ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Some new (2′-5′)oligoadenylate trimers, i.e., 22-28, containing the antiviral nucleoside ribavirin (= 1-(β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide; 7) and the synthetic cytokine 6-(benzylamino)purine riboside (= N6-benzyladenosine; 1) in different positions of the trimer, have been synthesized by the phosphotriester method. The selectively blocked nucleosides 2-6 and 8-11 and the 2′-phosphodiesters 13 and 14, used for the oligonucleotide syntheses, were synthesized from the corresponding unprotected ribonucleosides 1 and 7, and isolated by silica-gel column chromatography. The fully deblocked trimers 22-28 were purified by ion-exchange chromatography on DEAE-Senacell 23-SS. The newly synthesized compounds were characterized by physical means. The ability of synthesized trimers to inhibit HIV-1 replication and to improve RNase L activation were investigated. Some of the synthesized trimers showed also biological inhibition of HIV-1 reverse transcriptase and HIV-1-induced syncytia formation. It was shown that AdoBn-containing trimers inhibited HIV-1-induced syncytia formation 〉 1500-fold, independently of the position of the AdoBn residue in the oligomer chain.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19970800404