156699-37-5Relevant articles and documents
Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis
Nahrwold, Markus,Wei?, Christine,Bogner, Tobias,Mertink, Felix,Conradi, Jens,Sammet, Benedikt,Palmisano, Ralf,Royo Gracia, Soledad,Preu?e, Thomas,Sewald, Norbert
, p. 1853 - 1864 (2013/05/09)
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 β2-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.
NON-NATURAL AMINO ACIDS
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Page/Page column 60; Sheet 3, (2010/02/15)
This invention relates to non-natural desamino alkyl amino acid compounds, methods of making, and peptides containing these compounds as their N-terminus moieties. A preferred example is neurotensin (8-13) in which the N terminus is an alpha desamino, alpha methyl N,N dimethyl homolysine residue.
Stereochemical Definition and Chirospecific Synthesis of the Peptide Deformylase Inhibitor Sch 382583
Coats, Reed A.,Lee, Sheng-Lian,Davis, Kari A.,Patel, Kanu M.,Rhoads, Elaine K.,Howard, Michael H.
, p. 1734 - 1737 (2007/10/03)
The recently reported natural product Sch 382583 (1), an inhibitor of peptide deformylase, has been synthesized in 16 steps from commercially available starting materials. The three chiral centers were set by a combination of chiral auxiliary and chiral p