73-03-0
3'-deoxyadenosine
CAS: 73-03-0
Molecular Formula: C10H13N5O3
73-03-0 - Names and Identifiers
| Name | 3'-deoxyadenosine |
| Synonyms | 3'-dA Cordycepin Cipargamin CORDYCEPIN 3'-deoxy-adenosin 3'-deoxyadenosine 3'-deoxy-adenosin 3'-DEOXYADENOSINE 9-cordyceposidoadenine cordycepin crystalline Cordycepin from Cordyceps militaris 9-(3-deoxypentofuranosyl)-9H-purin-6-amine 9-(3-deoxy-beta-D-threo-pentofuranosyl)-9H-purin-6-amine |
| CAS | 73-03-0 |
| EINECS | 200-791-4 |
| InChI | InChI=1/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6-,10+/m0/s1 |
| InChIKey | OFEZSBMBBKLLBJ-BAJZRUMYSA-N |
73-03-0 - Physico-chemical Properties
| Molecular Formula | C10H13N5O3 |
| Molar Mass | 251.24 |
| Density | 1.2938 (rough estimate) |
| Melting Point | 225-229°C |
| Boling Point | 394.4°C (rough estimate) |
| Specific Rotation(α) | D20 -47°; D27 -42° |
| Flash Point | 333.1°C |
| Solubility | Soluble in water, hot ethanol and methanol, insoluble in benzene, ether and chloroform. |
| Vapor Presure | 1.36E-16mmHg at 25°C |
| Appearance | White needle or flake crystals |
| Color | White to Off-white |
| Maximum wavelength(λmax) | ['260nm(EtOH)(lit.)'] |
| Merck | 14,2529 |
| BRN | 35194 |
| pKa | 13?+-.0.60(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. |
| Refractive Index | 1.7610 (estimate) |
| MDL | MFCD00037998 |
73-03-0 - Risk and Safety
| Risk Codes | R40 - Limited evidence of a carcinogenic effect R36/37/38 - Irritating to eyes, respiratory system and skin. R25 - Toxic if swallowed R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S22 - Do not breathe dust. S36 - Wear suitable protective clothing. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 2811 |
| WGK Germany | 3 |
| RTECS | AU7358610 |
| FLUKA BRAND F CODES | 10-21 |
| HS Code | 29349990 |
| Hazard Class | 6.1 |
73-03-0 - Reference
| Reference Show more | 1. Wang Xueyan, Huang Yanping, Yang Ying, etc. Experimental study on the effect of two kinds of penetration methods on the transdermal penetration of cordycepin [J]. China medical cosmetology 2018 8(09):90-93. 2. Sun Lanfeng, Sun Qian, Pan Qi, et al. Analysis of nucleosides and cordycepin in enzymatic hydrolysate of Cordyceps militaris waste by HPLC [J]. Journal of Liaoning University of Traditional Chinese Medicine 2014(6):49-50. 3. Sun Lanfeng, Sun Qian, Pan Qi, et al. Determination of adenosine and cordycepin in enzymatic hydrolysate of Cordyceps militaris waste by HPLC [J]. Liaoning chemical industry, 2014 043(004):503-504. 4. Cai Shuilin, Zheng Yongbiao, Wang mingz, Lin Qingqiang, Huang, Yang, Huang Jianzhong. Optimization of mycelia production and cordycepin fermentation by Cordyceps militaris submerged culture using response surface methodology [J]. Agricultural Products Processing (journal) 2013(06):13-18 21. 5. Xiao Xuan, Yang Weichao, du Beibei, et al. Biotransformation of cordycepin by Lactobacillus casei [J]. Journal of Microbiology, 2019, 39(01):38-42. 6. Chang Zhengyi, Han Ping, Liu lie, etc. Optimization of extraction and determination of cordycepin from mycelial symbionts of Cordyceps militaris [J]. Science and Technology of Food Industry, 2016, 37(007):237-242. 7. Leaf Crystal, Zhang Jianfei, Cao Ningning, et al. Effects of adding silkworm pupa powder and changing pH of nutrient solution on the fruiting body yield and cordycepin content of cultured Cordyceps militaris. Sericulture science. 8. Study on protective effect of cordycepin on high glucose-induced apoptosis of human umbilical vein endothelial cells [J]. Chinese Journal of Clinical Pharmacology, 2020. 9. Zhang Tianzhu, Wu Guoliang, Yang Shihai, etc. Mechanism of cordycepin inhibiting lipopolysaccharide-induced airway epithelial cell injury [J]. Pharmacology and Clinic of Traditional Chinese Medicine, 2014, 29 (4):42-44. 10. Zhang Shanbai, Tu Chuan Hai, Xiao Yu, etc. Functional components and antioxidant activity of soybean residue from Cordyceps militaris solid-state fermentation [J]. Science and Technology of food industry, 2017, 038(024):69-74. 11. Zhao Chongyan, Yang Fang, Qu Qingsong, etc. Establishment of two-way fermentation system of Paecilomyces cicadae/Astragalus membranaceus and its components [J]. World Chinese medicine, 2018, 13(12):270-273. 12. Lin Aihua, Miao Liyun, Wang Junling, et al. Screening and optimization of Cordyceps acid extraction from Cordyceps militaris CNZ [J]. Hubei Agricultural sciences 2020(9). 13. Fan Zhenliang, Fang Yan, Jinglongfeng, et al. Effects of cordycepin and hirudin on inflammatory response, EMT and RIF in UUO rats [J]. Shi Zhen, Chinese medicine, 2019(10). 14. Guo Tao, Zhang Long, Wang Bing, et al. Determination of cordycepin and adenosine in Cordyceps militaris cultured in different culture media [J]. Sericulture Science, 2011, 37(006):1117-1122. 15. Liu Hong, Ma Hui, Cao Hong, et al. Production performance and taste substance analysis of different Cordyceps militaris coarse grain culture media [J]. Science and Technology of Food Industry 2019(12). 16. Shen Hong, Zhang Long, Wang Bing, etc. Growth and quality detection of Cordyceps militaris on silkworm body and pupa powder substitute medium [J]. Sericulture Science, 2012, 38(001):130-134. 17. Pan Qi, Sun Lanfeng. Analysis of four nucleosides in Cordyceps militaris [J]. China Contemporary Medicine, 2015, 000(009):85-87. 18. Zhang Zewen, Tan Jidan, Li Xiaohua, etc. Preliminary Study on Artificial culture conditions of Cordyceps cicadae [J]. Chemical and Biological Engineering, 2019, 036(007):12-14,28. 19. Li Mingbo, Duan Xiaobei, Zhang Hailin, etc. Ultrasonic extraction of nucleobases from cicada [J]. Guizhou agricultural sciences, 2014, 000(003):154-157. 20. Liu Sheng, Xu Weiqin, Deng shaohuan, Hui ailing, Zhang Wencheng. Determination of nucleosides in fresh and dried Cordyceps militaris from different areas [J]. Food industry, 2021,42(01):226-229. 21. [IF = 3.061] Jian Wang et al."Protective effect of Cordyceps militaris extract against against." Syst Biol Reprod Med. 2016;62(4):249-257 |
73-03-0 - Introduction
Pharmacological effects: It has various pharmacological effects such as anti-tumor, antibacterial and antiviral, immune regulation, and scavenging free radicals.
Last Update：2022-10-16 17:28:12
73-03-0 - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| trait | cordycepin exhibited acicular or patchy white crystals in appearance. |
| Use | (1) anti-tumor effect of cordycepin: at present, the researchers summarize the anti-tumor mechanism of cordycepin into two kinds: direct and indirect effects. Direct action refers to the anti-tumor component of cordycepin by interfering with the target cell nucleic acid, protein nucleic acid and glucose exchange, so as to directly inhibit the proliferation of tumor cells. Cordycepin can act on multiple cell signaling pathways, causing autophagy or apoptosis. Indirect effect means that the anti-tumor active ingredients in cordycepin play an anti-tumor role by promoting the proliferation and differentiation of human immune cells and thus enhancing the function of immune cells. (2) antiviral effect of cordycepin: cordycepin was first discovered and studied as a nucleoside antibiotic. It has extensive inhibitory effect on bacteria, fungi, Virus and other pathogenic microorganisms. (3) cordycepin anti-aging effect: cordycepin can increase the activity of SOD enzyme in the liver, inhibit the formation of superoxide compounds, and enhance the activity of one amine oxidase in the brain, which indicates that cordycepin has anti-aging effect. (4) cordycepin hypolipidemic, anti-hemagglutination: cordycepin can also increase the weight of the spleen, accelerate the liver nucleic acid and protein renewal rate, with anti-hypoxia, increase myocardial nutrient blood flow and reduce serum cholesterol. It also prevents the formation of blood clots. (5) cordycepin anti-inflammatory effect, immunomodulatory effect: a large number of documents show that cordycepin has a clear anti-infection, anti-inflammatory, immune regulation and anti-tumor effect, but also can act on oxidative damage, metabolic disorders and diseases of the nervous system. The mechanism of action of cordycepin is very complex, but at least we know that the role of cordycepin has been undisputed in the academic circle. In addition, the function of cordycepin in lowering blood sugar, treating and preventing obesity, anti-aging and improving memory all show that cordycepin is a rare nutrient. cordycepin has the function of improving human immune function, anti-aging, anti-fatigue, anti-cancer, anti-bacterial, anti-virus, lowering blood glucose and blood lipid, easily converted to cordyceps 5 '-triphosphate; Can be used as RNA 3'-terminal marker |
| plant extract | in 1951, a crystal, named cordycepin, was purified from Cordyceps militaris by a German scientist, after the foreign literature, the introduction of cordycepin anti-tumor, antiviral effect and extraction and purification research are from Cordyceps Militaris, but not extracted from Cordyceps sinensis, Cordyceps sinensis in the content of cordycepin is very small. cordycepin, also known as cordycepin and cordycepin, is the main active ingredient in Cordyceps militaris (especially nucleosides), which belongs to nucleoside drugs and purine alkaloids, it is also the first nucleoside antibiotic isolated from fungi. Because of the special effect of repairing cells and protecting the genetic code of life, it has become the leader of modern biological medicine. Cordycepin is a natural source of drugs, with anti-tumor, anti-bacterial, anti-virus, immune regulation, scavenging free radicals and other pharmacological effects, has a good clinical application prospect. At present, the research of cordycepin is becoming an extremely active field in medicinal chemistry. as a structural analog of adenosine, cordycepin can inhibit Bacillus subtilis, Mycobacterium avium and Ehrlich ascites cancer cells, and inhibit RNA and DNA synthesis of cancer cells, pharyngeal cancer (KD) cells have a strong inhibitory effect. Clinical use of cordycepin for adjuvant treatment of malignant tumors, symptoms improved in more than 91.7%; Mainly used for nasal cancer, pharyngeal cancer, lung cancer, leukemia, Patients with brain cancer and other malignancies. cordycepin is extracted from Cordyceps sinensis. It is the most nutritious active substance in Cordyceps sinensis, it is a kind of pure natural nutrient with health care function, which can activate dormant cells, repair diseased cells, replicate new living cells, clean up necrotic cells, and improve immunity and anti-fatigue, it is good to improve the energy of the body. |
| pharmacological effects | currently, it is known that most Cordyceps fungi contain cordycepin, which obviously plays an important role in anti-tumor effects. There are three reasons for the inhibition of tumorigenesis by cordycepin in Cordyceps fungi according to Jagger: (1) the free alcohol group of cordycepin can be incorporated into the DNA of cancer cells to act. (2) cordycepin can inhibit the phosphorylation of nucleosides or nucleotides to produce diphosphate and triphosphate derivatives, thereby inhibiting the synthesis of nucleic acids in tumor cells. (3) cordycepin can block the Amination of xanthate into guanosine. In, Müller et al. found that cordycepin had a strong inhibitory effect on the proliferation of L5718Y cells, and the ED50 was 0.27 μg, however, 2 '-deoxynucleoside could not be canceled; The tritium-labeled Cordyceps test showed that cordycepin could infiltrate into RNA but not DNA, and cordycepin could be phosphorylated into 3'-ATP in cells; 3 '-ATP had no effect on DNA-dependent DNA polymerase α and β activity in L5718Y cells, but had A strong inhibitory effect on nuclear Poly(A) polysaccharides, this is bound to lead to mRNA maturation disorder, which can affect the formation of mRNA and protein synthesis. The anti-tumor effect of cordycepin may be related to this mechanism. In 1997, the United States has been used in phase III clinical trials of cordycepin for the treatment of patients with acute pre-B and pre-T lymphocytic leukemia, activity against HIV Virus and selective inhibition of Clostridium bacteria. In 1985, the cytotoxic effects of Cordyceps sinensis and cultured hyphae (Qinghai) on ECA cells were observed by in vitro test in Zingiber officinale. Results for the ECA cells cultured in vitro, when the lowest effective concentration of the two was 0.405mg/ml and 25mg/ml respectively, the total staining rate was 100%, 80%, the results showed that the drugs had different cytotoxic effects on ECA. Comprehensive in vivo experiments suggest that the anti-tumor effect is related to the drug containing a certain amount of 3 '-deoxynucleoside and cordyceps polysaccharide and the immune regulation of the drug as a whole, and the maintenance of the relative balance of the immune function of the body. Cordyceps sinensis has a certain cytotoxic effect, which is consistent with the reported results of cordycepin resistance to L1210. |
| extraction and synthesis methods | cordycepin (3 '-deoxyadenosine), also known as cordycepin, cordycepin. It was first isolated in the Cordyceps militaris(Link.) puree liquid by Cunningham et al. in 1951, and this component has a variety of bioactive functions. At present, there are several main production processes of cordycepin: fermentation extraction The production of cordycepin in the original strain is not high, the culture method can increase the yield of cordycepin. biosynthesis Based on the study of Cordyceps militaris genome, a potential synthetic gene cluster was obtained by bioinformatics analysis. The gene functions of the four proteins encoded by the gene cluster were studied, and the production of cordycepin was mediated by adenosine 3 "-OH phosphorylation, dephosphorylation and redox reaction. chemical synthesis high purity cordycepin (HPLC purity up to 99%) was obtained from adenosine starting material by a mild and environmentally friendly method. |
| cordycepin and penseidin | in the fifties of the 20th century, the scientist Cunningham et al observed that the tissues of insects parasitic on cordyceps were not easy to rot, subsequently, a natural adenosine active substance was isolated and named cordycepin. Later through the cell experiment, it was found that it has antibacterial, insect-resistant and anticancer biological activity. Among them, "Pentostatin" (a potent inhibitor of adenosine deaminase "ADA"), found in bacteria, was confirmed to have anticancer activity. among more than 30 million species of plants in nature, cordycepin has been found in only a few genera of Cordyceps, and currently only in Cordyceps militaris was found in cordycepin and another anti-cancer activity molecule "pensitin 」. Pentostatin and cordycepin always occur concomitantly. Further studies have confirmed that "pensterine" is the protective umbrella of cordycepin. In the absence of pensinidin, cordycepin is susceptible to degradation. Professor Wang Chengshu revealed that in 2011, they sequenced the genome of Cordyceps militaris and published related papers, but in order to understand the synthesis pathway of cordycepin and pensitin, they took nearly seven more years. In 1991, the U. S. Food and Drug Administration (FDA) has approved pensitabine as a commercial drug (nipen) against Hairy cell leukemia. |
| production method | exists in pupa grass (Cordyceps militaris)[Cordyceps militaris (L.) the culture medium of Link] can also be chemically synthesized or biosynthesized |
Last Update：2024-04-09 21:54:55
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View History
73-03-0
(5R)-3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-[(phosphonooxy)methyl]-2-oxazolidinone
Ethyl N-benzhydrylideneglycinate
faropenem sodium
反-4-乙基环己醇
diethyl propan-2-ylpropanedioate
2-(4-(叔丁氧基羰基)哌嗪-1-基)-2-(4-(三氟甲基)苯基)乙酸
(5R)-3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-[(phosphonooxy)methyl]-2-oxazolidinone
Ethyl N-benzhydrylideneglycinate
faropenem sodium
反-4-乙基环己醇
diethyl propan-2-ylpropanedioate
2-(4-(叔丁氧基羰基)哌嗪-1-基)-2-(4-(三氟甲基)苯基)乙酸