic acetylcholine receptor antagonist. Reference: J Antibiot (Tokyo). 2006 Nov;59(11):685-92. https://pubmed.ncbi.nlm.nih.gov/17256466/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 489.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Nakae K, Nishimura Y, Ohba S, Akamatsu Y. Migrastatin acts as a muscarinic acetylcholine receptor antagonist. J Antibiot (Tokyo). 2006 Nov;59(11):685-92. doi: 10.1038/ja.2006.91. PMID: 17256466. 2. Nakae K, Yoshimoto Y, Sawa T, Homma Y, Hamada M, Takeuchi T, Imoto M. Migrastatin, a new inhibitor of tumor cell migration from Streptomyces sp. MK929-43F1. Taxonomy, fermentation, isolation and biological activities. J Antibiot (Tokyo). 2000 Oct;53(10):1130-6. doi: 10.7164/antibiotics.53.1130. PMID: 11132958.
In vitro protocol:
1. Nakae K, Nishimura Y, Ohba S, Akamatsu Y. Migrastatin acts as a muscarinic acetylcholine receptor antagonist. J Antibiot (Tokyo). 2006 Nov;59(11):685-92. doi: 10.1038/ja.2006.91. PMID: 17256466. 2. Nakae K, Yoshimoto Y, Sawa T, Homma Y, Hamada M, Takeuchi T, Imoto M. Migrastatin, a new inhibitor of tumor cell migration from Streptomyces sp. MK929-43F1. Taxonomy, fermentation, isolation and biological activities. J Antibiot (Tokyo). 2000 Oct;53(10):1130-6. doi: 10.7164/antibiotics.53.1130. PMID: 11132958.
In vivo protocol:
TBD
1: Alburquerque-González B, Bernabé-García M, Montoro-García S, Bernabé-García Á, Rodrigues PC, Ruiz Sanz J, López-Calderón FF, Luque I, Nicolas FJ, Cayuela ML, Salo T, Pérez-Sánchez H, Conesa-Zamora P. New role of the antidepressant imipramine as a Fascin1 inhibitor in colorectal cancer cells. Exp Mol Med. 2020 Feb;52(2):281-292. doi: 10.1038/s12276-020-0389-x. Epub 2020 Feb 20. PMID: 32080340; PMCID: PMC7062870. 2: Montoro-García S, Alburquerque-González B, Bernabé-García Á, Bernabé-García M, Rodrigues PC, den-Haan H, Luque I, Nicolás FJ, Pérez-Sánchez H, Cayuela ML, Salo T, Conesa-Zamora P. Novel anti-invasive properties of a Fascin1 inhibitor on colorectal cancer cells. J Mol Med (Berl). 2020 Mar;98(3):383-394. doi: 10.1007/s00109-020-01877-z. Epub 2020 Jan 29. PMID: 31996952. 3: Airan Y, Prasad KR. Furan Oxidation Strategy for the Synthesis of the Macrolactone Analogue of Migrastatin. J Org Chem. 2019 Nov 15;84(22):14974-14979. doi: 10.1021/acs.joc.9b02413. Epub 2019 Oct 30. PMID: 31615208. 4: Tavano S, Heisenberg CP. Migrasomes take center stage. Nat Cell Biol. 2019 Aug;21(8):918-920. doi: 10.1038/s41556-019-0369-3. PMID: 31371826. 5: Teijaro CN, Adhikari A, Shen B. Challenges and opportunities for natural product discovery, production, and engineering in native producers versus heterologous hosts. J Ind Microbiol Biotechnol. 2019 Mar;46(3-4):433-444. doi: 10.1007/s10295-018-2094-5. Epub 2018 Nov 13. PMID: 30426283; PMCID: PMC6405299. 6: Zhang B, Xu Z, Teng Q, Pan G, Ma M, Shen B. A Long-Range Acting Dehydratase Domain as the Missing Link for C17-Dehydration in Iso-Migrastatin Biosynthesis. Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7247-7251. doi: 10.1002/anie.201703588. Epub 2017 May 19. PMID: 28464455; PMCID: PMC5558199. 7: Giralt E, Lo Re D. The Therapeutic Potential of Migrastatin-Core Analogs for the Treatment of Metastatic Cancer. Molecules. 2017 Feb 9;22(2):198. doi: 10.3390/molecules22020198. PMID: 28208778; PMCID: PMC6155687. 8: Magpusao AN, Rutledge K, Hamlin TA, Lawrence JM, Mercado BQ, Leadbeater NE, Peczuh MW. Rules of Macrocycle Topology: A [13]-Macrodilactone Case Study. Chemistry. 2016 Apr 18;22(17):6001-11. doi: 10.1002/chem.201504684. Epub 2016 Mar 22. PMID: 27001347. 9: Zhang B, Yang D, Yan Y, Pan G, Xiang W, Shen B. Overproduction of lactimidomycin by cross-overexpression of genes encoding Streptomyces antibiotic regulatory proteins. Appl Microbiol Biotechnol. 2016 Mar;100(5):2267-77. doi: 10.1007/s00253-015-7119-7. Epub 2015 Nov 10. PMID: 26552797; PMCID: PMC4758858. 10: Lo Re D, Zhou Y, Mucha J, Jones LF, Leahy L, Santocanale C, Krol M, Murphy PV. Synthesis of Migrastatin Analogues as Inhibitors of Tumour Cell Migration: Exploring Structural Change in and on the Macrocyclic Ring. Chemistry. 2015 Dec 7;21(50):17993. doi: 10.1002/chem.201504167. Epub 2015 Nov 5. PMID: 26537992. 11: Lo Re D, Zhou Y, Mucha J, Jones LF, Leahy L, Santocanale C, Krol M, Murphy PV. Synthesis of Migrastatin Analogues as Inhibitors of Tumour Cell Migration: Exploring Structural Change in and on the Macrocyclic Ring. Chemistry. 2015 Dec 7;21(50):18109-21. doi: 10.1002/chem.201502861. Epub 2015 Nov 4. PMID: 26531227. 12: Lohman JR, Ma M, Osipiuk J, Nocek B, Kim Y, Chang C, Cuff M, Mack J, Bigelow L, Li H, Endres M, Babnigg G, Joachimiak A, Phillips GN Jr, Shen B. Structural and evolutionary relationships of "AT-less" type I polyketide synthase ketosynthases. Proc Natl Acad Sci U S A. 2015 Oct 13;112(41):12693-8. doi: 10.1073/pnas.1515460112. Epub 2015 Sep 29. PMID: 26420866; PMCID: PMC4611616. 13: Liu SP, Yu P, Yuan PH, Zhou ZX, Bu QT, Mao XM, Li YQ. Sigma factor WhiGch positively regulates natamycin production in Streptomyces chattanoogensis L10. Appl Microbiol Biotechnol. 2015 Mar;99(6):2715-26. doi: 10.1007/s00253-014-6307-1. Epub 2015 Jan 21. PMID: 25724582. 14: Seo JW, Ma M, Kwong T, Ju J, Lim SK, Jiang H, Lohman JR, Yang C, Cleveland J, Zazopoulos E, Farnet CM, Shen B. Comparative characterization of the lactimidomycin and iso-migrastatin biosynthetic machineries revealing unusual features for acyltransferase-less type I polyketide synthases and providing an opportunity to engineer new analogues. Biochemistry. 2014 Dec 16;53(49):7854-65. doi: 10.1021/bi501396v. Epub 2014 Dec 1. PMID: 25405956; PMCID: PMC4270375. 15: Lo Re D, Zhou Y, Nobis M, Anderson KI, Murphy PV. Synthesis of migrastatin and its macroketone analogue and in vivo FRAP analysis of the macroketone on E-cadherin dynamics. Chembiochem. 2014 Jul 7;15(10):1459-64. doi: 10.1002/cbic.201402061. Epub 2014 Jun 11. PMID: 24919421. 16: Majchrzak K, Lo Re D, Gajewska M, Bulkowska M, Homa A, Pawłowski K, Motyl T, Murphy PV, Król M. Migrastatin analogues inhibit canine mammary cancer cell migration and invasion. PLoS One. 2013 Oct 8;8(10):e76789. doi: 10.1371/journal.pone.0076789. PMID: 24116159; PMCID: PMC3792885. 17: Ma M, Kwong T, Lim SK, Ju J, Lohman JR, Shen B. Post-polyketide synthase steps in iso-migrastatin biosynthesis, featuring tailoring enzymes with broad substrate specificity. J Am Chem Soc. 2013 Feb 20;135(7):2489-92. doi: 10.1021/ja4002635. Epub 2013 Feb 11. PMID: 23394593; PMCID: PMC3582021. 18: Lecomte N, Njardarson JT, Nagorny P, Yang G, Downey R, Ouerfelli O, Moore MA, Danishefsky SJ. Emergence of potent inhibitors of metastasis in lung cancer via syntheses based on migrastatin. Proc Natl Acad Sci U S A. 2011 Sep 13;108(37):15074-8. doi: 10.1073/pnas.1015247108. Epub 2011 Aug 1. PMID: 21808037; PMCID: PMC3174672. 19: Wu X, Yang D, Zhu X, Feng Z, Lv Z, Zhang Y, Shen B, Xu Z. Iso-migrastatin Titer Improvement in the Engineered Streptomyces lividans SB11002 Strain by Optimization of Fermentation Conditions. Biotechnol Bioprocess Eng. 2010 Aug 1;15(4):664-669. doi: 10.1007/s12257-009-3129-6. PMID: 21625393; PMCID: PMC3100776. 20: Santos RN, Guido RV, Oliva G, Dias LC, Andricopulo AD. Quantitative structure-activity studies on a series of migrastatin analogs as inhibitors of cancer cell metastasis. Med Chem. 2011 May;7(3):155-64. doi: 10.2174/157340611795564240. PMID: 21486209.