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M9440

Sigma-Aldrich

Methyl-3,4-dephostatin

>98% (HPLC), powder

Synonyma:

3,4-Dihydroxy-N-methyl-N-nitrosoaniline

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About This Item

Empirický vzorec (Hillův zápis):
C7H8N2O3
Číslo CAS:
173043-84-0
Molekulová hmotnost:
168.15
MDL number:
MFCD01076450
UNSPSC Code:
12352200
PubChem Substance ID:
24278575
NACRES:
NA.77

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)

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
T Watanabe et al.
The Journal of antibiotics, 48(12), 1460-1466 (1995-12-01)
We have synthesized derivatives of dephostatin, a protein tyrosine phosphatase (PTPase) inhibitor, to study the structure-activity relationships of this inhibitor. Inactive analogs revealed some insight into structural requirements or PTPase inhibitory activity of dephostatin. Both a nitroso group and phenolic
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