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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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N R Jena et al.
Physical biology, 8(4), 046007-046007 (2011-06-15)
Methylated guanine damage at O6 position (i.e. O6MG) is dangerous due to its mutagenic and carcinogenic character that often gives rise to G:C-A:T mutation. However, the reason for this mutagenicity is not known precisely and has been a matter of
Anna V Knizhnik et al.
PloS one, 8(1), e55665-e55665 (2013-02-06)
Apoptosis, autophagy, necrosis and cellular senescence are key responses of cells that were exposed to genotoxicants. The types of DNA damage triggering these responses and their interrelationship are largely unknown. Here we studied these responses in glioma cells treated with
Takeshi Chihara et al.
Asian Pacific journal of cancer prevention : APJCP, 11(5), 1301-1304 (2011-01-05)
The scavenging capacity of reactive oxygen species, such as hydroxyl radicals, is reported not to decrease in boiled garlic (an odorless garlic preparation). We therefore examined the modifying effect of boiled garlic powder (BGP) on 1,2-dimethylhydrazine-induced mucin-depleted foci (MDF) and
J Vanden Bussche et al.
Journal of chromatography. A, 1257, 25-33 (2012-08-28)
O⁶-methylguanine (O⁶-MeG) and O⁶-carboxymethylguanine (O⁶-CMG) are characteristic promutagenic and toxic DNA adducts formed by nitrosated glycine derivates and N-nitrosopeptides. Since endogenous nitrosation has been hypothesised as a plausible origin for the association between red and processed meat intake and colorectal
Delia Chavarria et al.
Journal of molecular biology, 412(3), 325-339 (2011-08-09)
O(6)-methylguanine (O(6)-MeG) is a miscoding DNA lesion arising from the alkylation of guanine. This report uses the bacteriophage T4 DNA polymerase as a model to probe the roles of hydrogen-bonding interactions, shape/size, and nucleobase desolvation during the replication of this
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