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Sigma-Aldrich

6-O-Methylguanine

97%

Synonym(s):

2-Amino-6-methoxypurine, 6-Methoxyguanine

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About This Item

Empirical Formula (Hill Notation):
C6H7N5O
CAS Number:
20535-83-5
Molecular Weight:
165.15
Beilstein:
645384
MDL number:
MFCD00133009
UNSPSC Code:
12352100
PubChem Substance ID:
24862349
NACRES:
NA.22

Assay

97%

mp

>300 °C (lit.)

SMILES string

COc1nc(N)nc2[nH]cnc12

InChI

1S/C6H7N5O/c1-12-5-3-4(9-2-8-3)10-6(7)11-5/h2H,1H3,(H3,7,8,9,10,11)

InChI key

BXJHWYVXLGLDMZ-UHFFFAOYSA-N

Gene Information

human ... CDK2(1017) , MGMT(4255)

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General description

6-O-Methylguanine is a purine derivative and its binding affinity has been examined by B. subtilis xpt-pbuX guanine riboswitch (GR) using isothermal titration calorimetry (ITC). 6-O-Methylguanine is formed during the alkylation of a number of purified tRNA preparations, via reaction with the carcinogens, N-methyl-N-nitrosourea .

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Jihong Zhang et al.
Current molecular pharmacology, 5(1), 102-114 (2011-11-30)
Glioblastoma multiforme is the most common aggressive adult primary tumour of the central nervous system. Treatment includes surgery, radiotherapy and adjuvant temozolomide (TMZ) chemotherapy. TMZ is an alkylating agent prodrug, delivering a methyl group to purine bases of DNA (O6-guanine;
Sharon E Murphy et al.
Cancer prevention research (Philadelphia, Pa.), 4(11), 1752-1760 (2011-10-27)
Nicotine replacement therapy is often used to maintain smoking cessation. However, concerns exist about the safety of long-term nicotine replacement therapy use in ex-smokers and its concurrent use in smokers. In this study, we determined the effect of nicotine administration
Chiung-Wen Hu et al.
Analytical and bioanalytical chemistry, 402(3), 1199-1208 (2011-11-19)
Since methylation at the N-7 and O(6) positions of guanine and the N-3 position of adenine in DNA are the predominant reaction sites, N(7)-methylguanine (N(7)-MeG), O(6)-methylguanine (O(6)-MeG), and N(3)-methyladenine (N(3)-MeA) have been suggested as good biomarkers for assessing exposure to
V V Lylo et al.
TSitologiia i genetika, 45(6), 53-60 (2012-02-15)
The aim of our study was to investigate the effect of recombinant human cytokine EMAP II (endothelial monocyte-activating polypeptide II) on the expression of MGMT gene, encoding repair enzyme O6-methylguanine-DNA methyltransferase (MGMT) in human cell cultures. The influence of EMAP
Alkylation of transfer RNA by N-methyl-N-nitrosourea and N-ethyl-N-nitrosourea.
A E Pegg
Chemico-biological interactions, 6(6), 393-406 (1973-06-01)
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