INTRODUCTION OF A LIPOPHILIC THIOETHER TETHER IN THE MINOR-GROOVE OF NUCLEIC-ACIDS FOR ANTISENSE APPLICATIONS

被引:27
作者
MANOHARAN, M
JOHNSON, LK
TIVEL, KL
SPRINGER, RH
COOK, PD
机构
[1] Department of Medicinal Chemistry, Isis Pharmaceuticals, Carlsbad, CA 92008
关键词
D O I
10.1016/S0960-894X(01)80760-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A 2'-O-hexylthiotrityl adenosine phosphoramidite has been synthesized and incorporated into oligonucleotide phosphodiesters and phosphorothioates. This tether has potential antisense applications, offers a convenient nucleophile for conjugation of various moieties that would reside in the minor groove, and may form novel tertiary structures.
引用
收藏
页码:2765 / 2770
页数:6
相关论文
共 33 条
[1]  
Manoharan, Guinosso, Cook, Novel functionalization of the sugar moiety of nucleic acids for multiple labeling in the minor groove, Tetrahedron Letters, 32, (1991)
[2]  
Manoharan, Antisense Research and Applications, pp. 303-349, (1993)
[3]  
Manoharan, Johnson, McGee, Guinosso, Ramasamy, Springer, Bennett, Ecker, Vickers, Cowsert, Cook, Chemical Modifications to Improve Uptake and Bioavailability of Antisense Oligonucleotides, Annals of the New York Academy of Sciences, 660, (1992)
[4]  
Connolly, Rider, Chemical synthesis of oligonucleotides containing a free sulphydryl group and subsequent attachment of thiol specific probes, Nucleic Acids Research, 13, (1985)
[5]  
Sproat, Beijer, Rider, Neuner, The synthesis of protected 5′-mercapto-2′,5′-dideoxyribonucleoside-3′-0-phosphorainidites
[6]  
uses of 5′-mercapto-oligodeoxyribonucleotides, Nucleic Acids Research, 15, (1987)
[7]  
Zuckerman, Corey, Schultz, Efficient methods for attachment of thiol specific probes to the 3′-ends of synthetic oligodeoxyribonucleotides, Nucleic Acids Research, 15, (1987)
[8]  
Bischoff, Coull, Regnier, Introduction of 5′-terminal functional groups into synthetic oligonucleotides for selective immobilization, Analytical Biochemistry, 164, (1987)
[9]  
Sinha, Cook, The preparation and application of functionalised synthetic oligonucleotides: III. Use of H-phosphonate derivatives of protected amino-hexanol and mercapto-propanol or-hexanol, Nucleic Acids Research, 16, (1988)
[10]  
Sproat, Beiijer, Rider, Neuner, Synthesis of Modified Building Blocks Containing Amino or Thiol Moieties: Application of Modified Oligodeoxyribonucleotides, Nucleosides and Nucleotides, 7, (1988)