Genomes and Genes
Summary: Adenosine molecules which can be substituted in any position, but are lacking one hydroxyl group in the ribose part of the molecule.
- Challand M, Martins F, Roach P. Catalytic activity of the anaerobic tyrosine lyase required for thiamine biosynthesis in Escherichia coli. J Biol Chem. 2010;285:5240-8 pubmed publisher..The results of the substrate analogue studies and the product inhibition can be explained by a mechanistic hypothesis involving two reaction pathways, a product-forming pathway and a futile cycle. ..
- Lee S, Kim S, Choi W, Kim W, Moon S. Cordycepin causes p21WAF1-mediated G2/M cell-cycle arrest by regulating c-Jun N-terminal kinase activation in human bladder cancer cells. Arch Biochem Biophys. 2009;490:103-9 pubmed publisher..These results suggest that cordycepin could be an effective treatment for bladder cancer. ..
- Chang W, Lim S, Song H, Song B, Kim H, Cha M, et al. Cordycepin inhibits vascular smooth muscle cell proliferation. Eur J Pharmacol. 2008;597:64-9 pubmed publisher..Taken together, these data suggest that cordycepin may induce antiproliferation in RAoSMCs via the modulation of vessel wall remodeling. Therefore, cordycepin may be a potential therapeutic approach to treat restenosis. ..
- Wei H, Ye X, Chen Z, Zhong Y, Li P, Pu S, et al. Synthesis and pharmacokinetic evaluation of novel N-acyl-cordycepin derivatives with a normal alkyl chain. Eur J Med Chem. 2009;44:665-9 pubmed publisher..It indicated that N-octanoyl modification could decrease the metabolic velocity and increase the bioavailability of cordycepin to the maximum, thus it might be a promising prodrug of cordycepin. ..
- Yang F, Li S. Effects of sample preparation methods on the quantification of nucleosides in natural and cultured Cordyceps. J Pharm Biomed Anal. 2008;48:231-5 pubmed publisher..sinensis had no obvious variation among the three extraction methods. The results suggest that sample preparation has significant effect on the quantification of nucleosides in Cordyceps. ..
- Kawamoto A, Kodama E, Sarafianos S, Sakagami Y, Kohgo S, Kitano K, et al. 2'-deoxy-4'-C-ethynyl-2-halo-adenosines active against drug-resistant human immunodeficiency virus type 1 variants. Int J Biochem Cell Biol. 2008;40:2410-20 pubmed publisher..The present data suggest that EFdA, is a promising candidate for developing as a therapeutic agent for the treatment of individuals harboring multi-drug resistant HIV variants. ..
- Wu H, Min J, Zeng H, McCloskey D, Ikeguchi Y, Loppnau P, et al. Crystal structure of human spermine synthase: implications of substrate binding and catalytic mechanism. J Biol Chem. 2008;283:16135-46 pubmed publisher..An analysis to trace possible evolutionary origins of spermine synthase is also described. ..
- Ohrui H. 2'-deoxy-4'-C-ethynyl-2-fluoroadenosine, a nucleoside reverse transcriptase inhibitor, is highly potent against all human immunodeficiency viruses type 1 and has low toxicity. Chem Rec. 2006;6:133-43 pubmed
- Huang H, Das R, Basu A, Stone M. Structures of (5'S)-8,5'-Cyclo-2'-deoxyguanosine Mismatched with dA or dT. Chem Res Toxicol. 2012;25:478-90 pubmed publisher..For the S-cdG·dA mismatch pair, both S-cdG and dA intercalate, but no hydrogen bonding is observed between S-cdG and dA. This is consistent with the lower levels of S-cdG ? T transitions in E. coli. ..
- Wehbe Janek H, Shi Q, Kearney C. Cordycepin/Hydroxyurea synergy allows low dosage efficacy of cordycepin in MOLT-4 leukemia cells. Anticancer Res. 2007;27:3143-6 pubmed..HU was identified as a promising potential alternative for anti-cancer therapy with cordycepin, thus eliminating the need for the toxic deoxycoformycin. ..
- Shanmugam G, Goodenough A, Kozekov I, Guengerich F, Rizzo C, Stone M. Structure of the 1,N2-etheno-2'-deoxyguanosine adduct in duplex DNA at pH 8.6. Chem Res Toxicol. 2007;20:1601-11 pubmed..The 5'-neighbor T(5).A(20) base pair was destabilized with respect to Watson-Crick base pairing. The refined structure predicted a bend in the helical axis associated with the adduct site. ..
- Wu W, Hsiao J, Lian Y, Lin C, Huang B. The apoptotic effect of cordycepin on human OEC-M1 oral cancer cell line. Cancer Chemother Pharmacol. 2007;60:103-11 pubmed..05) in 12, 24 and 48 h cordycepin treatment. These results further confirmed the apoptotic event. In conclusion, cordycepin significantly induced cell apoptotsis in OEC-M1 human oral squamous cancer cells. ..
- Wu W, Stupi B, LITOSH V, Mansouri D, Farley D, Morris S, et al. Termination of DNA synthesis by N6-alkylated, not 3'-O-alkylated, photocleavable 2'-deoxyadenosine triphosphates. Nucleic Acids Res. 2007;35:6339-49 pubmed..A five-base experiment, illustrating the exquisite, stepwise addition through a homopolymer repeat, demonstrates the applicability of the N(6)-(2-nitrobenzyl)-dATP as an ideal RT for CRT sequencing. ..
- Chen Y, Chen Y, Lin Y, Huang S, Wang S. Cordycepin induces apoptosis of CGTH W-2 thyroid carcinoma cells through the calcium-calpain-caspase 7-PARP pathway. J Agric Food Chem. 2010;58:11645-52 pubmed publisher..In conclusion, the cordycepin-induced apoptosis of CGTH W-2 cells is mediated by the calcium-calpain-caspase 7-PARP pathway, and ARs are involved in the apoptotic effect of cordycepin. ..
- Nair U, Bartsch H, Nair J. Lipid peroxidation-induced DNA damage in cancer-prone inflammatory diseases: a review of published adduct types and levels in humans. Free Radic Biol Med. 2007;43:1109-20 pubmed
- Murphey Corb M, Rajakumar P, Michael H, Nyaundi J, Didier P, Reeve A, et al. Response of simian immunodeficiency virus to the novel nucleoside reverse transcriptase inhibitor 4'-ethynyl-2-fluoro-2'-deoxyadenosine in vitro and in vivo. Antimicrob Agents Chemother. 2012;56:4707-12 pubmed publisher..These results suggest that expanded studies with EFdA are warranted. ..
- Thomadaki H, Scorilas A, Tsiapalis C, Havredaki M. The role of cordycepin in cancer treatment via induction or inhibition of apoptosis: implication of polyadenylation in a cell type specific manner. Cancer Chemother Pharmacol. 2008;61:251-65 pubmed..However, inhibition of polyadenylation did not influence the cell lines Daudi and Molt-4 used, where alternative apoptotic pathways are induced through cleavage of DNA into high molecular weight fragments. ..
- Jaruga P, Dizdaroglu M. Identification and quantification of (5'R)- and (5'S)-8,5'-cyclo-2'-deoxyadenosines in human urine as putative biomarkers of oxidatively induced damage to DNA. Biochem Biophys Res Commun. 2010;397:48-52 pubmed publisher..We propose that R-cdA and S-cdA may be well-suited biomarkers for disease processes such as carcinogenesis. ..
- Navacchia M, Chatgilialoglu C, Montevecchi P. C5'-adenosinyl radical cyclization. A stereochemical investigation. J Org Chem. 2006;71:4445-52 pubmed
- Wong Y, Moon A, Duffin R, Barthet Barateig A, Meijer H, Clemens M, et al. Cordycepin inhibits protein synthesis and cell adhesion through effects on signal transduction. J Biol Chem. 2010;285:2610-21 pubmed publisher..We conclude that many of the reported biological effects of cordycepin are likely to be due to its effects on mTOR and AMPK signaling. ..
- Pande P, Das R, Sheppard C, Kow Y, Basu A. Repair efficiency of (5'S)-8,5'-cyclo-2'-deoxyguanosine and (5'S)-8,5'-cyclo-2'-deoxyadenosine depends on the complementary base. DNA Repair (Amst). 2012;11:926-31 pubmed publisher..This result adds to complexity of human NER, which discriminates the damaged base pairs on the basis of multiple criteria. ..
- Takahashi S, Tamai M, Nakajima S, Kato H, Johno H, Nakamura T, et al. Blockade of adipocyte differentiation by cordycepin. Br J Pharmacol. 2012;167:561-75 pubmed publisher..Cordycepin, by blocking both adipogenesis and lipid accumulation, may have potential as a therapeutic agent for effective treatment of obesity and obesity-related disorders. ..
- Pao H, Pan B, Leu S, Huang B. Cordycepin stimulated steroidogenesis in MA-10 mouse Leydig tumor cells through the protein kinase C Pathway. J Agric Food Chem. 2012;60:4905-13 pubmed publisher..In conclusion, cordycepin stimulated intracellular PLC/PKC and MAPK signal transduction pathways to induce steroidogenesis and cell death in MA-10 mouse Leydig tumor cells. ..
- Suzuki A, Takahashi N, Okada Y, Saito I, Nemoto N, Saito Y. Naphthalene-based environmentally sensitive fluorescent 8-substituted 2'-deoxyadenosines: application to DNA detection. Bioorg Med Chem Lett. 2013;23:886-92 pubmed publisher..We developed a new fluorescent probe containing (2,6dn)A that can be used for the detection of target DNA via a bulge formation regardless of the neighboring sequences. ..
- Yoshikawa N, Yamada S, Takeuchi C, Kagota S, Shinozuka K, Kunitomo M, et al. Cordycepin (3'-deoxyadenosine) inhibits the growth of B16-BL6 mouse melanoma cells through the stimulation of adenosine A3 receptor followed by glycogen synthase kinase-3beta activation and cyclin D1 suppression. Naunyn Schmiedebergs Arch Pharmacol. 2008;377:591-5 pubmed..In conclusion, this study demonstrated that cordycepin inhibits the proliferation of B16-BL6 cells by stimulating adenosine A3 receptors followed by the Wnt signaling pathway, including GSK-3beta activation and cyclin D1 inhibition. ..
- Kim H, Shrestha B, Lim S, Yoon D, Chang W, Shin D, et al. Cordycepin inhibits lipopolysaccharide-induced inflammation by the suppression of NF-kappaB through Akt and p38 inhibition in RAW 264.7 macrophage cells. Eur J Pharmacol. 2006;545:192-9 pubmed..Thus, cordycepin may provide a potential therapeutic approach for inflammation-associated disorders. ..
- Thomadaki H, Tsiapalis C, Scorilas A. The effect of the polyadenylation inhibitor cordycepin on human Molt-4 and Daudi leukaemia and lymphoma cell lines. Cancer Chemother Pharmacol. 2008;61:703-11 pubmed..The results showed that the differentiated modulations of PAP in the two cell lines may be a result of the additive effect of the changes in cell cycle and apoptotic pathway induced. ..
- Nyaga S, Jaruga P, Lohani A, Dizdaroglu M, Evans M. Accumulation of oxidatively induced DNA damage in human breast cancer cell lines following treatment with hydrogen peroxide. Cell Cycle. 2007;6:1472-8 pubmed..Furthermore, MCF-7 and HCC1937 cell lines were deficient in the excision repair of all the four lesions studied. These results suggest that oxidatively induced DNA damage and its repair may be critical in the etiology of breast cancer. ..
- Holbein S, Freimoser F, Werner T, Wengi A, Dichtl B. Cordycepin-hypersensitive growth links elevated polyphosphate levels to inhibition of poly(A) polymerase in Saccharomyces cerevisiae. Nucleic Acids Res. 2008;36:353-63 pubmed..Based on these observations, we suggest that binding of poly P to poly(A) polymerase negatively regulates its activity. ..
- Cho H, Cho J, Rhee M, Kim H, Lee H, Park H. Inhibitory effects of cordycepin (3'-deoxyadenosine), a component of Cordyceps militaris, on human platelet aggregation induced by thapsigargin. J Microbiol Biotechnol. 2007;17:1134-8 pubmed..Accordingly, our data demonstrated that cordycepin may have a beneficial effect on platelet aggregation-mediated thrombotic diseases through the [Ca2+]i-regulating system such as cGMP...
- Ohrui H, Kohgo S, Hayakawa H, Kodama E, Matsuoka M, Nakata T, et al. 2'-deoxy-4'-C-ethynyl-2-fluoroadenosine: a nucleoside reverse transcriptase inhibitor with highly potent activity against wide spectrum of HIV-1 strains, favorable toxic profiles, and stability in plasma. Nucleosides Nucleotides Nucleic Acids. 2007;26:1543-6 pubmed..The nucleoside will prevent or delay the emergence of drug-resistant HIV-1 variants and be an ideal therapeutic agent for both HIV-1 and HBV infections. ..
- Lee S, Moon G, Jung K, Kim W, Moon S. c-Jun N-terminal kinase 1 is required for cordycepin-mediated induction of G2/M cell-cycle arrest via p21WAF1 expression in human colon cancer cells. Food Chem Toxicol. 2010;48:277-83 pubmed publisher..Together, these results suggest a critical role for JNK1 activation in cordycepin-induced inhibition of cell growth and G2/M-phase arrest in human colon cancer cells. ..
- Chen L, Stellrecht C, Gandhi V. RNA-directed agent, cordycepin, induces cell death in multiple myeloma cells. Br J Haematol. 2008;140:682-391 pubmed publisher..Our results suggest that RNA-directed agents may be a new group of agents for the treatment of MM. ..
- Boussicault F, Kaloudis P, Caminal C, Mulazzani Q, Chatgilialoglu C. The fate of C5' radicals of purine nucleosides under oxidative conditions. J Am Chem Soc. 2008;130:8377-85 pubmed publisher..Rate constants for the reactions of the 2'-deoxyadenosin-5'-yl with cysteine and glutathione in water were determined by pulse radiolysis to be (2.1 +/- 0.5) x 10(7) and (4.9 +/- 0.6) x 10(7) M(-1) s(-1) at 22 degrees C, respectively. ..
- Karwowski B, Grand A, Cadet J. 5',8-Cyclo-2'-deoxyadenosine (cdA) formation by gamma-radiation. Theoretical quantum mechanics study. Acta Biochim Pol. 2009;56:655-62 pubmed..The O4'-exo conformation was found to be present in each of the discussed mechanisms. ..
- Jaruga P, Xiao Y, Nelson B, Dizdaroglu M. Measurement of (5'R)- and (5'S)-8,5'-cyclo-2'-deoxyadenosines in DNA in vivo by liquid chromatography/isotope-dilution tandem mass spectrometry. Biochem Biophys Res Commun. 2009;386:656-60 pubmed publisherOxidatively induced DNA lesions (5'R)- and (5'S)-8,5'-cyclo-2'-deoxyadenosines (R-cdA and S-cdA) are detectable and accumulate in vivo due to disease states and defects in DNA repair...
- Jaruga P, Xiao Y, Vartanian V, Lloyd R, Dizdaroglu M. Evidence for the involvement of DNA repair enzyme NEIL1 in nucleotide excision repair of (5'R)- and (5'S)-8,5'-cyclo-2'-deoxyadenosines. Biochemistry. 2010;49:1053-5 pubmed publisher..Further studies aimed at elucidating the mechanism of action of NEIL1 in NER are warranted. ..
- Zaliznyak T, Lukin M, de Los Santos C. Structure and stability of duplex DNA containing (5'S)-5',8-cyclo-2'-deoxyadenosine: an oxidatively generated lesion repaired by NER. Chem Res Toxicol. 2012;25:2103-11 pubmed publisher..The S-cdA·T duplex structure shows many similarities to and some intriguing differences from the recently reported structure of an S-cdG·dC duplex³¹ that suggest different lesion site dynamics. ..
- Petrova K, Jalluri R, Kozekov I, Rizzo C. Mechanism of 1,N2-etheno-2'-deoxyguanosine formation from epoxyaldehydes. Chem Res Toxicol. 2007;20:1685-92 pubmed..Also observed are products that appear to be derived from 2,3-epoxyoctanal, which can be formed through Schiff base formation of 4,5-epoxy-2-decenal with the dGuo followed by hydration of the double bond and retro-aldol reaction. ..
- Shi P, Huang Z, Tan X, Chen G. Proteomic detection of changes in protein expression induced by cordycepin in human hepatocellular carcinoma BEL-7402 cells. Methods Find Exp Clin Pharmacol. 2008;30:347-53 pubmed publisher..It is suggested that the effect of cordycepin on the growth of tumor cells is significantly related to the metabolism-associated protein expression induced by cordycepin. ..
- Jaruga P, Rozalski R, Jawien A, Migdalski A, Olinski R, Dizdaroglu M. DNA damage products (5'R)- and (5'S)-8,5'-cyclo-2'-deoxyadenosines as potential biomarkers in human urine for atherosclerosis. Biochemistry. 2012;51:1822-4 pubmed publisher..Our data suggest that R-cdA and S-cdA can be accurately and reproducibly measured in human urine as potential biomarkers of risk and diagnosis for atherosclerosis. ..
- Jaruga P, Dizdaroglu M. 8,5'-Cyclopurine-2'-deoxynucleosides in DNA: mechanisms of formation, measurement, repair and biological effects. DNA Repair (Amst). 2008;7:1413-25 pubmed publisher..Accumulation of cdA and cdG was observed in tissues in vivo in connection to disease and environmental conditions, suggesting an important role for these lesions in disease processes including carcinogenesis and neuronal death. ..
- Sun Y, Wang Y, Qu K, Zhu H. Beneficial effects of cordycepin on metabolic profiles of liver and plasma from hyperlipidemic hamsters. J Asian Nat Prod Res. 2011;13:534-46 pubmed publisher..Cordycepin afforded a little lipid-regulating activity on plasma but more beneficial effects on liver, implicating that cordycepin might have a protective effect on liver under fatty liver condition. ..
- Vu B, Boyer P, Siddiqui M, Marquez V, Hughes S. 4'-C-methyl-2'-deoxyadenosine and 4'-C-ethyl-2'-deoxyadenosine inhibit HIV-1 replication. Antimicrob Agents Chemother. 2011;55:2379-89 pubmed publisher..Experiments that measure the ability of the compounds to block DNA synthesis in infected cells suggest that this differential block to DNA synthesis also occurs in infected cells. ..
- Jeong J, Jin C, Park C, Hong S, Kim G, Jeong Y, et al. Induction of apoptosis by cordycepin via reactive oxygen species generation in human leukemia cells. Toxicol In Vitro. 2011;25:817-24 pubmed publisher..These results support a mechanism whereby cordycepin induces apoptosis of human leukemia cells through a signaling cascade involving a ROS-mediated caspase pathway. ..
- Karwowski B. Formation of 5',8-cyclo-2'-deoxyadenosine in single strand DNA. Theoretical quantum mechanics study. Org Biomol Chem. 2010;8:1603-9 pubmed publisher..Moreover, the investigated reaction paths have shown that the formation of the 5'R isomer is energetically favourable in both the aqueous and gaseous phases. Therefore, the presented results are in good agreement with experimental data. ..
- Lee E, Kim W, Moon S. Cordycepin suppresses TNF-alpha-induced invasion, migration and matrix metalloproteinase-9 expression in human bladder cancer cells. Phytother Res. 2010;24:1755-61 pubmed publisher..These results suggest that cordycepin maybe an effective therapeutic approach to treat bladder cancer. ..