MANUMYCIN A
MANUMYCIN A
  • CAS No.:52665-74-4
Other grades of this product :
MANUMYCIN A Basic information
Product Name:MANUMYCIN A
Synonyms:MANUMYCIN A;MANUMYCIN A, STREPTOMYCES PARVULUS;N-[5-Hydroxy-5-[7-[(2-hydroxy-5-oxo-1-cyclopenten-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;manumycin;manumycin A from streptomyces parvulus;(2E,4E)-N-[(5R)-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;NSC 622141;UCF 1C
CAS:52665-74-4
MF:C31H38N2O7
MW:550.64
EINECS:
Product Categories:Farnesyl transferase, RasG Proteins and Cyclic Nucleotides;D to;Enzyme Inhibitors by Enzyme;G Protein Function;Post-translational Modification
Mol File:52665-74-4.mol
MANUMYCIN A Chemical Properties
Boiling point 863.6±65.0 °C(Predicted)
density 1.26±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility Soluble in DMSO (up to 10 mg/ml), in Ethanol (up to 5 mg/ml) or in DMF (up to 20 mg/ml)
form Yellow to brown solid
pka3.80±0.30(Predicted)
color Yellow
Stability:Stable for 1 year from date of purchase as supplied. Solutions in DMSO, ethanol, or DMF may be stored at -20°C for up to 3 months.
Safety Information
WGK Germany 3
HS Code 2941900000
MSDS Information
ProviderLanguage
SigmaAldrich English
MANUMYCIN A Usage And Synthesis
DescriptionManumycin A is an antibiotic that acts as a potent and selective farnesyltransferase (FTase) inhibitor with anti-tumor activity. It inhibits rat brain FTase with a Ki value of 1.2 μM, thereby preventing Ras activation which requires farnesylation at the C-terminus for membrane attachment. It exhibits significant antitumor activity against Ki-ras-activated solid tumors in mice at a dose of 6.3 mg/kg. Manymycin A inhibits IκB kinase (IKK), independent of FTase inhibition, in an number of cells types with effective concentrations of 2-10 μM. In ApoE-deficient mice, Manumycin A treatment for 22 weeks at 5 mg/kg reduced aortic fatty streak lesion size to 43% of vehicle-treated animals, indicating FTase inhibition as a potential target for prevention or treatment of atherosclerosis.
UsesManumycin A from Streptomyces parvulus has been used to inhibit IκB kinase (IKK)b?nuclear κ-B essential modulator (NEMO) interaction in the homogeneous time-resolved fluorescence (HTRF)-based binding assay.
UsesManumycin A is an antibiotic that acts as a potent and selective farnesyltransferase (FTase) inhibitor with anti-tumor activity.
Biochem/physiol ActionsManumycin A is a natural monomeric epoxyquinoid. It has an ability to inhibit tumor necrosis factor (TNF) induced IκB kinase (IKK) activity in various cell types. In addition, manumycin A exhibits anti-tumor property by inhibiting farnesylation of oncogenic Ras.
References1) Hara?et al.?(1993),?Identification of Ras Farnesyltransferase inhibitors by microbial screening; Proc. Natl. Acad. Sci. USA,?90?2281 2) DiPaolo?et al.?(2000),?Manumycin inhibits ras signal transduction pathway and induces apoptosis in COLO320-DM human colon tumour cells; Br. J. Cancer,?82?905 3) Arenz?et al.?(2001),?Manumycin A and its analogies are irreversible inhibitors of neutral sphingomyelinase; Chem. Bio. Chem.,?2?141 4) Sharma?et al.?(2012),?Farnesyltransferase inhibitor manumycin targets IL1β-Ras-HIF-1α axis in tumor cells of diverse origin; Inflammation,?35?516 5) Saha and Nandi (2009),?Farnesyltransferase inhibitors reduce Ras activation and ameliorate acetaminophen-induced liver injury in mice; Hepatology,?50?1547 6) Singha?et al.?(2013),?Manumycin A inhibits triple-negative breast cancer growth through LC3-mediated cytoplasmic vacuolation death; Cell Death Dis.,?4?e457
MANUMYCIN A Preparation Products And Raw materials

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