Multicomponent non-covalent associations of β-cyclodextrin (β-CD)-drug inclusion complexes with diethanolamine (DEA). Detection and characterization of gaseous protonated 1 :1 :1 β-CD-drug-DEA adducts by ionspray ionization and tandem mass spectrometry

TLDR: In this article, a study by ionspray and tandem mass spectrometry (MS) of the multicomponent associations with diethanolamine (DEA) of β-cyclodextrin (β-CD) host-guest complexes of two drugs, namely glybenclamide and furosemide, allowed the detection and characterization of the gaseous protonated 1:1:1 drug β-CD-DEA adducts.

Abstract: The multicomponent non-covalent associations of β-cyclodextrin (β-CD)–drug host–guest complexes with appropriate molecules are of current interest to the pharmaceutical industry, as they can increase dramatically the solubility in water of scarcely soluble guest drugs. The present study by ionspray and tandem mass spectrometry (MS) of the multicomponent associations with diethanolamine (DEA) of the β-CD host–guest complexes of two drugs, namely glybenclamide and furosemide, allowed the detection and characterization of the gaseous protonated 1:1:1 drug–β-CD–DEA adducts. Their dissociation patterns upon collision activation provided interesting information on the relative strength of the interactions binding the components of such charged non-covalent associations in the gas phase. In particular, from the results above it clearly emerged that the stability of the 1:1 drug–β-CD inclusion complexes within such gaseous ternary associations was much weaker than that shown previously for the analogous 1:1 terfenadine (TFN)–β-CD complex originating by the tandem MS dissociation of the 1:1:1 TFN–β-CD–HA (HA = tartaric or citric acid) protonated adducts, generated by ionspray MS. Also, we noted that these findings appear consistent with the relative stability of the corresponding 1:1 drug–β-CD host–guest complexes in solution.