Synthesis, Hybridization Properties, Nuclease Stability, and Cellular Uptake of the Oligonucleotide-Amino-.beta.-cyclodextrins and Adamantane Conjugates

Synthesis of the oligonucleotides conjugated with amino derivatives of beta-cyclodextrin and adamantane, at the 3'-end of host oligonucleotide, has been described. The oligonucleotide conjugates were examined for their nuclease stability, hybridization properties, and cellular uptake. The oligo...

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Bibliographic Details
Published in:Bioconjugate chemistry 1995-07, Vol.6 (4), p.327-331
Main Authors: Habus, Ivan, Zhao, Qiuyan, Agrawal, Sudhir
Format: Article
Language:English
Subjects:
Adamantane
Amines
Base Sequence
Biological Transport
Cell Line
Chromatography, High Pressure Liquid
Cyclodextrins - chemistry
DNA-Directed DNA Polymerase
Glycoconjugates - chemical synthesis
Glycoconjugates - chemistry
Glycoconjugates - metabolism
Humans
Indicators and Reagents
Kinetics
Molecular Sequence Data
Nucleic Acid Hybridization
RNA, Complementary - chemistry
Structure-Activity Relationship
Substrate Specificity
Viral Proteins - metabolism
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Description
Summary:Synthesis of the oligonucleotides conjugated with amino derivatives of beta-cyclodextrin and adamantane, at the 3'-end of host oligonucleotide, has been described. The oligonucleotide conjugates were examined for their nuclease stability, hybridization properties, and cellular uptake. The oligonucleotide conjugates had increased nuclease resistance compared to their parent oligonucleotides. Conjugation of adamantane to the oligonucleotides did not adversely affect the ability of the oligonucleotides to hybridize with their complementary RNA. Conjugation with amino derivatives of beta-cyclodextrin, however, significantly destabilized the duplex formation. In the cellular uptake studies, we found that amino derivatives of beta-cyclodextrin attached at 3'-end of the oligonucleotides did not help to increase the uptake by cells. Cellular uptake of oligonucleotide-adamantane conjugates in association with 2-(hydroxypropyl)-beta-cyclodextrin (HPCD) as a "carrier" was significantly higher than that of control oligonucleotides.
ISSN:1043-1802
1520-4812
DOI:10.1021/bc00034a001