Oligocarbonate Molecular Transporters: Oligomerization-Based Syntheses and Cell-Penetrating Studies

被引:110
作者
Cooley, Christina B. [2 ,3 ]
Trantow, Brian M. [2 ,3 ]
Nederberg, Fredrik [1 ]
Kiesewetter, Matthew K. [2 ,3 ]
Hedrick, James L. [1 ]
Waymouth, Robert M. [2 ,3 ]
Wender, Paul A. [2 ,3 ]
机构
[1] IBM Corp, Almaden Res Ctr, San Jose, CA 95120 USA
[2] Stanford Univ, Dept Chem & Syst Biol, Stanford, CA 94305 USA
[3] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
基金
美国国家卫生研究院;
关键词
RING-OPENING POLYMERIZATION; DELIVERY VECTORS; DRUG-DELIVERY; INTERNALIZATION; PEPTIDES; MEMBRANE; ARGININE; DESIGN; CONJUGATION; ACTIVATION;
D O I
10.1021/ja907363k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new family of guanidinium-rich molecular transporters featuring a novel oligocarbonate backbone with 1,7-side chain spacing is described. Conjugates can be rapidly assembled irrespective of length in a one-step oligomerization strategy that can proceed with concomitant introduction of probes (or by analogy drugs). The new transporters exhibit excellent cellular entry as determined by flow cytometry and fluorescence microscopy, and the functionality of their drug delivery capabilities was confirmed by the delivery of the bioluminescent small molecule probe luciferin and turnover by its intracellular target enzyme.
引用
收藏
页码:16401 / +
页数:5
相关论文
共 35 条
[1]   Novel functional polycarbonate by lipase-catalyzed ring-opening polymerization of 5-methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one [J].
Al-Azemi, TF ;
Bisht, KS .
MACROMOLECULES, 1999, 32 (20) :6536-6540
[2]   Intrinsically cell-permeable miniature proteins based on a minimal cationic PPII motif [J].
Daniels, Douglas S. ;
Schepartz, Alanna .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) :14578-+
[3]   SUBSTRATE-BINDING PROPERTIES OF FIREFLY LUCIFERASE .I. LUCIFERIN-BINDING SITE [J].
DENBURG, JL ;
LEE, RT ;
MCELROY, WD .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1969, 134 (02) :381-&
[4]   Thiourea-based bifunctional organocatalysis: Supramolecular recognition for living polymerization [J].
Dove, AP ;
Pratt, RC ;
Lohmeijer, BGG ;
Waymouth, RM ;
Hedrick, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) :13798-13799
[5]   Overcoming multidrug resistance of small-molecule therapeutics through conjugation with releasable octaarginine transporters [J].
Dubikovskaya, Elena A. ;
Thorne, Steve H. ;
Pillow, Thomas H. ;
Contag, Christopher H. ;
Wender, Paul A. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2008, 105 (34) :12128-12133
[6]   Synthetic Mimic of Antimicrobial Peptide with Nonmembrane-Disrupting Antibacterial Properties [J].
Gabriel, Gregory J. ;
Madkour, Ahmad E. ;
Dabkowski, Jeffrey M. ;
Nelson, Christopher F. ;
Nusslein, Klaus ;
Tew, Gregory N. .
BIOMACROMOLECULES, 2008, 9 (11) :2980-2983
[7]   Cationic Amphiphilic Polyproline Helices: Side-Chain Variations and Cell-Specific Internalization [J].
Geisler, Iris ;
Chmielewski, Jean .
CHEMICAL BIOLOGY & DRUG DESIGN, 2009, 73 (01) :39-45
[8]   Intracellular cargo delivery by an octaarginine transporter adapted to target prostate cancer cells through cell surface protease activation [J].
Goun, Elena A. ;
Shinde, Rajesh ;
Dehnert, Karen W. ;
Adams-Bond, Angie ;
Wender, Paul A. ;
Contag, Christopher H. ;
Franc, Benjamin L. .
BIOCONJUGATE CHEMISTRY, 2006, 17 (03) :787-796
[9]   Molecular Dendritic Transporter Nanoparticle Vectors Provide Efficient Intracellular Delivery of Peptides [J].
Hamilton, Sharon K. ;
Harth, Eva .
ACS NANO, 2009, 3 (02) :402-410
[10]   Stimuli-responsive polyguanidino-oxanorbornene membrane transporters as multicomponent sensors in complex matrices [J].
Hennig, Andreas ;
Gabriel, Gregory J. ;
Tew, Gregory N. ;
Matile, Stefan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (31) :10338-10344