Bruni, Pia S.; Schürch, Stefan (2021). Mass Spectrometric Evaluation of β-Cyclodextrins as Potential Hosts for Titanocene Dichloride. International journal of molecular sciences, 22(18), p. 9789. MDPI 10.3390/ijms22189789
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Bent metallocene dichlorides (Cp2MCl2, M = Ti, Mo, Nb, ...) have found interest as anti-cancer drugs in order to overcome the drawbacks associated with platinum-based therapeutics. However, they suffer from poor hydrolytic stability at physiological pH. A promising approach to improve their hydrolytic stability is the formation of host-guest complexes with macrocyclic structures, such as cyclodextrins. In this work, we utilized nanoelectrospray ionization tandem mass spectrometry to probe the interaction of titanocene dichloride with β-cyclodextrin. Unlike the non-covalent binding of phenylalanine and oxaliplatin to β-cyclodextrin, the mixture of titanocene and β-cyclodextrin led to signals assigned as [βCD + Cp2Ti–H]+, indicating a covalent character of the interaction. This finding is supported by titanated cyclodextrin fragment ions occurring from col- lisional activation. Employing di- and trimethylated β-cyclodextrins as hosts enabled the elucidation of the influence of the cyclodextrin hydroxy groups on the interaction with guest structures. Masking of the hydroxy groups was found to impair the covalent interaction and enabling the encapsulation of the guest structure within the hydrophobic cavity of the cyclodextrin. Findings are further supported by breakdown curves obtained by gas-phase dissociation of the various complexes.
Item Type: |
Journal Article (Original Article) |
|---|---|
Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Bruni, Pia Simona, Schürch, Stefan |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry 500 Science |
ISSN: |
1422-0067 |
Publisher: |
MDPI |
Language: |
English |
Submitter: |
Stefan Schürch |
Date Deposited: |
17 Jan 2022 14:43 |
Last Modified: |
05 Dec 2022 15:57 |
Publisher DOI: |
10.3390/ijms22189789 |
PubMed ID: |
34575951 |
BORIS DOI: |
10.48350/162526 |
URI: |
https://boris.unibe.ch/id/eprint/162526 |
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