Bioconjugate Chemistry

, volume 28 , issue 10 , pages 2599-2607

Automated Solid-Phase Click Synthesis of Oligonucleotide Conjugates: From Small Molecules to Diverse N-Acetylgalactosamine Clusters

Valentina M Farzan ^{1, 2}

Egor Ulashchik ³

Egor A Ulashchik ⁴

Yury V Martynenko Makaev ³

Yury V. Martynenko-Makaev ⁴

Maksim V Kvach ³

Ilya O Aparin ⁵

V. A. Brylev ⁵

Vladimir A Brylev ⁵

Tatiana A Prikazchikova ^{1, 2}

Svetlana Maklakova ⁶

Svetlana Yu Maklakova ⁷

Alexander G. Majouga ^{6, 8}

A.V. Ustinov ⁵

Alexey V Ustinov ⁵

Г. А. Шипулин ⁹

German A. Shipulin ⁹

V.V. Shmanai ³

Vadim V Shmanai ⁴

Vladimir A. Korshun ^{5, 10}

Timofei S. Zatsepin ^{1, 2, 6, 7, 9}

Hide authors affiliations Show authors affiliations: 10 affiliations

Center of Translational Biomedicine, Skolkovo Institute of Science and Technology, Skolkovo, Moscow 143026, Russia |

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Surganova 13, Minsk 220072, Belarus |

⁴

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Surganova 13, Minsk 220072, Belarus |

⁵

Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, Moscow 117997, Russia |

⁶

Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 3, Moscow 119992, Russia |

⁷

Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 3, Moscow 119992, Russia |

⁸

National University of Science and Technology “MISiS”, Leninskiy Prospect 4, Moscow 119991, Russia |

⁹

Central Research Institute of Epidemiology, Novogireevskaya 3a, Moscow 111123, Russia |

¹⁰

Gause Institute of New Antibiotics, Bolshaya Pirogovskaya 11, Moscow 119021, Russia |

Publication type: Journal Article

Publication date: 2017-10-04

American Chemical Society (ACS)

Bioconjugate Chemistry

scimago Q1

wos Q1

SJR: 1.035

CiteScore: 7.5

Impact factor: 3.9

ISSN: 10431802, 15204812

DOI: 10.1021/acs.bioconjchem.7b00462

Copy DOI

PubMed ID: 28921968

Organic Chemistry

Pharmacology

Pharmaceutical Science

Biotechnology

Bioengineering

Biomedical Engineering

Abstract

We developed a novel technique for the efficient conjugation of oligonucleotides with various alkyl azides such as fluorescent dyes, biotin, cholesterol, N-acetylgalactosamine (GalNAc), etc. using copper-catalysed alkyne-azide cycloaddition on the solid phase and CuI·P(OEt)3 as a catalyst. Conjugation is carried out in an oligonucleotide synthesizer in fully automated mode and is coupled to oligonucleotide synthesis and on-column deprotection. We also suggest a set of reagents for the construction of diverse conjugates. The sequential double-click procedure using a pentaerythritol-derived tetraazide followed by the addition of a GalNAc or Tris-GalNAc alkyne gives oligonucleotide-GalNAc dendrimer conjugates in good yields with minimal excess of sophisticated alkyne reagents. The approach is suitable for high-throughput synthesis of oligonucleotide conjugates ranging from fluorescent DNA probes to various multi-GalNAc derivatives of 2'-modified siRNA.

Found

3 citations

Beloglazkina Elena

DSc in Chemistry, professor

296 publications, 3 214 citations, 11 reviews

h-index: 29

Lomonosov Moscow State University

2 citations

Zvereva Maria

DSc in Chemistry, professor

101 publications, 1 288 citations

h-index: 19

Lomonosov Moscow State University

2 citations

Novopashina Daria

77 publications, 723 citations, 9 reviews

h-index: 13

Institute of Chemical Biology and Fundamental Medicine of the Siberian Branch of the Russian Academy of Sciences

1 citation

Skvortsov Dmitry

🥼

PhD in Chemistry

128 publications, 1 834 citations, 1 review

h-index: 26

Lomonosov Moscow State University

1 citation

Mishin Alexander

PhD in Biological/biomedical sciences

81 publications, 2 755 citations, 9 reviews

h-index: 25

Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences

1 citation

Osolodkin Dmitry

🥼 🤝

PhD in Chemistry

80 publications, 1 707 citations

h-index: 22

Sechenov First Moscow State Medical University

M.P. Chumakov Federal Scientific Center for Research and Development of Immunobiological Drugs of the Russian Academy of Sciences

1 citation

Abakumov Maxim

PhD in Chemistry, associate professor

159 publications, 2 662 citations, 19 reviews

h-index: 28

National University of Science & Technology (MISiS)

Pirogov Russian National Research Medical University

1 citation

Nikitin Aleksey

🤝

PhD in Chemistry

46 publications, 635 citations

h-index: 14

National University of Science & Technology (MISiS)

Pirogov Russian National Research Medical University

Mendeleev University of Chemical Technology of Russia

Research interests

"Smart" materials

Inorganic Chemistry

Magnetic hyperthermia

Magnetic materials

Magnetic resonance imaging (MRI)

Nanoparticles of metal oxides

Nanotechnology

Synthesis of nanoparticles

Targeted drug delivery

1 citation

Uspenskaya Anastasia

🥼 🤝

PhD in Chemistry

21 publications, 230 citations

h-index: 9

Lomonosov Moscow State University

1 citation

Golovin Andrey

🥼 🤝

DSc in Chemistry

98 publications, 1 333 citations

h-index: 20

Lomonosov Moscow State University

Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences

1 citation

Perevyazova Tatyyana

17 publications, 119 citations

h-index: 6

Institute of Theoretical and Experimental Biophysics of the Russian Academy of Sciences

1 citation

Meschaninova Mariya

PhD in Chemistry

83 publications, 882 citations

h-index: 16

Institute of Chemical Biology and Fundamental Medicine of the Siberian Branch of the Russian Academy of Sciences

Catalytic nucleic acids

Chemistry of nucleic acids

DNA

Fluorescent samples

Interaction with biopolymers

Oligonucleotides

RNA

Synthesis

small interfering RNAs

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GOST Copy

Farzan V. M. et al. Automated Solid-Phase Click Synthesis of Oligonucleotide Conjugates: From Small Molecules to Diverse N-Acetylgalactosamine Clusters // Bioconjugate Chemistry. 2017. Vol. 28. No. 10. pp. 2599-2607.

GOST all authors (up to 50) Copy

Farzan V. M., Ulashchik E., Ulashchik E. A., Martynenko Makaev Y. V., Martynenko-Makaev Y. V., Kvach M. V., Aparin I. O., Brylev V. A., Brylev V. A., Prikazchikova T. A., Maklakova S., Maklakova S. Yu., Majouga A. G., Ustinov A., Ustinov A. V., Шипулин Г. А., Shipulin G. A., Shmanai V., Shmanai V. V., Korshun V. A., Zatsepin T. S. Automated Solid-Phase Click Synthesis of Oligonucleotide Conjugates: From Small Molecules to Diverse N-Acetylgalactosamine Clusters // Bioconjugate Chemistry. 2017. Vol. 28. No. 10. pp. 2599-2607.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/acs.bioconjchem.7b00462

UR - https://pubs.acs.org/doi/10.1021/acs.bioconjchem.7b00462

TI - Automated Solid-Phase Click Synthesis of Oligonucleotide Conjugates: From Small Molecules to Diverse N-Acetylgalactosamine Clusters

T2 - Bioconjugate Chemistry

AU - Farzan, Valentina M

AU - Ulashchik, Egor

AU - Ulashchik, Egor A

AU - Martynenko Makaev, Yury V

AU - Martynenko-Makaev, Yury V.

AU - Kvach, Maksim V

AU - Aparin, Ilya O

AU - Brylev, V. A.

AU - Brylev, Vladimir A

AU - Prikazchikova, Tatiana A

AU - Maklakova, Svetlana

AU - Maklakova, Svetlana Yu

AU - Majouga, Alexander G.

AU - Ustinov, A.V.

AU - Ustinov, Alexey V

AU - Шипулин, Г. А.

AU - Shipulin, German A.

AU - Shmanai, V.V.

AU - Shmanai, Vadim V

AU - Korshun, Vladimir A.

AU - Zatsepin, Timofei S.

PY - 2017

DA - 2017/10/04

PB - American Chemical Society (ACS)

SP - 2599-2607

IS - 10

VL - 28

PMID - 28921968

SN - 1043-1802

SN - 1520-4812

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2017_Farzan,

author = {Valentina M Farzan and Egor Ulashchik and Egor A Ulashchik and Yury V Martynenko Makaev and Yury V. Martynenko-Makaev and Maksim V Kvach and Ilya O Aparin and V. A. Brylev and Vladimir A Brylev and Tatiana A Prikazchikova and Svetlana Maklakova and Svetlana Yu Maklakova and Alexander G. Majouga and A.V. Ustinov and Alexey V Ustinov and Г. А. Шипулин and German A. Shipulin and V.V. Shmanai and Vadim V Shmanai and Vladimir A. Korshun and Timofei S. Zatsepin},

title = {Automated Solid-Phase Click Synthesis of Oligonucleotide Conjugates: From Small Molecules to Diverse N-Acetylgalactosamine Clusters},

journal = {Bioconjugate Chemistry},

year = {2017},

volume = {28},

publisher = {American Chemical Society (ACS)},

month = {oct},

url = {https://pubs.acs.org/doi/10.1021/acs.bioconjchem.7b00462},

number = {10},

pages = {2599--2607},

doi = {10.1021/acs.bioconjchem.7b00462}

}

MLA

Cite this

MLA Copy

Farzan, Valentina M., et al. “Automated Solid-Phase Click Synthesis of Oligonucleotide Conjugates: From Small Molecules to Diverse N-Acetylgalactosamine Clusters.” Bioconjugate Chemistry, vol. 28, no. 10, Oct. 2017, pp. 2599-2607. https://pubs.acs.org/doi/10.1021/acs.bioconjchem.7b00462.

Publisher

American Chemical Society (ACS)

Journal

Bioconjugate Chemistry

scimago Q1

wos Q1

SJR

1.035

CiteScore

7.5

Impact factor

3.9

ISSN

10431802 (Print)

15204812 (Electronic)

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