8-Nitroguanine

• CAT Number: R002299
• CAS Number: 168701-80-2
• Molecular Formula: C5H4N6O3
• Molecular Weight: 196.126
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: 2-amino-8-nitro-3,7-dihydropurin-6-one
• InChI: 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)
• InChIKey: IYHJRKNFFYAOGE-UHFFFAOYSA-N
• SMILES: C12=C(NC(=NC1=O)N)N=C(N2)[N+](=O)[O-]

8-Nitroguanine (CAS 168701-80-2) is a nitrative guanine derivative formed by oxidative damage to the guanine base in DNA by reactive nitrogen species (RNS) during inflammation and in vitro by reaction of DNA with peroxynitrite and other RNS reagents.It is mutagenic and induces G:C to T:A transversion in DNA. Incorporation of 8-nitroguanine as an 8-nitroG:anti-G base pair into a primer template stalls human DNA polymerase β and induces a 2:1 preference for deoxyadenosine (dA) insertion over deoxycytosine (dC). 8-Nitroguanine levels are increased in the lung tissue of mice with conditional expression of mutant K-Ras(G12V) that developed lung adenocarcinoma and in the lung tissue and peripheral lymphocyte DNA of cigarette smoke-exposed rats. 

 

Reference

1.Hiraku, Yusuke. "Formation of 8-nitroguanine, a nitrative DNA lesion, in inflammation-related carcinogenesis and its significance." Environmental health and preventive medicine 15.2 (2010): 63-72.
2.Ohshima, Hiroshi, Tomohiro Sawa, and Takaaki Akaike. "8-nitroguanine, a product of nitrative DNA damage caused by reactive nitrogen species: formation, occurrence, and implications in inflammation and carcinogenesis." Antioxidants & redox signaling 8.5-6 (2006): 1033-1045.
3.Bhamra, Inder, et al. "Base-pairing preferences, physicochemical properties and mutational behaviour of the DNA lesion 8-nitroguanine." Nucleic acids research 40.21 (2012): 11126-11138.
4.Ohnishi, Shiho, et al. "Nitrative and oxidative DNA damage caused by K-ras mutation in mice." Biochemical and biophysical research communications 413.2 (2011): 236-240.
5.Hsieh, Yih-Shou, et al. "Formation of 8-nitroguanine in tobacco cigarette smokers and in tobacco smoke-exposed Wistar rats." Chemico-biological interactions 140.1 (2002): 67-80.