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M9440

Sigma-Aldrich

Methyl-3,4-dephostatin

>98% (HPLC), powder

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Synonym(s):
3,4-Dihydroxy-N-methyl-N-nitrosoaniline
Empirical Formula (Hill Notation):
C7H8N2O3
Molecular Weight:
168.15
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

>98% (HPLC)

form

powder

color

red-brown

solubility

DMSO: soluble 18 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

CN(N=O)c1ccc(O)c(O)c1

InChI

1S/C7H8N2O3/c1-9(8-12)5-2-3-6(10)7(11)4-5/h2-4,10-11H,1H3

InChI key

XAKAQCMEMMZUEO-UHFFFAOYSA-N

Gene Information

human ... PTPN1(5770)

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M9440

Methyl-3,4-dephostatin

vibrant-m

E1904

Ethyl-3,4-dephostatin

vibrant-m

SML1887

APX2009

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SML2883

Paquinimod

assay

>98% (HPLC)

assay

>99% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

form

solid

form

powder

form

powder

color

red-brown

color

brown

color

white to beige

color

white to beige

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: soluble 18 mg/mL, H2O: insoluble

solubility

DMSO: soluble 22 mg/mL, H2O: soluble 8 mg/mL

solubility

DMSO: 10 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

Application

Methyl-3,4-dephostatin has been used as:
  • an inhibitor for methyltransferases
  • a kinase-related inhibitor for human transglutaminase
  • a cysteine binding compound for screening its effect on C-terminal domain (CTD) of human immunodeficiency virus (HIV-1) capsid protein

Biochem/physiol Actions

Methyl-3,4-dephostatin is a tyrphostin-related compound isolated from Streptomyces MJ742-NF5 strain. It favors nerve growth factor-based neurite formation in pheochromocytoma PC12 cells. Being a stable analog of the nitrosoaniline dephostatin, it can mimic phosphotyrosine substrate for Tyrosyl-DNA phosphodiesterase I (TdpI).
Stable analog of dephostatin; selective protein tyrosine phosphatase 1B and SHPTP-1 inhibitor; does not inhibit CD45-associated phosphatases.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Ebselen, a small-molecule capsid inhibitor of HIV-1 replication
Thenin-Houssier S, et al.
Antimicrobial Agents and Chemotherapy, 60(4), 2195-2208 (2016)
A high throughput scintillation proximity imaging assay for protein methyltransferases
Ibanez G, et al.
Combinatorial Chemistry & High Throughput Screening, 15(5), 359-371 (2012)
Thung-S Lai et al.
Chemistry & biology, 15(9), 969-978 (2008-09-23)
Human tissue transglutaminase (TGM2) is a calcium-dependent crosslinking enzyme involved in the posttranslational modification of intra- and extracellular proteins and implicated in several neurodegenerative diseases. To find specific inhibitors to TGM2, two structurally diverse chemical libraries (LOPAC and Prestwick) were
S Fujiwara et al.
Biochemical and biophysical research communications, 238(1), 213-217 (1997-09-23)
We studied the effect of the 3,4-dihydroxy analogue of dephostatin (3,4-dephostatin), an inhibitor of protein-tyrosine phosphatase (PTPase), on the differentiation of rat pheochromocytoma PC12 cells. 3,4-Dephostatin accelerated NGF-induced neurite formation in PC12h cells, a subline of PC12 cells, whereas the
Christophe Marchand et al.
Molecular cancer therapeutics, 8(1), 240-248 (2009-01-14)
Tyrosyl-DNA phosphodiesterase I (Tdp1) resolves topoisomerase I (Top1)-DNA adducts accumulated from natural DNA damage as well as from the action of certain anticancer drugs. Tdp1 catalyzes the hydrolysis of the phosphodiester bond between the catalytic tyrosine residue of topoisomerase I

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