Azidopropylvinylsulfonamide as a New Bifunctional Click Reagent for Bioorthogonal Conjugations: Application for DNA-Protein Cross-Linking

被引：22
|
作者：
Dadova, Jitka [1 ]
Vrabel, Milan [1 ]
Adamik, Matej [2 ]
Brazdova, Marie [2 ]
Pohl, Radek [1 ]
Fojta, Miroslav [2 ,4 ]
Hocek, Michal [1 ,3 ]
机构：
[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Gilead Sci & IOCB Res Ctr, Prague 16610 6, Czech Republic
[2] Acad Sci Czech Republ, Inst Biophys, CS-61265 Brno, Czech Republic
[3] Charles Univ Prague, Dept Organ Chem, Fac Sci, Prague 12843 2, Czech Republic
[4] Masaryk Univ, Cent European Inst Technol, Brno 62500, Czech Republic
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 45期
关键词：
biotransformations; click chemistry; conjugation; nucleic acids; proteins; GENETIC-CODE EXPANSION; SOLID-PHASE SYNTHESIS; NUCLEOSIDE TRIPHOSPHATES; POLYMERASE SYNTHESIS; ENZYMATIC-SYNTHESIS; AMINO-ACIDS; 2'-DEOXYRIBONUCLEOSIDE TRIPHOSPHATES; POSTSYNTHETIC MODIFICATION; MODIFIED OLIGONUCLEOTIDES; BUILDING-BLOCKS;
D O I：
10.1002/chem.201502209
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
N-(3-Azidopropyl)vinylsulfonamide was developed as a new bifunctional bioconjugation reagent suitable for the cross-linking of biomolecules through copper(I)-catalyzed azide-alkyne cycloaddition and thiol Michael addition reactions under biorthogonal conditions. The reagent is easily clicked to an acetylene-containing DNA or protein and then reacts with cysteine-containing peptides or proteins to form covalent cross-links. Several examples of bioconjugations of ethynyl- or octadiynyl-modified DNA with peptides, p53 protein, or alkyne-modified human carbonic anhydrase with peptides are given.
引用
收藏
页码：16091 / 16102
页数：12
相关论文
共 50 条
  • [21] DNA-protein cross-linking in nuclei of immature and mature chicken erythrocytes
    Eufemi, M
    Ferraro, A
    Altieri, F
    Cervoni, L
    Turano, C
    MOLECULAR BIOLOGY REPORTS, 2000, 27 (03) : 181 - 189
  • [22] Dependence of DNA-protein cross-linking on guanine radical protonation state
    Estonactoc, Alina J.
    Padigus, Jonah-Lynne
    Scala, Julianna
    Ott, Justine Danielle
    Madison, Amanda
    Stemp, Eric D. A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 284 - 284
  • [23] DNA-PROTEIN CROSS-LINKING BY CHEMICAL CARCINOGENS IN MAMMALIAN-CELLS
    FORNACE, AJ
    LITTLE, JB
    CANCER RESEARCH, 1979, 39 (03) : 704 - 710
  • [24] DNA-PROTEIN CROSS-LINKING BY HEAVY-METALS IN NOVIKOFF HEPATOMA
    WEDRYCHOWSKI, A
    SCHMIDT, WN
    HNILICA, LS
    ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1986, 251 (02) : 397 - 402
  • [25] DNA-protein cross-linking applications for chromatin studies in vitro and in vivo
    Pruss, D
    Gavin, IM
    Melnik, S
    Bavykin, SG
    CHROMATIN, 1999, 304 : 516 - 533
  • [26] Enzymatically Active DNA-Protein Nanogels with Tunable Cross-Linking Density
    Mariconti, Marina
    Morel, Mathieu
    Baigl, Damien
    Rudiuk, Sergii
    BIOMACROMOLECULES, 2021, 22 (08) : 3431 - 3439
  • [27] Trifunctional dinuclear platinum complexes as DNA-protein cross-linking agent
    Kloster, M
    Kostrhunova, H
    Zaludova, R
    Malina, J
    Kasparkova, J
    Brabec, V
    Farrell, N
    BIOCHEMISTRY, 2004, 43 (24) : 7776 - 7786
  • [28] Influence of guanine oxidation potential on DNA-protein cross-linking reactions
    Stemp, Eric D. A.
    Estonactoc, Alina
    Madison, Amanda
    Scala, Julianna
    Ochoa, Carmen E.
    Schaefer, Kathryn
    Kurbanyan, Kristina
    CHEMICAL RESEARCH IN TOXICOLOGY, 2007, 20 (12) : 2005 - 2006
  • [29] GLUTARALDEHYDE AS A PROTEIN CROSS-LINKING REAGENT
    RICHARDS, FM
    KNOWLES, JR
    JOURNAL OF MOLECULAR BIOLOGY, 1968, 37 (01) : 231 - &
  • [30] Proteomic Analysis of DNA-Protein Cross-Linking by Antitumor Nitrogen Mustards
    Loeber, Rachel L.
    Michaelson-Richie, Erin D.
    Codreanu, Simona G.
    Liebler, Daniel C.
    Campbell, Colin R.
    Tretyakova, Natalia Y.
    CHEMICAL RESEARCH IN TOXICOLOGY, 2009, 22 (06) : 1151 - 1162
12345