SML1761
AA-CW236
≥98% (HPLC)
Synonym(s):
4-(2-(5-(Chloromethyl)-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazol-1-yl)ethyl)-3,5-dimethylisoxazole
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About This Item
Empirical Formula (Hill Notation):
C17H16ClF3N4O2
CAS Number:
Molecular Weight:
400.78
UNSPSC Code:
12352200
NACRES:
NA.77
InChI
1S/C17H16ClF3N4O2/c1-10-14(11(2)27-23-10)7-8-25-15(9-18)16(22-24-25)12-3-5-13(6-4-12)26-17(19,20)21/h3-6H,7-9H2,1-2H3
InChI key
MPDMMSRZEHOFPA-UHFFFAOYSA-N
SMILES string
CC1=C(CCN2N=NC(C3=CC=C(OC(F)(F)F)C=C3)=C2CCl)C(C)=NO1
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 25 mg/mL protein, clear
storage temp.
2-8°C
Quality Level
Related Categories
Application
AA-CW236 has been used as an inhibitor of m6G DNA methyltransferase in mouse embryo fibroblasts.
Biochem/physiol Actions
AA-CW236 is a cell-permeable chloromethyl triazole (CMT) derivative that acts as a non-pseudosubstrate inhibitor against human O(6)-alkylguanine DNA methyltransferase (MGMT) by targeting MGMT active site Cys145 for covalent modification (KI = 24 nM, kinact = 0.03/min), displaying little affinity toward cysteines from other cellular proteins. AA-CW236 pretreatment (1 μM) effectively prevents MGMT from repairing DNA damage, causing significantly more upregulated O6-alkylguanine accumulation than the pseudosubstrate inhibitor Lomeguatrib (1 μM) when co-administered with the DNA-alkylating agent Temozolomide/TMZ (300 μM) in MCF-7 cells. Likewise, AA-CW236 is shown to boost TMZ toxicity in Caco-2 cultures (IC50 = 227 and 673 μM, respectively, with or without 3 μM AA-CW236 co-treatment).
AA-CW236 is a cell-permeable chloromethyl triazole (CMT) derivative that acts as a non-pseudosubstrate inhibitor against human O(6)-alkylguanine DNA methyltransferase (MGMT).
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Pennapa Thongararm et al.
Chemical research in toxicology, 33(2), 625-633 (2019-12-17)
DNA methylating agents are abundant in the environment and are sometimes used in cancer chemotherapy. They react with DNA to form methyl-DNA adducts and byproduct lesions that can be both toxic and mutagenic. Foremost among the mutagenic lesions is O6-methylguanine
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