| Identification | Back Directory | [Name]
MANUMYCIN A | [CAS]
52665-74-4 | [Synonyms]
UCF 1C
manumycin
NSC 622141
MANUMYCIN A
MANUMYCIN A, STREPTOMYCES PARVULUS
manumycin A from streptomyces parvulus
Manumycin A, Streptomyces parvulus - CAS 52665-74-4 - Calbiochem
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
(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
2,4-Decadienamide, N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxo-1,3,5-heptatrien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyl-, (2E,4E,6R)- | [Molecular Formula]
C31H38N2O7 | [MDL Number]
MFCD00920782 | [MOL File]
52665-74-4.mol | [Molecular Weight]
550.64 |
| Chemical Properties | Back Directory | [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 | [pka]
3.80±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. |
| Hazard Information | Back Directory | [Description]
Manumycin 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. | [Uses]
Manumycin 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. | [Uses]
Manumycin A is an antibiotic that acts as a potent and selective farnesyltransferase (FTase) inhibitor with anti-tumor activity. | [Definition]
ChEBI: Manumycin A is a polyketide with formula C31H38N2O7 initially isolated from Streptomyces parvulus as a result of a random screening program for farnesyl transferase (FTase) inhibitors. It is a natural product that exhibits anticancer and antibiotic properties. It has a role as an EC 1.8.1.9 (thioredoxin reductase) inhibitor, an EC 2.5.1.58 (protein farnesyltransferase) inhibitor, an antineoplastic agent, an apoptosis inducer, an antimicrobial agent, a bacterial metabolite, an antiatherosclerotic agent and a marine metabolite. It is a polyketide, an enamide, an epoxide, an organic heterobicyclic compound, a secondary carboxamide and a tertiary alcohol. | [Biochem/physiol Actions]
Manumycin 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. | [storage]
Store at -20°C | [References]
1) 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 |
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