Daminozide
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MedKoo CAT#: 326738

CAS#: 1596-84-5

Description: Daminozide is a plant growth regulator, a chemical sprayed on fruit to regulate their growth, make their harvest easier, and keep apples from falling off the trees before they are ripe. This makes sure they are red and firm for storage. Alar was first approved for use in the U.S. in 1963, it was primarily used on apples until 1989 when it was voluntarily withdrawn by the manufacturer after the U.S. Environmental Protection Agency proposed banning it based on concerns about cancer risks to consumers.


Chemical Structure

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Daminozide
CAS# 1596-84-5

Theoretical Analysis

MedKoo Cat#: 326738
Name: Daminozide
CAS#: 1596-84-5
Chemical Formula: C6H12N2O3
Exact Mass: 160.0848
Molecular Weight: 160.173
Elemental Analysis: C, 44.99; H, 7.55; N, 17.49; O, 29.97

Price and Availability

Size Price Availability Quantity
500.0mg USD 70.0 2 Weeks
1.0g USD 120.0 2 Weeks
2.0g USD 190.0 2 Weeks
5.0g USD 350.0 2 Weeks
10.0g USD 550.0 2 Weeks
20.0g USD 850.0 2 Weeks
50.0g USD 1250.0 2 Weeks
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Synonym: Aminozide; B 995; DIMG; DMASA; Kylar SADH; Succinic Acid; Daminozide.

IUPAC/Chemical Name: 4-(2,2-dimethylhydrazinyl)-4-oxobutanoic acid

InChi Key: NOQGZXFMHARMLW-UHFFFAOYSA-N

InChi Code: InChI=1S/C6H12N2O3/c1-8(2)7-5(9)3-4-6(10)11/h3-4H2,1-2H3,(H,7,9)(H,10,11)

SMILES Code: OC(CCC(NN(C)C)=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: Daminozide, a plant growth regulator, is a selective inhibitor of the human KDM2/7 histone demethylases, with IC50s of 0.55, 1.5 and 2.1 μM for PHF8, KDM2A, and KIAA1718, respectively.
In vitro activity: A formaldehyde dehydrogenase (FDH) coupled assay monitoring formaldehyde production confirmed the potency of daminozide against KDM2A (IC50 = 1.5±0.4 μM). To test further for subfamily selectivity, daminozide was screened against two other members of the KDM2/7 subfamily (PHF8 and KIAA1718, Table 1). The results indicate that daminozide is at least 100-fold selective as an inhibitor of the KDM2/7 subfamily over the other demethylase subfamily members tested, with IC50s of 2 μM or less against KDM2A, PHF8, and KIAA1718 and IC50s of 127 μM for KDM3A (a different subfamily of dimethyl lysine demethylase) or greater (mM range) against other demethylases (Table 1). No inhibition was observed (at 1 mM) against other biologically important 2OG oxygenases that catalyse hydroxylation, i.e. PHD2, FIH and BBOX1. Given its simple achiral structure and low molecular weight (160 Da), the degree of selectivity exhibited by daminozide is remarkable. The results do suggest a potential of daminozide or its derivatives to exert biological effects via the inhibition of 2OG oxygenases involved in epigenetics in animals and, potentially, in other organisms including plants Reference: J Med Chem. 2012 Jul 26; 55(14): 6639–6643. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4673902/
In vivo activity: The aim of the present work was to demonstrate the effect of Alar (Daminozide) on several life history traits, adult morphology, Hsp70 protein expression and in vivo DNA damage in the brain of the model organism Drosophila melanogaster. Alar treated flies exhibit a significant delay in pupation time and adult emergence time (p=0.003 and <0.0001 respectively in One-way ANOVA) in all experimental conditions than do the controls.A significant reduction in pupation height was obsereved in Alar treated flies (0.4μ0.2 cm.) in contrast to the control (4.0μ0.04 cm) in 400 ppm Alar medium. Similar results were obtained in other experimental conditions too (Table 2). Additionally, a significant reduction (p=0.0009 in One-way ANOVA) in mean daily egg production was recoreded in Alar treated groups with a span of over 20 days (Tables–3; Figure 3). Egg to adult survival rate was also decreased significantly in treated groups when compared to control (Tables 2–3; Figure 3). Larvae exposed to H2O2 (positive control) and to different concentrations of Alar (400, 10 000, 20 000 ppm) showed a significant increase in DNA damage in the cells of cerebral ganglia (Table 6). This observation unambiguously revealed that Alar is a neurotoxicant causing neurodegeneration in the cells of cerebral ganglia of treated larvae. Reference: nterdiscip Toxicol. 2018 May;11(1):27-37. https://pubmed.ncbi.nlm.nih.gov/30181710/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 41.0 255.97

Preparing Stock Solutions

The following data is based on the product molecular weight 160.173 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Rose NR, Woon EC, Tumber A, Walport LJ, Chowdhury R, Li XS, King ON, Lejeune C, Ng SS, Krojer T, Chan MC, Rydzik AM, Hopkinson RJ, Che KH, Daniel M, Strain-Damerell C, Gileadi C, Kochan G, Leung IK, Dunford J, Yeoh KK, Ratcliffe PJ, BurgessBrown N, von Delft F, Muller S, Marsden B, Brennan PE, McDonough MA, Oppermann U, Klose RJ, Schofield CJ, Kawamura A. Plant growth regulator daminozide is a selective inhibitor of human KDM2/7 histone demethylases. J Med Chem. 2012 Jul 26;55(14):6639-43. doi: 10.1021/jm300677j. Epub 2012 Jul 11. PMID: 22724510; PMCID: PMC4673902. 2. Chen JY, Li CF, Chu PY, Lai YS, Chen CH, Jiang SS, Hou MF, Hung WC. Lysine demethylase 2A promotes stemness and angiogenesis of breast cancer by upregulating Jagged1. Oncotarget. 2016 May 10;7(19):27689-710. doi: 10.18632/oncotarget.8381. PMID: 27029061; PMCID: PMC5053681. 3. Roy SS, Begum M, Ghosh S. Exploration of teratogenic and genotoxic effects of fruit ripening retardant Alar (Daminozide) on model organism Drosophila melanogaster. Interdiscip Toxicol. 2018 May;11(1):27-37. doi: 10.2478/intox-2018-0004. Epub 2018 Aug 6. PMID: 30181710; PMCID: PMC6117819. 4. National Toxicology Program. Bioassay of daminozide for possible carcinogenicity. Natl Cancer Inst Carcinog Tech Rep Ser. 1978;83:1-131. PMID: 12830215.
In vitro protocol: 1. Rose NR, Woon EC, Tumber A, Walport LJ, Chowdhury R, Li XS, King ON, Lejeune C, Ng SS, Krojer T, Chan MC, Rydzik AM, Hopkinson RJ, Che KH, Daniel M, Strain-Damerell C, Gileadi C, Kochan G, Leung IK, Dunford J, Yeoh KK, Ratcliffe PJ, BurgessBrown N, von Delft F, Muller S, Marsden B, Brennan PE, McDonough MA, Oppermann U, Klose RJ, Schofield CJ, Kawamura A. Plant growth regulator daminozide is a selective inhibitor of human KDM2/7 histone demethylases. J Med Chem. 2012 Jul 26;55(14):6639-43. doi: 10.1021/jm300677j. Epub 2012 Jul 11. PMID: 22724510; PMCID: PMC4673902. 2. Chen JY, Li CF, Chu PY, Lai YS, Chen CH, Jiang SS, Hou MF, Hung WC. Lysine demethylase 2A promotes stemness and angiogenesis of breast cancer by upregulating Jagged1. Oncotarget. 2016 May 10;7(19):27689-710. doi: 10.18632/oncotarget.8381. PMID: 27029061; PMCID: PMC5053681.
In vivo protocol: 1.. Roy SS, Begum M, Ghosh S. Exploration of teratogenic and genotoxic effects of fruit ripening retardant Alar (Daminozide) on model organism Drosophila melanogaster. Interdiscip Toxicol. 2018 May;11(1):27-37. doi: 10.2478/intox-2018-0004. Epub 2018 Aug 6. PMID: 30181710; PMCID: PMC6117819. 2. National Toxicology Program. Bioassay of daminozide for possible carcinogenicity. Natl Cancer Inst Carcinog Tech Rep Ser. 1978;83:1-131. PMID: 12830215.

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