Phenazine Methosulfate CAS 299-11-6

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Phenazine methosulfate, abbreviated as PMS, with the molecular formula C14H14N2O4S and CAS 299-11-6, is an important reagent in biochemistry. The research on enzymology is the latest artificial synthesis of hydrogenated compounds. Before the synthesis of this reagent, myocardial yellow enzyme is generally used as the hydrogen donor in the dehydrogenase reaction, but this reagent is a biological product and is not easy to handle and store. Artificially synthesized PMS not only has stable performance, but is also easy to handle and has good reaction effects. Compared with myocardial yellow enzyme, the reaction speed is tens of times faster. At present, this reagent is used instead of enzymes.

Phenazine methosulfate (PMS), also known as N-methylphenazine methylsulfate, is an extremely important reagent in biochemical research. Its chemical formula is C14H14N2O4S, which has demonstrated extensive application value in multiple fields.

1, Application in Biochemical Research

As an intermediate electronic carrier

 

5-methylphenazine methyl sulfate is widely used as an intermediate electron carrier in biochemical research. It can couple the generation of NADH (reduced state of nicotinamide adenine dinucleotide phosphate) or NADPH (reduced state of nicotinamide adenine dinucleotide phosphate) with the reduction of colored formazan tetrazolium salt. This characteristic makes 5-methylphenazine methyl sulfate play an important role in enzymatic research.

In enzymatic reactions, 5-methylphenazine methyl sulfate can accept electrons and transform into a reduced state. This reduced state of 5-methylphenazine methyl sulfate can further transfer electrons to other molecules, such as methyl tetrazolium salt, causing a reduction reaction and color change. By observing color changes, the degree of enzymatic reaction and enzyme activity can be indirectly determined.

Electron acceptors for enzyme detection

 

5-methylphenazine methyl sulfate is also commonly used as an electron acceptor for enzyme detection. In enzymatic research, in order to evaluate enzyme activity or detect the presence of a specific enzyme, it is usually necessary to mix the enzyme with a substrate and observe the conversion of the substrate. However, the conversion of some substrates is not intuitive and difficult to observe directly. At this point, 5-methylphenazine methyl sulfate can be introduced as an electron acceptor, which interacts with electrons generated by enzymatic reactions to produce easily observable color changes or fluorescence signals.
For example, in the activity detection of superoxide dismutase (SOD), the activity of SOD can be indirectly determined using the methyl cyanide generated by the reaction of 5-methylphenazine methyl sulfate with NBT (nitrotetrazolium blue). SOD can clear superoxide anion radicals, thereby inhibiting the reduction of NBT and the generation of formazan. By observing the production of Jia Zan, the activity of SOD can be indirectly evaluated.

 

Antioxidant performance evaluation

In the study of antioxidant substances, 5-methylphenazine methyl sulfate also plays an important role. Using NADH-PMS-NBT as the superoxide anion (O2 · -) generation system, the generation of O2 · - can be determined by NBT reduction method, thereby determining the antioxidant properties of the substance.
In this system, NADH releases electrons during the oxidation process, which are accepted by 5-methylphenazine methyl sulfate and converted into a reduced state. Subsequently, the reduced state of 5-methylphenazine methyl sulfate transfers electrons to NBT, reducing it to formazan. The amount of formaldehyde generated is directly proportional to the amount of superoxide anion radicals generated, so the antioxidant performance of a substance can be indirectly evaluated by measuring the amount of formaldehyde generated.

Industrial applications

 

 

In addition to biochemical research, 5-methylphenazine methyl sulfate is also widely used in the industrial field. For example, in fields such as environmental monitoring, food processing, and drug development, 5-methylphenazine methyl sulfate can be used as an indicator or reactant for detecting and analyzing various chemical substances.

1. Environmental monitoring
In environmental monitoring, 5-methylphenazine methyl sulfate can be used to detect pollutants in water bodies. Certain pollutants can undergo chemical reactions with 5-methylphenazine methyl sulfate, resulting in color changes or fluorescent signals. By observing these changes, the degree of water pollution and the types of pollutants can be preliminarily determined.

 

2. Food processing
In the food processing, 5-methylphenazine methyl sulfate can be used as a food additive or indicator. For example, in terms of food preservation and preservation, 5-methylphenazine methyl sulfate can be used to react with oxidative substances in food to produce products with antioxidant properties, thereby extending the shelf life of food. In addition, 5-methylphenazine methyl sulfate can also be used as an indicator to detect the content of nutrients or additives in food.

3. Drug development
In the process of drug development, 5-methylphenazine methyl sulfate can be used as a model compound or reactant for drug screening. Through chemical reactions or interactions with drug molecules, 5-methylphenazine methyl sulfate can reveal information about the active site, mechanism of action, and potential side effects of the drug. These pieces of information are of great significance for the development and optimization of drugs.

Phenazine methosulfate also has potential application value in the medical field. Although it has not yet been widely used in clinical diagnosis and treatment, studies have shown that it may have certain medical functions.

Method 1: Synthesis of Phenazine-1-ol

Add 5-methylphenazine methyl sulfate (604 mg, 1.97 mmol) to 600 mL of deionized water and place the resulting mixture under direct sunlight for 30 minutes until a dark green color is observed. Then place the reaction mixture in a window exposed to direct sunlight for 58 hours. Afterwards, slowly add 11.5 grams of sodium hydroxide to 35 milliliters of water into the reaction vessel and continue stirring for another 36 hours. Then transfer the obtained purple solution to a separatory funnel and wash with ether (to remove phenazine as a byproduct in the reaction). Then acidify the aqueous layer with 30mL of glacial acetic acid and extract with ether (2x). Collect the organic layer, dry with sodium sulfate, filter and concentrate. Purification of the desired product using rapid chromatography (2:1 hexane: ethyl acetate) was carried out to deliver 145 mg (37% yield) of phenazine-1-ol as a bright yellow solid.

Method 2:

The synthesis of 5-methylphenazine methyl sulfate is divided into three steps. Firstly, the synthesis and purification of phenazine, and finally, the synthesis of 5-methylphenazine methyl sulfate. The specific steps are as follows:

Step 1: Preparation of Phenazine: Take 200 milliliters of industrial aniline, 118 milliliters of nitrocellulose tea, 800 grams of granular sodium hydroxide, grind them, and place them in a beaker with a capacity of 1000 milliliters. Heat them in an oil bath to 180 ℃ for one hour. After the reaction is complete, keep them at 160 ℃ for half an hour. A black residue will form in the mixture. Pour out the solution from the beaker and inject distilled water to wash the residue once. Then add 200ml of 20% hydrochloric acid and 50ml of 14% nitric acid, stir while adding, stir well, and then heat to boiling. At this point, the solution turns dark brown (the undissolved black viscous substance can be repeatedly extracted 5-6 times as described above). Add concentrated ammonia water to the dark brown solution and neutralize until neutral. A brown precipitate will precipitate, and after filtration, 60 grams of crude product will be obtained.

Step 2: Purification by Sublimation Method: Place the crude phenol butterfly in a large evaporating dish, cover it with a piece of filter paper (cover the mouth of the evaporating dish), open a small circular hole in the center of the paper, and cover the evaporating dish with a large glass funnel for cooling. Heat the bottom of the evaporating dish with an alcohol spray lamp. At this time, the phenol butterfly rises as a gas, passes through the filter paper hole, meets the glass funnel cover, and is cooled to fall on the filter paper surface. Collect pale yellow needle shaped crystals on the filter paper, which are pure phenazine with a melting point of 171 ℃.

Step 3: Synthesis of 5-methylphenazine methyl sulfate: Take 90 mL of nitrobenzene, heat to boiling, then cool to 120 ° C, immediately add 5 g of phenazine, stir well, continue to cool to 100 ° C, then add 22.5 mL of methyl sulfate, stir well, heat in an oil bath to 100 ° C, hold for 7 minutes, and continue to cool to 0-5 ° C, where crystals precipitate. After filtration, wash the crystals twice with 60 mL of cold ether to obtain the product Phenazine methosulfate.

The research on phenazine methosulfate sulfate can be traced back to the 1930s. In 1934, German chemist Hans Fischer first reported the synthesis method of phenazine methyl sulfate while studying phenazine dyes. He successfully prepared this compound through the methylation reaction of phenazine and dimethyl sulfate, which was mainly used as a dye intermediate at that time. In the 1940s, with the increasing demand for dyes due to war, the industrial production process of methyl phenazine sulfate was improved. In 1947, American chemist Louis F. Fieser systematically studied the properties of phenazine compounds and found that phenazine methyl sulfate had special redox properties, which laid the foundation for subsequent biochemical applications. In the 1950s, with the development of paper chromatography and electrophoresis technology, phenazine methyl sulfate began to be used as a staining agent for biological samples. In 1956, British biochemist David Keilin made the first attempt to apply phenazine methyl sulfate to the study of the cytochrome system. Although no breakthrough was made at the time, it opened up new directions for future applications. The 1960s marked an important turning point in the application of phenazine methyl sulfate. In 1962, American biochemist Britton Chance systematically used phenazine sulfate methyl ester as an artificial electron acceptor while studying mitochondrial electron transport chains, successfully measuring the activity of various dehydrogenases. This groundbreaking work established its important position in enzymatic research. In the 1970s, with the deepening of research on bioenergy metabolism, the application of phenazine methyl sulfate rapidly expanded. In 1973, Japanese scientist Takashi Yamano developed a method for determining glucose-6-phosphate dehydrogenase based on phenazine sulfate methyl ester, which is still widely used today. In 1978, German biochemist Helmut Sies discovered that phenazine methyl sulfate could mediate the oxidation of NADPH in cells, providing a new tool for oxidative stress research. In the 1980s, with the development of molecular biology technology, significant progress was made in the application of phenazine methyl sulfate in microbiological research. In 1985, American scientist Arnold L. Demain first used it for the determination of microbial metabolites. In 1989, a British team reported a new application of phenazine methyl sulfate in bacterial respiratory chain research, providing a new method for studying the mechanism of antibiotic action.

Phenazine Methosulfate (PMS) is a synthetic heterocyclic compound that has become an indispensable tool in biochemical research. Its unique properties, including stability, solubility, and ability to facilitate electron transfer, make it suitable for a wide range of applications, from enzymatic assays to cell viability studies and toxicology research. However, it is important to handle PMS with care due to its potential health hazards and to follow proper storage and disposal procedures. As research continues to evolve, PMS is expected to play an increasingly important role in advancing our understanding of biological processes and developing new therapeutic strategies.

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