PMC:7204663 / 2796-5410
Annnotations
{"target":"http://pubannotation.org/docs/sourcedb/PMC/sourceid/7204663","sourcedb":"PMC","sourceid":"7204663","source_url":"https://www.ncbi.nlm.nih.gov/pmc/7204663","text":"If the pH of the molecular environment is lower (more acidic), more nitrogens are protonated, which in turn hinders the now-charged moieties from crossing membranes. This is particularly relevant for the intracellular distribution of basic drugs crossing between the cytosol (pH approx. 7.4) and the acidic lysosomal space (pH approx. 5.0). Fig. 2 shows this distribution conceptually. Basic compounds are in an equilibrium of a less polar unionized form (B) that can easily cross membranes, and a polar protonated form (BH+) that cannot easily cross membranes. As the unionized drug enters the acidic environment of the lysosome, it will be protonated and ‘trapped’ in the lysosome as the protonated form BH+ cannot easily diffuse back into the cytosol. As a result, high concentrations of the compound can accumulate in lysosomes. This concept of “ion-trapping” has been described and reviewed [7,8]. The magnitude of this accumulation depends on the mathematical relationship of the pKa of the compound of interest, its permeability, and the pH gradient between the two environments (e.g. cytosol [pH 7.4] and lysosome [pH 5.0]). If there is no permeability limitation, the expected ratio or concentration gradient can be calculated based on the well-known Henderson-Hasselbalch equation [8]. If the compound of interest has only one basic group, the ratio between the concentrations will be:(1) R=C1C2=H1+KaH2+Kawhere H1 and H2 are the respective proton concentrations (=10−pH) of the two environments (pH 5 and 7.4) and Ka is the dissociation constant (=10−pKa). Fig. 3 A shows the magnitude of the resulting accumulation as a function of the pKa value of the compound. Accumulation of up to 250-fold higher concentrations in lysosomes can be explained by the described mechanism.\nFig. 2 Concept of lysosomal ion-trapping. Basic compounds are in an equilibrium of a less polar unionized form (B) that can easily cross membranes, and a polar protonated form (BH+) that cannot easily cross membranes. As the unionized drug enters the acidic environment of a lysosome, it will be protonated and ‘trapped’ in the lysosome as the protonated form BH+ cannot easily diffuse back into the cytosol. As a result, high concentrations of the compound can accumulate in the lysosomes.\nFig. 3 Magnitude of lysosomal ion-trapping depending on the pKa of the compound of interest. For a monobasic compound (A), up to 250-fold higher concentrations are possible depending on pKa. For a dibasic compound (B), the accumulation can be over 60 000-fold. These simulations assume a pH gradient of 5.0 (lysosomes) and 7.4 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