Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4)

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4). / Zachariassen, Zack G; Thiele, Stefanie; Berg, Erik A; Rasmussen, Pernille; Fossen, Torgils; Rosenkilde, Mette M; Våbenø, Jon; Haug, Bengt Erik.

In: Bioorganic & Medicinal Chemistry, Vol. 22, No. 17, 01.09.2014, p. 4759-69.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Zachariassen, ZG, Thiele, S, Berg, EA, Rasmussen, P, Fossen, T, Rosenkilde, MM, Våbenø, J & Haug, BE 2014, 'Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4)', Bioorganic & Medicinal Chemistry, vol. 22, no. 17, pp. 4759-69. https://doi.org/10.1016/j.bmc.2014.07.004

APA

Zachariassen, Z. G., Thiele, S., Berg, E. A., Rasmussen, P., Fossen, T., Rosenkilde, M. M., Våbenø, J., & Haug, B. E. (2014). Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4). Bioorganic & Medicinal Chemistry, 22(17), 4759-69. https://doi.org/10.1016/j.bmc.2014.07.004

Vancouver

Zachariassen ZG, Thiele S, Berg EA, Rasmussen P, Fossen T, Rosenkilde MM et al. Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4). Bioorganic & Medicinal Chemistry. 2014 Sep 1;22(17):4759-69. https://doi.org/10.1016/j.bmc.2014.07.004

Author

Zachariassen, Zack G ; Thiele, Stefanie ; Berg, Erik A ; Rasmussen, Pernille ; Fossen, Torgils ; Rosenkilde, Mette M ; Våbenø, Jon ; Haug, Bengt Erik. / Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4). In: Bioorganic & Medicinal Chemistry. 2014 ; Vol. 22, No. 17. pp. 4759-69.

Bibtex

@article{60f61a7c967444a49b96f56ba0178322,
title = "Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4)",
abstract = "Structure-activity relationship studies of the cyclopentapeptide CXCR4 antagonists (cyclo(-l-/d-Arg(1)-Arg(2)-2-Nal(3)-Gly(4)-d-Tyr(5)-)) suggest that the l-/d-Arg(1)-Arg(2)-2-Nal(3) tripeptide sequence contained within these cyclopentapeptides serves as a recognition motif for peptidic CXCR4 antagonists. Starting by dissecting the cyclopentapeptide structure and reintroducing cyclic constraints in a stepwise manner, we here report a novel class of scaffold-based tripeptidomimetic CXCR4 antagonists based on the d-Arg-Arg-2-Nal motif. Biological testing of the prototype compounds showed that they represent new peptidomimetic hits; importantly, the modular nature of the scaffold provides an interesting starting point for future ligand optimization.",
keywords = "Dose-Response Relationship, Drug, Drug Design, Humans, Molecular Conformation, Peptides, Cyclic, Receptors, CXCR4, Structure-Activity Relationship",
author = "Zachariassen, {Zack G} and Stefanie Thiele and Berg, {Erik A} and Pernille Rasmussen and Torgils Fossen and Rosenkilde, {Mette M} and Jon V{\aa}ben{\o} and Haug, {Bengt Erik}",
note = "Copyright {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",
year = "2014",
month = sep,
day = "1",
doi = "10.1016/j.bmc.2014.07.004",
language = "English",
volume = "22",
pages = "4759--69",
journal = "Bioorganic & Medicinal Chemistry",
issn = "0968-0896",
publisher = "Pergamon Press",
number = "17",

}

RIS

TY - JOUR

T1 - Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4)

AU - Zachariassen, Zack G

AU - Thiele, Stefanie

AU - Berg, Erik A

AU - Rasmussen, Pernille

AU - Fossen, Torgils

AU - Rosenkilde, Mette M

AU - Våbenø, Jon

AU - Haug, Bengt Erik

N1 - Copyright © 2014 Elsevier Ltd. All rights reserved.

PY - 2014/9/1

Y1 - 2014/9/1

N2 - Structure-activity relationship studies of the cyclopentapeptide CXCR4 antagonists (cyclo(-l-/d-Arg(1)-Arg(2)-2-Nal(3)-Gly(4)-d-Tyr(5)-)) suggest that the l-/d-Arg(1)-Arg(2)-2-Nal(3) tripeptide sequence contained within these cyclopentapeptides serves as a recognition motif for peptidic CXCR4 antagonists. Starting by dissecting the cyclopentapeptide structure and reintroducing cyclic constraints in a stepwise manner, we here report a novel class of scaffold-based tripeptidomimetic CXCR4 antagonists based on the d-Arg-Arg-2-Nal motif. Biological testing of the prototype compounds showed that they represent new peptidomimetic hits; importantly, the modular nature of the scaffold provides an interesting starting point for future ligand optimization.

AB - Structure-activity relationship studies of the cyclopentapeptide CXCR4 antagonists (cyclo(-l-/d-Arg(1)-Arg(2)-2-Nal(3)-Gly(4)-d-Tyr(5)-)) suggest that the l-/d-Arg(1)-Arg(2)-2-Nal(3) tripeptide sequence contained within these cyclopentapeptides serves as a recognition motif for peptidic CXCR4 antagonists. Starting by dissecting the cyclopentapeptide structure and reintroducing cyclic constraints in a stepwise manner, we here report a novel class of scaffold-based tripeptidomimetic CXCR4 antagonists based on the d-Arg-Arg-2-Nal motif. Biological testing of the prototype compounds showed that they represent new peptidomimetic hits; importantly, the modular nature of the scaffold provides an interesting starting point for future ligand optimization.

KW - Dose-Response Relationship, Drug

KW - Drug Design

KW - Humans

KW - Molecular Conformation

KW - Peptides, Cyclic

KW - Receptors, CXCR4

KW - Structure-Activity Relationship

U2 - 10.1016/j.bmc.2014.07.004

DO - 10.1016/j.bmc.2014.07.004

M3 - Journal article

C2 - 25082513

VL - 22

SP - 4759

EP - 4769

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

SN - 0968-0896

IS - 17

ER -

ID: 137371407