Daminozide - CAS 1596-84-5
Catalog number: 1596-84-5
Category: Inhibitor
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Molecular Formula:
C6H12N2O3
Molecular Weight:
160.17
COA:
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Targets:
Others
Description:
Daminozide is a highly selective inhibitor of the human 2-oxoglutarate (JmjC) histone demethylases KDM2A, PHF8, and KDM7A with IC50 values of 1.5, 0.55, and 2.1 μM, respectively. When tested for inhibition of other demethylase subfamily members (KDM3, KDM4, KDM5, KDM6) and other 2OG oxygenases (FIH, PHD2, BBOX1), daminozide was considerably less potent (IC50s > 100 μM). Daminozide is known to retard plant growth and was widely used in the 1960s for agricultural and horticultural applications to control plant size and fruit ripening before it was withdrawn because of carcinogenicity concerns.
Purity:
>98%
Synonyms:
Alar; B 995; DMASA; SADH; Succinic Acid; Aminozide; Kylar; DIMG
MSDS:
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InChIKey:
NOQGZXFMHARMLW-UHFFFAOYSA-N
InChI:
InChI=1S/C6H12N2O3/c1-8(2)7-5(9)3-4-6(10)11/h3-4H2,1-2H3,(H,7,9)(H,10,11)
Canonical SMILES:
CN(C)NC(=O)CCC(=O)O
1. Inhibition of 2-oxoglutarate dependent oxygenases
Nathan R. Rose, Michael A. McDonough, Christopher J. Schofield*. Chem. Soc. Rev., 2011, 40, 4364–4397
The small molecule daminozide, or succinyl N,N-dimethyl hydrazide, was identified, together with maleyl N,N-dimethyl hydrazide (Fig. 8b), as a growth retardant when applied to plant foliage. The analogous phthalic acid derivatives were inactive as growth retardants. The maleic acid derivative was later shown to decompose in aqueous solution by intramolecular reaction, leading to the subsequent use of the succinic acid derivative, daminozide, in agricultural applications. The mechanism of action of daminozide was later shown to be, at least in part, inhibition of gibberellin biosynthesis as demonstrated by the ability of the compound to inhibit3β-hydroxylation of GA9 to GA4 in cell free extracts. Daminozide was used in agriculture, particularly to control pre-harvest ripening of apples, until concerns about its possible carcinogenicity led to its withdrawal from use, though it continues to find use in the cultivation of ornamental plants. Prohexadione and daminozide also inhibit flavanone 3β-hydroxylase, and likely inhibit other 2OG oxygenases as well.
2. Small-molecular modulators of cancer-associated epigenetic mechanisms
Yukihiro Itoh, Takayoshi Suzuki* and Naoki Miyata*. Mol. BioSyst., 2013, 9, 873-896
All of the JHDM inhibitors reported so far show competitive inhibition with the cofactor 2-oxoglutarate through binding to the catalytic iron in the active site (Fig. 9). Three simple compounds, N-oxalylglycine (NOG, 48), a-hydroxyglutarate (49) and daminozide (50), have been reported as JHDM inhibitors and several analogues, such as compound 51, have also been reported. In addition, 2,4-pyridinedicarboxylic acid (PCA, 52) and compound 53, pyridine derivatives, were reported to be potent inhibitors of KDM4A or KDM4E. All of the above-mentioned inhibitors have a structure that can chelate the iron ion in the catalytic site (Fig. 9). However, they are unlikely to be useful for cellular and animal assays because of their poor pharmacokinetics, low activity or poor selectivity among JHDM isozymes.
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CAS 1596-84-5 Daminozide

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