Methylene-blue

An organic cation that is phenothiazin-5-ium substituted by dimethylamino groups at positions 3 and 7. The chloride salt is the histological dye 'methylene blue'. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator (E-numbers for permitted antioxidant food additives are from E 300 to E 324). It inhibits guanylate cyclase, and has been used to treat cyanide poisoning and to lower levels of methemoglobin. Methylthioninium chloride (INN, or methylene blue, proposed trade name Rember) is an investigational drug being developed by the University of Aberdeen and TauRx Therapeutics that has been shown in early clinical trials to be an inhibitor of Tau protein aggregation. The drug is of potential interest for the treatment of patients with Alzheimer's disease

General

Type : Dye, Drug, Phenothiazine, anti-tau-aggregation, Multitarget, Sulfur Compound

Chemical_Nomenclature : [7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium

Canonical SMILES : CN(C)C1=CC2=C(C=C1)N=C3C=CC(=[N+](C)C)C=C3S2.[Cl-]

InChI : InChI=1S\/C16H18N3S.ClH\/c1-18(2)11-5-7-13-15(9-11)20-16-10-12(19(3)4)6-8-14(16)17-13\;\/h5-10H,1-4H3\;1H\/q+1\;\/p-1

InChIKey : RBTBFTRPCNLSDE-UHFFFAOYSA-N || CXKWCBBOMKCUKX-UHFFFAOYSA-M

Other name(s) : Methylene Blue cation  ||  3,7-bis(dimethylamino)phenothiazin-5-ium  ||  UNII-ZMZ79891ZH  ||  CHEMBL191083  ||  ZMZ79891ZH  ||  CHEBI:43830  ||  MBT  ||  Methylene blue  ||  Basic blue 9  ||  Swiss Blue  ||  Chromosmon  ||  Methylthioninium chloride  ||  Methylene Blue N


MW : 284.39

Formula : C16H18N3S

CAS_number : 61-73-4

PubChem : 4139,    6099

UniChem : RBTBFTRPCNLSDE-UHFFFAOYSA-N,    CXKWCBBOMKCUKX-UHFFFAOYSA-M

Wikipedia : Methylene_blue

Target

Families : Methylene-blue ligand of proteins in family
ACHE BCHE

Structure :
5E4T 5DLP

Protein :
torca-ACHE

References (14)

Title : The interactions of azure B, a metabolite of methylene blue, with acetylcholinesterase and butyrylcholinesterase - Petzer_2014_Toxicol.Appl.Pharmacol_274_488
Author(s) : Petzer A , Harvey BH , Petzer JP
Ref : Toxicol Appl Pharmacol , 274 :488 , 2014
Abstract :
PubMedSearch : Petzer_2014_Toxicol.Appl.Pharmacol_274_488
PubMedID: 24161345

Title : The specific interaction of the photosensitizer methylene blue with acetylcholinesterase provides a model system for studying the molecular consequences of photodynamic therapy - Silman_2013_Chem.Biol.Interact_203_63
Author(s) : Silman I , Roth E , Paz A , Triquigneaux MM , Ehrenshaft M , Xu Y , Shnyrov VL , Sussman JL , Deterding LJ , Ashani Y , Mason RP , Weiner L
Ref : Chemico-Biological Interactions , 203 :63 , 2013
Abstract :
PubMedSearch : Silman_2013_Chem.Biol.Interact_203_63
PubMedID: 23159732

Title : Binding of methylene blue to a surface cleft inhibits the oligomerization and fibrillization of prion protein - Cavaliere_2013_Biochim.Biophys.Acta_1832_20
Author(s) : Cavaliere P , Torrent J , Prigent S , Granata V , Pauwels K , Pastore A , Rezaei H , Zagari A
Ref : Biochimica & Biophysica Acta , 1832 :20 , 2013
Abstract :
PubMedSearch : Cavaliere_2013_Biochim.Biophys.Acta_1832_20
PubMedID: 23022479

Title : Determination of binding points of methylene blue and cationic phenoxazine dyes on human butyrylcholinesterase - Sezgin_2013_Arch.Biochem.Biophys_532_32
Author(s) : Sezgin Z , Biberoglu K , Chupakhin V , Makhaeva GF , Tacal O
Ref : Archives of Biochemistry & Biophysics , 532 :32 , 2013
Abstract :
PubMedSearch : Sezgin_2013_Arch.Biochem.Biophys_532_32
PubMedID: 23353050

Title : Resistance of human butyrylcholinesterase to methylene blue-catalyzed photoinactivation\; mass spectrometry analysis of oxidation products - Tacal_2013_Photochem.Photobiol_89_336
Author(s) : Tacal O , Li B , Lockridge O , Schopfer LM
Ref : Photochem Photobiol , 89 :336 , 2013
Abstract :
PubMedSearch : Tacal_2013_Photochem.Photobiol_89_336
PubMedID: 23136924

Title : Targeted oxidation of Torpedo californica acetylcholinesterase by singlet oxygen: identification of N-formylkynurenine tryptophan derivatives within the active-site gorge of its complex with the photosensitizer Methylene Blue - Triquigneaux_2012_Biochem.J_448_83
Author(s) : Triquigneaux MM , Ehrenshaft M , Roth E , Silman I , Ashani Y , Mason RP , Weiner L , Deterding LJ
Ref : Biochemical Journal , 448 :83 , 2012
Abstract :
PubMedSearch : Triquigneaux_2012_Biochem.J_448_83
PubMedID: 22888904

Title : Structural and functional characterization of the interaction of the photosensitizing probe methylene blue with Torpedo californica acetylcholinesterase - Paz_2012_Protein.Sci_21_1138
Author(s) : Paz A , Roth E , Ashani Y , Xu Y , Shnyrov VL , Sussman JL , Silman I , Weiner L
Ref : Protein Science , 21 :1138 , 2012
Abstract :
PubMedSearch : Paz_2012_Protein.Sci_21_1138
PubMedID: 22674800
Gene_locus related to this paper: torca-ACHE

Title : Comparative effects of cationic triarylmethane, phenoxazine and phenothiazine dyes on horse serum butyrylcholinesterase - Yucel_2008_Arch.Biochem.Biophys_478_201
Author(s) : Yucel YY , Tacal O , Ozer I
Ref : Archives of Biochemistry & Biophysics , 478 :201 , 2008
Abstract :
PubMedSearch : Yucel_2008_Arch.Biochem.Biophys_478_201
PubMedID: 18656440

Title : Multi-site inhibition of human plasma cholinesterase by cationic phenoxazine and phenothiazine dyes - Kucukkilinc_2007_Arch.Biochem.Biophys_461_294
Author(s) : Tuylu Kucukkilinc T , Ozer I
Ref : Archives of Biochemistry & Biophysics , 461 :294 , 2007
Abstract :
PubMedSearch : Kucukkilinc_2007_Arch.Biochem.Biophys_461_294
PubMedID: 17428437

Title : Methylene blue is a muscarinic antagonist in cardiac myocytes - Abi-Gerges_1997_Mol.Pharmacol_52_482
Author(s) : Abi-Gerges N , Eschenhagen T , Hove-Madsen L , Fischmeister R , Mery PF
Ref : Molecular Pharmacology , 52 :482 , 1997
Abstract :
PubMedSearch : Abi-Gerges_1997_Mol.Pharmacol_52_482
PubMedID: 9281611

Title : The interaction between methylene blue and the cholinergic system - Pfaffendorf_1997_Br.J.Pharmacol_122_95
Author(s) : Pfaffendorf M , Bruning TA , Batink HD , van Zwieten PA , Batnik HD
Ref : British Journal of Pharmacology , 122 :95 , 1997
Abstract :
PubMedSearch : Pfaffendorf_1997_Br.J.Pharmacol_122_95
PubMedID: 9298533

Title : Methaemoglobin production and reduction by methylene blue and the interaction of methylene blue with sodium nitrite in vivo - Marrs_1989_Hum.Toxicol_8_359
Author(s) : Marrs TC , Bright JE , Inns RH
Ref : Hum Toxicol , 8 :359 , 1989
Abstract :
PubMedSearch : Marrs_1989_Hum.Toxicol_8_359
PubMedID: 2807304

Title : Photo-oxidation of crystalline chymotrypsin in the presence of methylene blue -
Author(s) : Weil L , James S , Buchert AR
Ref : Archives of Biochemistry & Biophysics , 46 :266 , 1953
PubMedID:

Title : Methylene Blue as an Inhibitor of Acetylcholine-Esterase - Augustinsson_1950_Acta.Chem.Scand_4_536
Author(s) : Augustinsson KB
Ref : Acta Chemica Scandinavica , 4 :536 , 1950
Abstract :
PubMedSearch : Augustinsson_1950_Acta.Chem.Scand_4_536
PubMedID: