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M9948

Sigma-Aldrich

Mirin

≥98% (HPLC), powder

Synonym(s):

5-(4-Hydroxybenzylidene)-2-iminothiazolidin-4-one

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About This Item

Empirical Formula (Hill Notation):
C10H8N2O2S
CAS Number:
299953-00-7
Molecular Weight:
220.25
MDL number:
MFCD05885480
UNSPSC Code:
12352200
PubChem Substance ID:
329818100
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

red to orange

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

NC1=NC(=O)C(\S1)=C\c2ccc(O)cc2

InChI

1S/C10H8N2O2S/c11-10-12-9(14)8(15-10)5-6-1-3-7(13)4-2-6/h1-5,13H,(H2,11,12,14)/b8-5-

InChI key

YBHQCJILTOVLHD-YVMONPNESA-N

Gene Information

human ... MRE11A(4361)

Application

Mirin has been used:
  • as a small molecule inhibitor of meiotic recombination 11 (MRE11), in the pre-treatment of HCT116 wildtype cells before irradiation
  • as Mre11 inhibitior in BSC-1 cells infected with simian virus 40
  • in the pre-treatment of W12E cells for quantification of human papilloma virus (HPV) episome levels and to potentiate the effect of polyamide-25 (PA-25)

Biochem/physiol Actions

Mirin causes cell cycle arrest at G1 phase. Mirin sensitizes virus to antiviral polyamides (AVP). In human papilloma virus (HPV) episomes, mirin promotes damage by forming double stranded DNA breaks. It aids in reducing the inhibitory concentration (IC50s) of AVP.
Mirin is an inhibitor of the Mre11-Rad50-Nbs1 complex. It disrupts nuclease activity of Mre11 and thus, the ability to repair DNA double strand breaks.

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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J-Y Wang et al.
Oncogene, 35(13), 1657-1670 (2015-06-23)
DNA repair is critical for the maintenance of genome stability. Upon genotoxic stress, dysregulated DNA repair may induce apoptosis. Translin-associated factor X (TRAX), which was initially identified as a binding partner of Translin, has been implicated in genome stability. However
Antiviral activity of pyrrole-imidazole polyamides against SV40 and BK polyomaviruses
Edwards TG and Fisher C
Antiviral Research, 152(4), 68-75 (2018)
AKT overactivation can suppress DNA repair via p70S6 kinase-dependent downregulation of MRE11
Piscitello D, et al.
Oncogene, 37(4), 427-427 (2018)
DNA damage repair genes controlling human papillomavirus (HPV) episome levels under conditions of stability and extreme instability
Edwards TG, et al.
PLoS ONE, 8(10), e75406-e75406 (2013)
M Petroni et al.
Cell death and differentiation, 23(2), 197-206 (2015-06-13)
The MRE11/RAD50/NBS1 (MRN) complex is a major sensor of DNA double strand breaks, whose role in controlling faithful DNA replication and preventing replication stress is also emerging. Inactivation of the MRN complex invariably leads to developmental and/or degenerative neuronal defects
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