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M6418

Sigma-Aldrich

Manumycin A from Streptomyces parvulus

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About This Item

Empirical Formula (Hill Notation):
C31H38N2O7
CAS Number:
52665-74-4
Molecular Weight:
550.64
MDL number:
MFCD00920782
UNSPSC Code:
12352200
PubChem Substance ID:
24897011
NACRES:
NA.32

Assay

≥97% (HPLC)

Quality Level

200

form

powder

solubility

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

storage temp.

2-8°C

SMILES string

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

InChI key

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.

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.
Potent inhibitor of Ras farnesyltransferase.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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.
Binding of manumycin A inhibits IkappaB kinase beta activity
Bernier M, et al.
Test, 281(5), 2551-2561 (2006)
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
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