Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of 5-iodocytidine cas 1147-23-5 in China. Welcome to wholesale bulk high quality 5-iodocytidine cas 1147-23-5 for sale here from our factory. Good service and reasonable price are available.
5-Iodocytidine is an organic compound with the molecular formula C9H12IN3O5,CAS 1147-23-5, a white solid, and it is an iodine-containing pyrimidine nucleoside. Can be dissolved in water. Its UV absorption peak is located at 260 nm. X-ray crystal structure analysis can be performed in the solid state. It is an important chemical substance with certain reactivity and chemical properties. It can be applied in biochemistry, medicinal chemistry and other fields, and has potential application value in DNA repair and disease treatment.
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C.F |
C9H12IN3O5 |
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E.M |
369 |
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M.W |
369 |
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m/z |
369 (100.0%), 370 (9.7%), 370 (1.1%), 371 (1.0%) |
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E.A |
C, 29.29; H, 3.28; I, 34.38; N, 11.38; O, 21.67 |
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5-iodocytidine, chemical name 5-iodocytidin, molecular formula C9H12IN3O5, molecular weight 369.11. It is a white to off white crystalline or powder with photosensitivity, and should be stored in a dry, cool, and dark place at a temperature of 2-8 ° C. The melting point of 5-iodocytidin is greater than 160 ° C, the boiling point is 565.5 ± 60.0 ° C, and the density is 2.52 ± 0.1 g/cm3. It is slightly soluble in water, methanol, and DMSO, with an acidity coefficient (pKa) of 13.48 ± 0.70.
In the medical field
it can be used for the following purposes:
(1.)As the precursor of radionuclide, it is used in imaging research, such as radioactive iodine in the treatment of brain tumors, thyroid diseases, pancreatic cancer, etc.
(2.)For the treatment of viral infections, such as hepatitis B, hepatitis C, etc.
(3.)For the treatment of cancer, such as gastric cancer, lung cancer, liver cancer, etc. In these treatments, it is used in combination with chemotherapy or radiation therapy to enhance the effect of the treatment.
In the field of biology
it can be used for the following purposes:
(1.)For studying gene expression and regulation. By introducing it into cells, it is possible to study changes in gene expression and gain further insight into gene regulatory mechanisms.
(2.)For DNA methylation research. it is closely related to DNA methylation and can be used to study the function and mechanism of DNA methylation.
(3.)For RNA labeling and research. it can be used for RNA labeling to track the movement and metabolism of RNA in cells. At the same time, the structure and function of RNA can also be understood by studying it-labeled RNA.
In the field of chemistry
it can be used for the following purposes:
(1.)Used as a synthetic intermediate. Since it contains iodide ions, it can be used as an intermediate in organic synthesis for the preparation of various organic compounds.
(2.)For nucleotide modification and synthesis. it can be used to modify and synthesize DNA and RNA to obtain nucleic acid materials with special properties.
In conclusion, it is a multifunctional compound with broad application prospects and plays an important role in the fields of medicine, biology and chemistry.
Medical field
Antitumor drug:
It has wide applications in the field of medicine, especially in the field of anti-tumor drugs. As a cytidine analogue, it can exert anti-tumor effects by inhibiting DNA synthesis. It has been used in the treatment research of various tumors, such as leukemia, lymphoma, etc. The anti-tumor mechanism of 5-iodocycline mainly includes the following aspects:
Inhibition of DNA synthesis: It can be incorporated into DNA strands to replace normal cytidine, thereby interfering with the normal process of DNA synthesis.
Inducing cell apoptosis: It can activate the apoptotic signaling pathway within cells and induce tumor cell apoptosis.
Enhancing immune response: It can enhance the body's immune response and improve the immune system's ability to recognize and kill tumor cells.
Antiviral drugs
In addition to its anti-tumor effect, it also has certain antiviral activity. It can inhibit the replication process of certain viruses, such as hepatitis B virus (HBV) and hepatitis C virus (HCV). The antiviral mechanism of 5-iodocytidine may be related to its interference with the synthesis of viral nucleic acids. However, current research on the antiviral properties of 5-iodocytidin is still in its early stages, and its specific antiviral spectrum and mechanism require further in-depth study.
Biochemical research
Gene sequencing:
It also has important applications in biochemical research, especially in gene sequencing. As a cytidine analogue, it can be incorporated into DNA strands, thereby interfering with the normal synthesis process of DNA. This interference can be used to terminate the extension of DNA strands, thereby enabling the determination of specific gene sequences. The applications in gene sequencing mainly include the following aspects:
Chain termination sequencing: It can be used as a chain termination agent to be incorporated into the DNA chain during DNA synthesis, thereby terminating the extension of the DNA chain. By controlling the position and quantity of 5-iodocytidin incorporation, specific gene sequences can be determined.
Improving sequencing accuracy: The incorporation of 5-iodocytidin can alter the physicochemical properties of DNA strands, thereby enhancing sequencing accuracy.
Biomarkers and probes
It can also serve as a biomarker and probe for studying biological processes. For example, it can be used to label specific DNA sequences or proteins, enabling tracking and detection of these biomolecules. In addition, it can also be used to study intracellular signaling processes such as apoptosis and cell cycle regulation.
In the field of agriculture
Although there is currently limited research on the application of 5-iodocycline in the agricultural field, it may have certain plant growth regulation and pesticide activity. As a cytidine analogue, it may interfere with the nucleic acid metabolism process in plants, thereby affecting plant growth and development. In addition, it may also have certain antibacterial and antiviral activities, which can be used to develop new agricultural fungicides and antiviral drugs.
Other fields
In addition to the aforementioned fields, it may also be used in areas such as cosmetics and food additives. For example, it can be used to develop cosmetics with whitening, anti-aging and other functions; Or as a food additive, used to improve the quality and taste of food. However, the current research on the application of 5-iodocytidin in these fields is still in the exploratory stage, and its specific uses and effects need further verification.
5-Iodocytidine is a nucleotide molecule containing iodine, which is widely used in the field of biomedicine.
Several synthetic methods of 5-Iodocytidin will be introduced below.
(1) Pyrimidine method:
This synthesis method first reacts pyrimidine with ozone to obtain 5-oxopyrimidine, then reacts it with methyl iodide to obtain 5-iodo-2'-deoxyuridine, and finally reduces it with 1,3-dichloro-2-propanol The reaction yields product. The product synthesized by this method has high purity, but there are many steps and the requirements for reaction conditions are relatively high.
(2) Aldonic acid derivatization method:
The method first obtains 5-chloro-2'-deoxyuridine by esterifying 5-chlorouridine with 3,4,6-tri-O-acetylgluconic acid, and then performs iodination reaction to obtain 5-iodo- 2'-Deoxyuridine. Finally, it is obtained through reduction reaction. The method has the advantages of simple operation and high product purity.
(3) Acid sugar anhydride method:
This method first reacts 2',3'-di-O-methyl glucoside with fumaric acid to obtain 2',3'-di-O-methyluridine salt, and then converts it into 5 '-Iodine-2',3'-di-O-methyluridine salt, and finally it is obtained by removing the methyl group. The method has mild reaction conditions and high purity synthetic products, but requires relatively high purity raw materials.
(4) Bromination method:
This method obtains 5-bromouracil by reacting uracil with phosphorus tribromide, and then undergoes methylation reaction to obtain 5-bromo-2'-deoxyuridine. It is catalytically reduced by using sodium hydroxide and ammonium persulfate to give product. The method has fewer reaction steps, but the product has lower purity.
In short, there are many ways to synthesize 5-Iodocytidin, and different methods can be selected according to actual needs to obtain high-purity product.
Reactive nature:
It can react with a series of electrophiles (such as halogen, nitrosylation, phosphorylation, arylsulfonylation). For example, it can react with metal palmitic acid to form Palmitic acid product ester.
Chemical properties:
It as an iodine-containing pyrimidine nucleoside, can remove iodine under acidic conditions and generate 5-chloroglycoside or 5-bromoglycoside. In addition, it can tautomerize to 5-aminopurine nucleosides.
Adverse reactions
5-Iodocytidine is a halogenated pyrimidine nucleoside analogue, whose chemical structure involves the introduction of an iodine atom at the 5th carbon atom of cytidine. This modification significantly alters the metabolic pathway and biological activity of the drug.
Classification and manifestations of adverse reactions
Based on animal experiments and limited clinical observations, the adverse reactions of 5-Iodocytidine can be summarized as follows:
Bone marrow suppression manifests as a decrease in white blood cells and platelets, and in severe cases can lead to a decrease in whole blood cells. The direct inhibition of DNA synthesis in hematopoietic stem cells by drugs, combined with the radiation like effect of iodine atoms (although non radioactive, high atomic numbers may enhance local ionization). It usually reaches its peak 7-14 days after medication and recovers slowly (taking 2-4 weeks).
Hemolytic anemia: Rare report, possibly related to iodine atom induced oxidative damage to red blood cell membrane, manifested as jaundice and hemoglobinuria.
Digestive system response
Gastrointestinal mucosal injury is characterized by nausea and vomiting (with an incidence rate of about 60% -80%), diarrhea (which can be bloody in severe cases), and oral ulcers. The direct toxicity of drugs on gastrointestinal mucosal epithelial cells, combined with the local stimulating effect of iodine atoms. Compared with 5-fluorouracil, 5-Iodocytidine has a higher incidence of diarrhea, which may be related to the strong oxidative properties of iodine metabolites such as iodates.
Abnormal liver function is characterized by elevated transaminase levels (ALT/AST>3-fold upper limit) and mild elevation of bilirubin.
Direct damage to liver cells caused by drug metabolites, or immune-mediated liver cell necrosis.
The symptoms of the central nervous system include headache (30% -50%), dizziness, and drowsiness. In severe cases, cerebellar ataxia and cerebral palsy (rare) may occur. Drug metabolites (such as fluorocitric acid analogues) inhibit the tricarboxylic acid cycle, leading to neuronal energy metabolism disorders. Iodine atoms may pass through the blood-brain barrier and directly damage the membrane structure of neurons.
Peripheral neuropathy manifests as sensory abnormalities (such as glove sock like distribution) and muscle weakness. Axonal transport disorders or myelin sheath loss may be related to iodine atom interference with neuronal microtubule protein polymerization.
Skin and mucosal injuries
Hand foot syndrome is characterized by redness and pain on the palms and soles of the feet, and in severe cases, blisters and ulcers may appear. The drug concentrates in the sweat glands of the palms and soles of the feet, causing local high concentrations and leading to apoptosis of keratinocytes.
Pigmentation is manifested as blue black patches on the skin, nails, and mucous membranes (such as the mouth). Iodine atoms bind with melanin precursors (such as tyrosine) to form stable pigment complexes.
Allergic reactions manifest as rash (papules, urticaria), itching, and in severe cases, Stevens Johnson syndrome may occur. Iodine atoms act as haptens to induce delayed type hypersensitivity reactions mediated by T cells.
Frequently Asked Questions
Why does its melting point fluctuate in the catalogs of different suppliers?
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Purity, crystal habits, and measurement methods together create the melting point "Rashomon".
There are subtle differences in the data from various suppliers: Sigma Aldrich reports 101-104 ° C, TCI reports 97.0-101.0 ° C, and Fisher Scientific reports 95-99 ° C. The lesser known truth is that, in addition to purity factors (97% vs 95%), the crystal morphology, particle size, and heating rate of the capillary melting point analyzer of the sample can all cause a several degree drift in the apparent melting point - it is not a fixed point, but a "mass fingerprint".
How long can the prepared DMSO stock solution survive in the refrigerator?
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-Live for 1 month at 20 ° C and 6 months at -80 ° C, and repeated freezing and thawing are strictly prohibited.
The supplier clearly specifies the storage period for the solution: -20 ° C storage, which must be used up within one month; If placed in a -80 ° C ultra-low temperature refrigerator, it can be extended to 6 months. Cold mechanism: Molecular motion intensifies in solution state, and the ice crystal stress generated by repeated freezing and thawing may damage its structure.
Apart from conventional organic synthesis, what is its "hidden identity" in materials science?
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Can serve as candidate molecules for nonlinear optical (NLO) materials.
A systematic density functional theory (DFT) study in 2021 revealed that 5-iodoindole has significant nonlinear optical properties, and its theoretical calculation parameters indicate its potential application value in this field. This is another 'scientist persona' outside of its role as a drug intermediate.
What bacteria can it kill? Which bacteria are 'helpless' to deal with?
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It has selective antibacterial activity and is not a broad-spectrum fungicide.
Experiments have shown that 5-iodoindole has inhibitory effects on Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa, and Bacillus cereus, but is ineffective against other tested bacteria and yeast. Cold logic: Its biological activity is picky and not effective for all microorganisms.
What role does it play in the amino acid "decoration" project?
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It is a precise 'molecular brick' for constructing non natural amino acids.
The latest research (2024) shows that through palladium catalyzed C-H functionalization reaction, 5-iodoindole can be used as an arylation reagent, accurately installed on the amino acid skeleton, to construct non natural amino acids containing C5 indole structure, and has excellent diastereoselectivity (dr>95:5). This is a precise manifestation of its role as a 'block' in medicinal chemistry.
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