» Articles » PMID: 8382790

Facile Preparation of Nuclease Resistant 3' Modified Oligodeoxynucleotides

Overview
Specialty Biochemistry
Date 1993 Jan 11
PMID 8382790
Citations 23
Authors
Affiliations
Soon will be listed here.
Abstract

An efficient chemical procedure for the immobilization of carboxylate containing conjugate groups onto controlled pore glass (CPG) is described. The derivatized supports were used in the automated synthesis of an oligodeoxynucleotide (20-mer ODN) containing a 3' phosphodiester linked hexanol, aminohexyl, acridine, or cholesterol group. The stability of the oligomer in a hepatoma cell culture was found to be prolonged two to three fold by the presence of any of the 3' tails. By contrast, an aminohexyl group appended to the 5' terminus of the ODN only marginally improved its nuclease resistance. These data support the notion that antisense ODNs are primarily degraded by 3' exonucleases. Introduction of simple 3' tails which incorporate a normal phosphodiester linkage can increase ODN stability by interfering with these enzymes.

Citing Articles

Inhibition of transcription and antiproliferative effects in a cancer cell line using antigene oligonucleotides containing artificial nucleoside analogues.

Wang L, Notomi R, Sasaki S, Taniguchi Y RSC Med Chem. 2023; 14(8):1482-1491.

PMID: 37593572 PMC: 10429662. DOI: 10.1039/d3md00139c.


Development of Phosphoramidite Reagents for the Synthesis of Base-Labile Oligonucleotides Modified with a Linear Aminoalkyl and Amino-PEG Linker at the 3'-End.

Osawa T, Ren Q, Obika S Molecules. 2022; 27(23).

PMID: 36500594 PMC: 9736658. DOI: 10.3390/molecules27238501.


Oxidation of -[I]Iodobenzoic Acid and -[At]Astatobenzoic Acid Derivatives and Evaluation In Vivo.

Li Y, Chyan M, Hamlin D, Nguyen H, Corey E, Wilbur D Int J Mol Sci. 2022; 23(18).

PMID: 36142567 PMC: 9506049. DOI: 10.3390/ijms231810655.


RNA-Cholesterol Nanoparticles Function as Potent Immune Activators TLR7 and TLR8.

Obermann H, Lederbogen I, Steele J, Dorna J, Sander L, Engelhardt K Front Immunol. 2022; 12:658895.

PMID: 35126343 PMC: 8814444. DOI: 10.3389/fimmu.2021.658895.


Refilling drug delivery depots through the blood.

Brudno Y, Silva E, Kearney C, Lewin S, Miller A, Martinick K Proc Natl Acad Sci U S A. 2014; 111(35):12722-7.

PMID: 25139997 PMC: 4156738. DOI: 10.1073/pnas.1413027111.


References
1.
Petrie C, Reed M, Adams A, Meyer Jr R . An improved CPG support for the synthesis of 3'-amine-tailed oligonucleotides. Bioconjug Chem. 1992; 3(1):85-7. DOI: 10.1021/bc00013a014. View

2.
Zendegui J, Vasquez K, Tinsley J, Kessler D, Hogan M . In vivo stability and kinetics of absorption and disposition of 3' phosphopropyl amine oligonucleotides. Nucleic Acids Res. 1992; 20(2):307-14. PMC: 310371. DOI: 10.1093/nar/20.2.307. View

3.
Hinrichsen R, Fraga D, Reed M . 3'-modified antisense oligodeoxyribonucleotides complementary to calmodulin mRNA alter behavioral responses in Paramecium. Proc Natl Acad Sci U S A. 1992; 89(18):8601-5. PMC: 49968. DOI: 10.1073/pnas.89.18.8601. View

4.
Cantor C, WARSHAW M, Shapiro H . Oligonucleotide interactions. 3. Circular dichroism studies of the conformation of deoxyoligonucleotides. Biopolymers. 1970; 9(9):1059-77. DOI: 10.1002/bip.1970.360090909. View

5.
Knowles B, HOWE C, Aden D . Human hepatocellular carcinoma cell lines secrete the major plasma proteins and hepatitis B surface antigen. Science. 1980; 209(4455):497-9. DOI: 10.1126/science.6248960. View