WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 112127
CAS#: 168701-80-2
Description: 8-Nitroguanine is a nitrative guanine derivative formed by oxidative damage to the guanine base in DNA by reactive nitrogen species (RNS). It is mutagenic and induces G:C to T:A transversion in DNA.
MedKoo Cat#: 112127
Name: 8-Nitroguanine
CAS#: 168701-80-2
Chemical Formula: C5H4N6O3
Exact Mass: 196.0345
Molecular Weight: 196.13
Elemental Analysis: C, 30.62; H, 2.06; N, 42.85; O, 24.47
Synonym: 8-Nitroguanine; 8Nitroguanine; 8 Nitroguanine
IUPAC/Chemical Name: 2-amino-8-nitro-1,7-dihydro-6H-purin-6-one
InChi Key: IYHJRKNFFYAOGE-UHFFFAOYSA-N
InChi Code: InChI=1S/C5H4N6O3/c6-4-8-2-1(3(12)10-4)7-5(9-2)11(13)14/h(H4,6,7,8,9,10,12)
SMILES Code: O=C1C2=C(N=C(N1)N)N=C(N2)[N+]([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: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
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
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| 1 M NaOH | 50.0 | 254.93 |
The following data is based on the product molecular weight 196.13 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.
| 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 |
1: Ohshima H, Sawa T, Akaike T. 8-nitroguanine, a product of nitrative DNA damage caused by reactive nitrogen species: formation, occurrence, and implications in inflammation and carcinogenesis. Antioxid Redox Signal. 2006 May-Jun;8(5-6):1033-45. doi: 10.1089/ars.2006.8.1033. PMID: 16771693.
2: Alexander KJ, McConville M, Williams KR, Luzyanin KV, O'Neil IA, Cosstick R. Chemistry of the 8-Nitroguanine DNA Lesion: Reactivity, Labelling and Repair. Chemistry. 2018 Feb 26;24(12):3013-3020. doi: 10.1002/chem.201705541. Epub 2018 Feb 5. PMID: 29314291.
3: Horiike S, Kawanishi S, Kaito M, Ma N, Tanaka H, Fujita N, Iwasa M, Kobayashi Y, Hiraku Y, Oikawa S, Murata M, Wang J, Semba R, Watanabe S, Adachi Y. Accumulation of 8-nitroguanine in the liver of patients with chronic hepatitis C. J Hepatol. 2005 Sep;43(3):403-10. doi: 10.1016/j.jhep.2005.03.026. PMID: 16023246.
4: Hoki Y, Murata M, Hiraku Y, Ma N, Matsumine A, Uchida A, Kawanishi S. 8-Nitroguanine as a potential biomarker for progression of malignant fibrous histiocytoma, a model of inflammation-related cancer. Oncol Rep. 2007 Nov;18(5):1165-9. PMID: 17914567.
5: Hu CW, Chang YJ, Chen JL, Hsu YW, Chao MR. Sensitive Detection of 8-Nitroguanine in DNA by Chemical Derivatization Coupled with Online Solid-Phase Extraction LC-MS/MS. Molecules. 2018 Mar 8;23(3):605. doi: 10.3390/molecules23030605. PMID: 29517997; PMCID: PMC6017919.
6: Ma N, Tagawa T, Hiraku Y, Murata M, Ding X, Kawanishi S. 8-Nitroguanine formation in oral leukoplakia, a premalignant lesion. Nitric Oxide. 2006 Mar;14(2):137-43. doi: 10.1016/j.niox.2005.09.012. Epub 2005 Nov 14. PMID: 16290060.
7: Hiraku Y, Kawanishi S. Immunohistochemical analysis of 8-nitroguanine, a nitrative DNA lesion, in relation to inflammation-associated carcinogenesis. Methods Mol Biol. 2009;512:3-13. doi: 10.1007/978-1-60327-530-9_1. PMID: 19347269.
8: Pinlaor S, Yongvanit P, Hiraku Y, Ma N, Semba R, Oikawa S, Murata M, Sripa B, Sithithaworn P, Kawanishi S. 8-nitroguanine formation in the liver of hamsters infected with Opisthorchis viverrini. Biochem Biophys Res Commun. 2003 Sep 26;309(3):567-71. doi: 10.1016/j.bbrc.2003.08.039. PMID: 12963027.
9: Sawa T, Tatemichi M, Akaike T, Barbin A, Ohshima H. Analysis of urinary 8-nitroguanine, a marker of nitrative nucleic acid damage, by high-performance liquid chromatography-electrochemical detection coupled with immunoaffinity purification: association with cigarette smoking. Free Radic Biol Med. 2006 Feb 15;40(4):711-20. doi: 10.1016/j.freeradbiomed.2005.09.035. Epub 2005 Oct 21. PMID: 16458202.
10: Piao F, Li S, Li Q, Ye J, Liu S. Abnormal expression of 8-nitroguanine in the brain of mice exposed to arsenic subchronically. Ind Health. 2011;49(2):151-7. doi: 10.2486/indhealth.ms1058. Epub 2010 Dec 16. PMID: 21173536.
11: Ma N, Adachi Y, Hiraku Y, Horiki N, Horiike S, Imoto I, Pinlaor S, Murata M, Semba R, Kawanishi S. Accumulation of 8-nitroguanine in human gastric epithelium induced by Helicobacter pylori infection. Biochem Biophys Res Commun. 2004 Jun 25;319(2):506-10. doi: 10.1016/j.bbrc.2004.04.193. PMID: 15178435.
12: Hiraku Y. Formation of 8-nitroguanine, a nitrative DNA lesion, in inflammation-related carcinogenesis and its significance. Environ Health Prev Med. 2010 Mar;15(2):63-72. doi: 10.1007/s12199-009-0118-5. Epub 2009 Nov 19. PMID: 19921494; PMCID: PMC2824100.
13: Yermilov V, Rubio J, Ohshima H. Formation of 8-nitroguanine in DNA treated with peroxynitrite in vitro and its rapid removal from DNA by depurination. FEBS Lett. 1995 Dec 4;376(3):207-10. doi: 10.1016/0014-5793(95)01281-6. PMID: 7498543.
14: Hiraku Y, Sakai K, Shibata E, Kamijima M, Hisanaga N, Ma N, Kawanishi S, Murata M. Formation of the nitrative DNA lesion 8-nitroguanine is associated with asbestos contents in human lung tissues: a pilot study. J Occup Health. 2014;56(3):186-96. doi: 10.1539/joh.13-0231-oa. Epub 2014 Mar 4. PMID: 24598051.
