M9440
Methyl-3,4-dephostatin
>98% (HPLC), powder
Synonym(s):
3,4-Dihydroxy-N-methyl-N-nitrosoaniline
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About This Item
Empirical Formula (Hill Notation):
C7H8N2O3
CAS Number:
Molecular Weight:
168.15
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Product Name
Methyl-3,4-dephostatin, >98% (HPLC), powder
InChI key
XAKAQCMEMMZUEO-UHFFFAOYSA-N
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
assay
>98% (HPLC)
form
powder
color
red-brown
solubility
DMSO: soluble 18 mg/mL
H2O: insoluble
storage temp.
2-8°C
Quality Level
Gene Information
human ... PTPN1(5770)
Related Categories
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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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
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
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
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