Recent advances in oligonucleotide synthesis and their applications

Indian Journal of Biochemistry and Biophysics

Volumn 40, Issue 6, 2003, Pages 377-391

  Vaijayanthi, B ^a,b   Kumar, P ^a   Ghosh, P K ^c   Gupta, K C ^a  

^a CSIR INSTITUTE OF GENOMICS AND INTEGRATIVE BIOLOGY   (India)

^b UNIVERSITY OF DELHI   (India)

^c ZYDUS RESEARCH CENTRE   (India)

Author keywords

Conjugates; Immobilization; Microarray; Modifications; Oligonucleotides; Reusable support; Universal polymer support

Indexed keywords

NUCLEIC ACID; OLIGONUCLEOTIDE; PEPTIDE; POLYAMINE; POLYMER; REAGENT; RIBOZYME;

CONFORMATION; COST EFFECTIVENESS ANALYSIS; CROSS LINKING; DEPROTECTION REACTION; DNA BINDING; DNA MICROARRAY; DNA POLYMORPHISM; DNA SEQUENCE; DRUG SYNTHESIS; GENE MAPPING; GENE MUTATION; GENOMICS; GENOTYPE; SHORT SURVEY; SOLID STATE; TEMPERATURE DEPENDENCE;

AMINO ACID SEQUENCE; BIOPOLYMERS; CHEMISTRY TECHNIQUES, SYNTHETIC; COST-BENEFIT ANALYSIS; OLIGONUCLEOTIDE ARRAY SEQUENCE ANALYSIS; OLIGONUCLEOTIDES;

EID: 5444270975     PISSN: 03011208     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Short Survey

References (149)

1. Michelson A M & Todd A R (1955) J Chem Soc 2632-38.
2. Ghosh P K, Kumar P & Gupta K C (1998) J Indian Chem Soc 75, 206-18.
3. Gough G R, Brunden M J & Gilham P T (1983) Tetrahedron Lett 24, 5321-24.
4. Kumar P & Gupta K C (1999) Nucleic Acids Res 27, e2.
5. Gupta K C & Kumar P (1999) React Funct Polym 41, 197-204.
6. Azhayev A V (1999) Tetrahedron 55, 787-800.
7. Komiyama M & Yoshinari K (1997) J Org Chem 62, 2155-60.
8. Earnshaw D J & Gait M J (1998) Nucleic Acids Res 26, 5551-61.
9. Kumar P, Dhawan G, Chandra R & Gupta K C (2002) Nucleic Acids Res 30, e130.
10. Guzaev A P & Manoharan M (2003) J Am Chem Soc 125, 2380-81.
11. Pon R T, Shuyuan Yu, Zhiqiang G & Sanghvi Y S (1999) Nucleic Acids Res 27, 1533-38.
12. Hardy P M, Holland D, Scott S, Garman A J, Newton C R & McLean M J (1994) Nucleic Acids Res 22, 2998-3004.
13. Pon R T, Yu S & Sanghvi Y S (2001) Nucleosides Nucleotides Nucleic Acids 20, 985-89.
14. Pon R T, Yu S & Sanghvi Y S (2002) J Org Chem 67, 856-64.
15. Patnaik A K, Subba Rao N, Kumar P, Sharma A K, Garg B S & Gupta K C (2000) Helv Chim Acta 83, 322-26.
16. Manchanda R, Agarwal S K, Kumar P, Sharma A K & Gupta K C (2002) Helv Chim Acta 85, 2754-62.
17. Grimm G N, Boutorine A S, Lincoln P & Helene C (2001) Nucleosides Nucleotides Nucleic Acids 20, 909-14.
18. Privat E, Melvin T, Asseline U & Vigny P (2001) Photochem Photobiol 74, 532-41.
19. Koval V V, Chernonosov A A, Abramova T V, Ivanova T M, Fedorova O S, Derkacheva V M & Lukyanets E A (2001) Nucleosides Nucleotides Nucleic Acids 20, 1259-62.
20. Walton T A, Lyttle M H, Dick D J & Cook R M (2000) Bioconjug Chem 13, 1155-58.
21. Arimondo P B, Boutorine A, Baldeyrou B, Bailly C, Kuwahara M, Hecht S M, Sun J S, Garestier T & Helene C (2002) J Biol Chem 277, 3132-40.
22. Starke D, Lischka K, Pagels P, Uhlmann E, Kramer W, Wess G & Petzinger E (2001) BioMed Chem Lett 11, 945-49.
23. Sheppard T L, Wong C H & Joyce G F (2000) Angew Chem Int Ed Engl 39, 3660-63.
24. Bijsterbosch M K, Manoharan M, Dorland R, Van Veghel R, Biessen E A & Van Brekel T J (2002) J Pharmacol Exp Ther 302, 619-26.
25. Tung C H & Stein S (2000) Bioconjug Chem 11, 605-18.
26. Minard-Basquin C, Chaix C & Pichot C (2001) Nucleosides Nucleotides Nucleic Acids 20, 895-99.
27. Grimm G N, Boutorine A S & Helene C (2000) Nucleoside, Nucleotides Nucleic Acids 19, 1943-65.
28. Kumar P, Gupta K C, Rosch R & Seliger H (1996) BioMed Chem Lett 6, 2247-52.
29. Stetsenko D A & Gait M J (2001) Bioconjug Chem 12, 576-86.
30. Ghosh P K, Kumar P & Gupta K C (2000) J Indian Chem Soc 77, 109-18.
31. Stetsenko D A, Malakhov A D & Gait M J (2002) Org Lett 4, 3259-62.
32. Doronina S O, Guzaev A P & Manoharan M (2001) Nucleosides Nucleotides Nucleic Acids 20, 1007-10.
33. Haralambidis J, Duncan L & Tregear G W (1987) Tetrahedron Lett 28, 5199-5202.
34. Truffert J C, Lorthioir O, Asseline U, Thuong N T & Brack A (1994) Tetrahedron Lett 35, 2353-56.
35. Kubo T, Dubey K & Fujii M (2001) Nucleosides Nucleotides Nucleic Acids 20, 1321-24.
36. Robles J, Beltran M, Marchan V, Perez Y, Travesset I, Pedroso E & Grandas A (1999) Tetrahedron 55, 13251-64.
37. Chen C P, Li X X, Zhang L R, Min J M, Chan J Y, Fung K P, Wang S Q & Zhang L H (2002) Bioconjug Chem 13, 525-29.
38. Bergmann F & Bannwarth W (1995) Tetrahedron Lett 36, 1839-42.
39. Arar K, Aubertin A M, Roche A C, Monsigny M & Mayer R (1995) Bioconjug Chem 6, 573-77.
40. Mier W, Eritja R, Mohammed A, Haberkorn U & Eisenhut M (2000) Bioconjug Chem 11, 855-60.
41. Stetsenko D A & Gait M J (2000) Nucleosides Nucleotides Nucleic Acids 19, 1751-64.
42. Stetsenko D A & Gait M J (2000) J Org Chem 65, 4900-08.
43. Forget D, Boturyn D, Defrancq E, Lhomme J & Dumy P (2001) Chemistry 7, 3976-84.
44. Maruyama A, Saito M, Ueda M, Yamada M, Watanabe H & Akaike T (1999) Nucleic Acids Res Symp Ser 42, 97-98.
45. Zatsepin T S, Stetsenko D A, Arzumanov A A, Romanova E A, Gait M J & Oretskaya T S (2002) Bioconjug Chem 13, 822-30.
46. Bruick R K, Dawson P E, Kent S B, Usman N & Joyce G F (1996) Chem Biol 3, 49-56.
47. Zhu T, Wei Z, Tung C H, Dickerhof W A, Breslauer K J, Georgopoulos D E & Leibowitz M J (1993) Antisense Res Dev 3, 265-75.
48. Wei Z, Tung C H, Zhu T & Stein S (1994) Bioconjug Chem 5, 468-74.
49. Astriab-Fisher A, Sergueev D. Fisher M, Shaw B R & Juliano R L (2002) Pharm Res 19, 744-54.
50. Manoharan M (2002) Antisense Nucleic Acid Drug Dev 12, 103-28.
51. Crooke S T (2000) Methods Enzymol 313, 3-45.
52. Uhlmann E & Peyman A (1990) Chem Rev 90, 543-84.
53. Wang L, Prakash R K, Stein C A, Koehn R K & Ruffner D E (2003) Antisense Nucleic Acid Drug Dev 13, 169-89.
54. Zang Z, Li M, Wang H, Agrawal S & Zhang R (2003) Proc Natl Acad Sci (USA) 100, 11636-41.
55. Jahrsdorfer B & Weiner G J (2003) Curr Opin Investig Drugs 4, 686-90.
56. Rieger R & Kipps T J (2003) Cancer Res 63, 4128-35.
57. Davila E, Kennedy R & Celis E (2003) Cancer Res 63, 3281-8.
58. Rimmele M (2003) Chembiochem 4, 963-71.
59. Bi F, Liu N & Fan D (2003) Curr Gene Ther 3, 411-17.
60. Obika S, Mono K, Hari Y & Imanishi T (1999) BioMed Chem Lett 9, 515-18.
61. Kurreck J (2003) Eur J Biochem 270, 1628-44.
62. Venkatesan N, Kim S J & Kim B H (2003) Curr Med Chem 10, 1973-91.
63. While R E, Wade-Martins R, Hart S L, Frampton J, Huey B, Mehta A D, Cerosaletti K M, Concannon P & James M R J (2003) Gene Med 5, 883-92.
64. Corey D R, Munoz-Medellin D & Huang A (1995) Bioconjug Chem 6, 93-100.
65. Corey D R (1995) J Am Chem Soc 117, 9373-74.
66. Ede N J, Tregear G W & Haralambidis J (1994) Bioconjug Chem 5, 373-78.
67. Bendifallah N, Kristensen E, Dahl O, Koppelhus U & Nielsen P E (2003) Bioconjug Chem 4, 588-92.
68. Koppelhus U & Nielsen P E (2003) Adv Drug Deliv Rev 55, 267-80.
69. Asseline U, Thuong NT & Helene C (1997) New J Chem 21, 5-17.
70. Kuzuya A & Komiyama M (2000) Chem Lett, 1378-79.
71. Gottikh M B, Volkov E M, Romanova E A, Oretskaya T S & Shabarova Z A (1999) Nucleosides Nucleotides 18, 1645-46.
72. MacKellar C, Graham D, Will D W, Burgess S & Brown T (1992) Nucleic Acids Res 20, 3411-17.
73. Elsner H I & Mouritsen S (1994) Bioconjug Chem 5, 463-67.
74. Kurz M, Gu K & Lohse P A (2000) Nucleic Acids Res 28, e83.
75. Capobianco M L, De Champdore M, Francini L, Lena S, Garbesi A & Arcamone F (2001) Bioconjug Chem 12, 523-28.
76. Bhatia D, Yue-Ming L & Ganesh K N (1999) BioMed Chem Lett 9, 1789-94.
77. Arimondo P, Bailly C, Boutorine A, Asseline U, San J S, Garestier T & Helene C (2000) Nucleosides Nucleotides Nucleic Acids 19, 1205-18.
78. Trawick B N, Osiek T A & Bashkin J K (2001) Bioconjug Chem 12, 900-05.
79. Astrom H & Stromberg R (2001) Nucleosides Nucleotides Nucleic Acids 20, 1385-88.
80. Verbeure B, Lacey C J, Froeyen M, Rozenski J & Herdewijn P (2002) Bioconjug Chem 13, 333-50.
81. Minard-Basquin C, Chaix C, Pichot C & Mandrand B (2000) Bioconjug Chem 11, 795-804.
82. Jeong J H & Park T G (2001) Bioconjug Chem 12, 917-23.
83. Koch T, Jacobsen N, Fensholdt J, Boas U, Fenger M & Jacobsen M H (2000) Bioconjug Chem 11, 474-83.
84. Whittemore N A, Mullenix A N, Inamati G B, Manoharan M, Cook P D, Tuinman A A, Baker D C & Chambers J Q (1999) Bioconjug Chem 10, 261-70.
85. Balakin K V, Korshun V A, Mikhalev I I, Maleev G V, Malakhov A D, Prokhorenko I A & Berlin Yu A (1999) Biosens Bioelectron 13, 771-8.
86. Lewis F D, Wu Y & Liu X (2002) J Am Chem Soc 124, 12165-73.
87. Yamana K, Yoshikawa A & Nakano H (1996) Tetrahedron Lett 37, 637-40.
88. Yamana K, Yoshikawa A, Noda R & Nakano H (1998) Nucleosides Nucleotides 17, 233-42.
89. Asanuma H, Liang X, Yoshida T & Komiyama M (2001) Chembiochem 2, 39-44.
90. Asanuma H, Liang X & Komiyama M (2000) Tetrahedron Lett 41, 1055-58.
91. Liang X, Asanuma H & Komiyama M (2002) J Am Chem Soc 124, 1877-83.
92. Liang X, Asanuma H & Komiyama M (2001) Tetrahedron Lett 42, 6723-25.
93. Wang G & Stoisavljevic V (2000) Nucleosides Nucleotides Nucleic Acids 19, 1413-25.
94. Bednar M (2000) Med Sci Monit 6, 796-800.
95. Zammatteo N, Hamels S, De Longueville F, Alexandre I, Gala J L, Brasseur F, Remacle J (2002) Biotechnol Annu Rev 8, 85-101.
96. Heller M J (2002) Annu Rev Biomed Engg 4, 129-53.
97. Panda S, Sato T K, Hampton, G M & Hogenesch J B (2003) Trends Cell Biol 13, 151-56.
98. Vastag B (2003) JAMA 289, 155-56.
99. McGall G H & Christians F C (2002) Adv Biochem Engg Biotechnol 77, 21-42.
100. Southern E, Mir K & Shchepinov M (1999) Nature Genet (Suppl) 21, 5-9.
101. Kim I J, Kang H C, Park J H, Shin Y, Ku J L, Lim S B, Park S Y, Jung S Y, Kim H K & Park J G (2003) Clin Cancer Res 9, 2920-25.
102. Unger M A, Rishi M, Clemmer V B, Hartman J L, Keiper E A, Greshock J D, Chodosh L A, Liebman M N & Weber B L (2001) Breast Cancer Res 3, 336-41.
103. Bilban M, Buehler L K, Head S, Desoye G & Quaranta V (2002) Curr Issues Mol Biol 4, 57-64.
104. Brown P O & Botstein D (1999) Nat Genet 21, 33-37.
105. Ju J, Glazer A N & Mathies R A (1996) Nature Med 2, 246-49.
106. Smith L M, Sanders J Z, Kaiser R J, Hughes P, Dodd C, Connell C R, Heiner C, Kent S B H & Hood L E (1986) Nature (London) 321, 644-49.
107. !07 Ju J, Ruan C, Fuller C W, Glazer A N & Mathies R A (1995) Proc Natl Acad Sci (USA) 92, 4347-51.
108. Ju J, Khetrapal I, Scherer J A, Ruan C, Fuller C W, Glazer A N & Mathies R A (1995) Anal Biochem 231, 131-40.
109. Beaucage S L (2001) Curr Med Chem 8, 1213-44.
110. Cha T W, Boiadjiev V, Lozano J, Yang H & Zhu X Y (2002) Anal Biochem 311, 21-32.
111. Pease A C, Solas D, Sullivan E J, Cronin M T, Holmes C P & Fodor S P A (1994) Proc Natl Acad Sci USA 91, 5022-26.
112. Beier M & Hoheisel J D (1999) Nucleic Acids Res 27, 1970-77.
113. Beier M & Hoheisel J D (2000) Nucleic Acids Res 28, e11.
114. McGall G, Labadie J, Brock P, Wallraff G, Nguyen T & Hinsberg W (1996) Proc Natl Acad Sci (USA) 93, 13555-60.
115. Fodor S P, Read J L, Pirrung, M C, Stryer L, Lu A T & Solas D (1991) Science 251, 767-73.
116. Lipshutz R J, Fodor S P, Gingeras T R & Lockhart D J (1999) Nature Genet 21, 20-24.
117. Albert T J, Norton J, Ott M, Richmond T, Nuwaysir K, Nuwaysir E F, Stengele K -P & Green R D (2003) Nucleic Acids Res 31, e35.
118. Beier M & Hoheisel J D (2002) J Biotechnol 94, 15-22.
119. Elder J K, Johnson M, Milner N, Mir K U, Sohail M & Southern E M (1999) DNA Microarrays: A Practical Approach (Schena M, ed.), pp. 77, Oxford Press, New York.
120. Urdea M S & Horn T (1986) Tetrahedron Lett 27, 2933-36.
121. Kwiatkowski M, Fredriksson S, Isaksson A, Nilsson M & Landegren U (1999) Nucleic Acids Res 27, 4710-14.
122. Duggan D J, Bittner M, Chen Y, Meltzer P & Trent J M (1999) Nature Genet (Suppl) 21, 10-14.
123. Rogers Y -H, Jiang-Baucom P, Huang Z -J, Bogdanov V, Anderson S & Boyce Jacino M T (1999) Anal Biochem 266, 23-30.
124. Benters R, Niemeyer C M & Wohrle D (2001) Chembiochem 2, 686-94.
125. Zammatteo N, Jeanmart L, Hamels S, Courtois S, Louette P, Hevesi L & Remacle J (2000) Anal Biochem 280, 143-50.
126. Steel A, Torres M, Hartwell J, Yu Y-Y, Ting N, Hoke G, Yang H (2000) Microarray Biochip Technology (Schena M, ed), pp. 87, Eaton Press, Natick
127. Pirrung M C, Davis J D & Odenbaugh A L (2000) Langmuir 16, 2185-91.
128. Joos B, Kuster H & Cone R (1997) Anal Biochem 247, 96-101.
129. Belosludtsev Y, Iverson B, Lemeshko S, Eggers R, Wiese R, Lee S, Powdrill T & Hogan M (2001) Anal Biochem 292, 250-56.
130. Lamture J B, Beattie K L, Burke B E, Eggero H D, Ehrlich D J, Fowler R, Hollis M A, Kosicki B B, Reich R K, Smith S R, Varma R S & Hogan M E (1994) Nucleic Acids Res 22, 2121-25.
131. Adessi C, Matton G, Ayala G, Turcatti G, Mermod J -J, Mayer P & Kawashima E (2000) Nucleic Acids Res 28, e87.
132. Timofeev E N, Kochetkova S V, Mirzabekov A D & Florentiev V L (1996) Nucleic Acids Res 24, 3142-48.
133. Lee P H, Sawan S P, Modrusan Z, Arnold L J Jr & Reynolds M A (2002) Bioconjug Chem 13, 97-103.
134. Rehman F N, Audeh M, Abrams E S, Hammond P W, Kenney M & Boles C (1999) Nucleic Acids Res 27, 649-55.
135. Ghosh S S & Musso G F (1987) Nucleic Acids Res 15, 5353-72.
136. Strother T, Cai W, Zhao X, Hamers R J & Smith L M (2000) J Am Chem Soc 122, 1205-09.
137. Strother T, Hamers R J & Smith L M (2000) Nucleic Acids Res 28, 3535-41.
138. Okamoto T, Suzuki T & Yamamoto N (2000) Nature Biotechnol 18, 438-41.
139. Frutos A G, Smith L M & Corn R M (1998) J Am Chem Soc 120, 10277-82.
140. Smith E A, Wanat M J, Cheng Y, Barreira S V P, Frutos A G & Corn R M (2001) Langmuir 17, 2502-07.
141. Raddatz S, Mueller-Ibeler J, Kluge J, Wab L, Burdinski G, Havens J R, Onofrey T J, Wang D & Schweitzer M (2002) Nucleic Acids Res 30, 4793-802.
142. Podyminogin M A, Lukhtanov E A & Reed M W (2001) Nucleic Acids Res 29, 5090-98.
143. Kumar P & Gupta K C (2003) Bioconjug Chem 14, 507-12.
144. Zhao X, Nampalli S, Serino A J & Kumar S (2001) Nucleic Acids Res 29, 955-59.
145. Butler J H, Cronin M, Anderson K M, Biddison G M, Chatelain F, Cummer M, Davi D J, Fisher L, Frauendorf A W, Frueh F W, Gjerstad C, Harper T F, Kernahan S D, Long D Q, Pho M, Walker J A II & Brennan T M (2001) J Am Chem Soc 123, 8887-94.
146. Jung A, Stemmler I, Brecht A, Gauglitz G & Fresenius J (2001) Anal Chem 371, 128-36.
147. Diehl F, Grahlmann S, Beier M & Hoheisel J D (2001) Nucleic Acids Res 29, e38.
148. Faria M & Ulrich H (2002) Curr Cancer Drug Targets 2, 355-68.
149. Gilliam B L & Redfieid R R (2003) Curr Top Med Chem 3, 1536-53