299-11-6 Usage
Description
5-Methylphenazinium methosulfate, also known as Phenazine methosulfate (PMS), is a heterocyclic compound produced as secondary metabolites by bacteria. It is an electron transfer reactant used in various biochemical assays and has been found to induce oxidative DNA damage and apoptosis in certain cell lines. PMS appears as orange to light brown crystals or powder.
Uses
Used in the Hexosemonophosphate System:
5-Methylphenazinium methosulfate is used as an electron carrier in place of the flavine enzyme of Warburg in the hexosemonophosphate system, facilitating the transfer of electrons between enzymes and oxygen.
Used in Enzyme Preparation:
PMS is utilized in the preparation of succinic dehydrogenase, an enzyme involved in the citric acid cycle, as described by Green et al., J. Biol. Chem. 217, 551 (1955).
Used in Tyrosine Transaminase Test:
5-Methylphenazinium methosulfate is employed in the tyrosine transaminase test, an enzymic determination of ethanol in blood by the colorimetric micromethod.
Used in Nitric Oxide Reductase Activity Determination:
PMS is used with ascorbic acid to determine nitric oxide reductase activity, playing a crucial role in the assessment of this enzyme's function.
Used in Assays as an Electron Carrier:
Since the reduced PMS is easily oxidized by oxygen, it is used in assays as an electron carrier between enzymes and oxygen, cytochrome c, indophenols, or tetrazolium salts.
Used in Photosynthetic Experiments:
The reduced PMS is used as an electron donor to reduce cytochrome c or in photosynthetic experiments, contributing to the understanding of photosynthetic processes.
Used for Detection of Specific Dehydrogenases:
PMS has been reported for the detection of specific dehydrogenases, aiding in the identification and study of these enzymes.
Used in the Discovery of Antibacterial Agents:
Phenazine methosulfate is used in the discovery of potent bromophenazine antibacterial agents against Staphylococcus, contributing to the development of new treatments for bacterial infections.
Biochem/physiol Actions
Phenazine m ethosulfate (PMS) acts as a good electron acceptor. PMS is reduced non-enzymatically by (nicotinamide adenine dinucleotide) NADH and (nicotinamide adenine dinucleotide phosphate) NADPH.
Enzyme inhibitor
This redox-active reagent (FW = 306.34 g/mol; CAS 299-11-6; Eo’ = +0.080 V, pH = 7 and T = 30°C), also known as N-methylphenazoniummethosulfat, is frequently used as an artificial electron acceptor and carrier in studies of redox reactions. The reduced semiquinone, which may be prepared nonenzymatically from NADH or NADPH, is a colorless product (occasionally, a green color is reported) and can be used as an electron donor. This reduced compound is rapidly oxidized by dioxygen and will reduce cytochrome c, indophenol dyes, and many other electron acceptors. It is often used with ascorbic acid to determine nitric oxide reductase activity. Action as a Redox Substrate: Phenazine methosulfate (MTT) is a synthetic electron acceptor substtrate for many enzymes (e.g., succinate dehydrogenase, holine dehydrogenase, glycolate dehydrogenase, polyvinylalcohol dehydrogenase, (R)-pantolactone dehydrogenase, formate dihydrogenase, isoquinoline 1-oxidoreductase, quinaldate 4-oxidoreductase, aralkylamine dehydrogenase, glycine dehydrogenase (cyanide-forming), trimethylamine dehydrogenase, cytokinin dehydrogenase, and 4-cresol dehydrogenase (hydroxylating). When used in enzyme assays, MTT is converted to formazin, an intensely purple-colored product. To achieve high-sensitivity and a linear dependence, one must use a solubilization solution (usually either dimethyl sulfoxide, an acidified ethanol solution, or a solution of the detergent sodium dodecyl sulfate in diluted hydrochloric acid) to disperse/dissolve the otherwise insoluble formazan to obtain colored suspension/solution. The absorbance of this solution may then be quantified by measuring the wavelength between 500 and 600 nm in a spectrophotometer. The degree of light absorption depends on the solvent. Cell Viability Asaays: MTT has been widely employed in colorimetric assays for assessing the viability of cells. When tested under defined conditions, NAD(P)H-dependent cellular oxidoreductase enzymes catalyze the conversion of MTT to formazan, the intensity of which indicates cell viability. Other related tetrazolium dyes (including XTT, MTS and the WSTs) are used in conjunction with the intermediate electron acceptor, 1- methoxy phenazine methosulfate (PMS). Target(s): ferredoxin:NADPcyclase; photophosphorylation; progesterone monooxygenase; protein-Np -phosphohistidine:sugar phosphotransferase; stearoyl-CoA 9- desaturase; steroid 9a-monooxygenase; steroid 11bmonooxygenase; and testosterone 5a-reductase.
Purification Methods
It forms yellow-brown prisms from EtOH (charcoal), or EtOH/Et2O. Its solubility in H2O at 20o is 10%. In the presence of aqueous KI it forms a semiquinone which crystallises as blue leaflets from EtOH. [Wieland & Roseen Chem Ber 48 1117 1913, Voriskova Collect Czech Chem Commun 12 607 1947, Bülow Chem Ber 57 1431 1924, Campbell et al. J Chem Soc 404 1938, Morley J Chem Soc 4008 1952, Beilstein 23 I 59, 23 II 234, 23 III/IV 1658, 23/8 V 395.]
Check Digit Verification of cas no
The CAS Registry Mumber 299-11-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,9 and 9 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 299-11:
(5*2)+(4*9)+(3*9)+(2*1)+(1*1)=76
76 % 10 = 6
So 299-11-6 is a valid CAS Registry Number.
InChI:InChI=1/C13H11N2.CH4O4S/c1-15-12-8-4-2-6-10(12)14-11-7-3-5-9-13(11)15;1-5-6(2,3)4/h2-9H,1H3;1H3,(H,2,3,4)/q+1;
299-11-6Relevant articles and documents
The catalysed NADH reduction of resazurin to resorufin
Candeias, Luis P.,MacFarlane, Donald P. S.,McWhinnie, Sean L. W.,Maidwell, Nicola L.,Roeschlaub, Carl A.,Sammes, Peter G.,Whittlesey, Rachel
, p. 2333 - 2334 (1998)
Details are reported on the mechanism whereby NADH can be used for the reduction of resazurin 1 to give the fluorescent product resorufin 2, a process requiring the use of a catalyst, such as N-methylphenazinium methosulfate 3.
Hydrobromic acid-dimethyl sulfoxide reagent for dealkylation of 5,10-dialkyl-5,10-dihydrophenazines: Synthesis of 10-alkyl- 2(10H)-phenazinones
Sugimoto, Akira,Yoshino, Yasuyuki,Watanabe, Ryo,Mizuno, Kazuhiko,Uehara, Kaku
, p. 1057 - 1064 (2007/10/03)
By the reaction of 5,10-dialkyl-substituted 5,10- dihydrophenazine with hydrobromic acid in dimethyl sulfoxide at 90-110°, 10-alkyl-2(10H)-phenazinone was obtained as a major product. Brominated dihydrophenazine was isolated in the case of 1,6-dichloro-5,10-dimethyl-5,10-dihydrophenazine.
