Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis

Nahrwold M, Weiß C, Bogner T, Mertink F, Conradi J, Sammet B, Palmisano R, Royo Gracia S, Preuße T, Sewald N (2013)
Journal of medicinal chemistry 56(5): 1853-1864.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Tumor targeting anticancer drug conjugates that contain a tumor recognition motif (homing device) are of high current relevance. Cryptophycins, naturally occurring cytotoxic cyclo-depsipeptides, have been modified by total synthesis to provide analogues suitable for conjugation to peptide-based homing devices. An array of functionalized β(2)-amino acids was synthesized and incorporated into cryptophycins. All analogues proved to be highly active in the cytotoxicity assay using the human cervix carcinoma cell line KB-3-1 and its multidrug-resistant subclone KB-V1. Conformational analysis of cryptophycin-52 and two synthetic analogues was performed by NMR and MD methods to obtain information on the influence of the unit C configuration on the overall conformation. An azide-functionalized cryptophycin was connected by CuAAC to an alkyne-containing fluorescently labeled cyclic RGD-peptide as the homing device for internalization studies. Confocal fluorescence microscopy proved integrin-mediated internalization by endocytosis and final lysosomal localization of the cryptophycin prodrug.
Erscheinungsjahr
2013
Zeitschriftentitel
Journal of medicinal chemistry
Band
56
Ausgabe
5
Seite(n)
1853-1864
ISSN
0022-2623
eISSN
1520-4804
Page URI
https://pub.uni-bielefeld.de/record/2579007

Zitieren

Nahrwold M, Weiß C, Bogner T, et al. Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis. Journal of medicinal chemistry. 2013;56(5):1853-1864.
Nahrwold, M., Weiß, C., Bogner, T., Mertink, F., Conradi, J., Sammet, B., Palmisano, R., et al. (2013). Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis. Journal of medicinal chemistry, 56(5), 1853-1864. doi:10.1021/jm301346z
Nahrwold, M., Weiß, C., Bogner, T., Mertink, F., Conradi, J., Sammet, B., Palmisano, R., Royo Gracia, S., Preuße, T., and Sewald, N. (2013). Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis. Journal of medicinal chemistry 56, 1853-1864.
Nahrwold, M., et al., 2013. Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis. Journal of medicinal chemistry, 56(5), p 1853-1864.
M. Nahrwold, et al., “Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis”, Journal of medicinal chemistry, vol. 56, 2013, pp. 1853-1864.
Nahrwold, M., Weiß, C., Bogner, T., Mertink, F., Conradi, J., Sammet, B., Palmisano, R., Royo Gracia, S., Preuße, T., Sewald, N.: Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis. Journal of medicinal chemistry. 56, 1853-1864 (2013).
Nahrwold, Markus, Weiß, Christine, Bogner, Tobias, Mertink, Felix, Conradi, Jens, Sammet, Benedikt, Palmisano, Ralf, Royo Gracia, Soledad, Preuße, Thomas, and Sewald, Norbert. “Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis”. Journal of medicinal chemistry 56.5 (2013): 1853-1864.

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