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SML0586

Sigma-Aldrich

Lomeguatrib

≥98% (HPLC)

Synonym(s):

2-Amino-6-[(4-bromo-2-thienyl)methoxy]-9H-purine, O6-(4-bromothenyl)guanine

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About This Item

Empirical Formula (Hill Notation):
C10H8BrN5OS
CAS Number:
192441-08-0
Molecular Weight:
326.17
MDL number:
MFCD23703756
UNSPSC Code:
12352200
PubChem Substance ID:
329825566
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

room temp

SMILES string

Nc1nc(OCc2cc(Br)cs2)c3nc[nH]c3n1

InChI

1S/C10H8BrN5OS/c11-5-1-6(18-3-5)2-17-9-7-8(14-4-13-7)15-10(12)16-9/h1,3-4H,2H2,(H3,12,13,14,15,16)

InChI key

JUJPKFNFCWJBCX-UHFFFAOYSA-N

Biochem/physiol Actions

Lomeguatrib is a highly potent inactivator of O(6)-methylguanine-DNA methyltransferase (MGMT), a DNA repair protein which can confer resistance to some cancer chemotherapeutics, in particular the DNA alkylating agents such as Temozolomide, DTIC, Carmustine, etc. Lomeguatrib is a highly potent inactivator of MGMT and can be used to further investigate mechanisms of resistance. It is a potent irreversible inactivator of all mammalian O6-alkylguanine-DNA-alkyltransferases, so far tested with nanomolar activity in vitro and in vivo.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Kritsanawan Sae-Khow et al.
International journal of molecular sciences, 24(12) (2023-06-28)
The O6-methylguanine-DNA methyltransferase (MGMT) is a DNA suicide repair enzyme that might be important during sepsis but has never been explored. Then, the proteomic analysis of lipopolysaccharide (LPS)-stimulated wild-type (WT) macrophages increased proteasome proteins and reduced oxidative phosphorylation proteins compared
A Sabharwal et al.
Cancer chemotherapy and pharmacology, 66(5), 829-835 (2009-12-30)
Expression of the DNA repair protein O (6)-methylguanine-DNA methyltransferase (MGMT) correlates with resistance to irinotecan in colorectal cancer cell lines. This phase I study evaluated the maximum tolerated dose (MTD) of lomeguatrib, an inactivating pseudosubstrate of MGMT, in combination with
Patrizia Caporaso et al.
DNA repair, 6(8), 1179-1186 (2007-05-15)
Previous studies indicated that dacarbazine and Temozolomide could be highly effective against refractory acute leukaemia. Their activity relies mainly on the generation of methyl adducts at the O(6)-position of guanine in DNA. High levels of O(6)-methylguanine-DNA methyltransferase (MGMT) or a
O A Khan et al.
British journal of cancer, 98(10), 1614-1618 (2008-05-14)
To evaluate the tumour response to lomeguatrib and temozolomide (TMZ) administered for 5 consecutive days every 4 weeks in patients with metastatic colorectal carcinoma. Patients with stage IV metastatic colorectal carcinoma received lomeguatrib (40 mg) and TMZ (50-200 mg m(-2))
Malcolm Ranson et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 25(18), 2540-2545 (2007-06-20)
To evaluate tumor response, pharmacodynamic effects, and safety of a combination of lomeguatrib (LM), an O6-methylguanine DNA-methyltransferase (MGMT) inactivator, and temozolomide (TMZ), TMZ alone, and LM/TMZ after disease progression on TMZ alone in patients with advanced melanoma. Patients with unresectable
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