Migrastatin
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| Category | Others |
| Catalog number | BBF-02686 |
| CAS | 314245-65-3 |
| Molecular Weight | 489.60 |
| Molecular Formula | C27H39NO7 |
| Purity | 98% |
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Description
Migrastatin is a macrolide produced by Streptomyces sp. N4K929-43F1 and Str. platensis (NRRL 18993). It can inhibit the metastasis of cancer cells.
Specification
| Synonyms | (+)-migrastatin |
| IUPAC Name | 4-[(5S)-5-[(2R,3Z,5R,6S,7S,8E,12E)-6-hydroxy-7-methoxy-3,5-dimethyl-14-oxo-1-oxacyclotetradeca-3,8,12-trien-2-yl]-4-oxohexyl]piperidine-2,6-dione |
| Canonical SMILES | CC1C=C(C(OC(=O)C=CCCC=CC(C1O)OC)C(C)C(=O)CCCC2CC(=O)NC(=O)C2)C |
| InChI | 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 |
Properties
| Appearance | White Powder |
| Boiling Point | 707.9±60.0°C at 760 mmHg |
| Melting Point | 54-55°C |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1.Migrastatin analogues inhibit canine mammary cancer cell migration and invasion.
Majchrzak K1, Lo Re D, Gajewska M, Bulkowska M, Homa A, Pawłowski K, Motyl T, Murphy PV, Król M. PLoS One. 2013 Oct 8;8(10):e76789. doi: 10.1371/journal.pone.0076789. eCollection 2013.
BACKGROUND: Cancer spread to other organs is the main cause of death of oncological patients. Migration of cancer cells from a primary tumour is the crucial step in the complex process of metastasis, therefore blocking this process is currently the main treatment strategy. Metastasis inhibitors derived from natural products, such as, migrastatin, are very promising anticancer agents. Thus, the aim of our study was to investigate the effect of six migrastatin analogues (MGSTA-1 to 6) on migration and invasion of canine mammary adenocarcinoma cell lines isolated from primary tumours and their metastases to the lungs. Canine mammary tumours constitute a valuable tool for studying multiple aspect of human cancer.
2.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.
Seo JW1, Ma M, Kwong T, Ju J, Lim SK, Jiang H, Lohman JR, Yang C, Cleveland J, Zazopoulos E, Farnet CM, Shen B. Biochemistry. 2014 Dec 16;53(49):7854-65. doi: 10.1021/bi501396v. Epub 2014 Dec 1.
Lactimidomycin (LTM, 1) and iso-migrastatin (iso-MGS, 2) belong to the glutarimide-containing polyketide family of natural products. We previously cloned and characterized the mgs biosynthetic gene cluster from Streptomyces platensis NRRL 18993. The iso-MGS biosynthetic machinery featured an acyltransferase (AT)-less type I polyketide synthase (PKS) and three tailoring enzymes (MgsIJK). We now report cloning and characterization of the ltm biosynthetic gene cluster from Streptomyces amphibiosporus ATCC 53964, which consists of nine genes that encode an AT-less type I PKS (LtmBCDEFGHL) and one tailoring enzyme (LtmK). Inactivation of ltmE or ltmH afforded the mutant strain SB15001 or SB15002, respectively, that abolished the production of 1, as well as the three cometabolites 8,9-dihydro-LTM (14), 8,9-dihydro-8S-hydroxy-LTM (15), and 8,9-dihydro-9R-hydroxy-LTM (13). Inactivation of ltmK yielded the mutant strain SB15003 that abolished the production of 1, 13, and 15 but led to the accumulation of 14.
3.Synthesis of migrastatin and its macroketone analogue and in vivo FRAP analysis of the macroketone on E-cadherin dynamics.
Lo Re D1, Zhou Y, Nobis M, Anderson KI, Murphy PV. Chembiochem. 2014 Jul 7;15(10):1459-64. doi: 10.1002/cbic.201402061. Epub 2014 Jun 11.
An efficient and scalable synthesis of a key acyclic intermediate used for the preparation of migrastatin and its macroketone analogue is described; Brown alkoxyallylation is the key step for this synthesis. The macroketone was prepared on 100 mg scale by this route. Treatment of invasive pancreatic cancer cells grown on a cell-derived matrix or as subcutaneous tumours in nude mice with the macroketone inhibited E-cadherin dynamics in a manner consistent with increased cell adhesion and reduced invasive potential.
4.Post-polyketide synthase steps in iso-migrastatin biosynthesis, featuring tailoring enzymes with broad substrate specificity.
Ma M1, Kwong T, Lim SK, Ju J, Lohman JR, Shen B. J Am Chem Soc. 2013 Feb 20;135(7):2489-92. doi: 10.1021/ja4002635. Epub 2013 Feb 11.
The iso-migrastatin (iso-MGS) biosynthetic gene cluster from Streptomyces platensis NRRL 18993 consists of 11 genes, featuring an acyltransferase (AT)-less type I polyketide synthase (PKS) and three tailoring enzymes MgsIJK. Systematic inactivation of mgsIJK in S. platensis enabled us to (i) identify two nascent products of the iso-MGS AT-less type I PKS, establishing an unprecedented novel feature for AT-less type I PKSs, and (ii) account for the formation of all known post-PKS biosynthetic intermediates generated by the three tailoring enzymes MgsIJK, which possessed significant substrate promiscuities.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
