Methylglyoxal chemical formula CH3COCHO. Molecular weight 72.06. Yellow flowing liquid. It has a poignant scent and is hygroscopic. The boiling point is 72 ° C, the loved one density is 1.045524, and the refractive index is 1.400217.5. Soluble in water, soluble in ether and benzene for yellow, soluble in alcohol for colorless. It is quickly polymerized right into viscous semi-solid, soluble in water, releases warm, and go back to monomer remedy. Heating to form a yellow-green gas, which can last for a number of days in a shut tube. Products are usually 20% to 40% liquid remedy. Slightly acidic to litmus paper. Methylglyoxal Option is a regular metabolite in the human body, which can be generated by the metabolic rate of carbohydrates, lipids, and healthy proteins. Under normal physiological conditions, its synthesis in the body is extremely reduced, but it will boost significantly in hyperglycemic conditions such as diabetic patients. Glyoxal is an extremely responsive substance and is cytotoxic. As early as 1958, it was found that methylglyoxal not just had anti-malarial and anti-viral results however likewise had anti-tumor impacts, and afterwards individuals showed the anti-tumor results of methylglyoxal from artificial insemination, in vivo experiments and also scientific patients.
Methylglyoxal Solution Property
1.19 g/mL at 20 °C
25.09hPa at 20℃
Clear yellow to yellow-brown
>=10 g/100 mL at 17 ºC
Methylglyoxal Solution Uses
Methylglyoxal Solution is used as medicine, pesticide intermediate and biochemical reagent.
Methylglyoxal Solution can be used as raw materials for cimetidine, lactic acid, pyruvic acid, painkillers, anticancer, antihypertensive drugs, desensitizers, cosmetics, etc.
Anti-Tumor Mechanism of Methylglyoxal Solution
1. Inhibition of proliferation
As early as the 1860s, Methylglyoxal Solution was recognized as a natural growth regulator, a statin that prevents cell division. Methylglyoxal can inhibit the growth of human leukemia HL-60 cells, and can inhibit the growth of tumor-bearing mice inoculated with Ehrlicascites carcinoma (EAC) cells, leukemia L4946 cells, adenocarcinoma cells, and sarcoma S180 cells. Tumor growth, indicating that methylglyoxal can inhibit the proliferation of tumor cells. Studies have shown that the mechanism of its inhibition of proliferation lies in its ability to inhibit protein synthesis. Methylglyoxal can modify the guanylic acid residues of RNA, resulting in a decrease in the stability of protein polymers, thereby blocking the initial process of protein synthesis. Methylglyoxal can also react with the amino acid residue of DNA to modify it, thereby causing DNA double-strand breaks, forming DNA-protein cross-links, etc. to inhibit DNA synthesis, and Methylglyoxal Solution will also slightly affect RNA synthesis. . Subsequently, it was found that methylglyoxal can inhibit the proliferation of tumor cells by affecting metabolism. On the one hand, methylglyoxal can interfere with the glycolysis process of tumor cells. Studies have shown that 2mmol/L and 5mmol/L methyl ethyl After dialdehyde acts on ECA cells, the utilization of glucose is inhibited by 50% and 80%, respectively, and the production of lactic acid is inhibited by 55% and 90%, respectively, and it is found that methylglyoxal can greatly inhibit the 3 – the activity of glyceraldehyde phosphate dehydrogenase, because the raw material for the survival and rapid proliferation of tumor cells comes from its active hypoxic glycolysis process, so methylglyoxal can effectively and specifically inhibit its proliferation; another On the one hand, methylglyoxal directly inhibits the process of mitochondrial oxidative respiration, mainly by inhibiting the electron chain transfer involved in mitochondrial complex I, which leads to the reduction of oxygen consumption and ATP generation of tumor cells, thereby greatly reducing the energy supply. In addition, methylglyoxal can also prevent cells from transitioning from the early stage of DNA synthesis (G1 phase) to the DNA synthesis phase (S phase). It first down-regulates the expression of cyclin D1 in prostate cancer PC3 cells, and then down-regulates cyclin-dependent kinases 2 (cyclin-dependent kinase2, cdk2) and cdk4 dephosphorylate retinoblastoma protein (pRB) and eventually lead to G1 phase arrest and growth arrest. Therefore, methylglyoxal can inhibit the proliferation of tumor cells by inhibiting protein and DNA synthesis, inhibiting the glycolysis and oxidative phosphorylation process of tumor cells and regulating the cell cycle.
2. Induction of apoptosis
In recent years, it has been found that the main way for Methylglyoxal Solution to exert its anti-tumor effect is by inducing apoptosis. Studies have shown that Methylglyoxal can act on a variety of malignant tumors, including prostate cancer cells, liver cancer cells, and sarcoma cells. After tumor cells, the morphology of the cells changes greatly and lyses, and the DNA fragments in the cells increase and form apoptotic bodies. The mechanisms of methylglyoxal-induced apoptosis are as follows.
(1) Methylglyoxal Solution can increase the level of reactive oxygen species (ROS) in cells, the superoxide anion and hydrogen peroxide produced by methylglyoxal during the glycosylation reaction and its effect on ROS scavenging enzymes Inhibition increased the generation of intracellular ROS from two aspects: increasing the source and reducing the outlet, respectively. Elevated ROS can act as an upstream signaling molecule to activate mitogen-activated protein kinase p38 (p38MAPK), p42/44MAPK signaling pathway to mediate apoptosis; at the same time, the generation of ROS can also trigger mitochondria to release cytochrome c, thereby activating apoptosis The proteases caspase-3, caspase-9, and down-regulation of the DNA repair enzyme polyadenosine diphosphate-ribose polymerase (PARP) further damage cells.
(2) As a powerful glycosylation agent, Methylglyoxal Solution can undergo glycosylation reactions with other important intracellular components such as proteins to produce advanced glycation end products (AGEs). It can activate the nuclear factor NF-κB (nuclearfactor-KappaB) signaling pathway, trigger the mitochondrial apoptosis mechanism, and at the same time up-regulate the apoptosis protein Bax (Bcl-2-associatedXprotein), down-regulate Expression of the anti-apoptotic proteins Bcl-2 (B-celllymphoma-2) and Bcl-XL, ultimately leading to increased apoptosis; AP can also promote apoptosis by directly destroying the cytoskeletal proteins actin and tubulin α-tubulin apoptosis.
(3) In the study of sarcoma, it was found that in the process of reducing the activity of mitochondrial complex I, methylglyoxal can not only greatly reduce the production of ATP, but also reduce the mitochondrial transmembrane potential, thereby changing the mitochondrial membrane communication. Permeabilization, release of the mitochondrial pro-apoptotic factor cytochrome c, ultimately disrupts the integrity of the mitochondrial membrane and leads to cell death. Therefore, methylglyoxal can directly or indirectly activate the apoptotic signaling pathway and the mitochondrial apoptotic pathway to promote apoptosis. In addition, the MGDN adducts formed by the glycosylation of DNA residues by methylglyoxal can activate endonucleases. After the protein is modified, the biological activity and stability of the protein will be affected to a certain extent, and even be blocked by proteases. These are also one of the reasons why methylglyoxal promotes apoptosis.
3. Inhibition of invasion and adhesion
The adhesion, migration, and invasion abilities of tumor cells are essential factors for tumor metastasis. Methylglyoxal Solution can inhibit the adhesion and invasion of liver cancer Huh-7 and HepG2 cells. This inhibition is mediated by the tumor suppressor gene p53, and this inhibition does not exist when p53 is inhibited or interfered. Methylglyoxal can promote the translocation of p53 to the nucleus, enhance its transcriptional activity, and restore the conformation and activity of the Y220C mutant p53 to the conformation and activity of the wild-type p53. With the recovery of the function of the wild-type p53, the movement and invasion of tumor cells Inhibited, and the restoration of p53 function has been recommended as a kind of anti-tumor therapy, so methylglyoxal can inhibit the metastasis of liver cancer through the p53 pathway.
Immunomodulation has been considered as another option for the prevention and treatment of tumors. The defense mechanism of the immune system is to activate the body’s immune response through active or passive immunity to eliminate tumor cells and prevent tumor metastasis and recurrence. Studies have shown that Methylglyoxal Solution can increase the number and phagocytosis of macrophages in the mouse model of sarcoma 180 cells, as well as the production and killing effect of killer T cells, enhance the cellular immunity of mice to resist tumors, and at the same time, some immune regulation in mice Factors and surface receptors: interferon-γ (IFN-γ), tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), IL-6, Toll-like receptor-4 (TLR -4) and the expression of TLR-9 also significantly increased. Methylglyoxal mainly promotes the production of macrophages by regulating macrophage colony-stimulating factor, and p38MAPK and NF-κB signaling pathways are also involved. Therefore, methylglyoxal plays an important role in enhancing the activity of macrophages and lymphocytes and resisting tumors through immune regulation.
5. Improve chemotherapeutic drug sensitivity
High expression of glyoxalase I can cause multidrug resistance to doxorubicin, etoposide, mitomycin C and other chemotherapeutic drugs. Studies have found that the mRNA levels of glyoxalase I in many human tumor cell lines that are multidrug-resistant to existing clinical chemotherapy drugs are generally high. The cells also exhibit multi-drug resistance. The specific mechanism of the multi-drug resistance of chemotherapy drugs caused by the high expression of glyoxalase I is still unclear, but it is certain that it is closely related to methylglyoxal, and the glyoxalase I inhibitor p-bromobenzyl valley After the action of SGG on the cells, the content of methylglyoxal in the cells increased significantly, and the cells regained their sensitivity to anti-tumor drugs. In addition, it has been reported in the literature that methylglyoxal can enhance the killing effect of cisplatin on myeloma cells by activating the δ subunit of protein kinase C (proteinkinase C, PKC). About 4 times.
Preparation of Methylglyoxal Solution
Method 1: Add 160mL of water, 50mL of acetone, 37.2mL of glacial acetic acid and 4.0g of potassium chlorate into a 500mL four-necked bottle, and install a mechanical stirrer, a thermometer, a reflux condenser and a long-necked dropping funnel. Start mechanical stirring, control the temperature of the water bath at 60-75°C and the temperature in the bottle at about 60°C, add 35.4mL of bromine dropwise with a dropping funnel, and control the rate of addition so as not to accumulate unreacted bromine. After adding bromine, continue the reaction for 0.5h. After the color of the solution fades, add 80mL of ice water to dilute the reaction solution, and cool to 10°C, then add 100g of anhydrous sodium carbonate until the Congo red is neutral. The oil layer was separated, dried with 8g of anhydrous calcium chloride, distilled under reduced pressure, and the fraction at 40-42°C/1733Pa was collected, with a yield of 63.5% (50%-51% in literature). The collected fractions and DMSO were added into a 250mL three-neck flask according to the appropriate proportioning ratio, air was introduced, the temperature was controlled at an appropriate temperature, electromagnetic stirring was performed, and the reaction was refluxed for 8h. After the reaction was completed, fractional distillation was carried out at atmospheric pressure, and the fraction at 71.5-73.0°C was collected. The refractive index was n24.6D=1.3803 (documentation n20D=1.4209).
Method 2: Weigh 89.4g (0.3mol) of potassium dichromate dihydrate, dissolve it in 400mL of water, slowly add 63.9mL (1.2mol) of concentrated sulfuric acid dropwise while stirring, stir well, after cooling, transfer to the dropping funnel middle. In a 1000mL three-necked flask, first add 32.9mL (0.45mol) of 1,2-propanediol and 1.0g of manganese sulfate as a catalyst, and then connect a distillation device to the middle port, one port is connected to a dropping funnel, and the other port is inserted into a glass stopper. Glass tube, the lower port of the glass tube should be inserted below the liquid level. First introduce nitrogen gas into the three-necked bottle from the glass tube, and then heat the three-necked bottle with an electric heating mantle with a voltage regulator. After a few minutes, drop the prepared solution from the dropping funnel, and finish dropping in about 50-70 minutes.
Continue heating and distilling for 15 minutes after dropping (pay attention to closing the plunger of the dropping funnel), and collect about 250mL of yellow-green distillate. The distillate was extracted four times with 450 mL of anhydrous ether, the water layer was discarded after extraction, and the extracts were combined. Wash with saturated aqueous sodium bicarbonate until neutral, separate the water layer, and dry the ether layer with anhydrous magnesium sulfate for 4 h. Filtrate, evaporate diethyl ether in a water bath at 45-50°C, then fractionate in a boiling water bath, collect fractions at 71-73°C, and obtain a yellow-green liquid with a special odor, with a yield of 49%-50%. The product was stored at 0°C under nitrogen. After inspection, this fraction can make Schiff’s reagent appear purple, make Fehling’s reagent appear brick-red precipitate, and form orange-red precipitate with 2,4-dinitrobenzene trap (recrystallized in nitrobenzene), and measure its melting point It is 308-309°C (the literature is 308-309°C). After purification, the boiling point of Methylglyoxal Solution measured by trace method is 72°C (the literature is 72°C).
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