Tuning the Biological Activity of RGD Peptides with Halotryptophans

Kemker I, Schröder DC, Feiner R, Müller K, Marion A, Sewald N (2021)
Journal of Medicinal Chemistry 64(1): 586–601.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
An array of l- and d-halotryptophans with different substituents at the indole moiety was synthesized employing either enzymatic halogenation by halogenases or incorporation of haloindoles using tryptophan synthase. Introduction of these Trp derivatives into RGD peptides as a benchmark system was performed to investigate their influence on bioactivity. Halotryptophan-containing RGD peptides display increased affinity toward integrin αvβ3 and enhanced selectivity over integrin α5β1. In addition, bromotryptophan was exploited as a platform for late-stage diversification by Suzuki–Miyaura cross-coupling (SMC), resulting in new-to-nature biaryl motifs. These peptides show enhanced affinity toward αvβ3, good affinity to αvβ8, and remarkable selectivity over α5β1 and αIIbβ3 while featuring fluorogenic properties. Their feasibility as a probe was demonstrated in vitro. Extensive molecular dynamics simulations were undertaken to elucidate NMR and high-performance liquid chromatography (HPLC) data for these late-stage diversified cyclic RGD peptides and to further characterize their conformational preferences.
Erscheinungsjahr
2021
Zeitschriftentitel
Journal of Medicinal Chemistry
Band
64
Ausgabe
1
Seite(n)
586–601
ISSN
0022-2623
eISSN
1520-4804
Page URI
https://pub.uni-bielefeld.de/record/2949822

Zitieren

Kemker I, Schröder DC, Feiner R, Müller K, Marion A, Sewald N. Tuning the Biological Activity of RGD Peptides with Halotryptophans. Journal of Medicinal Chemistry. 2021;64(1):586–601.
Kemker, I., Schröder, D. C., Feiner, R., Müller, K., Marion, A., & Sewald, N. (2021). Tuning the Biological Activity of RGD Peptides with Halotryptophans. Journal of Medicinal Chemistry, 64(1), 586–601. https://doi.org/10.1021/acs.jmedchem.0c01536
Kemker, I., Schröder, D. C., Feiner, R., Müller, K., Marion, A., and Sewald, N. (2021). Tuning the Biological Activity of RGD Peptides with Halotryptophans. Journal of Medicinal Chemistry 64, 586–601.
Kemker, I., et al., 2021. Tuning the Biological Activity of RGD Peptides with Halotryptophans. Journal of Medicinal Chemistry, 64(1), p 586–601.
I. Kemker, et al., “Tuning the Biological Activity of RGD Peptides with Halotryptophans”, Journal of Medicinal Chemistry, vol. 64, 2021, pp. 586–601.
Kemker, I., Schröder, D.C., Feiner, R., Müller, K., Marion, A., Sewald, N.: Tuning the Biological Activity of RGD Peptides with Halotryptophans. Journal of Medicinal Chemistry. 64, 586–601 (2021).
Kemker, Isabell, Schröder, David C., Feiner, Rebecca, Müller, Kristian, Marion, Antoine, and Sewald, Norbert. “Tuning the Biological Activity of RGD Peptides with Halotryptophans”. Journal of Medicinal Chemistry 64.1 (2021): 586–601.
Material in PUB:
Dissertation, die diesen PUB Eintrag enthält
Conformational Analysis of Peptidotriazolamers and *cyclic* RGD Peptides
Schröder DC (2021)
Bielefeld: Universität Bielefeld.

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