Universität zu Köln

Bodero, Lizeth ORCID: 0000-0003-2552-0064, Parente, Sara, Arrigoni, Federico, Klimpel, Annika, Neundorf, Ines, Gazzola, Silvia ORCID: 0000-0001-6745-3598 and Piarulli, Umberto ORCID: 0000-0002-6952-1811 (2021). Synthesis and Biological Evaluation of an isoDGR-Paclitaxel Conjugate Containing a Cell-Penetrating Peptide to Promote Cellular Uptake. Eur. J. Org. Chem., 2021 (17). S. 2383 - 2388. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

Two new Drug Delivery Systems (DDS) cyclo[DKP-isoDGR]-PEG-4-Val-Ala-PTX (2) and cyclo[DKP-isoDGR]-PEG-4-sC18-Val-Ala-PTX (3), containing the cyclo[DKP-isoDGR] integrin ligand and the cytotoxic agent Paclitaxel (PTX), were synthesized to investigate the influence of a PEG-4 chain and of the sC18 cell-penetrating peptide (CPP) on the cellular uptake and the cytotoxicity of the constructs. A double click-reaction strategy was planned, to realize the connection of cyclo[DKP-isoDGR] and PTX to the CPP moiety. Anti-proliferative bioassays were performed on the alpha(V)beta(3)-positive U87 human glioblastoma cell line using a short contact time (15 min) followed by draining, washing of the cells, and re-incubation for 72 h. Compound 3 was significantly more potent (IC50=27.6 mu M) than compound 2 (IC50>100 mu M), and showed a reduced potency loss with respect to PTX (IC50=71 nM).

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Bodero, Lizeth UNSPECIFIED orcid.org/0000-0003-2552-0064 UNSPECIFIED Parente, Sara UNSPECIFIED UNSPECIFIED UNSPECIFIED Arrigoni, Federico UNSPECIFIED UNSPECIFIED UNSPECIFIED Klimpel, Annika UNSPECIFIED UNSPECIFIED UNSPECIFIED Neundorf, Ines UNSPECIFIED UNSPECIFIED UNSPECIFIED Gazzola, Silvia UNSPECIFIED orcid.org/0000-0001-6745-3598 UNSPECIFIED Piarulli, Umberto UNSPECIFIED orcid.org/0000-0002-6952-1811 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-570748
DOI:	10.1002/ejoc.202100241
Journal or Publication Title:	Eur. J. Org. Chem.
Volume:	2021
Number:	17
Page Range:	S. 2383 - 2388
Date:	2021
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1099-0690
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language BIFUNCTIONAL DIKETOPIPERAZINE SCAFFOLDS; CYCLIC RGD-PEPTIDOMIMETICS; DRUG-DELIVERY SYSTEMS; INTEGRIN; ISOASPARTATE; ALPHA(V)BETA(3); MECHANISM; ANTIBODY; LIGANDS; PROFILE Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/57074