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MANUMYCIN A

Product Name
MANUMYCIN A
CAS No.
52665-74-4
Chemical Name
MANUMYCIN A
Synonyms
UCF 1C;manumycin;NSC 622141;MANUMYCIN A;Chiromycin A;MANUMYCIN A, STREPTOMYCES PARVULUS;manumycin A from streptomyces parvulus;Manumycin A, Streptomyces parvulus;Manumycin A, Ras farnesyltransferase inhibitor;Manumycin A, Streptomyces parvulus - CAS 52665-74-4 - Calbiochem
CBNumber
CB1103133
Molecular Formula
C31H38N2O7
Formula Weight
550.64
MOL File
52665-74-4.mol
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MANUMYCIN A Property

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.
InChIKey
TWWQHCKLTXDWBD-MVTGTTCWSA-N
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Safety

WGK Germany 
3
HS Code 
2941900000
Storage Class
11 - Combustible Solids
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P337+P313IF eye irritation persists: Get medical advice/attention.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
M6418
Product name
Manumycin A from Streptomyces parvulus
Packaging
5mg
Price
$803
Updated
2025/07/31
Cayman Chemical
Product number
10010497
Product name
Manumycin A
Purity
≥98%
Packaging
1mg
Price
$111
Updated
2024/03/01
Cayman Chemical
Product number
10010497
Product name
Manumycin A
Purity
≥98%
Packaging
5mg
Price
$412
Updated
2024/03/01
TRC
Product number
M186000
Product name
Manumycin A,
Packaging
0.5mg
Price
$225
Updated
2021/12/16
Usbiological
Product number
207273
Product name
Manumycin A
Packaging
1mg
Price
$325
Updated
2021/12/16
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MANUMYCIN A Chemical Properties,Usage,Production

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.

in vivo

Manumycin A (5 mg/kg; once every two days; 2 weeks; i.p.) has anti-tumor effect in triple negative breast cancer mice[3]. Manumycin A (3 μg; once; i.m.) can correct abnormal splicing of Clcn1 in type 1 myotonic dystrophy (DM1) mice[5].

Animal Model:Female nude mice with breast cancer transplanted with MDAMB-231 cells[3].
Dosage:5 mg/kg
Administration:Intraperitoneal injection (i.p.); Once every two days; 2 weeks
Result:Inhibited tumor growth and increased levels of ER stress markers such as Bip, CHOP, LC3, and p62 proteins, as well as higher molecular weight ubiquitinated proteins.
Animal Model:HSALR transgenic mice[5].
Dosage:3 μg
Administration:Intramuscular injection (i.m.); once
Result:Reduced the content of Clcn1 exon 7A introns.

References

[1] M HARA. Identification of Ras farnesyltransferase inhibitors by microbial screening.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1993, 90 6: 2281-2285. DOI:10.1073/pnas.90.6.2281
[2] A DI PAOLO. Manumycin inhibits ras signal transduction pathway and induces apoptosis in COLO320-DM human colon tumourcells[J]. British Journal of Cancer, 2000, 82 4: 905-912. DOI:10.1054/bjoc.1999.1018
[3] CHRISTOPH ARENZ DIPL.-CHEM. Manumycin A and Its Analogues Are Irreversible Inhibitors of Neutral Sphingomyelinase[J]. ChemBioChem, 2001, 2 2: 141-143. DOI:10.1002/1439-7633(20010202)2:2<141::aid-cbic141>3.0.co;2-p
[4] VIVEK SHARMA. Farnesyltransferase inhibitor manumycin targets IL1β-Ras-HIF-1α axis in tumor cells of diverse origin.[J]. Inflammation, 2012, 35 2: 516-519. DOI:10.1007/s10753-011-9340-6
[5] BANISHREE SAHA  Dipankar N. Farnesyltransferase inhibitors reduce ras activation and ameliorate acetaminophen-induced liver injury in mice†[J]. Hepatology, 2009, 50 5: 1547-1557. DOI:10.1002/hep.23180
[6] P K SINGHA. Manumycin A inhibits triple-negative breast cancer growth through LC3-mediated cytoplasmic vacuolation death[J]. Cell Death & Disease, 2013, 4 1: e457-e457. DOI:10.1038/cddis.2012.192

MANUMYCIN A Preparation Products And Raw materials

Raw materials

Preparation Products

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MANUMYCIN A Suppliers

China 85 Europe 1 Japan 2 Switzerland 2 United Kingdom 5 United States 18 USA 1 Global 114
J & K SCIENTIFIC LTD.
Tel
18210857532; 18210857532
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
sales@meilune.com
Country
China
ProdList
4765
Advantage
58
Shanghai Tauto Biotech Co., Ltd.
Tel
021-51320588
Fax
0086-21-51320502
Email
tauto@tautobiotech.com
Country
China
ProdList
3988
Advantage
66
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4720
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55
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51395
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80
Shanghai EFE Biological Technology Co., Ltd.
Tel
021-65675885 18964387627
Fax
021-65675885
Email
info@efebio.com
Country
China
ProdList
9803
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58
Beijing Jin Ming Biotechnology Co., Ltd.
Tel
010-60605840 18892239720
Fax
010-60605840
Email
psaitong@jm-bio.com
Country
China
ProdList
12306
Advantage
58
Lynnchem
Tel
86-(0)29-85992781 17792393971
Email
info@lynnchem.com
Country
China
ProdList
4587
Advantage
58
Novachemistry
Tel
44-20819178-90 02081917890
Fax
(0)2080432064
Email
info@novachemistry.com
Country
United Kingdom
ProdList
4381
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58
Fan De(Beijing) Biotechnology Co., Ltd.
Tel
15911056312
Email
liming@bio-fount.com
Country
China
ProdList
9729
Advantage
58

52665-74-4, MANUMYCIN ARelated Search:

POLYGODIAL OUABAIN OCTAHYDRATE Cantharidin Mupirocin manumycin G manumycin E manumycin F MANUMYCIN A

  • 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
  • Manumycin A, Streptomyces parvulus - CAS 52665-74-4 - Calbiochem
  • 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)-
  • Chiromycin A
  • Manumycin A, Ras farnesyltransferase inhibitor
  • Manumycin A, <i>Streptomyces parvulus</i>
  • 52665-74-4
  • Cell Signaling and Neuroscience
  • Cell Biology
  • BioChemical
  • Post-translational Modification
  • G Proteins and Cyclic Nucleotides
  • G Protein Function
  • Farnesyl transferase, RasG Proteins and Cyclic Nucleotides
  • D to
  • Enzyme Inhibitors by Enzyme
  • G Protein Function
  • Post-translational Modification