Peptide-oligonucleotide phosphorothioate conjugates with membrane translocation and nuclear localization properties

被引：74

作者：

Antopolsky, M

Azhayeva, E

Tengvall, U

Auriola, S

Jääskeläinen, I

Rönkkö, S

Honkakoski, P

Urtti, A

Lönnberg, H

Azhayev, A ^{[1
]}

机构：

[1] Univ Kuopio, Dept Pharmaceut Chem, FIN-70211 Kuopio, Finland

[2] Univ Kuopio, Dept Pharmaceut, FIN-70211 Kuopio, Finland

[3] Univ Turku, Dept Chem, FIN-20014 Turku, Finland

来源：

BIOCONJUGATE CHEMISTRY | 1999年 / 10卷 / 04期

关键词：

D O I：

10.1021/bc980133y

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

Eighteen peptide - oligonucleotide phosphorothioate conjugates were prepared in good yield and thoroughly characterized with electrospray ionization mass spectra. When applied to the living cells, conjugates exhibiting membrane translocation and nuclear localization properties displayed efficient intracellular penetration but failed to show any serious antisense effect. Studies on the intracellular distribution of the fluorescein-labeled conjugates revealed their trapping in endosomes.

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页码：598 / 606

页数：9

相关论文

共 29 条

[1] Inhibitory properties of double helix forming circular oligonucleotides [J].

Azhayeva, E ;

Azhayev, A ;

Auriola, S ;

Tengvall, U ;

Urtti, A ;

Lönnberg, H .

NUCLEIC ACIDS RESEARCH, 1997, 25 (24) :4954-4961

[2] MASS AND SEQUENCE VERIFICATION OF MODIFIED OLIGONUCLEOTIDES USING ELECTROSPRAY TANDEM MASS-SPECTROMETRY [J].

BARRY, JP ;

VOUROS, P ;

VANSCHEPDAEL, A ;

LAW, SJ .

JOURNAL OF MASS SPECTROMETRY, 1995, 30 (07) :993-1006

[3] Synthesis and characterization of a peptide nucleic acid conjugated to a D-peptide analog of insulin-like growth factor 1 for increased cellular uptake [J].

Basu, S ;

Wickstrom, E .

BIOCONJUGATE CHEMISTRY, 1997, 8 (04) :481-488

[4] IMPROVED BIOLOGICAL-ACTIVITY OF ANTISENSE OLIGONUCLEOTIDES CONJUGATED TO A FUSOGENIC PEPTIDE [J].

BONGARTZ, JP ;

AUBERTIN, AM ;

MILHAUD, PG ;

LEBLEU, B .

NUCLEIC ACIDS RESEARCH, 1994, 22 (22) :4681-4688

[5] LIQUID-CHROMATOGRAPHY MASS-SPECTROMETRY OF ANTISENSE OLIGONUCLEOTIDES [J].

BOTHNER, B ;

CHATMAN, K ;

SARKISIAN, M ;

SIUZDAK, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (23) :2863-2868

[6] Template-directed ligation of peptides to oligonucleotides [J].

Bruick, RK ;

Dawson, PE ;

Kent, SB ;

Usman, N ;

Joyce, GF .

CHEMISTRY & BIOLOGY, 1996, 3 (01) :49-56

[7] Design of carrier peptide-oligonucleotide conjugates with rapid membrane translocation and nuclear localization properties [J].

Chaloin, L ;

Vidal, P ;

Lory, P ;

Méry, J ;

Lautredou, N ;

Divita, G ;

Heitz, F .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1998, 243 (02) :601-608

[8] HIGH-EFFICIENCY TRANSFORMATION OF MAMMALIAN-CELLS BY PLASMID DNA [J].

CHEN, C ;

OKAYAMA, H .

MOLECULAR AND CELLULAR BIOLOGY, 1987, 7 (08) :2745-2752

[9] Cellular delivery of oligonucleotides by synthetic import peptide carrier [J].

Dokka, S ;

Toledo-Velasquez, D ;

Shi, XL ;

Wang, LY ;

Rojanasakul, Y .

PHARMACEUTICAL RESEARCH, 1997, 14 (12) :1759-1764

[10]

EDGE NJ, 1994, BIOCONJUGATE CHEM, V5, P373