Haseloer, Alexander ORCID: 0000-0003-0480-7568, Luetzenburg, Tamara, Strache, Joss Pepe, Neudoerfl, Joerg, Neundorf, Ines and Klein, Axel ORCID: 0000-0003-0093-9619 . Building up Pt-II-Thiosemicarbazone-Lysine-sC18 Conjugates. ChemBioChem. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1439-7633

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Abstract

Three chiral tridentate N<^>N<^>S coordinating pyridine-carbaldehyde (S)-N4-(alpha-methylbenzyl)thiosemicarbazones (HTSCmB) were synthesised along with lysine-modified derivatives. One of them was selected and covalently conjugated to the cell-penetrating peptide sC18 by solid-phase peptide synthesis. The HTSCmB model ligands, the HTSCLp derivatives and the peptide conjugate rapidly and quantitatively form very stable Pt-II chlorido complexes [Pt(TSC)Cl] when treated with K2PtCl4 in solution. The Pt(CN) derivatives were obtained from one TSCmB model complex and the peptide conjugate complex through Cl--> CN- exchange. Ligands and complexes were characterised by NMR, IR spectroscopy, HR-ESI-MS and single-crystal XRD. Intriguingly, no decrease in cell viability was observed when testing the biological activity of the lysine-tagged HdpyTSCLp, its sC18 conjugate HdpyTSCL-sC18 or the PtCl and Pt(CN) conjugate complexes in three different cell lines. Thus, given the facile and effective preparation of such Pt-TSC-peptide conjugates, these systems might pave the way for future use in late-stage labelling with Pt radionuclides and application in nuclear medicine.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Haseloer, AlexanderUNSPECIFIEDorcid.org/0000-0003-0480-7568UNSPECIFIED
Luetzenburg, TamaraUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Strache, Joss PepeUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Neudoerfl, JoergUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Neundorf, InesUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Klein, AxelUNSPECIFIEDorcid.org/0000-0003-0093-9619UNSPECIFIED
URN: urn:nbn:de:hbz:38-312009
DOI: 10.1002/cbic.202000564
Journal or Publication Title: ChemBioChem
Publisher: WILEY-V C H VERLAG GMBH
Place of Publication: WEINHEIM
ISSN: 1439-7633
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
PLATINUM(II) COMPLEXES; CYTOTOXIC ACTIVITY; ANTITUMOR-ACTIVITY; BIS(THIOSEMICARBAZONE) COMPLEXES; ANTIPROLIFERATIVE ACTIVITY; PALLADIUM(II) COMPLEXES; CRYSTAL-STRUCTURE; BASIS-SETS; THIOSEMICARBAZONE; PEPTIDEMultiple languages
Biochemistry & Molecular Biology; Chemistry, MedicinalMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/31200

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