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MedKoo Cat#: 540182 | Name: Glycidamide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Glycidamide is a carcinogen and metabolite of acrylamide that induces DNA adduct formation and mutations.

Chemical Structure

Glycidamide
Glycidamide
CAS#5694-00-8

Theoretical Analysis

MedKoo Cat#: 540182

Name: Glycidamide

CAS#: 5694-00-8

Chemical Formula: C3H5NO2

Exact Mass: 87.0320

Molecular Weight: 87.08

Elemental Analysis: C, 41.38; H, 5.79; N, 16.09; O, 36.75

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Synonym
Glycidamide; HSDB 7804; HSDB7804; HSDB-7804; LS-1386; LS1386; LS 1386
IUPAC/Chemical Name
oxirane-2-carboxamide
InChi Key
FMAZQSYXRGRESX-UHFFFAOYSA-N
InChi Code
InChI=1S/C3H5NO2/c4-3(5)2-1-6-2/h2H,1H2,(H2,4,5)
SMILES Code
O=C(C1OC1)N
Appearance
Solid powder
Purity
>97% (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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Glycidamide is a carcinogen and metabolite of acrylamide that induces DNA adduct formation and mutations.
In vitro activity:
Therefore, 1 μM of GA (glycidamide) was chosen to determine the migratory abilities of the GA-treated prostate cancer cells using a migration transwell assay. As shown in Figure 1C–D, the migratory abilities significantly increased by about by 3-fold, 2-fold, and 2.5-fold in GA-treated LNCap, DU145 and PC3, respectively. Taken together, these results showed that GA promotes cell growth and migration and contributes to malignant phenotypes of prostate cancer cells. Reference: Int J Mol Sci. 2019 May 4;20(9):2199. https://pubmed.ncbi.nlm.nih.gov/31060254/
In vivo activity:
Drinking water administration of glycidamide to F334/N rats resulted in a dose-related increase in brain gliosis in both sexes (Table 4). In male rats, the incidence of gliosis was increased in the 0.70 mM glycidamide dose group, while in female rats the incidence was increased at 0.175, 0.35, and 0.70 mM glycidamide. Male F344/N rats also had glycidamide-related increases in hepatocyte degeneration and necrosis in the liver. Additional non-neoplastic lesions associated with glycidamide exposure in female F344/N rats included axonal degeneration of the spinal cord and uterine endometrial hyperplasia. Reference: Food Chem Toxicol. 2015 Dec;86:104-15. https://pubmed.ncbi.nlm.nih.gov/26429628/

Preparing Stock Solutions

The following data is based on the product molecular weight 87.08 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. Ekanem TI, Huang CC, Wu MH, Lin DY, Lai WT, Lee KH. Glycidamide Promotes the Growth and Migratory Ability of Prostate Cancer Cells by Changing the Protein Expression of Cell Cycle Regulators and Epithelial-to-Mesenchymal Transition (EMT)-Associated Proteins with Prognostic Relevance. Int J Mol Sci. 2019 May 4;20(9):2199. doi: 10.3390/ijms20092199. PMID: 31060254; PMCID: PMC6540322. 2. Lauvås AJ, Lislien M, Holme JA, Dirven H, Paulsen RE, Alm IM, Andersen JM, Skarpen E, Sørensen V, Macko P, Pistollato F, Duale N, Myhre O. Developmental neurotoxicity of acrylamide and its metabolite glycidamide in a human mixed culture of neurons and astrocytes undergoing differentiation in concentrations relevant for human exposure. Neurotoxicology. 2022 Jul 11;92:33-48. doi: 10.1016/j.neuro.2022.07.001. Epub ahead of print. PMID: 35835329. 3. Aras D, Cakar Z, Ozkavukcu S, Can A, Cinar O. In Vivo acrylamide exposure may cause severe toxicity to mouse oocytes through its metabolite glycidamide. PLoS One. 2017 Feb 9;12(2):e0172026. doi: 10.1371/journal.pone.0172026. PMID: 28182799; PMCID: PMC5300229. 4. Beland FA, Olson GR, Mendoza MC, Marques MM, Doerge DR. Carcinogenicity of glycidamide in B6C3F1 mice and F344/N rats from a two-year drinking water exposure. Food Chem Toxicol. 2015 Dec;86:104-15. doi: 10.1016/j.fct.2015.09.017. Epub 2015 Sep 30. PMID: 26429628; PMCID: PMC5066397.
In vitro protocol:
1. Ekanem TI, Huang CC, Wu MH, Lin DY, Lai WT, Lee KH. Glycidamide Promotes the Growth and Migratory Ability of Prostate Cancer Cells by Changing the Protein Expression of Cell Cycle Regulators and Epithelial-to-Mesenchymal Transition (EMT)-Associated Proteins with Prognostic Relevance. Int J Mol Sci. 2019 May 4;20(9):2199. doi: 10.3390/ijms20092199. PMID: 31060254; PMCID: PMC6540322. 2. Lauvås AJ, Lislien M, Holme JA, Dirven H, Paulsen RE, Alm IM, Andersen JM, Skarpen E, Sørensen V, Macko P, Pistollato F, Duale N, Myhre O. Developmental neurotoxicity of acrylamide and its metabolite glycidamide in a human mixed culture of neurons and astrocytes undergoing differentiation in concentrations relevant for human exposure. Neurotoxicology. 2022 Jul 11;92:33-48. doi: 10.1016/j.neuro.2022.07.001. Epub ahead of print. PMID: 35835329.
In vivo protocol:
1. Aras D, Cakar Z, Ozkavukcu S, Can A, Cinar O. In Vivo acrylamide exposure may cause severe toxicity to mouse oocytes through its metabolite glycidamide. PLoS One. 2017 Feb 9;12(2):e0172026. doi: 10.1371/journal.pone.0172026. PMID: 28182799; PMCID: PMC5300229. 2. Beland FA, Olson GR, Mendoza MC, Marques MM, Doerge DR. Carcinogenicity of glycidamide in B6C3F1 mice and F344/N rats from a two-year drinking water exposure. Food Chem Toxicol. 2015 Dec;86:104-15. doi: 10.1016/j.fct.2015.09.017. Epub 2015 Sep 30. PMID: 26429628; PMCID: PMC5066397.
1: Wang ET, Chen DY, Liu HY, Yan HY, Yuan Y. Protective effect of allicin against glycidamide-induced toxicity in male and female mice. Gen Physiol Biophys. 2015 Apr;34(2):177-87. doi: 10.4149/gpb_2014038. Epub 2015 Mar 2. PubMed PMID: 25730897. 2: Beland FA, Olson GR, Mendoza MC, Marques MM, Doerge DR. Carcinogenicity of glycidamide in B6C3F1 mice and F344/N rats from a two-year drinking water exposure. Food Chem Toxicol. 2015 Dec;86:104-15. doi: 10.1016/j.fct.2015.09.017. Epub 2015 Sep 30. PubMed PMID: 26429628; PubMed Central PMCID: PMC5066397. 3: Fennell TR, Snyder R, Hansen B, Friedman M. Dosimetry of Acrylamide and Glycidamide Over the Lifespan in a 2-Year Bioassay of Acrylamide in Wistar Han Rats. Toxicol Sci. 2015 Aug;146(2):386-94. doi: 10.1093/toxsci/kfv104. Epub 2015 Jul 3. PubMed PMID: 26141391; PubMed Central PMCID: PMC4517054. 4: Gutzkow KB, Duale N, Danielsen T, von Stedingk H, Shahzadi S, Instanes C, Olsen AK, Steffensen IL, Hofer T, Törnqvist M, Brunborg G, Lindeman B. Enhanced susceptibility of obese mice to glycidamide-induced sperm chromatin damage without increased oxidative stress. Andrology. 2016 Nov;4(6):1102-1114. doi: 10.1111/andr.12233. Epub 2016 Aug 30. PubMed PMID: 27575329. 5: Luo YS, Long TY, Shen LC, Huang SL, Chiang SY, Wu KY. Synthesis, characterization and analysis of the acrylamide- and glycidamide-glutathione conjugates. Chem Biol Interact. 2015 Jul 25;237:38-46. doi: 10.1016/j.cbi.2015.05.002. Epub 2015 May 15. PubMed PMID: 25980586. 6: Von Tungeln LS, Doerge DR, Gamboa da Costa G, Matilde Marques M, Witt WM, Koturbash I, Pogribny IP, Beland FA. Tumorigenicity of acrylamide and its metabolite glycidamide in the neonatal mouse bioassay. Int J Cancer. 2012 Nov 1;131(9):2008-15. doi: 10.1002/ijc.27493. Epub 2012 Mar 28. PubMed PMID: 22336951; PubMed Central PMCID: PMC4810677. 7: Kim TH, Shin S, Kim KB, Seo WS, Shin JC, Choi JH, Weon KY, Joo SH, Jeong SW, Shin BS. Determination of acrylamide and glycidamide in various biological matrices by liquid chromatography-tandem mass spectrometry and its application to a pharmacokinetic study. Talanta. 2015 Jan;131:46-54. doi: 10.1016/j.talanta.2014.07.042. Epub 2014 Jul 24. PubMed PMID: 25281071. 8: de Lima JP, Silva SN, Rueff J, Pingarilho M. Glycidamide genotoxicity modulated by Caspases genes polymorphisms. Toxicol In Vitro. 2016 Aug;34:123-7. doi: 10.1016/j.tiv.2016.03.018. Epub 2016 Apr 5. PubMed PMID: 27062911. 9: Manjanatha MG, Guo LW, Shelton SD, Doerge DR. Acrylamide-induced carcinogenicity in mouse lung involves mutagenicity: cII gene mutations in the lung of big blue mice exposed to acrylamide and glycidamide for up to 4 weeks. Environ Mol Mutagen. 2015 Jun;56(5):446-56. doi: 10.1002/em.21939. Epub 2015 Jan 29. PubMed PMID: 25639614. 10: Obón-Santacana M, Freisling H, Peeters PH, Lujan-Barroso L, Ferrari P, Boutron-Ruault MC, Mesrine S, Baglietto L, Turzanski-Fortner R, Katzke VA, Boeing H, Quirós JR, Molina-Portillo E, Larrañaga N, Chirlaque MD, Barricarte A, Khaw KT, Wareham N, Travis RC, Merritt MA, Gunter MJ, Trichopoulou A, Lagiou P, Naska A, Palli D, Sieri S, Tumino R, Fiano V, Galassom R, Bueno-de-Mesquita HB, Onland-Moret NC, Idahl A, Lundin E, Weiderpass E, Vesper H, Riboli E, Duell EJ. Acrylamide and glycidamide hemoglobin adduct levels and endometrial cancer risk: A nested case-control study in nonsmoking postmenopausal women from the EPIC cohort. Int J Cancer. 2016 Mar 1;138(5):1129-38. doi: 10.1002/ijc.29853. Epub 2015 Oct 1. PubMed PMID: 26376083; PubMed Central PMCID: PMC4716289. 11: Obón-Santacana M, Lujan-Barroso L, Travis RC, Freisling H, Ferrari P, Severi G, Baglietto L, Boutron-Ruault MC, Fortner RT, Ose J, Boeing H, Menéndez V, Sánchez-Cantalejo E, Chamosa S, Castaño JM, Ardanaz E, Khaw KT, Wareham N, Merritt MA, Gunter MJ, Trichopoulou A, Papatesta EM, Klinaki E, Saieva C, Tagliabue G, Tumino R, Sacerdote C, Mattiello A, Bueno-de-Mesquita HB, Peeters PH, Onland-Moret NC, Idahl A, Lundin E, Weiderpass E, Vesper HW, Riboli E, Duell EJ. Acrylamide and Glycidamide Hemoglobin Adducts and Epithelial Ovarian Cancer: A Nested Case-Control Study in Nonsmoking Postmenopausal Women from the EPIC Cohort. Cancer Epidemiol Biomarkers Prev. 2016 Jan;25(1):127-34. doi: 10.1158/1055-9965.EPI-15-0822. Epub 2015 Nov 23. PubMed PMID: 26598536. 12: Pingarilho M, Oliveira NG, Martins C, Gomes BC, Fernandes AS, Martins V, Labilloy A, de Lima JP, Rueff J, Gaspar JF. Induction of sister chromatid exchange by acrylamide and glycidamide in human lymphocytes: role of polymorphisms in detoxification and DNA-repair genes in the genotoxicity of glycidamide. Mutat Res. 2013 Apr 15;752(1-2):1-7. doi: 10.1016/j.mrgentox.2012.12.013. Epub 2013 Jan 31. PubMed PMID: 23376767. 13: Feng CH, Lu CY. Modification of major plasma proteins by acrylamide and glycidamide: Preliminary screening by nano liquid chromatography with tandem mass spectrometry. Anal Chim Acta. 2011 Jan 17;684(1-2):80-6. doi: 10.1016/j.aca.2010.10.042. Epub 2010 Nov 9. PubMed PMID: 21167989. 14: von Stedingk H, Vikström AC, Rydberg P, Pedersen M, Nielsen JK, Segerbäck D, Knudsen LE, Törnqvist M. Analysis of hemoglobin adducts from acrylamide, glycidamide, and ethylene oxide in paired mother/cord blood samples from Denmark. Chem Res Toxicol. 2011 Nov 21;24(11):1957-65. doi: 10.1021/tx200284u. Epub 2011 Sep 15. PubMed PMID: 21882862. 15: Li M, Sun J, Zou F, Bai S, Jiang X, Jiao R, Ou S, Zhang H, Su Z, Huang Y, Bai W. Glycidamide inhibits progesterone production through reactive oxygen species-induced apoptosis in R2C Rat Leydig Cells. Food Chem Toxicol. 2016 Oct 28. pii: S0278-6915(16)30342-8. doi: 10.1016/j.fct.2016.09.035. [Epub ahead of print] PubMed PMID: 27984162. 16: Bandarra S, Fernandes AS, Magro I, Guerreiro PS, Pingarilho M, Churchwell MI, Gil OM, Batinic-Haberle I, Gonçalves S, Rueff J, Miranda JP, Marques MM, Beland FA, Castro M, Gaspar JF, Oliveira NG. Mechanistic insights into the cytotoxicity and genotoxicity induced by glycidamide in human mammary cells. Mutagenesis. 2013 Nov;28(6):721-9. doi: 10.1093/mutage/get052. Erratum in: Mutagenesis. 2014 Jan;29(1):97. PubMed PMID: 24150595. 17: Ehlers A, Lenze D, Broll H, Zagon J, Hummel M, Lampen A. Dose dependent molecular effects of acrylamide and glycidamide in human cancer cell lines and human primary hepatocytes. Toxicol Lett. 2013 Feb 27;217(2):111-20. doi: 10.1016/j.toxlet.2012.12.017. Epub 2012 Dec 31. PubMed PMID: 23287710. 18: Hemgesberg MN, Bonck T, Merz KH, Sun Y, Schrenk D. Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acryl-amide. Acta Crystallogr E Crystallogr Commun. 2016 Jul 22;72(Pt 8):1179-82. doi: 10.1107/S2056989016010859. eCollection 2016 Aug 1. PubMed PMID: 27536408; PubMed Central PMCID: PMC4971867. 19: Costa LG, Deng H, Calleman CJ, Bergmark E. Evaluation of the neurotoxicity of glycidamide, an epoxide metabolite of acrylamide: behavioral, neurochemical and morphological studies. Toxicology. 1995 Apr 12;98(1-3):151-61. PubMed PMID: 7740544. 20: Watzek N, Scherbl D, Schug M, Hengstler JG, Baum M, Habermeyer M, Richling E, Eisenbrand G. Toxicokinetics of acrylamide in primary rat hepatocytes: coupling to glutathione is faster than conversion to glycidamide. Arch Toxicol. 2013 Aug;87(8):1545-56. doi: 10.1007/s00204-013-1054-0. Epub 2013 Apr 9. PubMed PMID: 23568512.

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