Synthesis and biophysical properties of 5'-thio-2',4'-BNA/LNA oligonucleotide

被引：10

作者：

Islam, Md Ariful ^{[1
,2
]}

Fujisaka, Aki ^{[1
,3
]}

Mori, Shohei ^{[1
]}

Ito, Kosuke Ramon ^{[1
]}

Yamaguchi, Takao ^{[1
]}

Obika, Satoshi ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, 1-6 Yamadaoka, Suita, Osaka 5650871, Japan

[2] Noakhali Sci & Technol Univ, Dept Pharm, Sonapur 3814, Noakhali, Bangladesh

[3] Osaka Ohtani Univ, Fac Pharm, Nishikiori Kita 3-11-1, Tondabayashi, Osaka 5848540, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2018年 / 26卷 / 12期

关键词：

Phosphorothiolate; 2'; 4'-BNA; LNA; Synthesis; Binding affinity; Nuclease stability; SOLID-PHASE SYNTHESIS; RNA-SYNTHESIS; ANALOGS; OLIGODEOXYNUCLEOTIDES; HYBRIDIZATION; SUBSTRATE;

D O I：

10.1016/j.bmc.2018.05.040

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Phosphorothioate modification of oligonucleotides is one of the most promising chemical modifications in nucleic acid therapeutics. Structurally similar 5'-thio or phosphorothiolate-modified nucleotides, in which the 5'bridging oxygen atom is replaced with a sulfur atom, are attracting attention and gaining importance in oligonucleotide- based research. In our present study, we synthesized 5'-thio-2', 4'-BNA/LNA monomers bearing thymine or 5-methylcytosine nucleobase. The 5'-thio-2', 4'-BNA/LNA monomers were successfully incorporated into target oligonucleotides, and their nuclease stability and binding affinity with complementary strands were evaluated.

引用

页码：3634 / 3638

页数：5

共 50 条

[31] 4′-thio-5-ethyl-2′-deoxyuridine 5′-phosphonates:: Synthesis and antiviral properties
Alexandrova, LA
Ilyicheva, TN
Fedyuk, NV
Karpenko, IL
Pokrovsky, AG
CHEMISTRY OF NUCLEIC ACID COMPONENTS, 2002, 5 : 295 - 298
[32] Rationale of 5-125I-iodo-4′-thio-2′-deoxyuridine as a potential iodinated proliferation marker
Toyohara, J
Hayashi, A
Sato, M
Tanaka, H
Haraguchi, K
Yoshimura, Y
Yonekura, Y
Fujibayashi, Y
JOURNAL OF NUCLEAR MEDICINE, 2002, 43 (09) : 1218 - 1226
[33] DNA containing 4'-thio-2'-deoxycytidine inhibits methylation by HhaI methyltransferase
Kumar, S
Horton, JR
Jones, GD
Walker, RT
Roberts, RJ
Cheng, X
NUCLEIC ACIDS RESEARCH, 1997, 25 (14) : 2773 - 2783
[34] SYNTHESIS, STRUCTURE AND PROPERTIES OF 2-THIO-4-IMINO-5-SPIROCYCLOHEXANE HYDANTOINS
MEDVEDEVA, LA
ZOLOTOI, AB
POLYAKOV, AI
DYACHENKO, OA
ATOVMYAN, LO
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1989, (04): : 485 - 492
[35] Evaluation of radiobromine-labeled 5-bromo-4′-thio-2′-deoxyuridine as a tumor proliferation imaging agent
Kiyono, Yasushi
Sano, Keisuke
Nakayama, Yosuke
Mori, Tetsuya
Toyohara, Jun
Pozo, Miguel Martinez
Mandap, Katheryn
Asai, Tatsuya
Okazawa, Hidehiko
Fujibayashi, Yasuhisa
JOURNAL OF NUCLEAR MEDICINE, 2010, 51
[36] Superior Silencing by 2 ',4 '-BNA(NC)-Based Short Antisense Oligonucleotides Compared to 2 ',4 '-BNA/LNA-Based Apolipoprotein B Antisense Inhibitors
Yamamoto, Tsuyoshi
Yasuhara, Hidenori
Wada, Fumito
Harada-Shiba, Mariko
Imanishi, Takeshi
Obika, Satoshi
JOURNAL OF NUCLEIC ACIDS, 2012, 2012
[37] In vitro and in vivo biophysical properties of oligonucleotides containing 5 '-thio nucleosides
Islam, Md Ariful
Waki, Reiko
Fujisaka, Aki
Ito, Kosuke Ramon
Obika, Satoshi
DRUG DISCOVERIES AND THERAPEUTICS, 2016, 10 (05): : 263 - 270
[38] Pharmacokinetics and tissue fractionation studies of 5-[125I]iodo-4'-thio-2'-deoxyuridine.
Toyohara, J
Gogami, A
Hayashi, A
Yonekura, Y
Fujibayashi, Y
JOURNAL OF NUCLEAR MEDICINE, 2003, 44 (05) : 302P - 302P
[39] C5-amino acid functionalized LNA: Synthesis, evaluation of biophysical properties, and potential for antisense therapeutics
Guenther, Dale C.
Kumar, Pawan
Hrdlicka, Patrick J.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[40] Synthesis and biophysical properties of nucleobase-functionalized LNA (locked nucleic acid)
Hrdlicka, Patrick J.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248

← 1 2 3 4 5 →