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Synthe­sis and Charac­ter­i­za­tion of biofunc­tion­al­ized organ­otin chalco­genide clusters

Martina Kämpfe — Hector Fellow Stefanie Dehnen

The cytotox­i­c­ity of organic tin compounds makes them inter­est­ing for cancer chemother­apy. Organ­otin chalco­genide clusters release under acidic decom­po­si­tion not only an organic tin compound but also an even more toxic hydro­gen chalco­genide. To enable biocom­pat­i­bil­ity of those clusters, they must be deriva­tized with biomol­e­cules. This project aims to synthe­size biofunc­tion­al­ized organ­otin chalco­genide clusters and to inves­ti­gate their decom­po­si­tion behavior.

Organ­otin chalco­genide clusters are a highly versa­tile group of molecules consist­ing of an inorganic core composed of tin and chalco­gen atoms as well as organic substituents on the outside of the cluster. Due to the cytotox­i­c­ity of tin compounds, one poten­tial area of appli­ca­tion is chemother­apy. When the clusters are decom­posed in an acidic environ­ment, as is often the case in cancer cells, they release not only a cytotoxic organ­otin species but also highly toxic hydro­gen chalco­genide (e.g. H2S). To enable biocom­pat­i­bil­ity of the clusters, they must be deriva­tized with biomol­e­cules as organic substituents.

The first step in this project is to lay the synthetic founda­tions. The aim is to develop a synthe­sis of biofunc­tion­al­ized organ­otin chalco­genide clusters of the adaman­tane type using a novel linker system between tin and the biomol­e­cule, which should enable modifi­ca­tion with a broad spectrum of biomol­e­cules such as amino acids, peptides, DNA bases and sugars. Further­more, a synthe­sis for the function­al­iza­tion of ‘double-decker’ type clusters, which have already been modified with amino acids and peptides, with other biomol­e­cules such as DNA bases and sugars is to be developed.

Subse­quently, the decom­po­si­tion proper­ties of the clusters will be inves­ti­gated and compared in order to inves­ti­gate the influ­ence of the struc­ture of the cluster cores and the biomolecules.

Synthesis and Characterization of biofunctionalized organotin chalcogenide clusters

Schematic repre­sen­ta­tion of the synthe­sis of biofunc­tion­al­ized organ­otin chalco­genide clusters of the adaman­tane type (top) and the “double-decker” type (bottom). E describes the used chalco­gen atoms sulfur, selenium, or tellurium, and Rbio describes the biomolecules.

Florent Draye

Martina Kämpfe

Karlsruhe Insti­tute of Technology

Super­vised by

Prof. Dr.

Stefanie Dehnen

Chemistry

Hector Fellow since 2024Disziplinen Stefanie Dehnen