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M6418

Sigma-Aldrich

Manumycin A from Streptomyces parvulus

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About This Item

Formule empirique (notation de Hill):
C31H38N2O7
Numéro CAS:
52665-74-4
Poids moléculaire :
550.64
Numéro MDL:
MFCD00920782
Code UNSPSC :
12352200
ID de substance PubChem :
24897011
Nomenclature NACRES :
NA.32

Pureté

≥97% (HPLC)

Niveau de qualité

200

Forme

powder

Solubilité

methanol: 9.80-10.20 mg/mL, clear, yellow to very deep yellow

Température de stockage

2-8°C

Chaîne SMILES 

CCCC[C@@H](C)\C=C(C)\C=C(/C)C(=O)NC1=C[C@@](O)(\C=C\C=C\C=C\C(=O)NC2=C(O)CCC2=O)[C@@H]3O[C@H]3C1=O

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

Clé InChI

TWWQHCKLTXDWBD-YCWSEAROSA-N

Application

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.

Actions biochimiques/physiologiques

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.
Potent inhibitor of Ras farnesyltransferase.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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P K Singha et al.
Cell death & disease, 4, e457-e457 (2013-01-19)
Therapy resistance can be attributed to acquisition of anti-apoptotic mechanisms by the cancer cells. Therefore, developing approaches that trigger non-apoptotic cell death in cancer cells to compensate for apoptosis resistance will help to treat cancer effectively. Triple-negative breast cancers (TNBC)
William Stein et al.
The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation, 30(7), 761-769 (2011-04-05)
In this study we systematically dissect the prenylation pathway to better define the mechanism behind statin inhibition in chronic allograft rejection in heart transplants, or transplant coronary artery disease (TCAD). Utilizing a murine heterotopic heart transplant model, animals received daily
Qingming Xiong et al.
Journal of medical microbiology, 60(Pt 6), 744-749 (2011-02-26)
Anaplasma phagocytophilum is an obligately intracellular bacterium and is the causative agent of human granulocytic anaplasmosis (HGA), an emerging and major tick-borne disease in the USA and other parts of the world. This study showed that the prenylation inhibitor manumycin
Binding of manumycin A inhibits IkappaB kinase beta activity
Bernier M, et al.
Test, 281(5), 2551-2561 (2006)
M Hara et al.
Proceedings of the National Academy of Sciences of the United States of America, 90(6), 2281-2285 (1993-03-15)
A microbial screen using a yeast strain with conditional deficiency in the GPA1 gene was carried out to search for inhibitors of protein farnesyltransferase (PFT). A strain of Streptomyces was found to produce active compounds named UCF1-A, UCF1-B, and UCF1-C.
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Oncogenes and Tumor Suppressors Reprogram Metabolism

We present an article about how proliferating cells require the biosynthesis of structural components for biomass production and for genomic replication.

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