Protolysis of Amino Acid‐Functionalized Tin Sulfide Clusters

In order to gain information about the behavior of tin sulfide clusters with bio‐organic ligand shells under acidic conditions, such as found in undesirable cells for instance, we systematically treated amino acid‐functionalized tin sulfide clusters with different acids. For Boc‐protected amino acid...

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Bibliographic Details
Published in:European journal of inorganic chemistry 2020-08, Vol.2020 (29), p.2809-2815
Main Authors: Engel, Annikka, Dewald, Hendrik, Reuter, Anna, Klippstein, Josefin, Dehnen, Stefanie
Format: Article
Language:English
Subjects:
Amino acids
Chlorides
Cluster compounds
Clusters
H2S release
Hydrogen sulfide
Inorganic chemistry
Organotin sulfides
Organotin trichlorides
Protolysis
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Summary:In order to gain information about the behavior of tin sulfide clusters with bio‐organic ligand shells under acidic conditions, such as found in undesirable cells for instance, we systematically treated amino acid‐functionalized tin sulfide clusters with different acids. For Boc‐protected amino acid derivatives, we could show that this treatment causes either cleavage of the protecting group of the amino acid or protolysis of the tin sulfide core under release of H2S and formation of the correspondingly functionalized organotin trichloride, depending on the nature of the acid. This points towards a potential future use of such species for targeted cytotoxic applications. Organotin sulfide clusters were tested towards de‐protection of their Boc‐protected amino acid ligands and towards controlled degradation under acidic conditions. (a) The preconditions for growing oligopeptides on the ligand shell of such clusters to make them compatible with physiologic conditions, and (b) their potential use for targeted release of H2S as a cytotoxic species were probed with different acids: (partial) de‐protection and H2S release were achieved.
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.202000290