Methylene blue trihydrateAn inhibitor of cGMP-mediated processes and guanylyl cyclase, a useful stain, and a redox indicator

Methylene blue trihydrate (CAS 7220-79-3)

Methylene blue trihydrate | CAS 7220-79-3 is rated 5.0 out of 5 by 1.
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Synonym: C.I. Basic Blue 9, trihydrate (8CI); Methylthionine chloride
Application: An inhibitor of cGMP-mediated processes and guanylyl cyclase, a useful stain, and a redox indicator
CAS Number: 7220-79-3
Molecular Weight: 373.90
Molecular Formula: C16H18N3S•Cl•3H2O
* Refer to Certificate of Analysis for lot specific data (including water content).
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Methylene Blue acts as a GCS (guanylyl cyclase) inhibitor, biological stain and redox indicator. Methylene Blue inhibits tau filament formation. Additionally, Methylene Blue is also reported to inhibit NOSs (nitric oxide synthase). Methylene Blue is widely used to inhibit cGMP-mediated processes. Methylene Blue has been observed to dose-dependently induce cytotoxicity in U-373 MG human astrocytoma and SK-N-MC human neuroblastoma cells. Furthermore Methylene Blue is reported to bind to the M2 subtype of muscarinic receptors in rat cardiac myocytes, and thus exhibit antimuscarinic effects on IK, ACh and ICa. Methylene Blue has also been reported to inhibit endothelium-dependent relaxation of isolated blood vessels.


References

1. Mayer, B., et al. 1993. Biochem. Pharmacol. 45: 367-374. PMID: 7679577
2. Mayer, B., et al. 1993. Eur. Heart J. 14: 22-26. PMID: 7507438
3. Lee, Y.S., et al. 1995. Cancer Lett. 88: 141-145. PMID: 7874686
4. Abi-Gerges, N., et al. 1997. Mol. Pharmacol. 52: 482-490. PMID: 9281611
5. González, M.C., et al. 1998. Brain Res. Bull. 46: 229-231. PMID: 9667816

Appearance :
Crystalline powder
Physical State :
Solid
Solubility :
Soluble in water (50 mg/ml), ethanol (70 mg/ml), alcohol, and chloroform. Insoluble in ether.
Storage :
Store at room temperature
Melting Point :
190° C
IC50 :
Plasmodium falciparum: IC50 = 5.4 nM; Glutathione reductase: IC50 = 6.4 µM (Plasmodium falciparum 3D7); Apaf-1: IC50 = 15.5 µM (human); Glutathione reductase: IC50 = 16 µM (human)
pK Values :
pKb: 4.89 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
SP5740000
PubChem CID :
104827
Merck Index :
14: 6060
MDL Number :
MFCD00150008
EC Number :
200-515-2
Beilstein Registry :
3599847
SMILES :
CN(C)C1=CC2=C(C=C1)N=C3C=CC(=[N+](C)C)C=C3S2.O.O.O.[Cl-]

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Methylene blue trihydrate  Product Citations

See how others have used Methylene blue trihydrate. Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 12750356  Pivarcsi, A. et al. 2003. Int Immunol. 15: 721-730.

PMID: # 12679308  Simmons, R. et al. 2003. Ann. Surg. Oncol. 10: 242-247.

PMID: # 9443418  Sheng, H. et al. 1998. Cancer Res. 58: 362-366.

Citations 1 to 3 of 3 total
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Rated 5 out of 5 by from Lee et al Lee et al. (PubMed ID 7874686) found that the guanylyl cyclase inhibitor, methylene blue (MB), activated cytotoxicity in human brain tumor cells.
Date published: 2015-06-17
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