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MedKoo Cat#: 564856 | Name: Manumycin A
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Description:

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

Manumycin A is a Farnesyltransferase inhibitor which suppresses exosome biogenesis and secretion via targeted inhibition of Ras/Raf/ERK1/2 signaling and hnRNP H1 in castration-resistant prostate cancer cells, inhibiting IKKβ activity through covalent cross-linking of IKKβ monomers via C179.

Chemical Structure

Manumycin A
Manumycin A
CAS#52665-74-4

Theoretical Analysis

MedKoo Cat#: 564856

Name: Manumycin A

CAS#: 52665-74-4

Chemical Formula: C31H38N2O7

Exact Mass: 550.2679

Molecular Weight: 550.65

Elemental Analysis: C, 67.62; H, 6.96; N, 5.09; O, 20.34

Price and Availability

Size Price Availability Quantity
1mg USD 315.00 2 weeks
5mg USD 850.00 2 weeks
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Related CAS #
No Data
Synonym
Manumycin A
IUPAC/Chemical Name
(2E,4E,6R)-N-[(1S,5S,6R)-5-Hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienamide
InChi Key
TWWQHCKLTXDWBD-MVTGTTCWSA-N
InChi Code
InChI=1S/C31H38N2O7/c1-5-6-11-19(2)16-20(3)17-21(4)30(38)32-22-18-31(39,29-28(40-29)27(22)37)15-10-8-7-9-12-25(36)33-26-23(34)13-14-24(26)35/h7-10,12,15-19,28-29,34,39H,5-6,11,13-14H2,1-4H3,(H,32,38)(H,33,36)/b8-7+,12-9+,15-10+,20-16+,21-17+/t19-,28-,29-,31+/m1/s1
SMILES Code
CCCC[C@@H](C)/C=C(C)/C=C(C)/C(NC1=C[C@](/C=C/C=C/C=C/C(NC2=C(O)CCC2=O)=O)(O)[C@]3([H])O[C@]3([H])C1=O)=O
Appearance
Solid powder
Purity
>98% (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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 550.65 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
1: Castro-Falcón G, Creamer KE, Chase AB, Kim MC, Sweeney D, Glukhov E, Fenical W, Jensen PR. Structure and Candidate Biosynthetic Gene Cluster of a Manumycin- Type Metabolite from Salinispora pacifica. J Nat Prod. 2022 Apr 22;85(4):980-986. doi: 10.1021/acs.jnatprod.1c01117. Epub 2022 Mar 9. PMID: 35263117; PMCID: PMC9209988. 2: Hagemann A, Altrogge PK, Kehrenberg MCA, Diehl D, Jung D, Weber L, Bachmann HS. Analyzing the postulated inhibitory effect of Manumycin A on farnesyltransferase. Front Chem. 2022 Dec 6;10:967947. doi: 10.3389/fchem.2022.967947. PMID: 36561140; PMCID: PMC9763582. 3: Catalano M, O'Driscoll L. Inhibiting extracellular vesicles formation and release: a review of EV inhibitors. J Extracell Vesicles. 2019 Dec 19;9(1):1703244. doi: 10.1080/20013078.2019.1703244. PMID: 32002167; PMCID: PMC6968539. 4: Tuladhar A, Rein KS. Manumycin A Is a Potent Inhibitor of Mammalian Thioredoxin Reductase-1 (TrxR-1). ACS Med Chem Lett. 2018 Mar 5;9(4):318-322. doi: 10.1021/acsmedchemlett.7b00489. PMID: 29670693; PMCID: PMC5900327. 5: Tuladhar A, Hondal RJ, Colon R, Hernandez EL, Rein KS. Effectors of thioredoxin reductase: Brevetoxins and manumycin-A. Comp Biochem Physiol C Toxicol Pharmacol. 2019 Mar;217:76-86. doi: 10.1016/j.cbpc.2018.11.015. Epub 2018 Nov 23. PMID: 30476593; PMCID: PMC7485175. 6: Cecrdlova E, Petrickova K, Kolesar L, Petricek M, Sekerkova A, Svachova V, Striz I. Manumycin A downregulates release of proinflammatory cytokines from TNF alpha stimulated human monocytes. Immunol Lett. 2016 Jan;169:8-14. doi: 10.1016/j.imlet.2015.11.010. Epub 2015 Nov 18. PMID: 26602157. 7: Gorniaková D, Petříček M, Kahoun D, Grabic R, Zelenka T, Chroňáková A, Petříčková K. Activation of a Cryptic Manumycin-Type Biosynthetic Gene Cluster of Saccharothrix espanaensis DSM44229 by Series of Genetic Manipulations. Microorganisms. 2021 Mar 8;9(3):559. doi: 10.3390/microorganisms9030559. PMID: 33800500; PMCID: PMC8000086. 8: Xiong Q, Rikihisa Y. The prenylation inhibitor manumycin A reduces the viability of Anaplasma phagocytophilum. J Med Microbiol. 2011 Jun;60(Pt 6):744-749. doi: 10.1099/jmm.0.029231-0. Epub 2011 Feb 24. PMID: 21349982; PMCID: PMC3167922. 9: Sojka DR, Hasterok S, Vydra N, Toma-Jonik A, Wieczorek A, Gogler-Pigłowska A, Scieglinska D. Inhibition of the Heat Shock Protein A (HSPA) Family Potentiates the Anticancer Effects of Manumycin A. Cells. 2021 Jun 7;10(6):1418. doi: 10.3390/cells10061418. PMID: 34200371; PMCID: PMC8229576. 10: Cho JJ, Chae JI, Kim KH, Cho JH, Jeon YJ, Oh HN, Yoon G, Yoon DY, Cho YS, Cho SS, Shim JH. Manumycin A from a new Streptomyces strain induces endoplasmic reticulum stress-mediated cell death through specificity protein 1 signaling in human oral squamous cell carcinoma. Int J Oncol. 2015 Nov;47(5):1954-62. doi: 10.3892/ijo.2015.3151. Epub 2015 Sep 8. PMID: 26352011. 11: Datta A, Kim H, Lal M, McGee L, Johnson A, Moustafa AA, Jones JC, Mondal D, Ferrer M, Abdel-Mageed AB. Manumycin A suppresses exosome biogenesis and secretion via targeted inhibition of Ras/Raf/ERK1/2 signaling and hnRNP H1 in castration-resistant prostate cancer cells. Cancer Lett. 2017 Nov 1;408:73-81. doi: 10.1016/j.canlet.2017.08.020. Epub 2017 Aug 24. PMID: 28844715; PMCID: PMC5628151. 12: Zajičková T, Kyzek S, Ďurovcová I, Ševčovičová A, Gálová E. Ratio-dependent effects of photoactivated hypericin and manumycin A on their genotoxic and mutagenic potential. Chem Biol Interact. 2023 Apr 1;374:110421. doi: 10.1016/j.cbi.2023.110421. Epub 2023 Feb 23. PMID: 36828245. 13: Ali BR, Pal A, Croft SL, Taylor RJ, Field MC. The farnesyltransferase inhibitor manumycin A is a novel trypanocide with a complex mode of action including major effects on mitochondria. Mol Biochem Parasitol. 1999 Oct 25;104(1):67-80. doi: 10.1016/s0166-6851(99)00131-0. PMID: 10589982. 14: Egler J, Zierle J, Lang F. Stimulating Effect of Manumycin A on Suicidal Erythrocyte Death. Cell Physiol Biochem. 2016;38(3):1147-56. doi: 10.1159/000443065. Epub 2016 Mar 11. PMID: 26962870. 15: Chanadech S, Ruen-Ngam D, Intaraudom C, Pittayakhajonwut P, Chongruchiroj S, Pratuangdejkul J, Thawai C. Isolation of manumycin-type derivatives and genome characterization of a marine Streptomyces sp. C1-2. Res Microbiol. 2021 Mar;172(2):103812. doi: 10.1016/j.resmic.2021.103812. Epub 2021 Jan 23. PMID: 33497762. 16: Singha PK, Pandeswara S, Venkatachalam MA, Saikumar P. Manumycin A inhibits triple-negative breast cancer growth through LC3-mediated cytoplasmic vacuolation death. Cell Death Dis. 2013 Jan 17;4(1):e457. doi: 10.1038/cddis.2012.192. PMID: 23328664; PMCID: PMC3563980. 17: Bernier M, Kwon YK, Pandey SK, Zhu TN, Zhao RJ, Maciuk A, He HJ, Decabo R, Kole S. Binding of manumycin A inhibits IkappaB kinase beta activity. J Biol Chem. 2006 Feb 3;281(5):2551-61. doi: 10.1074/jbc.M511878200. Epub 2005 Nov 30. PMID: 16319058. 18: Macejová M, Sačková V, Hradická P, Jendželovský R, Demečková V, Fedoročko P. Combination of photoactive hypericin and Manumycin A exerts multiple anticancer effects on oxaliplatin-resistant colorectal cells. Toxicol In Vitro. 2020 Aug;66:104860. doi: 10.1016/j.tiv.2020.104860. Epub 2020 Apr 13. PMID: 32298799. 19: Kim KH, Chae JI, Oh H, Cho JH, Lee RH, Yoon G, Cho SS, Cho YS, Lee MH, Liu K, Lee HJ, Shim JH. Manumycin A induces apoptosis in malignant pleural mesothelioma through regulation of Sp1 and activation of the mitochondria- related apoptotic pathway. Oncol Rep. 2016 Jul;36(1):117-24. doi: 10.3892/or.2016.4801. Epub 2016 May 10. PMID: 27176604. 20: Carey GB, Roy SK, Daino H. The natural tumorcide Manumycin-A targets protein phosphatase 1α and reduces hydrogen peroxide to induce lymphoma apoptosis. Exp Cell Res. 2015 Mar 1;332(1):136-45. doi: 10.1016/j.yexcr.2014.12.009. Epub 2014 Dec 30. PMID: 25556058; PMCID: PMC9976551.

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