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Cordycepin Basic information Plant extracts Pharmacological effects Uses Product Name: Cordycepin Synonyms: CORDYCEPIN;3’-deoxy-adenosin;9-cordyceposidoadenine;3'-DEOXYADENOSINE;3'-dA;Cordycepin from Cordyceps militaris;Cipargamin;9-(3-deoxypentofuranosyl)-9H-purin-6-amine CAS: 73-03-0 MF: C10H13N5O3 MW: 251.24 EINECS: 200-791-4 Product Categories: Miscellaneous Natural Products;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors Mol File: 73-03-0.mol   Cordycepin Chemical Properties Melting point  225-229 °C alpha  D20 -47°; D27 -42° Boiling point  394.4°C (rough estimate) density  1.2938 (rough estimate) refractive index  1.7610 (estimate) storage temp.  Keep in dark place,Inert atmosphere,Store in freezer, under -20°C solubility  Soluble in DMSO (up to 25 mg/ml). pka 13 +-.0.60(Predicted) form  Powder color  White to Off-white λmax 260nm(EtOH)(lit.) Merck  14,2529 BRN  35194 Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. InChIKey OFEZSBMBBKLLBJ-BAJZRUMYSA-N CAS DataBase Reference 73-03-0(CAS DataBase Reference) EPA Substance Registry System Adenosine, 3'-deoxy- (73-03-0)   Safety Information Hazard Codes  Xn,T Risk Statements  40-36/37/38-25-20/21/22 Safety Statements  22-36-45-26 RIDADR  UN 2811 WGK Germany  3 RTECS  AU7358610 F  10-21 HazardClass  6.1 HS Code  29349990 MSDS Information Provider Language 3'-Deoxyadenosine English SigmaAldrich English   Cordycepin Usage And Synthesis Plant extracts In 1951, German scientist Cunningham had purified a crystal from the Cordyceps militaris and named it cordycepin. From then on, the crordycepin reported in published literature abroad regarding to its antitumor, antiviral efficacy as well as extraction and purification had been all obtained from Cordyceps instead of being from Cordyceps sinensis which contains only trace amount of Cordycepin. Cordyceps is the major active ingredient contained in Cordyceps (especially nucleoside). It belongs to a kind of nucleoside drugs, purine alkaloids and is also the first kind of nuclear glycosides antibiotics isolated from fungus. Owing to its special efficacy in repairing cells and protection of the genetic code of life, it has become one of the leaders in modern biomedicine. Cordycepin is a drug of natural source with various kinds of pharmacological effects such as anti-tumor, antibacterial and antiviral, immunomodulatory as well as free radical-scavenging, etc., and has good prospects for clinical application. At present time, the research on cordycepin present study is becoming an extremely active area in the field of pharmaceutical chemistry. As a structural analogue of adenosine, cordycepin can inhibit Bacillus subtilis, Mycobacterium tuberculosis of birds and Ehrlich ascites tumor cells with inhibitory effect on the RNA and DNA synthesis inhibition of cancer cells, therefore having very strong inhibitory effect on the human nose and pharynx cancer (KD) cells. The clinically applied cordycepin is mostly used for adjuvant treatment of malignant tumors with the cases of improved clinical symptoms accounting for more than 91.7%; it is mainly used for the treatment of patients of nasal cancer, throat cancer, lung cancer, leukemia, brain cancer and other malignant tumor. Cordycepin is extracted from the Cordyceps and is the mostly nutritious active substance inside Cordyceps. Its major composition is Cordyceps polysaccharide, Cordyceps acid as well as Cordyceps SOD and is a kind of natural nutrients of high health function. It can activate dormant cells, repair diseased cells, propagate the new living cells, clean up dead cells and is of great value in improving immunity, anti-fatigue as well as improving the body's energy. Pharmacological effects Most currently known Cordyceps fungus contains Cordycepin, which obviously plays an important role in the anti-tumor effect. Jagger believes the cordycepin contained in Cordyceps fungus can inhibit tumorigenesis through three possible mechanisms: 1. The free alcoholic group contained in cordycepin can be incorporated into the DNA of cancer cells and takes effect. 2. Cordycepin can inhibit the phosphorylation of nucleoside or nucleotide to generate the derivatives of diphosphate and triphosphate, thereby inhibiting the synthesis of nucleic acids in tumor cell. 3. Cordycepin can block the amination of xanthylic acid into guanylate. In 1977, Müller et al found that cordycepin had strong inhibitory effect against the proliferation of L5718Y cell with the ED50 being 0.27μg; this inhibitory effect can be eliminated by adenosine but not 2'-deoxy-nucleosides; The tritium marked Cordyceps trial have showed that cordycepin can be incorporated into RNA rather than DNA. The cordycepin, inside the cell, can be phosphorylated to 3'-ATP; 3'-ATP has no effect on the activity of the DNA-dependent DNA polymerase α and β in L5718Y cells, but has strong inhibitory effect on the nuclear Poly (a) polysaccharide which will inevitably lead to a maturation defect of mRNA, further negatively affecting the formation of mRNA and protein synthesis. The anti-tumor effects of Cordyceps may be related to this mechanism. In 1997, the United States has applied cordycepin to third-period clinical trials for the treatment of pre-B and pre-T acute lymphocytic leukemia, while cordycepin also exhibit strong anti-fungal, anti-HIV viral and selective inhibition activity on the activity of Clostridium genus. In 1985, with in vitro experiments, Jiang ping et al observed the cytotoxicity of Cordyceps sinensis and cultured mycelium (Qinghai) on ECA cells. For the treatment of in vitro cell culture ECA, the result showed that when they two were at the lowest effective concentration 0.405mg/ml and 25mg/ml, the total infection rate was 100%, 80%, respectively, indicating that the drug has different strengths of ECA cytotoxicity. Comprehensive in vivo tests speculated that the anti-tumor effect is correlated with the certain amount of 3'-deoxy-nucleosides contained in the drug and Cordyceps polysaccharides as well as the relative balance between the overall immune regulatory function of the drugs and its effect of maintaining body immunity. Cordyceps sinensis has certain cytotoxic effect, which is consistent with the report regarding to the strong cytotoxicity of cordycepin-resistant L1210. The above information is edited by the chemicalbook of Dai Xiongfeng. Uses Cordycepin is known to have various kinds of effects of improving immune skill, anti-aging, anti-fatigue, anti-cancer, anti-bacterial, anti-virus, lowering blood glucose and lipid and male hormone. Description Cordycepin (73-03-0) is an adenosine analog lacking the hydroxyl at the 3’ position. Inhibits PARP1 and polyadenylation2. Displays anti-inflammatory effects1,3 and neuroprotective effects by inhibiting Aβ-induced apoptosis in hippocampal neurons4. Induces apoptosis in a variety of cancer cell lines5. Displays antiobesity effects.6 Inhibits cell senescence via activation of AMPK.7 Maintains stem cell pluripotency and increases iPS cell generation efficiency.8 Chemical Properties Crystalline Solid Uses First reported nucleoside antibiotic. General Description Chemical structure: nucleoside Biological Activity Nucleoside analog that acts as an anticancer and antifungal agent. Can be converted to 3'-deoxyadenosine triphosphate (3'-dATP), which inhibits ATP-dependent DNA synthesis. Inhibits growth of various tumor cells in vitro . Biochem/physiol Actions Cordycepin is an adenosine analogue that is readily converted to cordycepin 5′-triphosphate; can be used for 3′-end labeling of RNA. Purification Methods 3'-Deoxyadenosine forms needles from EtOH, n-BuOH and n-PrOH, and a monohydrate from H2O. It has max 260nm ( 14,600) in EtOH. The picrate has m 195o(dec, yellow crystals from H2O). [Kaczka et al. Biochim Biophys Acta 14 456 1964, Todd & Ulbricht J Chem Soc 3275 1960, Lee et al. J Am Chem Soc 83 1906 1961, Walton et al. J Am Chem Soc 86 2952 1964, Beilstein 26 III/IV 3594.] References 1) Kim et al. (2011), Cordycepin blocks lung injury-associated inflammation and promotes BRCA1-deficient breast cancer cell killing by effectively inhibiting PARP; Mol. Med. 17 893 2) Kondrashov et al. (2012), Inhibition of polyadenylation reduces inflammatory gene induction; RNA 18 2236 3)Yang et al. (2017), Cordycepin inhibits LPS-induced inflammatory response by modulating NOD-Like Receptor Protein 3 inflammasome activation; Biomed. Pharmacother. 95 1777 4) Song et al. (2018), Neuroprotective effects of cordycepin inhibit Aβ-induced apoptosis in hippocampal neurons; Neurotoxicology 68 73 5) Zhang et al. (2018), Cordycepin induces apoptosis in human pancreatic cancer cells via the mitochondrial-mediated intrinsic pathway and suppresses tumor growth in vivo; OncoTargets Ther. 11 4479 6) Li et al. (2018), Cordycepin modulates body weight by reducing prolactin via an adenosine A1 receptor; Curr. Pharm. Des., 24 3240 7) Wang et al (2019) Cordycepin prevents radiation ulcer by inhibiting cell senescence via NRF2 and SMPK in rodents; Nat. Commun. 10 2538 8) Wang et al. (2020) The novel application of cordycepin in maintaining stem cell pluripotency and increasing iPS cell generation efficiency; Sci. Rep. 10 2187   Cordycepin Preparation Products And Raw materials Tag:Cordycepin(73-03-0) Related Product Information

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Leader Biochemical Group is a large leader incorporated industry manufacturers and suppliers of advanced refined raw materials From the year of 1996 when our factory was put into production to year of 2020, our group has successively invested in more than 52 factories with shares and subordinates.We focus on manufacture Pharm & chemicals, functional active ingredients, nutritional Ingredients, health care products, cosmetics, pharmaceutical and refined feed, oil, natural plant ingredients industries to provide top quality of GMP standards products.All the invested factories' product lines cover API and intermediates, vitamins, amino acids, plant extracts, daily chemical products, cosmetics raw materials, nutrition and health care products, food additives, feed additives, essential oil products, fine chemical products and agricultural chemical raw materials And flavors and fragrances. Especially in the field of vitamins, amino acids, pharmaceutical raw materials and cosmetic raw materials, we have more than 20 years of production and sales experience. All products meet the requirements of high international export standards and have been recognized by customers all over the world. Our manufacture basement & R&D center located in National Aerospace Economic & Technical Development Zone Xi`an Shaanxi China. Now not only relying on self-cultivation and development as well as maintains good cooperative relations with many famous research institutes and universities in China. Now, we have closely cooperation with Shanghai Institute of Organic Chemistry of Chinese Academy of Science, Beijing Institute of Material Medical of Chinese Academy of Medical Science, China Pharmaceutical University, Zhejiang University. Closely cooperation with them not only integrating Science and technology resources, but also increasing the R&D speed and improving our R&D power. Offering Powerful Tech supporting Platform for group development. Keep serve the manufacture and the market as the R&D central task, focus on the technical research.  Now there are 3 technology R & D platforms including biological extract, microorganism fermentation and chemical synthesis, and can independently research and develop kinds of difficult APIs and pharmaceutical intermediates. With the strong support of China State Institute of Pharmaceutical Industry (hereinafter short for CSIPI), earlier known as Shanghai Institute of Pharmaceutical Industry (SIPI), we have unique advantages in the R & D and industrialization of high-grade, precision and advanced products.  Now our Group technical force is abundant, existing staff more that 1000 people, senior professional and technical staff accounted for more than 50% of the total number of employees, including 15 PhD research and development personnel, 5 master′ S degree in technical and management personnel 9 people. We have advanced equipment like fermentation equipment and technology also extraction, isolation, purification, synthesis with rich production experience and strict quality control system, According to the GMP required, quickly transforming the R&D results to industrial production in time, it is our advantages and our products are exported to North and South America, Europe, Middle East, Africa, and other five continents and scale the forefront in the nation, won good international reputation.  We believe only good quality can bring good cooperation, quality is our key spirit during our production, we are warmly welcome clients and partner from all over the world contact us for everlasting cooperation, Leader will be your strong, sincere and reliable partner in China.

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