299-11-6 Usage
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 academic research and scientific papers
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.
A Simple and Efficient Flow Preparation of Pyocyanin a Virulence Factor of Pseudomonas aeruginosa
Mortzfeld, Frederik B.,Pietruszka, J?rg,Baxendale, Ian R.
, p. 5424 - 5433 (2019/06/13)
The synthesis of the naturally occurring toxin pyocyanin has been realized in a short 4 step sequence. The key photochemical reaction and isolation of the final product have been facilitated by the use of flow chemistry techniques and immobilised reagents. Using these procedures gram quantities of pyocyanin were easily prepared in high yield and purity.
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.
Synthesis of 5'-polyarene-tethered oligo-DNAs and the thermal stability and spectroscopic properties of their duplexes and triplexes
Puri, Nitin,Zamaratski, Edouard,Sund, Christian,Chattopadhyaya, Jyoti
, p. 10409 - 10432 (2007/10/03)
Eleven different planar hydroxy alkylated polyarenes 1-11 with different geometry, bulk and electronic characteristics were synthesised, and used for tethering to the 5'-phosphate of a 9-mer and a 18-mer DNA sequences through solid-phase synthesis. The 5'-polyarene-tethered 9-mers 30-40 were tested for their ability to form stable duplexes with four complementary target DNA-strands 25-28 of different length. The 5'-polyarene-tethered 18-mers 44-54 were tested for their ability to form stable triplexes with a 24-mer duplex target 41+42. The T(m) measurements of duplexes at low salt and pH 7.3 showed that the angular nitro phenanthrene and phenanthrene conjugates 31 and 30 gave the highest duplex stabilisations with targets 25 (ΔT(m) 13.8°C and 11.8°C) and 26 (ΔT(m), 12.3°C and 11.9°C). With the mismatch sequence 28, only 30 and 31 gave a high ΔT(m), of 11.6°C and 10.8°C respectively, while lower ΔT(m), values were observed for other conjugates (ΔT(m), -4.0-5.0°C). The T(m) measurements of triplexes between 43-54 and duplex target 41+42 at low salt and pH 7.3, 6.5 and 6.0 without Mg2+ showed that the nitro phenanthrene conjugate 45 gave the best triplex stabilisation (ΔT(m), 4.1-5.4°C). The stabilisation of nitro phenanthrene conjugate 45 compared to phenanthrene conjugate 44 increased more remarkably when Mg2+ was present: 45 (ΔT(m), 15°C), 44 (ΔT(m), 10°C). These results imply that the electron density of the chromophore influences the π-π stacking interactions between the chromophore and nucleobases, and thereby influencing the duplex and triplex stability. Fluorescence measurements on single strand to double strand transition indicated that the 5'-tethered polyarenes are stacked only on the neighbouring nucleobases of the opposite strand. In case of 5'-9-N-ethylphenazinium conjugate 36, a comparative NMR and fluorescence measurement has unambiguously shown that the tethered phenazinium ion is indeed intercalated between the nucleotides of the opposite target strand 26. Thermodynamic calculations showed the most stable ΔG°(298K) for 30, 31(+targets 25, 26, 28) and 35, 36(+targets 25, 26) compared to the blank 29 ΔΔG°(298K) ~-10kJ mol-1). The non-palindromic target 27 was shown by T(m) measurements to form a stable tertiary structure, which was very little affected by addition of any 5'-tethered conjugate, thereby showing the importance of the tertiary structures of an in vivo antisense target and its implication in regard to its bioavailablity to complementary antisense probes.
