Structures and Functions of Nucleic Acids Modified with S, Se, and Te and Complexed with Small Molecules

Medicinal Chemistry of Nucleic Acids

Volumn , Issue , 2011, Pages 101-141

  Zhang, Wen ^a   Sheng, Jia ^a   Huang, Zhen ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

Nucleic acids; Se nucleic acids; Tellurium derivatized nucleic acids (TeNA)

Indexed keywords

EID: 84885977521     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118092804.ch2     Document Type: Chapter

References (245)

1. Benoff, B., Yang, H., Lawson, C., Parkinson, G., Liu, J., Blatter, E., Ebright, Y., Berman, H., Ebright, R., Structural basis of transcription activation: the CAP-alpha CTD-DNA complex. Science 2002, 297 (5586), 1562.
2. Dynan, W., Tjian, R., Control of eukaryotic messenger RNA synthesis by sequencespecific DNA-binding proteins. Nature 1985, 316 (6031), 774-778.
3. Watson, J., Crick, F., Molecular structure of nucleic acids: a structure for deoxyribose nucleic acid. Nature 1953, 171 (4356), 737-738.
4. Storz, G., An expanding universe of noncoding RNAs. Science 2002, 296 (5571), 1260.
5. Eddy, S., Non-coding RNA genes and the modern RNA world. Nature Reviews Genetics 2001, 2 (12), 919-929.
6. DiPaolo, J., Alvarez-Salas, L., Advances in the development of therapeutic nucleic acids against cervical cancer. Expert Opinion on Biological Therapy 2004, 4 (8), 1251-1264.
7. Gitlin, L., Andino, R., Nucleic acid-based immune system: the antiviral potential of mammalian RNA silencing. Journal of Virology 2003, 77 (13), 7159.
8. Opalinska, J., Gewirtz, A., Nucleic-acid therapeutics: basic principles and recent applications. Nature Reviews Drug Discovery 2002, 1 (7), 503-514.
9. Olie, R., Simões-Wüst, A., Baumann, B., Leech, S., Fabbro, D., Stahel, R., Zangemeister-Wittke, U., A novel antisense oligonucleotide targeting survivin expression induces apoptosis and sensitizes lung cancer cells to chemotherapy. Cancer Research 2000, 60 (11), 2805.
10. Mulamba, G., Hu, A., Azad, R., Anderson, K., Coen, D., Human cytomegalovirus mutant with sequence-dependent resistance to the phosphorothioate oligonucleotide fomivirsen (ISIS 2922). Antimicrobial Agents and Chemotherapy 1998, 42 (4), 971.
11. Reynolds, A., Leake, D., Boese, Q., Scaringe, S., Marshall, W., Khvorova, A., Rational siRNA design for RNA interference. Nature Biotechnology 2004, 22 (3), 326-330.
12. Cech, T., Zaug, A., Grabowski, P., In vitro splicing of the ribosomal RNA precursor of Tetrahymena: involvement of a guanosine nucleotide in the excision of the intervening sequence. Cell 1981, 27 (3), 487-496.
13. Rowe, P., Ribozymes enter clinical trials for HIV-1 treatment. Lancet 1996, 348 (9037), 1302.
14. Calin, G., Sevignani, C., Dumitru, C., Hyslop, T., Noch, E., Yendamuri, S., Shimizu, M., Rattan, S., Bullrich, F., Negrini, M., Human microRNA genes are frequently located at fragile sites and genomic regions involved in cancers. Proceedings of the National Academy of Sciences of the United States of America 2004, 101 (9), 2999.
15. Ng, E., Shima, D., Calias, P., Cunningham, E., Guyer, D., Adamis, A., Pegaptanib, a targeted anti-VEGF aptamer for ocular vascular disease. Nature Reviews Drug Discovery 2006, 5 (2), 123-132.
16. Kadokura, M., Wada, T., Seio, K., Sekine, M., Synthesis of 4-Thiouridine, 6- Thioinosine, and 6-Thioguanosine 3', 5'-O-Bisphosphates as Donor Molecules for RNA Ligation and Their Application to the Synthesis of Photoactivatable TMGCapped U1 snRNA Fragments. J. Org. Chem 2000, 65 (17), 5104-5113.
17. Carrasco, N., Caton Williams, J., Brandt, G., Wang, S., Huang, Z., Efficient Enzymatic Synthesis of Phosphoroselenoate RNA by Using Adenosine 5'-(a-P- Seleno) triphosphate. Angewandte Chemie 2006, 118 (1), 100-103.
18. Brandt, G., Carrasco, N., Huang, Z., Efficient Substrate Cleavage Catalyzed by Hammerhead Ribozymes Derivatized with Selenium for X-Ray Crystallography†. Biochemistry 2006, 45 (29), 8972-8977.
19. Wolfe, M., Ahmed, F., Lacourciere, G., Lauhon, C., Stadtman, T., Larson, T., Functional Diversity of the Rhodanese Homology Domain. Journal of Biological Chemistry 2004, 279 (3), 1801.
20. Veres, Z., Tsai, L., Scholz, T., Politino, M., Balaban, R., Stadtman, T., Synthesis of 5-methylaminomethyl-2-selenouridine in tRNAs: 31P NMR studies show the labile selenium donor synthesized by the selD gene product contains selenium bonded to phosphorus. Proceedings of the National Academy of Sciences of the United States of America 1992, 89 (7), 2975.
21. Shohda, K., Okamoto, I., Wada, T., Seio, K., Sekine, M., Synthesis and properties of 2'-O-methyl-2-thiouridine and oligoribonucleotides containing 2'-O-methyl-2- thiouridine. Bioorganic & Medicinal Chemistry Letters 2000, 10 (16), 1795-1798.
22. Sintim, H., Kool, E., Enhanced base pairing and replication efficiency of thiothymidines, expanded-size variants of thymidine. Journal of the American Chemical Society 2006, 128 (2), 396-397.
23. Agrawal, S., Goodchild, J., Civeira, M., Thornton, A., Sarin, P., Zamecnik, P., Oligodeoxynucleoside phosphoramidates and phosphorothioates as inhibitors of human immunodeficiency virus. Proceedings of the National Academy of Sciences of the United States of America 1988, 85 (19), 7079.
24. Uhlmann, E., Peyman, A., Antisense oligonucleotides: a new therapeutic principle. Chemical Reviews 1990, 90 (4), 543-584.
25. Chanfreau, G., Jacquier, A., Catalytic site components common to both splicing steps of a group II intron. Science 1994, 266 (5189), 1383.
26. Padgett, R., Podar, M., Boulanger, S., Perlman, P., The stereochemical course of group II intron self-splicing. Science 1994, 266 (5191), 1685.
27. Usman, N., Cedergren, R., Exploiting the chemical synthesis of RNA. Trends in Biochemical Sciences 1992, 17 (9), 334-339.
28. Cramer, F., Modified nucleotides as tools in nucleic acid research. Accounts of Chemical Research 1969, 2 (11), 338-344.
29. Verma, S., Eckstein, F., Modified oligonucleotides: synthesis and strategy for users. Annual Review of Biochemistry 1998, 67 (1), 99-134.
30. Zon, G., Automated synthesis of phosphorus-sulfur analogs of nucleic acids-25 years on: potential therapeutic agents and proven utility in biotechnology. New Journal of Chemistry 2010, 34 (5), 795-804.
31. Morris, M., Lucion, A., Antisense oligonucleotides in the study of neuroendocrine systems. Journal of Neuroendocrinology 1995, 7 (7), 493-500.
32. Manoharan, M., RNA interference and chemically modified small interfering RNAs. Current Opinion in Chemical Biology 2004, 8 (6), 570-579.
33. Ichikawa, E., Kato, K., Sugar-modified nucleosides in past 10 years, a review. Current Medicinal Chemistry 2001, 8 (4), 385-423.
34. Imazawa, M., Ueda, T., Synthesis of 2'-deoxy-2'-mercaptouridine. Tetrahedron Letters 1970, 55, 4807.
35. Acton, E., Ryan, K., Goodman, L., Synthesis of 2-thio-D-ribose and 2'-thioadenosine derivatives. The Journal of Organic Chemistry 1971, 36 (18), 2646-2657.
36. Bradbury, E., Nagyvary, J., Preparation of 2'-thio-2'-deoxycytidine 2': 3'- phosphorothioate. Nucleic Acids Research 1976, 3 (10), 2437.
37. Patel, A., Schrier, W., Nagyvary, J., Synthesis and properties of 2'-deoxy-2'- thiocytidine. The Journal of Organic Chemistry 1980, 45 (24), 4830-4834.
38. Divakar, K., Mottoh, A., Reese, C., Sanghvi, Y., Approaches to the synthesis of 2'-thio analogues of pyrimidine ribosides. Journal of the Chemical Society, Perkin Transactions 1 1990, 1990, (4), 969-974.
39. Dantzman, C., Kiessling, L., Reactivity of a 2'-Thio Nucleotide Analog. Journal of the American Chemical Society 1996, 118 (47), 11715-11719.
40. Fraser, A., Wheeler, P., Cook, P., Sanghvi, Y., Synthesis and conformational properties of 2'-deoxy-2'-methylthio-pyrimidine and-purine nucleosides: Potential antisense applications. Journal of Heterocyclic Chemistry 1993, 30 (5), 1277-1287.
41. Cosstick, R., Vyle, J., Synthesis and phosphorus-sulphur bond cleavage of 3'- thiothymidylyl (3'-5') thymidine. Journal of the Chemical Society, Chemical Communications 1988, 1988 (15), 992-993.
42. Cosstick, R., Vyle, J., Solid phase synthesis of oligonucleotides containing 3'- thiothymidine. Tetrahedron Letters 1989, 30 (35), 4693-4696.
43. Weinstein, L., Earnshaw, D., Cosstick, R., Cech, T., Synthesis and Characterization of an RNA Dinucleotide Containing a 3'-S-Phosphorothiolate Linkage. Journal of the American Chemical Society 1996, 118 (43), 10341-10350.
44. Cosstick, R., Vyle, J., Synthesis and properties of dithymidine phosphate analogues containing 3'-thiothymidine. Nucleic acids research 1990, 18 (4), 829.
45. Vyle, J., Li, X., Cosstick, R., New methods for the synthesis of 3'-Sphosphorothiolate internucleoside linkages. Tetrahedron Letters 1992, 33 (21), 3017-3020.
46. Sabbagh, G., Fettes, K., Gosain, R., O'Neil, I., Cosstick, R., Synthesis of phosphorothioamidites derived from 3' thio 3' deoxythymidine and 3' thio 2', 3' dideoxycytidine and the automated synthesis of oligodeoxynucleotides containing a 3S phosphorothiolate linkage. Nucleic Acids Research 2004, 32 (2), 495.
47. Sun, S., Yoshida, A., Piccirilli, J., Synthesis of 3'-thioribonucleosides and their incorporation into oligoribonucleotides via phosphoramidite chemistry. RNA 1997, 3 (11), 1352.
48. Li, X., Scott, G., Baxter, A., Taylor, R., Vyle, J., Cosstick, R., Application of the Michaelis-Arbusov reaction to the synthesis of internucleoside 3-Sphosphorothiolate inkages. Journal of the Chemical Society, Perkin Transactions 1 1994, (15), 2123-2129.
49. Liu, X., Reese, C., 3'-Thiouridylyl-(3' →5')-uridine. Tetrahedron Letters 1996, 37 (6), 925-928.
50. Horton, N., Connolly, B., Perona, J., Inhibition of EcoRV Endonuclease by Deoxyribo-3'-S-phosphorothiolates: a High-Resolution X-ray Crystallographic Study. Journal of the American Chemical Society 2000, 122 (14), 3314-3324.
51. Warnecke, J., Sontheimer, E., Piccirilli, J., Hartmann, R., Active site constraints in the hydrolysis reaction catalyzed by bacterial RNase P: analysis of precursor tRNAs with a single 3'-S-phosphorothiolate internucleotide linkage. Nucleic Acids Research 2000, 28 (3), 720.
52. Brautigam, C., Sun, S., Piccirilli, J., Steitz, T., Structures of normal single-stranded DNA and Deoxyribo-3-S-phosphorothiolates bound to the 3'-5'Exonucleolytic active site of DNA polymerase I from Escherichia coli . ‡. Biochemistry 1999, 38 (2), 696-704.
53. Reist, E., Gueffroy, D., Goodman, L., Synthesis of 4-Thio-D-and-L-ribofuranose and the Corresponding Adenine Nucleosides1, 2. Journal of the American Chemical Society 1964, 86 (24), 5658-5663.
54. Bobek, M., Whistler, R., Bloch, A., Preparation and activity of the 4'-thio-derivatives of some 6-substituted purines nucleosides. Journal of Medicinal Chemistry 1970, 13 (3), 411-413.
55. Reist, E., Fisher, L., Goodman, L., Thio Sugars. Synthesis of the adenine nucleosides of 4-thio-D-xylose and 4-thio-D-arabinose. The Journal of Organic Chemistry 1968, 33 (1), 189-192.
56. Rahim, S., Trivedi, N., Bogunovic-Batchelor, M., Hardy, G., Mills, G., Selway, J., Snowden, W., Littler, E., Coe, P., Basnak, I.,Synthesis and anti-herpes virus activity of 2'-deoxy-4'-thiopyrimidine nucleosides. Journal of Medicinal Chemistry 1996, 39 (3), 789-795.
57. Van Draanen, N., Freeman, G., Short, S., Harvey, R., Jansen, R., Szczech, G., Koszalka, G., Synthesis and Antiviral Activity of 2'-Deoxy-4'-thio Purine Nucleosides. Journal of Medicinal Chemistry 1996, 39 (2), 538-542.
58. Verri, A., Focher, F., Duncombe, R., Basnak, I., Walker, R., Coe, P., De Clercq, E., Andrei, G., Snoeck, R., Balzarini, J., Anti-(herpes simplex virus) activity of 4'-thio- 2'-deoxyuridines: a biochemical investigation for viral and cellular target enzymes. Biochemical Journal 2000, 351 (Pt 2), 319.
59. Carbon, J., David, H., Studier, M., Thiobases in Escherchia coli Transfer RNA: 2- Thiocytosine and 5-Methylaminomethyl-2-thiouracil. Science (New York, NY) 1968, 161 (3846), 1146.
60. Baczynskyj, L., Biemann, K., Hall, R., Sulfur-containing nucleoside from yeast transfer ribonucleic acid: 2-thio-5 (or 6)-uridine acetic acid methyl ester. Science 1968, 159 (3822), 1481-1483.
61. Ueda, T., Iida, Y., Ikeda, K., Mizuno, Y., Synthesis of 2, 4-dithiouridine and 2- thiocytidine. Chemical & Pharmaceutical Bulletin 1966, 14 (6), 666.
62. Vormbrock, R., Morawietz, R., Gassen, H., Codon-Anticodon interaction studied with trinucleoside diphosphates containing 2-thiouridine, 4-thiouridine, 2, 4- dithiouridine, or 2-thiocytidine. Biochimica et Biophysica Acta (BBA)-Nucleic Acids and Protein Synthesis 1974, 340 (3), 348-358.
63. Connolly, B., Newman, P., Synthesis and properties of oligonucleotides containing 4-thiothyniidine, 5-methyl-2-pyrunidinone-1-β-D (2'-dexoyriboside) and 2- thiothvmidine. Nucleic Acids Research 1989, 17 (13), 4957.
64. Rajeev, K., Prakash, T., Manoharan, M., 2'-Modified-2-thiothymidine Oligonucleotides. Org. Lett 2003, 5 (17), 3005-3008.
65. Kumar, R., Davis, D., Synthesis of oligoribonucleotides containing 2-thiouridine: Incorporation of 2-thiouridine phosphoramidite without base protection. The Journal of Organic Chemistry 1995, 60 (24), 7726-7727.
66. Coleman, R., Kesicki, E., Synthesis and Postsynthetic Modification of Oligodeoxynucleotides Containing 4-Thio-2'-deoxyuridine (ds4U). Journal of the American Chemical Society 1994, 116 (26), 11636-11642.
67. Nikiforov, T., Cornolly, B., The synthesis of oligodeoxynucleotides containing 4- thiothymidine residues. Tetrahedron Letters 1991, 32 (31), 3851-3854.
68. Xu, Y., Zheng, Q., Swann, P., Synthesis of DNA containing modified bases by post-synthetic substitution. Synthesis of oligomers containing 4-substituted thymine: O4-alkylthymine, 5-methylcytosine, N4-dimethylamino-5-methylcytosine, and 4- thiothymine. The Journal of Organic Chemistry 1992, 57 (14), 3839-3845.
69. Coleman, R., Siedlecki, J., Synthesis of a 4-thio-2'-deoxyuridine containing oligonucleotide. Development of the thiocarbonyl group as a linker element. Journal of the American Chemical Society 1992, 114 (23), 9229-9230.
70. Nikiforov, T., Connolly, B., Straightforward preparation and use in oligodeoxynucleotide synthesis of 5'-O-(4, 4'-dimethoxytrityl)-4-[S-(2-cyanoethyl)]- thiothymidine. Tetrahedron Letters 1992, 33 (17), 2379-2382.
71. Clivio, P., Fourrey, J., Gasche Annie, J., Favre, A., Synthesis and purification of oligonucleotides containing sulfur substituted nucleobases: 4-thiouracil, 4- thiothymine and 6-mercaptopurine. Tetrahedron Letters 1992, 33 (1), 65-68.
72. Rao, T., Jayaraman, K., Durland, R., Revankar, G., A novel synthesis of S6- cyanoethyl-2'-deoxy-6-thioguanosine and its incorporation into triple helix forming oligonucleotides. Tetrahedron Letters 1992, 33 (50), 7651-7654.
73. Christopherson, M., Broom, A., Synthesis of oligonucleotides containing 2'-deoxy- 6-thioguanosine at a predetermined site. Nucleic Acids Research 1991, 19 (20), 5719.
74. Rappaport, H.,The 6-thioguanine/5-methyl-2-pyrimidinone base pair. Nucleic Acids Research 1988, 16 (15), 7253.
75. Xu, Y., Zheng, Q., Swann, P., Synthesis by post-synthetic substitution of oligomers containing guanine modified at the 6-position with S-, N-, O-derivatives. Tetrahedron 1992, 48 (9), 1729-1740.
76. Held, H., Benner, S., Challenging artificial genetic systems: thymidine analogs with 5 position sulfur functionality. Nucleic Acids Research 2002, 30 (17), 3857.
77. Held, H., Roychowdhury, A., Benner, S., C-5 modified nucleosides: Direct insertion of alkynyl-thio functionality in pyrimidines. Nucleosides, Nucleotides and Nucleic Acids 2003, 22 (4), 391-404.
78. Coleman, R., Pires, R., Covalent cross-linking of duplex DNA using 4-thio-2- deoxyuridine as a readily modifiable platform for introduction of reactive functionality into oligonucleotides. Nucleic Acids Research 1997, 25 (23), 4771.
79. Nikiforov, T., Connolly, B., Oligodeoxynucleotides containing 4-thiothymidine and 6-thiodeoxyguanosine as affinity labels for the Eco RV restriction endonuclease and modification methylase. Nucleic Acids Research 1992, 20 (6), 1209.
80. Lennard, L., Van Loon, J., Lilleyman, J., Weinshilboum, R., Thiopurine pharmacogenetics in leukemia: correlation of erythrocyte thiopurine methyltransferase activity and 6-thioguanine nucleotide concentrations. Clinical Pharmacology & Therapeutics 1987, 41 (1), 18-25.
81. Connolly, B., Potter, B., Eckstein, F., Pingoud, A., Grotjahn, L., Synthesis and characterization of an octanucleotide containing the EcoRI recognition sequence with a phosphorothioate group at the cleavage site. Biochemistry 1984, 23 (15), 3443-3453.
82. Matsukura, M., Zon, G., Shinozuka, K., Stein, C., Mitsuya, H., Cohen, J., Broder, S., Synthesis of phosphorothioate analogues of oligodeoxyribonucleotides and their antiviral activity against human immunodeficiency virus (HIV). Gene 1988, 72 (1-2), 343-347.
83. Eckstein, F., Gindl, H., Synthesis of nucleoside 5'-polyphosphorothioates. Biochimica et Biophysica Acta (BBA)-Nucleic Acids and Protein Synthesis 1967, 149 (1), 35-40.
84. Eckstein, F., Nucleoside phosphorothioates. Journal of the American Chemical Society 1970, 92 (15), 4718-4723.
85. Eckstein, F., Simonson, L., Baer, H., Adenosine 3', 5'-cyclic phosphorothioate. Synthesis and biological properties. Biochemistry 1974, 13 (18), 3806-3810.
86. Burgers, P., Eckstein, F., Diastereomers of 5'-O-adenosyl 3'-O-uridyl phosphorothioate: chemical synthesis and enzymic properties. Biochemistry 1979, 18 (4), 592-596.
87. Burgers, P., Eckstein, F., Synthesis of dinucleoside monophosphorothioates via addition of sulphur to phosphite triesters. Tetrahedron Letters 1978, 19 (40), 3835-3838.
88. Stec, W., Zon, G., Egan, W., Automated solid-phase synthesis, separation, and stereochemistry of phosphorothioate analogs of oligodeoxyribonucleotides. Journal of the American Chemical Society 1984, 106 (20), 6077-6079.
89. Froehler, B., Deoxynucleoside H-phosphonate diester intermediates in the synthesis of internucleotide phosphate analogues. Tetrahedron Letters 1986, 27 (46), 5575-5578.
90. Ott, J., Eckstein, F., Protection of oligonucleotide primers against degradation by DNA polymerase I. Biochemistry 1987, 26 (25), 8237-8241.
91. Vu, H., Hirschbein, B., Internucleotide phosphite sulfurization with tetraethylthiuram disulfide. Phosphorothioate oligonucleotide synthesis via phosphoramidite chemistry. Tetrahedron Letters 1991, 32 (26), 3005-3008.
92. Bielinska, A., Shivdasani, R., Zhang, L., Nabel, G., Regulation of gene expression with double-stranded phosphorothioate oligonucleotides. Science 1990, 250 (4983), 997.
93. Monia, B., Johnston, J., Geiger, T., Muller, M., Fabbro, D., Antitumor activity of a phosphorothioate antisense oligodeoxynucleotide targeted against C-raf kinase. Nature Medicine 1996, 2 (6), 668-675.
94. Gaur, R., Sharma, P., Gupta, K., A simple method for the introduction of thiol group at 5'-termini of oligodeoxynucleotides. Nucleic Acids Research 1989, 17 (11), 4404.
95. Yau, H., Chan, H., Yang, M., Electrochemical properties of DNA-intercalating doxorubicin and methylene blue on n-hexadecyl mercaptan-doped 5'-thiol-labeled DNAmodified gold electrodes. Biosensors and Bioelectronics 2003, 18 (7), 873-879.
96. Adessi, C., Matton, G., Ayala, G., Turcatti, G., Mermod, J., Mayer, P., Kawashima, E., Solid phase DNA amplification: characterisation of primer attachment and amplification mechanisms. Nucleic Acids Research 2000, 28 (20), e87.
97. Kelley, S., Barton, J., Jackson, N., McPherson, L., Potter, A., Spain, E., Allen, M., Hill, M., Orienting DNA helices on gold using applied electric fields. Langmuir 1998, 14 (24), 6781-6784.
98. Kelley, S., Jackson, N., Hill, M., Barton, J., Long-range electron transfer through DNA films. Angewandte Chemie International Edition 1999, 38 (7), 941-945.
99. Mirkin, C., Letsinger, R., Mucic, R., Storhoff, J., A DNA-based method for rationally assembling nanoparticles into macroscopic materials. 1996, 382 (6592), 607-609.
100. Li, Z., Jin, R., Mirkin, C., Letsinger, R., Multiple thiol-anchor capped DNA-gold nanoparticle conjugates. Nucleic Acids Research 2002, 30 (7), 1558.
101. Jin, R., Wu, G., Li, Z., Mirkin, C., Schatz, G., What controls the melting properties of DNA-linked gold nanoparticle assemblies ? Journal of the American Chemical Society 2003, 125 (6), 1643-1654.
102. Rosi, N., Giljohann, D., Thaxton, C., Lytton-Jean, A., Han, M., Mirkin, C., Oligonucleotide-modified gold nanoparticles for intracellular gene regulation. Science 2006, 312 (5776), 1027.
103. Rosi, N., Mirkin, C., Nanostructures in biodiagnostics. Chem. Rev 2005, 105 (4), 1547-1562.
104. Jencks, W., RNA catalysis. Evolution on fast-forward. Nature 1992, 358 (6387), 543.
105. Venkateswarlu, D., Lind, K., Mohan, V., Manoharan, M., Ferguson, D., Structural properties of DNA: RNA duplexes containing 2'-O-methyl and 2'-S-methyl substitutions: a molecular dynamics investigation. Nucleic Acids Research 1999, 27 (10), 2189.
106. Pallan, P., Prakash, T., Li, F., Eoff, R., Manoharan, M., Egli, M., A conformational transition in the structure of a 2-thiomethyl-modified DNA visualized at high resolution. Chemical Communications 2009, (15), 2017-2019.
107. Lima, W., Nichols, J., Wu, H., Prakash, T., Migawa, M., Wyrzykiewicz, T., Bhat, B., Crooke, S., Structural requirements at the catalytic site of the heteroduplex substrate for human RNase H1 catalysis. Journal of Biological Chemistry 2004, 279 (35), 36317.
108. Secrist III, J., Tiwari, K., Riordan, J., Montgomery, J., Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides. Journal of Medicinal Chemistry 1991, 34 (8), 2361-2366.
109. Dyson, M., Coe, P., Walker, R., The synthesis and antiviral activity of some 4'- thio-2'-deoxy nucleoside analogs. Journal of Medicinal Chemistry 1991, 34 (9), 2782-2786.
110. Basnak, I., Hancox, E., Connolly, B., Walker, R. In The synthesis and some properties of some 5-substituted pyrimidine 4'-thio-2'-deoxynucleosides and oligodeoxynucleotides containing 4'-thiothymidine, Nucleic Acids Symposium Series 1993, 29 (1), 101-102.
111. 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 Research 1997, 25 (14), 2773.
112. Watts, J., Choubdar, N., Sadalapure, K., Robert, F., Wahba, A., Pelletier, J., Mario Pinto, B., Damha, M., 2'-Fluoro-4'-thioarabino-modified oligonucleotides: conformational switches linked to siRNA activity. Nucleic Acids Research 2007.
113. Hancox, E., Connolly, B., Walker, R., Synthesis and properties of oligodeoxynucleotides containing the analogue 2'-deoxy-4'-thiothemidine. Nucleic Acids Research 1993, 21 (15), 3485-3492.
114. Jones, G., Lesnik, E., Owens, S., Risen, L., Walker, R., Investigation of some properties of oligodeoxynucleotides containing 4'-thio-2'-deoxynucleotides: duplex hybridization and nuclease sensitivity. Nucleic Acids Research 1996, 24 (21), 4117-4122.
115. Takahashi, M., Minakawa, N., Matsuda, A., Synthesis and characterization of 2'- modified-4'-thioRNA: a comprehensive comparison of nuclease stability. Nucleic Acids Research 2009, 37 (4), 1353-1362.
116. Boggon, T., Hancox, E., McAuley-Hecht, K., Connolly, B., Hunter, W., Brown, T., Walker, R., Leonard, G., The crystal structure analysis of d (CGCGAASSCGCG) 2, a synthetic DNA dodecamer duplex containing four 4'-thio-2'-deoxythymidine nucleotides. Nucleic Acids Research 1996, 24 (5), 951-961.
117. Takahashi, M., Daidouji, S., Shiro, M., Minakawa, N., Matsuda, A., Synthesis and crystal structure of 2'-deoxy-2'-fluoro-4'-thioribonucleosides: substrates for the synthesis of novel modified RNAs. Tetrahedron 2008, 64 (19), 4313-4324.
118. Testa, S., Disney, M., Turner, D., Kierzeks, R., Thermodynamics of RNA- RNA Duplexes with 2-or 4-Thiouridines: Implications for Antisense Design and Targeting a Group I Intron†. Biochemistry 1999, 38 (50), 16655-16662.
119. Diop-Frimpong, B., Prakash, T., Rajeev, K., Manoharan, M., Egli, M., Stabilizing contributions of sulfur-modified nucleotides: crystal structure of a DNA duplex with 2'-O-[2-(methoxy) ethyl]-2-thiothymidines. Nucleic Acids Research 2005, 33 (16), 5297.
120. Sismour, A., Benner, S., The use of thymidine analogs to improve the replication of an extra DNA base pair: a synthetic biological system. Nucleic Acids Research 2005, 33 (17), 5640.
121. Braasch, D., Paroo, Z., Constantinescu, A., Ren, G., Ö z, O., Mason, R., Corey, D., Biodistribution of phosphodiester and phosphorothioate siRNA. Bioorganic & Medicinal Chemistry Letters 2004, 14 (5), 1139-1143.
122. Slim, G., Gait, M., Configurationally defined phosphorothioate-containing oligoribonucleotides in the study of the mechanism of cleavage of hammerhead ribozymes. Nucleic Acids Research 1991, 19 (6), 1183-1188.
123. Koizumi, M., Ohtsuka, E., Effects of phosphorothioate and 2-amino groups in hammerhead ribozymes on cleavage rates and magnesium binding. Biochemistry 1991, 30 (21), 5145-5150.
124. Gleave, M., Monia, B., Antisense therapy for cancer. Nature Reviews Cancer 2005, 5 (6), 468-479.
125. Nakamaye, K., Eckstein, F., Inhibition of restriction endonuclease Nel I cleavage by phosphorothioate groups and its application to oligonucleotide-directed mutagenesis. Nucleic Acids Research 1986, 14 (24), 9679-9698.
126. Sayers, J., Schmidt, W., Eckstein, F., 5'-3'exonucleases in phosphorothioatebased oligonucleotide-directed mutagenesis. Nucleic Acids Research 1988, 16 (3), 791-802.
127. Loke, S., Stein, C., Zhang, X., Avigan, M., Cohen, J., Neckers, L., Delivery of c-myc antisense phosphorothioate oligodeoxynucleotides to hematopoietic cells in culture by liposome fusion: specific reduction in c-myc protein expression correlates with inhibition of cell growth and DNA synthesis. Current Topics in Microbiology and Immunology 1988, 141, 282.
128. Matsukura, M., Zon, G., Shinozuka, K., Robert-Guroff, M., Shimada, T., Stein, C., Mitsuya, H., Wong-Staal, F., Cohen, J., Broder, S., Regulation of viral expression of human immunodeficiency virus in vitro by an antisense phosphorothioate oligodeoxynucleotide against rev (art/trs) in chronically infected cells. Proceedings of the National Academy of Sciences of the United States of America 1989, 86 (11), 4244-4248.
129. Alvarez-Salas, L., Nucleic acids as therapeutic agents. Current Topics in Medicinal Chemistry 2008, 8 (15), 1379-1404.
130. Van Tol, H., Buzayan, J., Feldstein, P., Eckstein, F., Bruening, G., Two autolytic processing reactions of a satellite RNA proceed with inversion of configuration. Nucleic Acids Research 1990, 18 (8), 1971-1975.
131. Scott, E., Uhlenbeck, O., A re-investigation of the thio effect at the hammerhead cleavage site. Nucleic Acids Research 1999, 27 (2), 479-484.
132. Yoshinari, K., Taira, K., A further investigation and reappraisal of the thio effect in the cleavage reaction catalyzed by a hammerhead ribozyme. Nucleic Acids Research 2000, 28 (8), 1730-1742.
133. Manoharan, M., Johnson, L., McGee, D., Guinosso, C., Ramasamy, K., Springer, R., Bennett, C., Ecker, D., Vickers, T., Cowsert, L., Chemical modifications to improve uptake and bioavailability of antisense oligonucleotides. Annals of the New York Academy of Sciences 1992, 660 (1), 306-309.
134. Sandberg, J., Parker, V., Blanchard, K., Sweedler, D., Powell, J., Kachensky, A., Bellon, L., Usman, N., Rossing, T., Borden, E., Pharmacokinetics and tolerability of an antiangiogenic ribozyme (ANGIOZYME) in healthy volunteers. The Journal of Clinical Pharmacology 2000, 40 (12), 1462-1469.
135. Weng, D., Masci, P., Radka, S., Jackson, T., Weiss, P., Ganapathi, R., Elson, P., Capra, W., Parker, V., Lockridge, J., A phase I clinical trial of a ribozyme-based angiogenesis inhibitor targeting vascular endothelial growth factor receptor-1 for patients with refractory solid tumors. Molecular Cancer Therapeutics 2005, 4 (6), 948-955.
136. Gryaznov, S., Oligonucleotide N3 P5 Phosphoramidates and Thio Phoshoramidates as Potential Therapeutic Agents. Chemistry & Biodiversity 2010, 7 (3), 477-493.
137. CROOKE, S., Vitravene™-another piece in the mosaic. Antisense and Nucleic Acid Drug Development 1998, 8 (4), 1089.
138. Merki, E., Graham, M., Mullick, A., Miller, E., Crooke, R., Pitas, R., Witztum, J., Tsimikas, S., Antisense oligonucleotide directed to human apolipoprotein B-100 reduces lipoprotein (a) levels and oxidized phospholipids on human apolipoprotein B-100 particles in lipoprotein (a) transgenic mice. Circulation 2008, 118 (7), 743-753.
139. Akdim, F., Stroes, E., Sijbrands, E., Tribble, D., Trip, M., Jukema, J., Flaim, J., Su, J., Yu, R., Baker, B., Efficacy and safety of mipomersen, an antisense inhibitor of apolipoprotein B, in hypercholesterolemic subjects receiving stable statin therapy. Journal of the American College of Cardiology 2010, 55 (15), 1611-1618.
140. Yu, R., Geary, R., Flaim, J., Riley, G., Tribble, D., vanVliet, A., Wedel, M., Lack of Pharmacokinetic Interaction of Mipomersen Sodium (ISIS 301012), a 2-OMethoxyethyl Modified Antisense Oligonucleotide Targeting Apolipoprotein B-100 Messenger RNA, with Simvastatin and Ezetimibe. Clinical Pharmacokinetics 2009, 48 (1), 39-50.
141. Chi, K., Eisenhauer, E., Fazli, L., Jones, E., Goldenberg, S., Powers, J., Tu, D., Gleave, M., A phase I pharmacokinetic and pharmacodynamic study of OGX-011, a 2'-methoxyethyl antisense oligonucleotide to clusterin, in patients with localized prostate cancer. JNCI Cancer Spectrum 2005, 97 (17), 1287-1296.
142. Chia, S., Dent, S., Ellard, S., Ellis, P., Vandenberg, T., Gelmon, K., Powers, J., Walsh, W., Seymour, L., Eisenhauer, E., Phase II trial of OGX-011 in combination with docetaxel in metastatic breast cancer. Clinical Cancer Research 2009, 15 (2), 708.
143. Ko, Y., Falcao, C., Torchilin, V., Cationic liposomes loaded with proapoptotic peptide D-(KLAKLAK) 2 and Bcl-2 antisense oligodeoxynucleotide G3139 for enhanced anticancer therapy. Molecular Pharmaceutics 2009, 6 (3), 971-977.
144. Raab, R., Sparano, J., Ocean, A., Christos, P., Ramirez, M., Vinciguerra, V., Kaubisch, A., A Phase I Trial of Oblimersen Sodium in Combination with Cisplatin and 5-Fluorouracil in patients with Advanced esophageal, Gastroesophageal Junction, and Gastric Carcinoma. American Journal of Clinical Oncology 2010, 33 (1), 61.
145. Dean, E., Jodrell, D., Connolly, K., Danson, S., Jolivet, J., Durkin, J., Morris, S., Jowle, D., Ward, T., Cummings, J., Phase I trial of AEG35156 administered as a 7- day and 3-day continuous intravenous infusion in patients with advanced refractory cancer. Journal of Clinical Oncology 2009, 27 (10), 1660-1666.
146. Hamilton, A., Baulcombe, D., A species of small antisense RNA in posttranscriptional gene silencing in plants. Science 1999, 286 (5441), 950-952.
147. Dorsett, Y., Tuschl, T., siRNAs: applications in functional genomics and potential as therapeutics. Nature Reviews Drug Discovery 2004, 3 (4), 318-329.
148. Rana, T., Illuminating the silence: understanding the structure and function of small RNAs. Nature Reviews Molecular Cell Biology 2007, 8 (1), 23-36.
149. Wilson, C., Keefe, A., Building oligonucleotide therapeutics using non-natural chemistries. Current Opinion in Chemical Biology 2006, 10 (6), 607-614.
150. Braasch, D., Jensen, S., Liu, Y., Kaur, K., Arar, K.,White, M., Corey, D., RNA Interference in Mammalian Cells by Chemically-Modified RNA†. Biochemistry 2003, 42 (26), 7967-7975.
151. Harborth, J., Elbashir, S., Vandenburgh, K., Manninga, H., Scaringe, S., Weber, K., Tuschl, T., Sequence, chemical, and structural variation of small interfering RNAs and short hairpin RNAs and the effect on mammalian gene silencing. Antisense and Nucleic Acid Drug Development 2003, 13 (2), 83-105.
152. Spankuch-Schmitt, B., Bereiter-Hahn, J., Kaufmann, M., Strebhardt, K., Effect of RNA silencing of polo-like kinase-1 (PLK1) on apoptosis and spindle formation in human cancer cells. JNCI Cancer Spectrum 2002, 94 (24), 1863.
153. Coma, S., Noe, V., Lavarino, C., Adán, J., Rivas, M., López-Matas, M., Pagan, R., Mitjans, F., Vilaró, S., Piulats, J., Use of siRNAs and antisense oligonucleotides against survivin RNA to inhibit steps leading to tumor angiogenesis. Oligonucleotides 2004, 14 (2), 100-113.
154. Nowak, J., Age-related macular degeneration (AMD): pathogenesis and therapy. Pharmacol Rep 2006, 58 (3), 353-363.
155. Frank-Kamenetsky, M., Grefhorst, A., Anderson, N., Racie, T., Bramlage, B., Akinc, A., Butler, D., Charisse, K., Dorkin, R., Fan, Y., Therapeutic RNAi targeting PCSK9 acutely lowers plasma cholesterol in rodents and LDL cholesterol in nonhuman primates. Proceedings of the National Academy of Sciences 2008, 105 (33), 11915.
156. Soutschek, J., Akinc, A., Bramlage, B., Charisse, K., Constien, R., Donoghue, M., Elbashir, S., Geick, A., Hadwiger, P., Harborth, J., Therapeutic silencing of an endogenous gene by systemic administration of modified siRNAs. Nature 2004, 432 (7014), 173-178.
157. Wright, L., Kearney, P., Current status of ribozymes as gene therapy agents for cancer. Cancer Investigation 2001, 19 (5), 495-509.
158. Sarver, N., Cantin, E., Chang, P., Zaia, J., Ladne, P., Stephens, D., Rossi, J., Ribozymes as potential anti-HIV-1 therapeutic agents. Science 1990, 247 (4947), 1222-1225.
159. Weng, D., Usman, N., Angiozyme: a novel angiogenesis inhibitor. Current Oncology Reports 2001, 3 (2), 141-146.
160. Kobayashi, H., Gail Eckhardt, S., Lockridge, J., Rothenberg, M., Sandler, A., O'Bryant, C., Cooper, W., Holden, S., Aitchison, R., Usman, N., Safety and pharmacokinetic study of RPI. 4610 (ANGIOZYME), an anti-VEGFR-1 ribozyme, in combination with carboplatin and paclitaxel in patients with advanced solid tumors. Cancer Chemotherapy and Pharmacology 2005, 56 (4), 329-336.
161. James, H., Gibson, I., The therapeutic potential of ribozymes. Blood 1998, 91 (2), 371.
162. Mulhbacher, J., St-Pierre, P., Lafontaine, D., Therapeutic applications of ribozymes and riboswitches. Current Opinion in Pharmacology 2010, 10 (5), 551-556.
163. Isaka, Y., DNAzymes as potential therapeutic molecules. Current Opinion in Molecular Therapeutics 2007, 9 (2), 132.
164. Schubert, S., Gul, D., Grunert, H., Zeichhardt, H., Erdmann, V., Kurreck, J., RNA cleaving'10-23'DNAzymes with enhanced stability and activity. Nucleic Acids Research 2003, 31 (20), 5982-5992.
165. Jian-ping, Z., Pre-clinical application and perspective of ribozyme and DNAzyme [J]. China Biotechnology 2010, 6.
166. Chan, C., Khachigian, L., DNAzymes and their therapeutic possibilities. Internal Medicine Journal 2009, 39 (4), 249-251.
167. Ireson, C., Kelland, L., Discovery and development of anticancer aptamers. Molecular Cancer Therapeutics 2006, 5 (12), 2957.
168. Nimjee, S., Rusconi, C., Sullenger, B., Aptamers: an emerging class of therapeutics. Medicine 2005, 56 (1), 555.
169. Proske, D., Blank, M., Buhmann, R., Resch, A., Aptamers-basic research, drug development, and clinical applications. Applied Microbiology and Biotechnology 2005, 69 (4), 367-374.
170. Yang, X., Wang, H., Beasley, D., Volk, D., Zhao, X., Luxon, B., Lomas, L., Herzog, N., Aronson, J., Barrett, A., Selection of thioaptamers for diagnostics and therapeutics. Annals of the New York Academy of Sciences 2006, 1082 (Oligonucleotide Therapeutics: First Annual Meeting of the Oligonucleotide Therapeutics Society), 116-119.
171. Fennewald, S., Scott, E., Zhang, L., Yang, X., Aronson, J., Gorenstein, D., Luxon, B., Shope, R., Beasley, D., Barrett, A., Thioaptamer decoy targeting of AP-1 proteins influences cytokine expression and the outcome of arenavirus infections. Journal of General Virology 2007, 88 (3), 981-990.
172. Tombelli, S., Minunni, M., Mascini, M., Analytical applications of aptamers. Biosensors and Bioelectronics 2005, 20 (12), 2424-2434.
173. Kocisko, D., Vaillant, A., Lee, K., Arnold, K., Bertholet, N., Race, R., Olsen, E., Juteau, J., Caughey, B., Potent antiscrapie activities of degenerate phosphorothioate oligonucleotides. Antimicrobial Agents and Chemotherapy 2006, 50 (3), 1034-1044.
174. Weiss, S., Proske, D., Neumann, M., Groschup, M., Kretzschmar, H., Famulok, M., Winnacker, E., RNA aptamers specifically interact with the prion protein PrP. Journal of Virology 1997, 71 (11), 8790-8797.
175. Hoffman, J., McConnell, K., The presence of 4-selenouridine in Escherichia coli tRNA. Biochimica et Biophysica Acta (BBA)-Nucleic Acids and Protein Synthesis 1974, 366 (1), 109-113.
176. Zhang, J.,Wang, X., Xu, T., Elemental selenium at nano size (Nano-Se) as a potential chemopreventive agent with reduced risk of selenium toxicity: comparison with se-methylselenocysteine in mice. Toxicological Sciences 2008, 101 (1), 22-31.
177. Schrauzer, G., Selenomethionine: a review of its nutritional significance, metabolism and toxicity. Journal of Nutrition 2000, 130 (7), 1653.
178. Stadtman, T., Selenocysteine. Annual Review of Biochemistry 1996, 65 (1), 83-100.
179. Carrasco, N., Ginsburg, D., Du, Q., Huang, Z., Synthesis of selenium-derivatized nucleosides and oligonucleotides for X-ray crystallography. Nucleosides, Nucleotides and Nucleic Acids 2001, 20 (9), 1723-1734.
180. Carrasco, N., Huang, Z., Enzymatic synthesis of phosphoroselenoate DNA using thymidine 5'-( -P-seleno) triphosphate and DNA polymerase for x-ray crystallography via MAD. J. Am. Chem. Soc 2004, 126 (2), 448-449.
181. Sheng, J., Huang, Z., Selenium derivatization of nucleic acids for phase and structure determination in nucleic acid X-ray crystallography. International Journal of Molecular Sciences 2008, 9 (3), 258-271.
182. Caton-Williams, J., Huang, Z., Biochemistry of selenium-derivatized naturally occurring and unnatural nucleic acids. Chemistry & Biodiversity 2008, 5 (3), 396-407.
183. Salon, J., Sheng, J., Jiang, J., Chen, G., Caton-Williams, J., Huang, Z., Oxygen replacement with selenium at the thymidine 4-position for the Se base pairing and crystal structure studies. Journal of the American Chemical Society 2007, 129 (16), 4862-4863.
184. Salon, J., Jiang, J., Sheng, J., Gerlits, O., Huang, Z., Derivatization of DNAs with selenium at 6-position of guanine for function and crystal structure studies. Nucleic Acids Research 2008, 36 (22), 7009-7018.
185. Sheng, J., Salon, J., Gan, J., Huang, Z., Synthesis and crystal structure study of 2 -Se-adenosine-derivatized DNA. Science China Chemistry 2010, 53 (1), 78-85.
186. Sheng, J., Huang, Z., Selenium derivatization of nucleic acids for x ray crystal structure and Function Studies. Chemistry & Biodiversity 2010, 7 (4), 753-785.
187. Inagaki, Y., Minakawa, N., Matsuda, A. In Synthesis of 4'-selenoribo nucleosides, Nucleic Acids Symposium Series 2007, 51 (1), 139-140.
188. Salon, J., Chen, G., Portilla, Y., Germann, M., Huang, Z., Synthesis of a 2'-Seuridine Phosphoramidite and its incorporation into oligonucleotides for structural study. Organic Letters 2005, 7 (25), 5645-5648.
189. Wilds, C., Pattanayek, R., Pan, C., Wawrzak, Z., Egli, M., Selenium-assisted nucleic acid crystallography: use of phosphoroselenoates for MAD phasing of a DNA structure. Journal of the American Chemical Society 2002, 124 (50), 14910-14916.
190. Hassan, A., Sheng, J., Zhang, W., Huang, Z., High fidelity of base pairing by 2- selenothymidine in DNA. Journal of the American Chemical Society 2010, 132 (7), 2120-2121.
191. Du, Q., Carrasco, N., Teplova, M., Wilds, C., Egli, M., Huang, Z., Internal derivatization of oligonucleotides with selenium for X-ray crystallography using MAD. Journal of the American Chemical Society 2002, 124 (1), 24-25.
192. Sheng, J., Jiang, J., Salon, J., Huang, Z., Synthesis of a 2'-Se-thymidine Phosphoramidite and its incorporation into oligonucleotides for crystal structure study. Organic Letters 2007, 9 (5), 749-752.
193. Jeong, L., Tosh, D., Kim, H., Wang, T., Hou, X., Yun, H., Kwon, Y., Lee, S., Choi, J., Zhao, L., First synthesis of 4-selenonucleosides showing unusual southern conformation. Organic Letters 2008, 10 (2), 209-212.
194. Watts, J., Johnston, B., Jayakanthan, K., Wahba, A., Pinto, B., Damha, M., Synthesis and biophysical characterization of oligonucleotides containing a 4'- selenonucleotide. Journal of the American Chemical Society 2008, 130 (27), 8578-8579.
195. Hassan, A., Sheng, J., Jiang, J., Zhang, W., Huang, Z., Synthesis and crystallographic analysis of 5-Se-thymidine DNAs. Organic Letters 2009, 11 (12), 2503-2506.
196. Mori, K., Boiziau, C., Cazenave, C., Matsukura, M., Subasinghe, C., Cohen, J., Broder, S., Toulmé, J., Stein, C., Phosphoroselenoate oligodeoxynucleotides: synthesis, physico-chemical characterization, anti-sense inhibitory properties and anti-HIV activity. Nucleic Acids Research 1989, 17 (20), 8207-8219.
197. Stawinski, J., Thelin, M., Nucleoside H-phosphonates. 14. Synthesis of nucleoside phosphoroselenoates and phosphorothioselenoates via stereospecific selenization of the corresponding H-phosphonate and H-phosphonothioate diesters with the aid of new selenium-transfer reagent, 3H-1, 2-benzothiaselenol-3-one. The Journal of Organic Chemistry 1994, 59 (1), 130-136.
198. Holloway, G., Pavot, C., Scaringe, S., Lu, Y., Rauchfuss, T., An organometallic route to oligonucleotides containing phosphoroselenoate. ChemBioChem 2002, 3 (11), 1061-1065.
199. Tram, K., Wang, X., Yan, H., Facile synthesis of oligonucleotide phosphoroselenoates. Organic Letters 2007, 9 (24), 5103-5106.
200. Caton Williams, J., Huang, Z., Synthesis and DNA polymerase incorporation of colored 4 selenothymidine triphosphate for polymerase recognition and DNA visualization. Angewandte Chemie International Edition 2008, 47 (9), 1723-1725.
201. Hendrickson, W., Horton, J., LeMaster, D., Selenomethionyl proteins produced for analysis by multiwavelength anomalous diffraction (MAD): a vehicle for direct determination of three-dimensional structure. The EMBO Journal 1990, 9 (5), 1665-1672.
202. Lee, Y., Ogata, C., Pflugrath, J., Levitt, D., Sarma, R., Banaszak, L., Pilkis, S., Crystal structure of the rat liver fructose-2, 6-bisphosphatase based on selenomethionine multiwavelength anomalous dispersion phases. Biochemistry 1996, 35 (19), 6010-6019.
203. Doublie, S., Preparation of selenomethionyl proteins for phase determination. Methods in Enzymology 1997, 276, 523-530.
204. Deacon, A., Ealick, S., Selenium-based MAD phasing: setting the sites on larger structures. 1999, 7 (7), 161-166.
205. Xiong, Y., Sundaralingam, M., Crystal structure of a DNA· RNA hybrid duplex with a polypurine RNA r (gaagaagag) and a complementary polypyrimidine DNA d (CTCTTCTTC). Nucleic Acids Research 2000, 28 (10), 2171-2176.
206. Ogata, C., Hendrickson, W., Gao, X., Patel, D. In Crystal structure of chromomycin-DNA complex, Journal Abstracts of American Crystallographic Association Meeting Series 2 . 1989; 17 53.
207. Jiang, J., Sheng, J., Carrasco, N., Huang, Z., Selenium derivatization of nucleic acids for crystallography. Nucleic Acids Research 2006, 35 (2), 477-485.
208. Teplova, M., Wilds, C., Wawrzak, Z., Tereshko, V., Du, Q., Carrasco, N., Huang, Z., Egli, M., Covalent incorporation of selenium into oligonucleotides for X-ray crystal structure determination via MAD: proof of principle. Biochimie 2002, 84 (9), 849-858.
209. Thota, N., Li, X., Bingman, C., Sundaralingam, M., High-resolution refinement of the hexagonal A-DNA octamer d (GTGTACAC) at 1.4 A. Acta Crystallographica Section D: Biological Crystallography 1993, 49 (2), 282-291.
210. Beach, J., Kim, H., Jeong, L., Nampalli, S., Islam, Q., Ahn, S., Babu, J., Chu, C., A highly stereoselective synthesis of anti-HIV 2', 3'-dideoxy-and 2', 3'- didehydro-2', 3'-dideoxynucleosides. The Journal of Organic Chemistry 1992, 57 (14), 3887-3894.
211. Haraguchi, K., Tanaka, H., Maeda, H., Itoh, Y., Saito, S., Miyasaka, T., Selenoxide elimination for the synthesis of unsaturated-sugar uracil nucleosides. The Journal of Organic Chemistry 1991, 56 (18), 5401-5408.
212. Diaz, Y., El-Laghdach, A., Matheu, M., Castillon, S., Stereoselective synthesis of 2, 3-dideoxynucleosides by addition of selenium electrophiles to glycals. A formal synthesis of D4T from 2-deoxyribose. J. Org. Chem 1997, 62 (5), 1501-1505.
213. Ramadan, S., Razak, A., Ragab, A., El-Meleigy, M., Incorporation of tellurium into amino acids and proteins in a tellurium-tolerant fungi. Biological Trace Element Research 1989, 20 (3), 225-232.
214. Boles, J., Lewinski, K., Kunkle, M., Odom, J., Dunlap, R., Lebioda, L., Hatada, M., Bio-incorporation of telluromethionine into buried residues of dihydrofolate reductase. Nature Structural & Molecular Biology 1994, 1 (5), 283-284.
215. Moroder, L., Isosteric replacement of sulfur with other chalcogens in peptides and proteins. Journal of Peptide Science 2005, 11 (4), 187-214.
216. Sheng, J., Hassan, A., Huang, Z., Synthesis of the First Tellurium Derivatized Oligonucleotides for Structural and Functional Studies. Chemistry-A European Journal 2009, 15 (39), 10210-10216.
217. Sheng, J., Hassan, A., Huang, Z., New Telluride-Mediated Elimination for Novel Synthesis of 2',3'-dideoxynucleosides. The Journal of Organic Chemistry 2008, 73 (10), 3725-3729.
218. Rose, P. G., Bundy, B. N., Watkins, E. B., Thigpen, J. T., Deppe, G., Maiman, M. A., Clarke-Pearson, D. L., Insalaco, S., Concurrent cisplatin-based radiotherapy and chemotherapy for locally advanced cervical cancer. New England Journal of Medicine 1999, 340 (15), 1144-1153.
219. Morris, M., Eifel, P. J., Lu, J., Grigsby, P. W., Levenback, C., Stevens, R. E., Rotman, M., Gershenson, D. M., Mutch, D. G., Pelvic radiation with concurrent chemotherapy compared with pelvic and para-aortic radiation for high-risk cervical cancer. New England Journal of Medicine 1999, 340 (15), 1137-43.
220. Keys, H. M., Bundy, B. N., Stehman, F. B., Muderspach, L. I., Chafe, W. E., Suggs, C. L., 3rd, Walker, J. L., Gersell, D., Cisplatin, radiation, and adjuvant hysterectomy compared with radiation and adjuvant hysterectomy for bulky stage IB cervical carcinoma. New England Journal of Medicine 1999, 340 (15), 1154-61.
221. Wang, K., Lu, J., Li, R., The events that occur when cisplatin encounters cells. Coordination Chemistry Reviews. 1996, 151, 53-58.
222. Lippard, S. J., New chemistry of an old molecule: cis-[Pt(NH3)2Cl2]. Science 1982, 218 (4577), 1075-1082.
223. Takahara, P. M., Rosenzweig, A. C., Frederick, C. A., Lippard, S. J., Crystal structure of double-stranded DNA containing the major adduct of the anticancer drug cisplatin. Nature 1995, 377 (6550), 649-652.
224. Ohndorf, U. M., Rould, M. A., He, Q., Pabo, C. O., Lippard, S. J., Basis for recognition of cisplatin-modified DNA by high-mobility-group proteins. Nature 1999, 399 (6737), 708-712.
225. Jamieson, E., Lippard, S., Structure, Recognition, and Processing of Cisplatin- DNA Adducts. Chem. Rev 1999, 99 (9), 2467-2498.
226. Todd, R. C., Lippard, S. J., Structure of duplex DNA containing the cisplatin 1,2-{Pt(NH3)2}2+-d(GpG) cross-link at 1.77 A resolution. Journal of Inorganic Biochemistry 2010, 104 (9), 902-908.
227. Zlatanova, J., Yaneva, J., Leuba, S. H., Proteins that specifically recognize cisplatindamaged DNA: a clue to anticancer activity of cisplatin. The Journal of the Federation of American Societies for Experimental Biology 1998, 12 (10), 791-799.
228. Reiβner, T., Schneider, S., Schorr, S., Carell, T., Crystal Structure of a Cisplatin-(1, 3 GTG) Cross Link within DNA Polymerase ?. Angewandte Chemie International Edition 2010, 49 (17), 3077-3080.
229. Bruijnincx, P. C., Sadler, P. J., New trends for metal complexes with anticancer activity. Current Opinion in Chemical Biology 2008, 12 (2), 197-206.
230. Zimmer, C., Effects of the antibiotics netropsin and distamycin A on the structure and function of nucleic acids. Progress in Nucleic Acid Research and Molecular Biology 1975, 15 285-318.
231. Wartell, R. M., Larson, J. E., Wells, R. D., Netropsin. A specific probe for A-T regions of duplex deoxyribonucleic acid. Journal of Biological Chemistry 1974, 249 (21), 6719-6731.
232. Kopka, M. L., Yoon, C., Goodsell, D., Pjura, P., Dickerson, R. E., The molecular origin of DNA-drug specificity in netropsin and distamycin. Proceedings of the National Academy of Sciences of the United States of America 1985, 82 (5), 1376-1380.
233. Schultz, P. G., Dervan, P. B., Distamycin and penta-N-methylpyrrolecarboxamide binding sites on native DNA. A comparison of methidiumpropyl-EDTA-Fe(II) footprinting and DNA affinity cleaving. Journal of Biomolecular Structural Dynamics 1984, 1 (5), 1133-1147.
234. Nunn, C. M., Garman, E., Neidle, S., Crystal structure of the DNA decamer d(CGCAATTGCG) complexed with the minor groove binding drug netropsin. Biochemistry 1997, 36 (16), 4792-4799.
235. Chen, X., Mitra, S. N., Rao, S. T., Sekar, K., Sundaralingam, M., A novel end-to-end binding of two netropsins to the DNA decamers d(CCCCCIIIII)2, d(CCCBr5CCIIIII)2 and d(CBr5CCCCIIIII)2. Nucleic Acids Research 1998, 26 (23), 5464-5471.
236. Tevis, D. S., Kumar, A., Stephens, C. E., Boykin, D. W., Wilson, W. D., Large, sequence-dependent effects on DNA conformation by minor groove binding compounds. Nucleic Acids Research 2009, 37 (16), 5550-5558.
237. Kielkopf, C. L., White, S., Szewczyk, J. W., Turner, J. M., Baird, E. E., Dervan, P. B., Rees, D. C., A structural basis for recognition of A.T and T.A base pairs in the minor groove of B-DNA. Science 1998, 282 (5386), 111-115.
238. Squire, C. J., Baker, L. J., Clark, G. R., Martin, R. F., White, J., Structures of m-iodo Hoechst-DNA complexes in crystals with reduced solvent content: implications for minor groove binder drug design. Nucleic Acids Res 2000, 28 (5), 1252-1258.
239. Neidle, S., Mann, J., Rayner, E., Baron, A., Boahen, Y., Simpson, I. J., Smith, N. J., Fox, K. R., Hartley, J. A., Kelland, L. R., Symmetric bis-benzimidazoles: new sequence-selective DNA-binding molecules. Chemical Communications. 1999, 929-930.
240. Aymami, J., Nunn, C. M., Neidle, S., DNA minor groove recognition of a nonself- complementary AT-rich sequence by a tris-benzimidazole ligand. Nucleic Acids Research 1999, 27 (13), 2691-2698.
241. Neidle, S., Crystallographic insights into DNA minor groove recognition by drugs. Biopolymers 1997, 44 (1), 105-121.
242. Goodwin, K. D., Long, E. C., Georgiadis, M. M., A host-guest approach for determining drug-DNA interactions: an example using netropsin. Nucleic Acids Research 2005, 33 (13), 4106-4116.
243. Richards, A., Rodger, A., Synthetic metallomolecules as agents for the control of DNA structure. Chemical Society Reviews 2007, 36 (3), 471-483.
244. Salon, J., Sheng, J., Gan, J.-H., Huang, Z., Synthesis and crystal structure of 2'-Semodified guanosine containing DNA. Journal of Organic Chemistry 2010, 75 (3), 637-641.
245. Sheng, J., Hassan, A. E. A., Zhang, W., Zhou, J., Xu, B., Soares, A. S., Huang, Z., Synthesis, structure and imaging of oligodeoxyribonucleotides with telluriumnucleobase derivatization. Nucleic Acids Research 2011, 39 (9), 3962-3971.