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363057

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:
Molecular Weight:
165.15
Beilstein:
645384
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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

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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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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
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
Sunny D Gilbert et al.
Structure (London, England : 1993), 17(6), 857-868 (2009-06-16)
Purine riboswitches discriminate between guanine and adenine by at least 10,000-fold based on the identity of a single pyrimidine (Y74) that forms a Watson-Crick base pair with the ligand. To understand how this high degree of specificity for closely related
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;

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