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构建 Pt-硫代半卡巴腙-赖氨酸-sC18 轭合物。

Building up Pt -Thiosemicarbazone-Lysine-sC18 Conjugates.

机构信息

Universität zu Köln, Department für Chemie, Institut für Anorganische Chemie, Greinstraße 6, 50939, Köln, Germany.

Universität zu Köln, Department für Chemie, Institut für Biochemie, Zülpicher Strasse 47a, 50674, Köln, Germany.

出版信息

Chembiochem. 2021 Feb 15;22(4):694-704. doi: 10.1002/cbic.202000564. Epub 2020 Nov 6.

DOI:10.1002/cbic.202000564
PMID:32909347
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7894172/
Abstract

Three chiral tridentate N^N^S coordinating pyridine-carbaldehyde (S)-N4-(α-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 chlorido complexes [Pt(TSC)Cl] when treated with K PtCl 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.

摘要

三种手性三齿 N^N^S 配位吡啶-醛（S）-N4-（α-甲基苄基）硫代半卡巴腙（HTSCmB）与赖氨酸修饰的衍生物一起合成。其中一种通过固相肽合成被共价连接到穿膜肽 sC18 上。HTSCmB 模型配体、HTSCLp 衍生物和肽缀合物在溶液中用 KPtCl 处理时，迅速且定量地形成非常稳定的 Pt 氯代配合物[Pt(TSC)Cl]。通过 Cl → CN 交换从一个 TSCmB 模型配合物和肽缀合物配合物中获得 Pt(CN)衍生物。配体和配合物通过 NMR、IR 光谱、高分辨率电喷雾质谱（HR-ESI-MS）和单晶 XRD 进行了表征。有趣的是，在三种不同的细胞系中测试赖氨酸标记的 HdpyTSCLp、其 sC18 缀合的 HdpyTSCL-sC18 或 PtCl 和 Pt(CN)缀合配合物的生物活性时，未观察到细胞活力下降。因此，鉴于此类 Pt-TSC-肽缀合物的制备既简便又有效，这些系统可能为将来使用 Pt 放射性核素进行晚期标记以及在核医学中的应用铺平道路。

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