Mitochondrial Affinity of Guanidine-rich Molecular Transporters Built on myo- and scyllo-Inositol Scaffolds: Stereochemistry Dependency

被引：9

作者：

Ghosh, Subhash C. ^{[1
]}

Kim, Boram ^{[1
]}

Im, Jungkyun ^{[1
]}

Lee, Woo Sirl ^{[1
]}

Im, Chang-Nim ^{[2
,3
]}

Chang, Young-Tae ^{[2
,3
]}

Kim, Wanil ^{[4
]}

Kim, Kyong-Tai ^{[4
]}

Chung, Sung-Kee ^{[1
]}

机构：

[1] Pohang Univ Sci & Technol, Dept Chem, Pohang 790784, South Korea

[2] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

[3] Agcy Sci Technol & Res A STAR Biopolis, Singapore Bioimaging Consortium, Lab Bioimaging Probe Dev, Singapore 138667, Singapore

[4] Pohang Univ Sci & Technol, Dept Life Sci, Pohang 790784, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2010年 / 31卷 / 12期

关键词：

Blood-brain barrier; Cellular membrane; Drug delivery; Inositol scaffold; Mitochondrial affinity; CELLULAR UPTAKE; LIPOPHILICITY DETERMINATION; DESIGN; TRANSLOCATION; EFFICIENT; PEPTIDE; TOOL;

D O I：

10.5012/bkcs.2010.31.12.3623

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We prepared several novel molecular transporters built on myo- and scyllo-inositol scaffolds with variations in the number of guanidine residues, linker chain lengths and patterns. Some of these transporters were found to localize in mitochondria, and the mitochondrial affinity seems to be substantially related to the scaffold stereochemistry.

引用

收藏

页码：3623 / 3631

页数：9

相关论文

共 32 条

[1] p53 mediates cellular dysfunction and behavioral abnormalities in Huntington's disease [J].

Bae, BI ;

Xu, H ;

Igarashi, S ;

Fujimuro, M ;

Agrawal, N ;

Taya, Y ;

Hayward, SD ;

Moran, TH ;

Montell, C ;

Ross, CA ;

Snyder, SH ;

Sawa, A .

NEURON, 2005, 47 (01) :29-41

[2] Novel Guanidine-Containing Molecular Transporters Based on Lactose Scaffolds: Lipophilicity Effect on the Intracellular Organellar Selectivity [J].

Biswas, Goutam ;

Jeon, Ock-Youm ;

Lee, Woo Sirl ;

Kim, Dong-Chan ;

Kim, Kyong-Tai ;

Lee, Suho ;

Chang, Sunghoe ;

Chung, Sung-Kee .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (30) :9161-9168

[3] Dendritic oligoguanidines as intracellular translocators [J].

Chung, HH ;

Harms, G ;

Seong, CM ;

Choi, BH ;

Min, CH ;

Taulane, JP ;

Goodman, M .

BIOPOLYMERS, 2004, 76 (01) :83-96

[4] Synthesis of all possible regioisomers of scyllo-inositol phosphate [J].

Chung, SK ;

Kwon, YU ;

Chang, YT ;

Sohn, KH ;

Shin, JH ;

Park, KH ;

Hong, BJ ;

Chung, IH .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (11) :2577-2589

[5] Recent advances in cell-penetrating, non-peptide molecular carriers [J].

Chung, Sung-Kee ;

Maiti, Kaustabh K. ;

Lee, Woo Sirl .

INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2008, 354 (1-2) :16-22

[6] Maiming mitochondria in familial ALS [J].

Dawson, VL .

NATURE MEDICINE, 2004, 10 (09) :905-906

[7] Highly efficient, nonpeptidic oligoguanidinium vectors that selectively internalize into mitochondria [J].

Fernandex-Carneado, J ;

Van Gool, M ;

Martos, V ;

Castel, S ;

Prados, P ;

de Mendoza, J ;

Giralt, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (03) :869-874

[8] Mitochondria and apoptosis [J].

Green, DR ;

Reed, JC .

SCIENCE, 1998, 281 (5381) :1309-1312

[9] EVALUATION OF A SIMPLE HPLC CORRELATION METHOD FOR THE ESTIMATION OF THE OCTANOL-WATER PARTITION-COEFFICIENTS OF ORGANIC-COMPOUNDS [J].

HAKY, JE ;

YOUNG, AM .

JOURNAL OF LIQUID CHROMATOGRAPHY, 1984, 7 (04) :675-689

[10] Targeting mitochondria [J].

Hoye, Adam T. ;

Davoren, Jennifer E. ;

Wipf, Peter ;

Fink, Mitchell P. ;

Kagan, Valerian E. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (01) :87-97

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