Fine-tuning furan toxicity: fast and quantitative DNA interchain crosslink formation upon selective oxidation of a furan containing oligonucleotide

被引：36

作者：

Halila, S ^{[1
]}

Velasco, T ^{[1
]}

De Clercq, P ^{[1
]}

Madder, A ^{[1
]}

机构：

[1] State Univ Ghent, Dept Organ Chem, Lab Organ & Biomimet Chem, B-9000 Ghent, Belgium

来源：

CHEMICAL COMMUNICATIONS | 2005年 / 07期

关键词：

D O I：

10.1039/b415092a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oligonucleotides containing a furan modified internal nucleoside have been synthesized; selective in situ oxidation of the furan moiety to a reactive enal species in the presence of a complementary DNA strand gives rise to fast and efficient formation of an interstrand cross-link.

引用

页码：936 / 938

页数：3

共 17 条

[1] The effect of cross-links on the conformational dynamics of duplex DNA [J].

Cain, RJ ;

Glick, GD .

NUCLEIC ACIDS RESEARCH, 1997, 25 (04) :836-842

[2] Characterization of amino acid on glutathione adducts of cis-2-butene-1,4-dial, a reactive metabolite of furan [J].

Chen, LJ ;

Hecht, SS ;

Peterson, LA .

CHEMICAL RESEARCH IN TOXICOLOGY, 1997, 10 (08) :866-874

[3] Covalent cross-linking of duplex DNA using 4-thio-2'-deoxyuridine as a readily modifiable platform for introduction of reactive functionality into oligonucleotides [J].

Coleman, RS ;

Pires, RM .

NUCLEIC ACIDS RESEARCH, 1997, 25 (23) :4771-4777

[4] TEMPLATE-DIRECTED CROSS-LINKING OF OLIGONUCLEOTIDES - SITE-SPECIFIC COVALENT MODIFICATION OF DG-N7 WITHIN DUPLEX DNA [J].

COLEMAN, RS ;

KESICKI, EA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6252-6253

[5] Internal labeling of oligonucleotide probes by Diels-Alder cycloaddition [J].

Graham, D ;

Grondin, A ;

McHugh, C ;

Fruk, L ;

Smith, WE .

TETRAHEDRON LETTERS, 2002, 43 (27) :4785-4788

[6] INCORPORATION OF 2'-AMIDO-NUCLEOSIDES IN OLIGODEOXYNUCLEOTIDES AND OLIGORIBONUCLEOTIDES AS A MODEL FOR 2'-LINKED CONJUGATES [J].

HENDRIX, C ;

DEVREESE, B ;

ROZENSKI, J ;

VANAERSCHOT, A ;

DEBRUYN, A ;

VANBEEUMEN, J ;

HERDEWIJN, P .

NUCLEIC ACIDS RESEARCH, 1995, 23 (01) :51-57

[7] SEQUENCE-SPECIFIC MODIFICATION OF DNA FRAGMENTS BY OLIGONUCLEOTIDE DERIVATIVES CONTAINING ALKYLATING GROUPS AT THE C5 POSITION OF DEOXYURIDINE [J].

KHALIMSKAYA, LM ;

LEVINA, AS ;

ZARYTOVA, VF .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (08) :1083-1088

[8] Efficient conditions for conversion of 2-substituted furans into 4-oxygenated 2-enoic acids and its application to synthesis of (+)-aspicilin, (+)-patulolide A, and (-)-pyrenophorin [J].

Kobayashi, Y ;

Nakano, M ;

Kumar, GB ;

Kishihara, K .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7505-7515

[9] DNA interchain cross-links formed by acrolein and crotonaldehyde [J].

Kozekov, ID ;

Nechev, LV ;

Moseley, MS ;

Harris, CM ;

Rizzo, CJ ;

Stone, MP ;

Harris, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) :50-61

[10] A new reactive nucleoside analogue for highly reactive and selective cross-linking reaction to cytidine under neutral conditions [J].

Nagatsugi, F ;

Tokuda, N ;

Maeda, M ;

Sasaki, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (19) :2577-2579

← 1 2 →