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Colchicine powder , white crystalline solid, or colorless to light yellow crystal, solid at room temperature. It is a bitter and highly toxic natural alkaloid with a chemical formula of C22H25NO6, CAS 64-86-8, and a relative molecular weight of 399.44. The water solubility is low, and only 0.5g of Colchicine can be accommodated per 100ml of water. However, it is easily soluble in organic solvents such as alcohol, ethanol, and chloroform, and can react with other compounds in its solution to form new compounds. It is a very stable molecule, so it is not easily affected by other factors in nature. It also has no obvious magnetic and electrical properties. It also has some special physical properties, for example, it can play an important role in the formation of Cytoskeleton protein. Colchicine can also intercalate into DNA double strands, thereby affecting its topology and structure, thereby disrupting DNA replication and cell division processes. It is an alkaloid with various pharmacological activities such as anti-cancer, anti-gout, anti-inflammation, and immunosuppression. It is made from Colchicum autumnale of the plant family Colchicaceae. It is an alkaloid with multiple pharmacological activities such as anti-cancer, anti-gout, anti-inflammation, and immunosuppression, and is widely used in medicine, life sciences, and agriculture.
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Chemical Formula |
C22H25NO6 |
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Exact Mass |
399 |
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Molecular Weight |
399 |
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m/z |
399 (100.0%), 400 (23.8%), 401 (2.7%), 401 (1.2%) |
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Elemental Analysis |
C, 66.15; H, 6.31; N, 3.51; O, 24.03 |
Colchicine powder has various pharmacological effects, but it also comes with certain toxic side effects and exhibits some other effects.
Anti gouty arthritis: It is an effective medication for treating gouty arthritis, which can alleviate pain and reduce inflammation. Its mechanism of action includes reducing the levels of cytokines such as IL-6, IL-1 β, TNF - α, reducing inflammatory cell infiltration, and inhibiting sodium urate induced arthritis.
Antipancreatitis: It can alleviate the inflammatory response in rats with acute pancreatitis, improve microcirculation, reduce oxidative stress products in pancreatic and lung tissues, and decrease the production of reactive oxygen species.
Anti hepatitis: It can repair liver cells in mice with toxic hepatitis, improve liver function, and treat early cirrhosis. Its mechanism of action includes stimulating collagenase activity, promoting collagen degradation, and reducing serum bilirubin levels.
Anti pneumonia: As a clinical anti-inflammatory drug, it can alleviate cytokine storm and reduce mortality in COVID-19 patients by inhibiting neutrophil function, inhibiting NLRP3 inflammasome activation, delaying cell pyroptosis, and other pathways.
Treatment of angina pectoris: Low dose colchicine can reduce the levels of hs CRP, IL-6, and angiotensin II in serum, effectively treating angina pectoris combined with acute gout.
Treatment of myocardial fibrosis: It can reduce the levels of inflammatory factors such as OPN, TGF - β 1, PAI-1, and immunoglobulin, and delay myocardial fibrosis in patients with primary hypertension and hyperuricemia.
Protecting atrial tissue: may reduce the mRNA level of acetylcholine dependent potassium channel gene (Kir 3.4) in idiopathic atrial fibrillation, decrease the inflammatory response of atrial muscle tissue, and thus reduce the occurrence of rapid atrial arrhythmia in a rabbit model of aseptic pericarditis.
Treating myocardial infarction: It can have a therapeutic effect on acute myocardial infarction by reducing uric acid levels and improving inflammatory factors.
Treatment of heart failure and coronary heart disease: it can reduce the production of interleukin-18 and interleukin-1 β, and long-term use can reduce the incidence rate of coronary heart disease. Low doses of this substance can improve inflammation and endothelial function in acute coronary syndrome, and reduce the incidence of cardiovascular adverse events.
Inhibition of fibroblast proliferation: The proliferation of thyroid associated ophthalmopathy can be inhibited by suppressing its cell cycle, and RF cell proliferation may be inhibited by suppressing the secretion of TGF - β derived from human renal fibroblasts.
Inhibition of cancer cell proliferation: A series of derivatives synthesized from colchicine exhibit significant anti proliferative activity against human myeloid leukemia cell line K562. Colchicine powder ointment and Zhenguang 81 have also been used for the treatment of breast cancer and skin cancer. Colchicine microspheres are toxic to human breast cancer cells and can inhibit their growth.
Colchicine site inhibitors can inhibit the mRNA and protein expression of P-glycoprotein, exhibiting multidrug resistance in anti-tumor cells. They can also overcome the MDR effect of A549/Taxol cells by inhibiting the cell cycle of paclitaxel resistant human lung cancer cells.
Inhibition of glioma cell proliferation: Within a certain dosage range, it can inhibit liver cell apoptosis to alleviate liver damage caused by Paragonimus westermani, and the inhibition of apoptosis is positively correlated with the dosage of the medication. The ability to inhibit the growth of mouse glioma cells (G422) is positively correlated with drug concentration and significantly inhibits the growth of C6 glioma cells.
It can inhibit the formation of spindle fibers and cause the already formed spindle fibers to disintegrate, thereby suppressing the formation of spindle bodies. The specific mechanism is as follows:
(1) The C-ring of the chemical structure binds to microtubule proteins, interfering with the function of the spindle. The spindle is assembled from microtubule proteins and is a necessary structure for evenly distributing chromosomes to the poles during cell division. Microtubules are a metastable dynamic structure composed of heterodimers of alpha and beta microtubule proteins and a small amount of microtubule binding proteins. The C-ring of the chemical structure of colchicine is cross-linked with amino acid residues 1-46 and 214-241 of β - tubulin. When the β subunit of colchicine is assembled to the end of the microtubule, other microtubule subunits are difficult to assemble at that location, thereby inhibiting microtubule polymerization, disrupting microtubule formation, inhibiting spindle formation, and suppressing cell mitosis.
(2) It is also a microtubule depolymerizer that can promote the depolymerization of microtubule proteins. When colchicine comes into contact with a cell undergoing mitosis, colchicine binds to the above specific localization points of tubulin, destroying the dimer structure formed by α and β tubulin, causing the original microtubule depolymerization, resulting in the cell being unable to form spindle filaments normally, even if the sisters chromatids can be separated, they cannot be pulled to the two poles of the cell, thus doubling the number of chromosomes.
Its function is reversible. When the colchicine in the organism is metabolized and degraded, its effect disappears, and it no longer inhibits the formation of microtubules and spindle fibers, allowing cells to continue dividing.
The source of Colchicine Powder is limited and the content is low, so people have sought a series of synthetic methods.
1. Summary method
- Fritsch-Buttenberg-Wiechell Rearrangement method
The Fritsch-Buttenberg-Wiechell Rearrangement method is one of the earliest synthesis methods of Colchicine. Its reaction steps are as follows:
Starting material: N-acetyl-N-phenyl-β-bromoacetamide (1)
(1) 1 is deacetylated by base catalysis to generate methylenephenol-N-benzoylvinylamine (2);
(2) Mannich reaction of 2 with N-benzoyl-D-alanine methyl ester (3) catalyzed by K2CO3 to generate Schöpf acid (4);
(3) 4 generates N-acetyl-3-bromobenzoylmethyl acrylate (5) through dehydration, and then undergoes a rearrangement reaction through heating and Loveman rearrangement to generate Colchicine (6).
The main advantage of this method is that there are fewer reaction steps, but multi-step reactions are required to form key intermediates, the operation is cumbersome, and the product yield is low.
- Trost synthesis method
The Trost synthesis method is a comprehensive method based on olefin synthesis, and its reaction steps are as follows:
Raw material: β-dimethylaminoacrylate (7)
(1) 7 undergoes a semi-addition reaction catalyzed by Pd(0) to generate 8;
(2) 8 undergoes a chemical reaction with an amide anion to generate 9;
(3) 9 undergoes an asymmetric cyclization reaction catalyzed by nonafluorobiphenol chromium to generate 10;
(4) 10 undergoes deprotection and HBr-catalyzed hydrogenation to generate Colchicine (6).
The advantage of this method is that there are few reaction steps, easy synthesis of intermediates, high product yield and wide application range, but higher technical requirements are required.
- Leimgruber-Batcho method
Leimgruber-Batcho method is a kind of total method that adopts 2,3,4,6-tetramethoxybenzophenone as starting material, and its reaction steps are as follows:
Starting material: 2,3,4,6-tetramethoxybenzophenone (11)
(1) 11 undergoes an etherification reaction to generate 12;
(2) 12 undergoes o-phosphite acylation reaction to generate 13;
(3) 13 generates 14 through dehydration reaction;
(4) 14 undergoes Schöpf acid reaction to produce Colchicine (6).
The advantage of this method is that the intermediate is easy to synthesize, the reaction steps are few, and the operation is simple, but the product yield is low.
2. Semi-synthetic method
In addition to the general method, there are some semi-synthetic methods that can be used for the synthesis of Colchicine. These methods mainly utilize the natural Colchicine skeleton to produce Colchicine analogs through chemical modification or biotransformation.
- Demethylation method
Demethylation method is a semi-synthetic method using natural Colchicine skeleton. Its reaction steps are as follows:
Ingredients: Natural Colchicine (15)
(1) 15 reacts with methyl bromide and KOH to form 16;
(2) 16 generates 17 through quinoid metathesis;
(3) 17 generates 18 through dehydration reaction;
(4) 18 undergoes appropriate protection and deprotection reactions to generate Colchicine (6).
The advantage of this method is that the semi-synthetic method is relatively simple to operate, and natural Colchicine can be used as a raw material, but there are many steps and the product yield is not high.
- Biocatalytic method
The Biocatalytic method is to introduce the Colchicine skeleton into microorganisms, and realize the synthesis of Colchicine analogs through the action of metabolic enzymes. The advantage of this method is that the product diversity and stereoselectivity are high, and natural biotransformation is utilized, and it has good environmental friendliness.
For example, a study showed that the O-demethylase enzyme expressed in Pichia pastoris can convert the methoxy group of natural Colchicine to hydroxyl group and produce hydroxylated Colchicine derivatives.
In conclusion, there are various synthetic methods of Colchicine, including total method and semi-synthetic method. Among them, the sum method involves many important organic synthesis reactions, such as Mannich reaction, Lovelock-Ross reaction, etc., which has high theoretical and practical significance. The semi-synthetic method is to use natural Colchicine as the starting material to realize the synthesis of Colchicine Powder analogues through chemical modification or biotransformation, which has the advantages of simple operation and high product diversity. In general, different synthesis methods can be selected according to the specific situation to achieve the best synthesis effect.
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