A. D. Malakhov

New Pyrene Derivatives for Fluorescent Labeling of Oligonucleotides

Abstract A series of pyrene-containing reagents have been synthesized and used for the fluorescent labeling of oligonucleotides.

[Synthesis and fluorescent properties of 5-(1-pyrenylethynyl)-2'- deoxyuridine-containing oligodeoxynucleotides].

Novel reagents for the fluorescent labeling of oligo- and polynucleotides have been prepared: 5-(1-pyrenylethynyl)-2′-deoxyuridine 3′-phosphoramidite and a solid support carrying this nucleoside. Oligo-nucleotides containing one or several modified units have been synthesized, and the fluorescence of these probes has been shown to change upon hybridization with the complementary sequence.

New Fluorescent Nucleoside Derivatives -5-Alkynylated 2-Deoxyuridines

Abstract Four fluorescent nucleosides, 5-(4-pyrenylethynyl)-, 5-(l-pyrenylbutadiynyl)-, 5-(3-perylenylethynyl)-, and 5-[4-(2-benzoxazolyl)phenylethynyl]-2′-deoxyuridines, were synthesized.

A Pyrene Seco-Pseudonucleoside in Constructing Interaction-Sensitive Fluorescent DNA Probes

Abstract Based on 4-(1-pyrenyl)-1, 3-butanediol, a pyrene seco-pseudonucleoside, we prepared a nonnucleotide phosphoramidite reagent and a pyrene-modified LCAA-CPG-support and employed them in solid-phase synthesis of pyrene-labeled oligonucleotides with varying numbers and positions of the pseudonucleoside residues. Changes in the fluorescence intensity and the spectral curve shape upon hybridization were observed that depended on the position(s) of the modified unit(s) in the probe.

Perylene attached to DNA through stiff or flexible linker: duplex stability and FRET.

Two fluorescent nucleosides, 5-(perylen-3-ylethynyl)-2′-deoxyuridine and 5-[(perylen-3-yl)methoxypropyn-1-yl]-2′-deoxyuridine, were incorporated into synthetic oligodeoxyribonucleotides and spectral properties of the conjugates and their duplexes were studied.

Synthesis and evaluation of anti-HSV activity of new 5-alkynyl-2'-deoxyuridines.

Eight 5-alkynyl-2′deoxyuridines containing different bulky substituents have been prepared and tested against HSV-1 in Vero cells. The compounds show positive antiviral activity. There is no obvious correlation between activity and substituent size. The nature of the linker between uracil and a substituent appears to be more important for antiviral properties: nucleosides containing arylethynyl groups show higher activity.

Synthesis and Fluorescent Characteristics of Oligodeoxynucleotides Containing a Novel Fluorescent Label, p-(2-Benzoxazolyl)tolane

A functional (dihydroxybutyl) derivative of p-(2-benzoxazolyl)tolane, a fluorescent label novel for biopolymers, was synthesized. The functionalized solid support obtained on its basis was employed in the synthesis of oligodeoxynucleotides 3-terminally labeled with benzoxazolyltolane (these oligonucleotides also contained 1-phenylethynylpyrene residues). This fluorophore within its dihydroxybutyl derivative and the oligonucleotides modified with it display an intensive fluorescence characterized by a high Stokes shift. The oligonucleotides labeled with this fluorophore are potential probes sensitive to the bioplymer microenvironment.