Functionalized triazolopeptoids - a novel class for mitochondrial targeted delivery

被引：20

作者：

Althuon, Daniela ^{[1
]}

Roenicke, Franziska ^{[2
]}

Fuerniss, Daniel ^{[1
]}

Quan, Jasmin ^{[1
]}

Wellhoefer, Isabelle ^{[2
]}

Jung, Nicole ^{[1
,2
]}

Schepers, Ute ^{[2
]}

Braese, Stefan ^{[1
,2
]}

机构：

[1] Karlsruhe Inst Technol, Inst Organ Chem, D-76131 Karlsruhe, Germany

[2] Karlsruhe Inst Technol, Inst Toxicol & Genet, D-76344 Eggenstein Leopoldshafen, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 14期

关键词：

CLICK; PEPTOIDS; BINDING; INHIBITORS; OLIGOMERS; WATER; SHAPE; DYES;

D O I：

10.1039/c5ob00250h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we introduce linear 1,4-triazolopeptoids as a novel class of cell penetrating peptidomimetics suitable as organ targeting molecular transporters of bioactive cargo. Repetitive triazole moieties with up to three residues were assembled on solid supports using copper-catalyzed alkyne-azide cycloadditions (CuAAC) in a submonomer approach. Depending on the lipophilicity of their side chain appendages the 1,4-triazolopeptoids showed either endosomal localization or a strong colocalization with the mitochondria of HeLa cells with moderate toxicity. While the basic triazolopeptoids mainly target the neuromast cells in zebrafish embryos, the lipophilic ones colocalize with either cartilage in the jaws and the blood vessel system.

引用

页码：4226 / 4230

页数：5

共 40 条

[1] Synthesis of novel polyesteramine dendrimers by divergent and convergent methods [J].

Akiyama, Hitoshi ;

Miyashita, Kazuyuki ;

Hari, Yoshiyuki ;

Obika, Satoshi ;

Imanishi, Takeshi .

TETRAHEDRON, 2013, 69 (33) :6810-6820

[2] Residue-based control of helix shape in beta-peptide oligomers [J].

Appella, DH ;

Christianson, LA ;

Klein, DA ;

Powell, DR ;

Huang, XL ;

Barchi, JJ ;

Gellman, SH .

NATURE, 1997, 387 (6631) :381-384

[3] Investigating Rhodamine B-Labeled Peptoids: Scopes and Limitations of Its Applications [J].

Birtalan, Esther ;

Rudat, Birgit ;

Koelmel, Dominik K. ;

Fritz, Daniel ;

Vollrath, Sidonie B. L. ;

Schepers, Ute ;

Braese, Stefan .

BIOPOLYMERS, 2011, 96 (05) :694-701

[4] First synthesis of 1,2,3-triazolo-linked (1,6)-α-D-oligomannoses (triazolomannoses) by iterative Cu(I)-catalyzed alkyne-azide cycloaddition [J].

Cheshev, Pavel ;

Marra, Alberto ;

Dondoni, Alessandro .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (17) :3225-3227

[5] Passage of Trojan Peptoids into Plant Cells [J].

Eggenberger, Kai ;

Birtalan, Esther ;

Schroeder, Tina ;

Braese, Stefan ;

Nick, Peter .

CHEMBIOCHEM, 2009, 10 (15) :2504-2512

[6] A facile synthesis of N-C linked 1,2,3-triazole-oligomers [J].

Fiandanese, Vito ;

Iannone, Francesco ;

Marchese, Giuseppe ;

Punzi, Angela .

TETRAHEDRON, 2011, 67 (29) :5254-5260

[7] Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry [J].

Fuerniss, Daniel ;

Mack, Timo ;

Hahn, Frank ;

Vollrath, Sidonie B. L. ;

Koroniak, Katarzyna ;

Schepers, Ute ;

Braese, Stefan .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :56-63

[8] Triazole-Linked DNA as a Primer Surrogate in the Synthesis of First-Strand cDNA [J].

Fujino, Tomoko ;

Yasumoto, Ken-ichi ;

Yamazaki, Naomi ;

Hasome, Ai ;

Sogawa, Kazuhiro ;

Isobe, Hiroyuki .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (11) :2956-2960

[9]

Fujino Tomoko, 2007, Nucleic Acids Symp Ser (Oxf), P267

[10] Transport characteristics of peptides and peptidomimetics:: II.: Hydroxyethylamine bioisostere-containing peptidomimetics as substrates for the oligopeptide transporter and P-glycoprotein in the intestinal mucosa [J].

Gao, J ;

Winslow, SL ;

Vander Velde, D ;

Aubé, J ;

Borchardt, RT .

JOURNAL OF PEPTIDE RESEARCH, 2001, 57 (05) :361-373

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