thionucleosides

Summary

Summary: Nucleosides in which the base moiety is substituted with one or more sulfur atoms.

Top Publications

  1. Dande P, Prakash T, Sioufi N, Gaus H, Jarres R, Berdeja A, et al. Improving RNA interference in mammalian cells by 4'-thio-modified small interfering RNA (siRNA): effect on siRNA activity and nuclease stability when used in combination with 2'-O-alkyl modifications. J Med Chem. 2006;49:1624-34 pubmed
    ..These optimized 4'-thio-siRNAs may be valuable for developing stable siRNAs for therapeutic applications. ..
  2. Albers E. Metabolic characteristics and importance of the universal methionine salvage pathway recycling methionine from 5'-methylthioadenosine. IUBMB Life. 2009;61:1132-42 pubmed publisher
    ..Thus, promising targets for antimicrobial agents have been identified. Other medical topics to which this pathway has connections are cancer, apoptosis, and inflammatory response. ..
  3. Simile M, Banni S, Angioni E, Carta G, De Miglio M, Muroni M, et al. 5'-Methylthioadenosine administration prevents lipid peroxidation and fibrogenesis induced in rat liver by carbon-tetrachloride intoxication. J Hepatol. 2001;34:386-94 pubmed
    ..MTA and SAM protect against oxidative liver injury through partially different mechanisms. ..
  4. Sekowska A, Dénervaud V, Ashida H, Michoud K, Haas D, Yokota A, et al. Bacterial variations on the methionine salvage pathway. BMC Microbiol. 2004;4:9 pubmed
    ..The thermophile T. tengcongensis, that thrives in the absence of oxygen, appears to possess the pathway. It will be an interesting link to uncover the missing reactions in anaerobic environments. ..
  5. Andreu Pérez P, Hernandez Losa J, Moline T, Gil R, Grueso J, Pujol A, et al. Methylthioadenosine (MTA) inhibits melanoma cell proliferation and in vivo tumor growth. BMC Cancer. 2010;10:265 pubmed publisher
    ..MTA inhibits melanoma cell proliferation and in vivo tumor growth particularly in BRAF mutant melanoma cells. These data reveal a naturally occurring drug potentially useful for melanoma treatment. ..
  6. Hoshika S, Minakawa N, Matsuda A. Synthesis and physical and physiological properties of 4'-thioRNA: application to post-modification of RNA aptamer toward NF-kappaB. Nucleic Acids Res. 2004;32:3815-25 pubmed
    ..The results presented in this paper will, it is hoped, contribute to the development of 4'-thioRNA as a new generation of artificial RNA. ..
  7. Collins C, Volik S, Lapuk A, Wang Y, Gout P, Wu C, et al. Next generation sequencing of prostate cancer from a patient identifies a deficiency of methylthioadenosine phosphorylase, an exploitable tumor target. Mol Cancer Ther. 2012;11:775-83 pubmed publisher
    ..The combination of genome sequencing and patient-derived xenografts can identify candidate therapeutic agents and evaluate them for personalized oncology...
  8. Kumar S, Horton J, Jones G, Walker R, Roberts R, Cheng X. DNA containing 4'-thio-2'-deoxycytidine inhibits methylation by HhaI methyltransferase. Nucleic Acids Res. 1997;25:2773-83 pubmed
    ..This inhibitory effect can be partially overcome after a considerably long time in the crystal environment where the packing prevents complex dissociation and the target is accurately positioned within the active site. ..
  9. Lee S, Cho Y. Induction of apoptosis in leukemia U937 cells by 5'-deoxy-5'-methylthioadenosine, a potent inhibitor of protein carboxylmethyltransferase. Exp Cell Res. 1998;240:282-92 pubmed

More Information

Publications62

  1. Takahashi M, Nagai C, Hatakeyama H, Minakawa N, Harashima H, Matsuda A. Intracellular stability of 2'-OMe-4'-thioribonucleoside modified siRNA leads to long-term RNAi effect. Nucleic Acids Res. 2012;40:5787-93 pubmed publisher
  2. Ansorena E, García Trevijano E, Martinez Chantar M, Huang Z, Chen L, Mato J, et al. S-adenosylmethionine and methylthioadenosine are antiapoptotic in cultured rat hepatocytes but proapoptotic in human hepatoma cells. Hepatology. 2002;35:274-80 pubmed
    ..These effects may participate in the hepatoprotective and chemopreventive properties of this safe and well-tolerated drug. ..
  3. Avila M, García Trevijano E, Lu S, Corrales F, Mato J. Methylthioadenosine. Int J Biochem Cell Biol. 2004;36:2125-30 pubmed
    ..Finally, observations carried out in models of liver damage and cancer demonstrate a therapeutic potential for MTA that deserves further consideration. ..
  4. Jasamai M, Balzarini J, Simons C. 6-Azathymidine-4'-thionucleosides: synthesis and antiviral evaluation. J Enzyme Inhib Med Chem. 2008;23:56-61 pubmed
  5. Singh J, Tabita F. Roles of RubisCO and the RubisCO-like protein in 5-methylthioadenosine metabolism in the Nonsulfur purple bacterium Rhodospirillum rubrum. J Bacteriol. 2010;192:1324-31 pubmed publisher
    ..Moreover, the aerobic and anaerobic sulfur salvage pathways appear to be differentially controlled, with novel and previously undescribed steps apparent for sulfur salvage in this organism. ..
  6. Stevens A, Spangler B, Wallner S, Kreutz M, Dettmer K, Oefner P, et al. Direct and tumor microenvironment mediated influences of 5'-deoxy-5'-(methylthio)adenosine on tumor progression of malignant melanoma. J Cell Biochem. 2009;106:210-9 pubmed publisher
    ..In summary, we demonstrated a tumor-supporting role of MTA. ..
  7. Inoue N, Kaga D, Minakawa N, Matsuda A. Practical synthesis of 2'-deoxy-4'-thioribonucleosides: substrates for the synthesis of 4'-thioDNA. J Org Chem. 2005;70:8597-600 pubmed
    ..2'-deoxy-4'-thiopurine nucleosides were synthesized using the same radical reaction of the corresponding 2'-beta-bromo derivatives. ..
  8. Lauhon C. Requirement for IscS in biosynthesis of all thionucleosides in Escherichia coli. J Bacteriol. 2002;184:6820-9 pubmed
    ..presence of [(35)S]cysteine showed that only a small fraction of 2-thiocytidine was present, while the other thionucleosides were absent when cells were isolated during log phase...
  9. Li T, Zhang Q, Oh P, Xia M, Chen H, Bemanian S, et al. S-Adenosylmethionine and methylthioadenosine inhibit cellular FLICE inhibitory protein expression and induce apoptosis in colon cancer cells. Mol Pharmacol. 2009;76:192-200 pubmed publisher
    ..One molecular mechanism identified is the inhibition of cFLIP expression. SAMe and MTA may be attractive agents in the chemoprevention and treatment of colon cancer. ..
  10. Hevia H, Varela Rey M, Corrales F, Berasain C, Martinez Chantar M, Latasa M, et al. 5'-methylthioadenosine modulates the inflammatory response to endotoxin in mice and in rat hepatocytes. Hepatology. 2004;39:1088-98 pubmed
    ..In conclusion, these observations demonstrate novel immunomodulatory properties for MTA that may be of value in the management of inflammatory diseases. ..
  11. Ansorena E, Berasain C, López Zabalza M, Avila M, García Trevijano E, Iraburu M. Differential regulation of the JNK/AP-1 pathway by S-adenosylmethionine and methylthioadenosine in primary rat hepatocytes versus HuH7 hepatoma cells. Am J Physiol Gastrointest Liver Physiol. 2006;290:G1186-93 pubmed
  12. Moreno B, Hevia H, Santamaria M, Sepulcre J, Munoz J, García Trevijano E, et al. Methylthioadenosine reverses brain autoimmune disease. Ann Neurol. 2006;60:323-34 pubmed
    ..MTA has a remarkable immunomodulatory activity and may be beneficial for multiple sclerosis and other autoimmune diseases. ..
  13. Bonora G. Large-scale preparation of conjugated oligonucleoside phosphorothioates by the high-efficiency liquid-phase (HELP) method. Curr Protoc Nucleic Acid Chem. 2005;Chapter 4:Unit 4.27 pubmed publisher
    ..The use of N, N'-disuccinimidyl carbonate for the activation of the terminal OH groups of the PEG was preferred. ..
  14. Kierzek E, Kierzek R. The synthesis of oligoribonucleotides containing N6-alkyladenosines and 2-methylthio-N6-alkyladenosines via post-synthetic modification of precursor oligomers. Nucleic Acids Res. 2003;31:4461-71 pubmed
  15. Chen Z, Olopade O, Savarese T. Expression of methylthioadenosine phosphorylase cDNA in p16-, MTAP- malignant cells: restoration of methylthioadenosine phosphorylase-dependent salvage pathways and alterations of sensitivity to inhibitors of purine de novo synthesis. Mol Pharmacol. 1997;52:903-11 pubmed
    ..g. antifolates) whose mechanism of action in part involves the de novo purine pathway. These findings provide a theoretical basis for the relatively selective action certain antifolates may have against MTAP-deficient malignancies. ..
  16. Zhao Y, Yuan Z. [A new coumarin glycoside from Glehnia littoralis]. Yao Xue Xue Bao. 2007;42:1070-3 pubmed
    ..Compound 1 is a new coumarin glycoside, compounds 2 and 7 were isolated from this genus for the first time. ..
  17. Jeong L, Gunaga P, Kim H, Tosh D, Lee H, Choe S, et al. Stereoselective synthesis of 1'-functionalized-4'-thionucleosides. Nucleosides Nucleotides Nucleic Acids. 2007;26:1011-4 pubmed
    Stereoselective functionalization of the 1'-position of 4'-thionucleosides was achieved using a stereoselective S(N)2 reaction controlled by 5-membered ring coordination.
  18. Lee J, Luong W, Huang D, Cornell K, Riscoe M, Howell P. Mutational analysis of a nucleosidase involved in quorum-sensing autoinducer-2 biosynthesis. Biochemistry. 2005;44:11049-57 pubmed
    ..Furthermore, mutation of Arg193 to alanine shows that the nucleophilic water is able to direct its attack without assistance from the enzyme. This mutagenesis study has allowed a reevaluation of the catalytic mechanism. ..
  19. Tsoukala E, Manta S, Tzioumaki N, Kiritsis C, Komiotis D. Keto-fluorothiopyranosyl nucleosides: a convenient synthesis of 2- and 4-keto-3-fluoro-5-thioxylopyranosyl thymine analogs. Carbohydr Res. 2011;346:2011-5 pubmed publisher
    ..Oxidation of the free hydroxyl group in the 2'-position and concomitant displacement of the benzoyl group by an acetyl gave target 1-(4'-O-acetyl-3'-deoxy-3'-fluoro-?-d-xylopyranosyl-2'-ulose)thymine (15). ..
  20. Dervieux T, Blanco J, Krynetski E, Vanin E, Roussel M, Relling M. Differing contribution of thiopurine methyltransferase to mercaptopurine versus thioguanine effects in human leukemic cells. Cancer Res. 2001;61:5810-6 pubmed
  21. Micioni Di Bonaventura M, Cifani C, Lambertucci C, Volpini R, Cristalli G, Massi M. A2A adenosine receptor agonists reduce both high-palatability and low-palatability food intake in female rats. Behav Pharmacol. 2012;23:567-74 pubmed publisher
    ..They may potentially be useful pharmacological agents to control binge-related eating disorders and to reduce food overconsumption associated with obesity. ..
  22. Warlick B, Imker H, Sriram J, Tabita F, Gerlt J. Mechanistic diversity in the RuBisCO superfamily: RuBisCO from Rhodospirillum rubrum is not promiscuous for reactions catalyzed by RuBisCO-like proteins. Biochemistry. 2012;51:9470-9 pubmed publisher
    ..Thus, although RuBisCOs can be functionally promiscuous, RuBisCO from R. rubrum is not promiscuous for either of the known RLP-catalyzed reactions...
  23. Regenold J, Illes P. Inhibitory adenosine A1-receptors on rat locus coeruleus neurones. An intracellular electrophysiological study. Naunyn Schmiedebergs Arch Pharmacol. 1990;341:225-31 pubmed
    ..In conclusion, both exogenous and endogenous adenosine activates somatic and/or dendritic A1-receptors of LC neurones leading to an enhancement of potassium conductance and thereby to a decreased firing rate and a hyperpolarization. ..
  24. Kikuchi Y, Yamazaki N, Tarashima N, Furukawa K, Takiguchi Y, Itoh K, et al. Gene suppression via U1 small nuclear RNA interference (U1i) machinery using oligonucleotides containing 2'-modified-4'-thionucleosides. Bioorg Med Chem. 2013;21:5292-6 pubmed publisher
    ..U1 adaptors consisting of a 'target domain' and a 'U1 domain', we prepared adaptor ONs using 2'-modified-4'-thionucleosides developed by our group, and evaluated their U1i activity...
  25. Pang P, Deng X, Wang Z, Xie W. Structural and biochemical insights into the 2'-O-methylation of pyrimidines 34 in tRNA. FEBS J. 2017;284:2251-2263 pubmed publisher
    ..The atomic coordinates and structural factors have been deposited in the Protein Data Bank with accession number 5CO4. ..
  26. Harris D, Beechey R, Linstead D, Barrett J. Nucleoside uptake by Trichomonas vaginalis. Mol Biochem Parasitol. 1988;29:105-16 pubmed
    ..Adenosine uptake could not be completely inhibited by nitrobenzylthionucleosides. The rate of nucleoside uptake by T. vaginalis is sufficient to sustain growth. ..
  27. Hammerland L, Johansson M, Malmström J, Mattsson J, Minidis A, Nilsson K, et al. Structure-activity relationship of thiopyrimidines as mGluR5 antagonists. Bioorg Med Chem Lett. 2006;16:2467-9 pubmed
    ..Structure-activity relationship investigations of the thiopyrimidine (1), an HTS hit with micromolar activity as a metabotropic glutamate receptor 5 (mGluR5) antagonist, led to compounds with sub-micromolar activity. ..
  28. Hughes J, Tattersall M. Potentiation of methotrexate lymphocytotoxicity in vitro by inhibitors of nucleoside transport. Br J Cancer. 1989;59:381-4 pubmed
    ..Nucleoside transport inhibitors isolate the cellular effects of nucleic acid antimetabolites, and provide a tool to study mechanisms of antifolate cytotoxicity. ..
  29. Yang H, Sadda M, Li M, Zeng Y, Chen L, Bae W, et al. S-adenosylmethionine and its metabolite induce apoptosis in HepG2 cells: Role of protein phosphatase 1 and Bcl-x(S). Hepatology. 2004;40:221-31 pubmed
  30. Wu Y, Zhang X, Meng W, Qing F. Synthesis of new 2',3'-dideoxy-6',6'-difluoro-3'-thionucleoside from gem-difluorohomoallyl alcohol. Org Lett. 2004;6:3941-4 pubmed
    ..The construction of pyrimidine ring with the amino group of compound 15 gave the target compound 1. ..
  31. Melnychuk S, Neverov A, Brown R. Catalytic decomposition of simulants for chemical warfare V agents: highly efficient catalysis of the methanolysis of phosphonothioate esters. Angew Chem Int Ed Engl. 2006;45:1767-70 pubmed
  32. Hansen E, Seamon K, Cravens S, Stivers J. GTP activator and dNTP substrates of HIV-1 restriction factor SAMHD1 generate a long-lived activated state. Proc Natl Acad Sci U S A. 2014;111:E1843-51 pubmed publisher
    ..This property would be important in resting CD4(+) T cells, where dNTP pools are reduced to nanomolar levels to restrict infection by HIV-1. ..
  33. Benkov K, Lu Y, Patel A, Rahhal R, Russell G, Teitelbaum J. Role of thiopurine metabolite testing and thiopurine methyltransferase determination in pediatric IBD. J Pediatr Gastroenterol Nutr. 2013;56:333-40 pubmed publisher
    ..Routine and repetitive metabolite testing has little or no role in patients who are doing well and taking an acceptable dose of a TP. ..
  34. Limm K, Ott C, Wallner S, Mueller D, Oefner P, Hellerbrand C, et al. Deregulation of protein methylation in melanoma. Eur J Cancer. 2013;49:1305-13 pubmed publisher
    ..The effects of endogeneous MTA on PRMTs as presented in this study can strongly support the migratory and invasive phenotype of melanoma cells. ..
  35. Wang Y, Lattmann E, Zheng Q. Preparation of 6-thioguanosine phosphoramidite for oligoribonucleotide synthesis. Nucleosides Nucleotides Nucleic Acids. 2003;22:1247-9 pubmed
    ..The results show that the monomer was stable under the conditions of RNA synthesis and suitable for incorporation of thioguanine into oligoribonucleotides. ..
  36. Sullivan K, Reddy A, Dietzmann K, Suriano A, Kocieda V, Stewart M, et al. Epigenetic regulation of tumor necrosis factor alpha. Mol Cell Biol. 2007;27:5147-60 pubmed
    ..These studies demonstrate the importance of epigenetic regulation in the control of TNF-alpha expression. These findings may have relevance for inflammatory disorders in which TNF-alpha is overproduced. ..
  37. Zlatopolskiy B, Morgenroth A, Urusova E, Dinger C, Kull T, Pape M, et al. Towards to hENT1-nucleoside transporter selective imaging agents. Synthesis and in vitro evaluation of the radiolabeled SAENTA analogues. Bioorg Med Chem Lett. 2009;19:5151-4 pubmed publisher
    ..131)I-5 showed high hENT(1)-specific binding (up to 54% ID) to 6 from 7 tested tumor cell lines and was chosen for further in vivo study. ..
  38. Lucas M, Encinar J, Arribas E, Oyenarte I, Garc a I, Kortazar D, et al. Binding of S-methyl-5'-thioadenosine and S-adenosyl-L-methionine to protein MJ0100 triggers an open-to-closed conformational change in its CBS motif pair. J Mol Biol. 2010;396:800-20 pubmed publisher
  39. Lee J, Cornell K, Riscoe M, Howell P. Expression, purification, crystallization and preliminary X-ray analysis of Escherichia coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase. Acta Crystallogr D Biol Crystallogr. 2001;57:150-2 pubmed
    ..On the basis of density calculations, two monomers are predicted per asymmetric unit (Matthews coefficient, V(M) = 2.37 A(3) Da(-1)), with a solvent content of 48%. ..
  40. Marjon K, Cameron M, Quang P, Clasquin M, Mandley E, Kunii K, et al. MTAP Deletions in Cancer Create Vulnerability to Targeting of the MAT2A/PRMT5/RIOK1 Axis. Cell Rep. 2016;15:574-587 pubmed publisher
    ..Furthermore, this vulnerability extends to PRMT5 co-complex proteins such as RIOK1. Thus, the unique biochemical features of PRMT5 create an axis of targets vulnerable in CDKN2A/MTAP-deleted cancers. ..
  41. Parker W, Allan P, Ealick S, Sorscher E, Hassan A, Silamkoti A, et al. Design and evaluation of 5'-modified nucleoside analogs as prodrugs for an E. coli purine nucleoside phosphorylase mutant. Nucleosides Nucleotides Nucleic Acids. 2005;24:387-92 pubmed
  42. Gero A. Induction of nucleoside transport sites into the host cell membrane of Babesia bovis infected erythrocytes. Mol Biochem Parasitol. 1989;35:269-76 pubmed
    ..bovis infected erythrocytes has characteristics different from either human erythrocytes or erythrocytes infected with the malarial parasites Plasmodium falciparum or Plasmodium yoelii. ..
  43. Jeong L, Pal S, Choe S, Choi W, Jacobson K, Gao Z, et al. Structure-activity relationships of truncated D- and l-4'-thioadenosine derivatives as species-independent A3 adenosine receptor antagonists. J Med Chem. 2008;51:6609-13 pubmed publisher
    ..5 nM), but a N(6)-(3-bromobenzyl) derivative 7d showed the optimal species-independent binding affinity. ..
  44. El Tayeb A, Griessmeier K, Muller C. Synthesis and preliminary evaluation of [3H]PSB-0413, a selective antagonist radioligand for platelet P2Y12 receptors. Bioorg Med Chem Lett. 2005;15:5450-2 pubmed
    ..57nM. Human platelets had a high density of P2Y(12) receptors exhibiting a B(max) value of 7.66pmol/mg of protein. ..
  45. Tisdale M, Kemp S, Parry N, Larder B. Rapid in vitro selection of human immunodeficiency virus type 1 resistant to 3'-thiacytidine inhibitors due to a mutation in the YMDD region of reverse transcriptase. Proc Natl Acad Sci U S A. 1993;90:5653-6 pubmed
    ..Assessment of the interactive effects of multiple drug-resistance mutations may help to establish a rationale for using these drugs in the future therapy of HIV disease. ..
  46. Dai Y, Pochapsky T, Abeles R. Mechanistic studies of two dioxygenases in the methionine salvage pathway of Klebsiella pneumoniae. Biochemistry. 2001;40:6379-87 pubmed
    ..A cyclopropyl substrate analogue inactivates both enzymes after multiple turnovers, providing evidence that a radical mechanism may be involved in the formation of the peroxide anion intermediate. ..
  47. Onizuka K, Taniguchi Y, Sasaki S. A new odorless procedure for the synthesis of 2'-deoxy-6-thioguanosine and its incorporation into oligodeoxynucleotides. Nucleosides Nucleotides Nucleic Acids. 2009;28:752-60 pubmed publisher
    ..The results showed that 2-ethylhexyl 3-mercaptopropionate is useful as an odor less reagent and also as an S-protecting group of 2'-deoxy-6-thioguanosine. ..
  48. Durant P, Bajji A, Sundaram M, Kumar R, Davis D. Structural effects of hypermodified nucleosides in the Escherichia coli and human tRNALys anticodon loop: the effect of nucleosides s2U, mcm5U, mcm5s2U, mnm5s2U, t6A, and ms2t6A. Biochemistry. 2005;44:8078-89 pubmed
    ..Wobble modifications, t(6)A37, and magnesium each make unique contributions toward promoting canonical tRNA structure in the fundamentally dynamic tRNA(Lys)(UUU) anticodon. ..
  49. Park A, Hayakawa S, Honda E, Mine Y, Yoshida K, Munakata H. Conditioned media from lung cancer cell line A549 and PC9 inactivate pulmonary fibroblasts by regulating protein phosphorylation. Arch Biochem Biophys. 2012;518:133-41 pubmed publisher
    ..These results show that A549 and PC9 conditioned media have the ability to inactivate myofibroblasts, and that CREB-phosphorylation plays a central role in this process. ..
  50. Haraguchi K, Horii C, Yoshimura Y, Ariga F, Tadokoro A, Tanaka H. An access to the ?-anomer of 4'-thio-C-ribonucleosides: hydroboration of 1-C-aryl- or 1-C-heteroaryl-4-thiofuranoid glycals and its regiochemical outcome. J Org Chem. 2011;76:8658-69 pubmed publisher
    ..These 1'-boranes were converted into either the ring-opened structure or the 2'-deoxy derivatives depending upon their stability. ..
  51. Zheng Q, Wang Y, Lattmann E. Synthesis of S6-(2,4-dinitrophenyl)-6-thioguanosine phosphoramidite and its incorporation into oligoribonucleotides. Bioorg Med Chem Lett. 2003;13:3141-4 pubmed
    ..The identity of the oligonucleotides was confirmed by UV spectrophotometry and nucleoside composition analysis. ..
  52. Reichardt C, Guo C, Crespo Hernandez C. Excited-state dynamics in 6-thioguanosine from the femtosecond to microsecond time scale. J Phys Chem B. 2011;115:3263-70 pubmed publisher
    ..Finally, the experimental and computational results for 6-thioguanosine are compared with those reported for the DNA/RNA guanine monomers. ..
  53. Yu J, Wu Q, Zhang Q, Liu Y, Li Y, Zhou Z. Synthesis and antitumor activity of novel 2',3'-dideoxy-2',3'-diethanethionucleosides bearing 1,2,3-triazole residues. Bioorg Med Chem Lett. 2010;20:240-3 pubmed publisher
    ..Nucleosides with a triazole ring, 16a-16c, showed significantly improved activity towards a broad range of tumor cell lines. ..