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
MDL number:
UNSPSC Code:
12352200
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)
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 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
Regulatory Information
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A high throughput scintillation proximity imaging assay for protein methyltransferases
Ibanez G, et al.
Combinatorial Chemistry & High Throughput Screening, 15(5), 359-371 (2012)
Ebselen, a small-molecule capsid inhibitor of HIV-1 replication
Thenin-Houssier S, et al.
Antimicrobial Agents and Chemotherapy, 60(4), 2195-2208 (2016)
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
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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