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M6418

Manumycin A

Name: Manumycin A
Brand: SIGMA

from Streptomyces parvulus, ≥97% (HPLC), Ras farnesyltransferase inhibitor, powder

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About This Item

Empirical Formula (Hill Notation):

C₃₁H₃₈N₂O₇

CAS Number:

52665-74-4

Molecular Weight:

550.64

UNSPSC Code:

12352200

PubChem Substance ID:

24897011

NACRES:

NA.32

MDL number:

MFCD00920782

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Properties

Product Name

Manumycin A from Streptomyces parvulus,

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

Description

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

0000419116

0000138489

0000218760

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Binding of manumycin A inhibits IkappaB kinase beta activity

Bernier M, et al.

Test, 281(5), 2551-2561 (2006)

Identification of Ras farnesyltransferase inhibitors by microbial screening.

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.

Reversal of age-dependent nuclear morphology by inhibition of prenylation does not affect lifespan in Caenorhabditis elegans.

Daniel Z Bar et al.

Nucleus (Austin, Tex.), 1(6), 499-505 (2011-02-18)

Fibroblasts derived from Hutchinson-Gilford progeria syndrome (HGPS) patients and dermal cells derived from healthy old humans in culture display age-dependent progressive changes in nuclear architecture due to accumulation of farnesylated lamin A. Treating human HGPS cells or mice expressing farnesylated

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Global Trade Item Number

SKU	GTIN
M6418-5MG	04061833026502