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C3394 Sigma

Cordycepin

from Cordyceps militaris

Synonym: 3′-Deoxyadenosine

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Description

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.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide and Gene Regulation research. Discover more featured Cyclic Nucleotide and Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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DISCOVER Bioactive Small Molecules

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Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T
Risk Statements (Europe) 
Safety Statements (Europe) 
26-45
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
AU7358610

Protocols & Articles

Articles

Discover Bioactive Small Molecules for Cyclic Nucleotides

Transmission of an extracellular signal across the cell membrane is initiated by activation of many types of hormone and neurotransmitter receptors, such as G-protein coupled receptors (GPCRs), and c...
Keywords: Antivirals, Cancer, Cardiovascular, Cellular processes, Diabetes, Diseases, Hormones, Neurotransmitters

Discover Bioactive Small Molecules for Gene Regulation

The loss of regulation of gene expression is a key component to many human disease states, including neurodegenerative disorders, autoimmune conditions and, most prominently, cancers. Regulation of g...
Keywords: Acetylations, Epigenetics, Gene expression, Genomics, Methylations, Post translational modifications, Transcription

Peer-Reviewed Papers

References

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Antileukemic activity and mechanism of action of cordycepin against terminal deoxynucleotidyl transferase-positive (TdT+) leukemic cells. Kodama, E.N., et al. Biochem. Pharmacol. 59, 273-281, (2000)

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Genomic Islands Of Uropathogenic Escherichia Coli Contribute To Virulence. Lloyd, A.L., et al. J. Bacteriol. 191, 3469-81, (2009)

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The polyadenylation inhibitor cordycepin (3'dA) causes a decline in c-MYC mRNA levels without affecting c-MYC protein levels. Ioannidis, P., et al. Oncogene 18, 117-125, (1999)

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Cordycepin blocks recovery of non-heat-shock mRNA translation following heat shock in Drosophila. Duncan, R.F. Eur. J. Biochem. 233, 784-792, (1995)

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Structure-activity relationships of synthetic cordycepin analogues as experimental therapeutics for African trypanosomiasis. Vodnala SK, Lundbäck T, Yeheskieli E, et al. J. Med. Chem. 56(24), 9861-73, (2013)

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[Fast determination of adenosine and cordycepin in Cordyceps and its deserted solid medium]. Li C, Yan A, Cai C, et al. Se Pu 30(7), 711-5, (2012)

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Changes in mRNA stability associated with cold stress in Arabidopsis cells. Chiba Y, Mineta K, Hirai MY, et al. Plant Cell Physiol. 54(2), 180-94, (2013)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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mRNAs containing the histone 3' stem-loop are degraded primarily by decapping mediated by oligouridylation of the 3' end. Su W, Slepenkov SV, Slevin MK, et al. RNA 19(1), 1-16, (2013)

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Ethanol extracts of fruiting bodies of Antrodia cinnamomea exhibit anti-migration action in human adenocarcinoma CL1-0 cells through the MAPK and PI3K/AKT signaling pathways. Chen YY, Chou PY, Chien YC, et al. Phytomedicine 19(8-9), 768-78, (2012)

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Cordycepin stimulated steroidogenesis in MA-10 mouse Leydig tumor cells through the protein kinase C Pathway. Pao HY, Pan BS, Leu SF, et al. J. Agric. Food Chem. 60(19), 4905-13, (2012)

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Cordycepin (3'-deoxyadenosine) attenuates age-related oxidative stress and ameliorates antioxidant capacity in rats. Ramesh T, Yoo SK, Kim SW, et al. Exp. Gerontol. 47(12), 979-87, (2012)

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The nucleoside antagonist cordycepin causes DNA double strand breaks in breast cancer cells. Lee HJ, Burger P, Vogel M, et al. Invest. New Drugs 30(5), 1917-25, (2012)

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Inhibition of polyadenylation reduces inflammatory gene induction. Kondrashov A, Meijer HA, Barthet-Barateig A, et al. RNA 18(12), 2236-50, (2012)

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Cordycepin suppresses TNF-α-induced NF-κB activation by reducing p65 transcriptional activity, inhibiting IκBα phosphorylation, and blocking IKKγ ubiquitination. Ren Z, Cui J, Huo Z, et al. Int. Immunopharmacol. 14(4), 698-703, (2012)

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Blockade of adipocyte differentiation by cordycepin. Takahashi S, Tamai M, Nakajima S, et al. Br. J. Pharmacol. 167(3), 561-75, (2012)

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High-resolution structures of complexes of plant S-adenosyl-L-homocysteine hydrolase (Lupinus luteus). Brzezinski K, Dauter Z, and Jaskolski M Acta Crystallogr. D Biol. Crystallogr. 68(Pt 3), 218-31, (2012)

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Cordycepin: a bioactive metabolite with therapeutic potential. Tuli HS, Sharma AK, Sandhu SS, et al. Life Sci. 93(23), 863-9, (2013)

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Cordycepin induces apoptosis of C6 glioma cells through the adenosine 2A receptor-p53-caspase-7-PARP pathway. Chen Y, Yang SH, Hueng DY, et al. Chem. Biol. Interact. 216, 17-25, (2014)

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Ras/ERK1 pathway regulation of p27KIP1-mediated G1-phase cell-cycle arrest in cordycepin-induced inhibition of the proliferation of vascular smooth muscle cells. Jung SM, Park SS, Kim WJ, et al. Eur. J. Pharmacol. 681(1-3), 15-22, (2012)

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Cordycepin as a sensitizer to tumour necrosis factor (TNF)-α-induced apoptosis through eukaryotic translation initiation factor 2α (eIF2α)- and mammalian target of rapamycin complex 1 (mTORC1)-mediated inhibition of nuclear factor (NF)-κB. Kadomatsu M, Nakajima S, Kato H, et al. Clin. Exp. Immunol. 168(3), 325-32, (2012)

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Effects of selenium and light wavelengths on liquid culture of Cordyceps militaris Link. Dong JZ, Liu MR, Lei C, et al. Appl. Biochem. Biotechnol. 166(8), 2030-6, (2012)

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Apoptosis induction of human prostate carcinoma cells by cordycepin through reactive oxygen species‑mediated mitochondrial death pathway. Lee HH, Park C, Jeong JW, et al. Int. J. Oncol. 42(3), 1036-44, (2013)

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Protective roles of Cordyceps on lung fibrosis in cellular and rat models. Chen M, Cheung FW, Chan MH, et al. J. Ethnopharmacol. 143(2), 448-54, (2012)

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Effect of cordycepin purified from Cordyceps militaris on Th1 and Th2 cytokines in mouse splenocytes. Jeong MH, Seo MJ, Park JU, et al. J. Microbiol. Biotechnol. 22(8), 1161-4, (2012)

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Blockade of Smad signaling by 3'-deoxyadenosine: a mechanism for its anti-fibrotic potential. Gu L, Johno H, Nakajima S, et al. Lab. Invest. 93(4), 450-61, (2013)

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Synthesis and pharmacokinetic evaluation of novel N-acyl-cordycepin derivatives with a normal alkyl chain. H-P Wei et al Eur. J. Med. Chem. 44, 665-9, (2009)

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Cordycepin induces apoptosis in human neuroblastoma SK-N-BE(2)-C and melanoma SK-MEL-2 cells. Baik JS, Kwon HY, Kim KS, et al. Indian J. Biochem. Biophys. 49(2), 86-91, (2012)

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Cordycepin (3'-deoxyadenosine) pentostatin (deoxycoformycin) combination treatment of mice experimentally infected with Trypanosoma evansi. Dalla Rosa L, da Silva AS, Gressler LT, et al. Parasitology 140(5), 663-71, (2013)

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Effect of long-term administration of cordycepin from Cordyceps militaris on testicular function in middle-aged rats. Sohn SH, Lee SC, Hwang SY, et al. Planta Med. 78(15), 1620-5, (2012)

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Suppression of T-cell activation in vitro and in vivo by cordycepin from Cordyceps militaris. Xiong Y, Zhang S, Xu L, et al. J. Surg. Res. 185(2), 912-22, (2013)

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Cultivation of medicinal caterpillar fungus, Cordyceps militaris (Ascomycetes), and production of cordycepin using the spent medium from levan fermentation. Wu FC, Chen YL, Chang SM, et al. Int. J. Med. Mushrooms 15(4), 393-405, (2013)

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Optimization of solid state culture conditions for the production of adenosine, cordycepin, and D-mannitol in fruiting bodies of medicinal caterpillar fungus Cordyceps militaris (L.:Fr.) Link (Ascomycetes). Lim L, Lee C, and Chang E Int. J. Med. Mushrooms 14(2), 181-7, (2012)

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Early viral protein synthesis is necessary for NF-kappaB activation in modified vaccinia Ankara (MVA)-infected 293 T fibroblast cells. Martin S and Shisler JL Virology 390(2), 298-306, (2009)

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Influence of treatment with 3'-deoxyadenosine associated deoxycoformycin on hematological parameters and activity of adenosine deaminase in infected mice with Trypanosoma evansi. Dalla Rosa L, Da Silva AS, Ruchel JB, et al. Exp. Parasitol. 135(2), 357-62, (2013)

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Triacetyl-3-hydroxyphenyladenosine, a derivative of cordycepin, attenuates atherosclerosis in apolipoprotein E-knockout mice. Zhao Z, Song G, Tian H, et al. Exp. Biol. Med. (Maywood.) 237(11), 1262-72, (2012)

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Effect of cordycepin on the expression of the inflammatory cytokines TNF-alpha, IL-6, and IL-17A in C57BL/6 mice. Seo MJ, Kim MJ, Lee HH, et al. J. Microbiol. Biotechnol. 23(2), 156-60, (2013)

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Merck 14,2529

Beil. 26,IV,3594

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