A preorganized β-amino acid bearing a guanidinium side chain and its use in cell-penetrating peptides

被引：36

作者：

Demizu, Yosuke ^{[1
,2
]}

Oba, Makoto ^{[3
]}

Okitsu, Koyo ^{[2
,4
]}

Yamashita, Hiroko ^{[2
,4
]}

Misawa, Takashi ^{[2
]}

Tanaka, Masakazu ^{[3
]}

Kurihara, Masaaki ^{[2
,4
]}

Gellman, Samuel H. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53707 USA

[2] Natl Inst Hlth Sci Setagaya, Tokyo 1588501, Japan

[3] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

[4] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Yokohama, Kanagawa 2268501, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 20期

基金：

美国国家科学基金会;

关键词：

ALPHA-HELIX MIMICRY; INTRACELLULAR DELIVERY; POLYPLEX MICELLES; DESIGN; FOLDAMERS; MOLECULES; ANTIBACTERIAL; TRANSLOCATION; TRANSFECTION; TRANSPORTERS;

D O I：

10.1039/c5ob00389j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cyclic beta-amino acid (APC(Gu)) bearing a side-chain guanidinium group has been developed. The APC(Gu) residue was incorporated into an alpha/beta-peptide based on the Tat(47-57) fragment, leading to an oligomer with substantial helicity in methanol that enters HeLa cells much more readily than does the corresponding Tat alpha-peptide.

引用

页码：5617 / 5620

页数：4

共 39 条

[1] Evaluation of Diverse α/β-Backbone Patterns for Functional α-Helix Mimicry: Analogues of the Bim BH3 Domain [J].

Boersma, Melissa D. ;

Haase, Holly S. ;

Peterson-Kaufman, Kimberly J. ;

Lee, Erinna F. ;

Clarke, Oliver B. ;

Colman, Peter M. ;

Smith, Brian J. ;

Horne, W. Seth ;

Fairlie, W. Douglas ;

Gellman, Samuel H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) :315-323

[2] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[3]

Dupont E, 2011, METHODS MOL BIOL, V683, P21, DOI 10.1007/978-1-60761-919-2_2

[4] Diprotected triflylguanidines: A new class of guanidinylation reagents [J].

Feichtinger, K ;

Zapf, C ;

Sings, HL ;

Goodman, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :3804-3805

[5] Recent advances in the use of cell-penetrating peptides for medical and biological applications [J].

Fonseca, Sonali B. ;

Pereira, Mark P. ;

Kelley, Shana O. .

ADVANCED DRUG DELIVERY REVIEWS, 2009, 61 (11) :953-964

[6] Temperature-, concentration- and cholesterol-dependent translocation of L- and D-octa-arginine across the plasma and nuclear membrane of CD34+ leukaemia cells [J].

Fretz, Marjan M. ;

Penning, Neal A. ;

Al-Taei, Saly ;

Futaki, Shiroh ;

Takeuchi, Toshihide ;

Nakase, Ikuhiko ;

Storm, Gert ;

Jones, Arwyn T. .

BIOCHEMICAL JOURNAL, 2007, 403 (02) :335-342

[7] Oligoarginine vectors for intracellular delivery: Design and cellular-uptake mechanisms [J].

Futaki, S .

BIOPOLYMERS, 2006, 84 (03) :241-249

[8] Foldamers: A manifesto [J].

Gellman, SH .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180

[9] Foldamers as versatile frameworks for the design and evolution of function [J].

Goodman, Catherine M. ;

Choi, Sungwook ;

Shandler, Scott ;

DeGrado, William F. .

NATURE CHEMICAL BIOLOGY, 2007, 3 (05) :252-262

[10] Intracellular delivery of large molecules and small particles by cell-penetrating proteins and peptides [J].

Gupta, B ;

Levchenko, TS ;

Torchilin, VP .

ADVANCED DRUG DELIVERY REVIEWS, 2005, 57 (04) :637-651

← 1 2 3 4 →