Membrane activity of biotechnological peptide drugs

Abstract

Charged Langmuir-Blodgett monolayers deposited at an immobilised liquid-liquid interface have been used as a simple model for a biological membrane to investigate the membrane activity of biotechnological oligopeptide drugs.

Ion transfer voltammetry of tryptamine, serotonin, and tryptophan at the nitrobenzene/water interface

“…Ion transfer voltammetry of aromatic amines, including amino acids, dipeptides, neurotransmitters, and anesthetics, at the organic solvent (O)|water (W) interface has been studied by many authors [7][8][9][10][11][12][13][14][15][16][17][18]. Much attention has been paid to the hydrophobicity of protonated cations of the aromatic amines, as determined by the reversible half-wave potentials of the voltammograms, and to the relationship to their biological or pharmacological activities.…”

Voltammetric Insights in the Transfer of Ionizable Drugs Across Biomimetic Membranes - Recent Achievements

“…Chronoamperometry using a micropipette has also been successfully used for charge transference and diffusion coefficient determination of this type of polypeptide protamine [17]. Kontturi et al [18] evaluated the partition coefficient values from cyclic voltammetric measurements at a polarized water-NPOE interface of drugs used in therapy, like those structurally related to aminoacridines: aminacrine ( log P w NPOE =-1.63), proflavine ( log P w NPOE = -1.65), tacrine ( log P w NPOE =-1.97), and velnacrine ( log P w NPOE =-0.24). The results obtained on the study of drug membrane activity, by combining a theoretical model to electrochemical impedance spectroscopy experiments, permitted the justification of some of the differences found between their therapeutic activities [18].…”

“…These drugs possess different abilities to pass through biological membranes since positive interactions were observed between velnacrine and proflavine ionic forms and the polar groups of the various phosphatidylcholine fattyacids, which has been used as modifiers of the liquid-liquid interface. The electrochemistry of the protonated forms of two structurally related decapeptides of pharmaceutical interest (LHRH-leutinising hormone releasing hormone, and nafarelin) at the distearoyl phosphatidylcholine monolayer-modified water-nitrophenyloctyl ether interface was studied [56]. Although nafarelin is more lipophilic than LHRH, their membrane activities have been found to be in divergence.…”

“…The membrane activities of four ionisable therapeutic important drugs (aminacrine, tacrine, velnacrine and proflavine) were obtained by cyclic voltammetry and electrochemical impedance spectroscopy at water and nitrophenyloctyl ether interface [18]. These drugs possess different abilities to pass through biological membranes since positive interactions were observed between velnacrine and proflavine ionic forms and the polar groups of the various phosphatidylcholine fattyacids, which has been used as modifiers of the liquid-liquid interface.…”

“…Kontturi et al [18] evaluated the partition coefficient values from cyclic voltammetric measurements at a polarized water-NPOE interface of drugs used in therapy, like those structurally related to aminoacridines: aminacrine ( log P w NPOE =-1.63), proflavine ( log P w NPOE = -1.65), tacrine ( log P w NPOE =-1.97), and velnacrine ( log P w NPOE =-0.24). The results obtained on the study of drug membrane activity, by combining a theoretical model to electrochemical impedance spectroscopy experiments, permitted the justification of some of the differences found between their therapeutic activities [18]. A facilitated (assisted) ion transfer study of the protonated neurotransmitter dopamine (often used in neuropsychosis treatment) using dibenzo-18-crown-6 crown ether was reported by Zhan et al [19] and Beni et al [20].…”