Mirin
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MedKoo CAT#: 407310

CAS#: 1198097-97-0

Description: Mirin is a Mre11-Rad50-Nbs1 (MRN)-ATM pathway inhibitor.

Chemical Structure

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Mirin
CAS# 1198097-97-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 407310
Name: Mirin
CAS#: 1198097-97-0
Chemical Formula: C10H8N2O2
Exact Mass: 220.03
Molecular Weight: 220.246
Elemental Analysis: C, 54.53; H, 3.66; N, 12.72; O, 14.53; S, 14.56

Price and Availability

Size Price Availability Quantity
10mg USD 90 Ready to ship
25mg USD 180 Ready to ship
50mg USD 300 Ready to ship
100mg USD 500 Ready to ship
200mg USD 750 Ready to ship
500mg USD 1550 Ready to ship
1g USD 2650 Ready to ship
2g USD 3850 Ready to ship
5g USD 6250 2 weeks
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Synonym: Mirin

IUPAC/Chemical Name: Z-5-(4-Hydroxybenzylidene)-2-imino-1,3-thiazolidin-4-one

InChi Key: YBHQCJILTOVLHD-YVMONPNESA-N

InChi Code: 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-

SMILES Code: O=C1NC(S/C1=C\C2=CC=C(O)C=C2)=N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Mirin is a small-molecule inhibitor of MRN (Mre11, Rad50, and Nbs1) complex.
In vitro activity: Consistently, mirin induced accumulation of 53BP1 nuclear bodies, a known marker of replication-associated DNA damage, and DNA DSBs, in MNA but not MNSC cells (Fig. 3a, b). Furthermore, it induced H2AX and p53 phosphorylation in all MNA but not in MNSC cells (Fig. 3c), indicating the activation of a DDR. Early accumulation of DNA damage and DDR ended up in apoptotic cell death in MNA but not MNSC cells, as indicated by the trypan blue exclusion assay, expression of the cleaved forms of PARP1 and Caspase-3 and TUNEL staining (Fig. 3c, d). Reference: Cell Death Dis. 2018 Sep; 9(9): 895. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6117286/
In vivo activity: As an alternative approach the study used the small molecule inhibitor mirin, which inhibits nuclease activity of MRE11 and prevents MRN-dependent signal amplification in somatic cells. Treatment of prophase I arrested GV-stage mouse oocytes with 100 µM mirin for 1 h did not affect the number of γH2AX/MDC1 foci (Fig. 4C-D), whereas when DNA damage was induced by NCS (neocarzinostatin) in the presence of mirin the number of γH2AX/MDC1 foci was significantly reduced compared to NCS only (Fig. 4C-E). Inhibition of MRE11 during meiotic maturation by mirin substantially decreased the amount of chromatin-associated phosphorylated H2AX and MDC1 binding in MI oocytes (Fig. 4C-F), followed by the increase in γH2AX foci number on metaphase II chromosomes (Fig. 4C-D). The number of MII eggs with at least one γH2AX focus was highly increased after mirin treatment during meiotic maturation (Fig. 4G). Reference: Cell Cycle. 2016; 15(4): 546–558. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5056612/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 31.8 144.18
DMF 30.0 136.21
Ethanol 0.3 1.14

Preparing Stock Solutions

The following data is based on the product molecular weight 220.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Jividen K, Kedzierska KZ, Yang CS, Szlachta K, Ratan A, Paschal BM. Genomic analysis of DNA repair genes and androgen signaling in prostate cancer. BMC Cancer. 2018 Oct 10;18(1):960. doi: 10.1186/s12885-018-4848-x. PMID: 30305041; PMCID: PMC6180441. 2. Petroni M, Sardina F, Infante P, Bartolazzi A, Locatelli E, Fabretti F, Di Giulio S, Capalbo C, Cardinali B, Coppa A, Tessitore A, Colicchia V, Sahùn Roncero M, Belardinilli F, Di Marcotullio L, Soddu S, Comes Franchini M, Petricci E, Gulino A, Giannini G. MRE11 inhibition highlights a replication stress-dependent vulnerability of MYCN-driven tumors. Cell Death Dis. 2018 Aug 30;9(9):895. doi: 10.1038/s41419-018-0924-z. PMID: 30166519; PMCID: PMC6117286. 3. Mayer A, Baran V, Sakakibara Y, Brzakova A, Ferencova I, Motlik J, Kitajima TS, Schultz RM, Solc P. DNA damage response during mouse oocyte maturation. Cell Cycle. 2016;15(4):546-58. doi: 10.1080/15384101.2015.1128592. Epub 2016 Jan 8. PMID: 26745237; PMCID: PMC5056612. 4. Rozier L, Guo Y, Peterson S, Sato M, Baer R, Gautier J, Mao Y. The MRN-CtIP pathway is required for metaphase chromosome alignment. Mol Cell. 2013 Mar 28;49(6):1097-107. doi: 10.1016/j.molcel.2013.01.023. Epub 2013 Feb 21. PMID: 23434370; PMCID: PMC3615147.
In vitro protocol: 1. Jividen K, Kedzierska KZ, Yang CS, Szlachta K, Ratan A, Paschal BM. Genomic analysis of DNA repair genes and androgen signaling in prostate cancer. BMC Cancer. 2018 Oct 10;18(1):960. doi: 10.1186/s12885-018-4848-x. PMID: 30305041; PMCID: PMC6180441. 2. Petroni M, Sardina F, Infante P, Bartolazzi A, Locatelli E, Fabretti F, Di Giulio S, Capalbo C, Cardinali B, Coppa A, Tessitore A, Colicchia V, Sahùn Roncero M, Belardinilli F, Di Marcotullio L, Soddu S, Comes Franchini M, Petricci E, Gulino A, Giannini G. MRE11 inhibition highlights a replication stress-dependent vulnerability of MYCN-driven tumors. Cell Death Dis. 2018 Aug 30;9(9):895. doi: 10.1038/s41419-018-0924-z. PMID: 30166519; PMCID: PMC6117286.
In vivo protocol: 1. Mayer A, Baran V, Sakakibara Y, Brzakova A, Ferencova I, Motlik J, Kitajima TS, Schultz RM, Solc P. DNA damage response during mouse oocyte maturation. Cell Cycle. 2016;15(4):546-58. doi: 10.1080/15384101.2015.1128592. Epub 2016 Jan 8. PMID: 26745237; PMCID: PMC5056612. 2. Rozier L, Guo Y, Peterson S, Sato M, Baer R, Gautier J, Mao Y. The MRN-CtIP pathway is required for metaphase chromosome alignment. Mol Cell. 2013 Mar 28;49(6):1097-107. doi: 10.1016/j.molcel.2013.01.023. Epub 2013 Feb 21. PMID: 23434370; PMCID: PMC3615147.

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1: Garner KM, Pletnev AA, Eastman A. Corrected structure of mirin, a
small-molecule inhibitor of the Mre11-Rad50-Nbs1 complex. Nat Chem Biol. 2009
Mar;5(3):129-30; author reply 130. doi: 10.1038/nchembio0309-129. PubMed PMID:
19219009; PubMed Central PMCID: PMC3881006.