Receiver-amplifier, self-immolative dendritic device

被引:50
作者
Amir, Roey J. [1 ]
Danieli, Eyal [1 ]
Shabat, Doron [1 ]
机构
[1] Tel Aviv Univ, Sch Chem, Fac Exact Sci, Dept Organ Chem, IL-69978 Tel Aviv, Israel
关键词
dendrimers; enzymes; fluorescence; prodrugs; self-immolative;
D O I
10.1002/chem.200601263
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Self-immolative dendrimers disassemble through a domino-like chain fragmentation initiated by a single cleavage at the dendrimer core. We have designed and synthesized dendritic molecules that resemble dendritic architectures present in nature. The unique design allows a cleavage signal received by any one of the multiple triggers on one side of the dendrimer to be transferred convergently to a focal point. The signal is divergently amplified through to the other side of the dendrimer, reporter units are released, and fluorescence is emitted. During signal propagation, the dendritic molecule disassembles in a self-immolative manner into small fragments. These compounds are the longest dendritic system ever reported to disassemble through sequential self-immolative reactions. The synthesized dendritic molecules have an architecture and signal-conducting activity related to that of neurons.
引用
收藏
页码:812 / 821
页数:10
相关论文
共 27 条
[1]  
Amir R., 2003, Angew. Chem., V115, P4632
[2]  
Amir R.J., 2005, ANGEW CHEM, V117, P4452, DOI DOI 10.1002/ANGE.200500842
[3]   Prodrug activation gated by a molecular "OR" logic trigger [J].
Amir, RJ ;
Popkov, M ;
Lerner, RA ;
Barbas, CF ;
Shabat, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (28) :4378-4381
[4]   Self-immolative dendrimer biodegradability by multi-enzymatic triggering [J].
Amir, RJ ;
Shabat, D .
CHEMICAL COMMUNICATIONS, 2004, (14) :1614-1615
[5]   Self-immolative dendrimers [J].
Amir, RJ ;
Pessah, N ;
Shamis, M ;
Shabat, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (37) :4494-4499
[6]   Synthetic peptides in the form of dendrimers become resistant to protease activity [J].
Bracci, L ;
Falciani, C ;
Lelli, B ;
Lozzi, L ;
Runci, Y ;
Pini, A ;
De Montis, MG ;
Tagliamonte, A ;
Neri, P .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (47) :46590-46595
[7]   BACTERIAL PENICILLIN AMIDASE [J].
CLARIDGE, CA ;
GOUREVITCH, A ;
LEIN, J .
NATURE, 1960, 187 (4733) :237-238
[8]  
de Groot F. M. H., 2003, ANGEW CHEM, V115, P4628
[9]   Cascade-release dendrimers liberate all end groups upon a single triggering event in the dendritic core [J].
de Groot, FMH ;
Albrecht, C ;
Koekkoek, R ;
Beusker, PH ;
Scheeren, HW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (37) :4490-4494
[10]   Some new aspects of dendrimer applications [J].
Flomenbom, O ;
Amir, RJ ;
Shabat, D ;
Klafter, J .
JOURNAL OF LUMINESCENCE, 2005, 111 (04) :315-325