Mitochondriotropics: A review of their mode of action, and their applications for drug and DNA delivery to mammalian mitochondria

Synthesis of betulin derivatives and the determination of their relative lipophilicities using reversed‐phase thin‐layer chromatography

“…Also logP values calculated from R M0 for cholesterol are in agreement with the data presented by others (presumably theoretical) in the literature -9.9 (Westover and Covey, 2006) and 8.47 (Berthod, 2006). According to Horobin et al (2007) all the studied compounds were superlipophilic (logP > 8) except for 30-methoxybetulin, which was strongly lipophilic (8 > logP > 5) and lipophilic 17b-estradiol (5 > logP > 0). The RP-TLC method allowed for rapid measurement of parameters related to the molecular structure of the studied superlipophilic and highly lipophilic compounds.…”

Challenges of Antibacterial Discovery

“…Recent modeling studies by Trapp and coauthors have approached the flux of neutral and ionic compounds into plants and animal cells and organelles by using a dynamic cell model based on the "Fick-Nernst-Planck" equation (a combination of Fick's first law and the Nernst-Planck equation describing the electrochemical potential) (162,(365)(366)(367). Adapting and enhancing this model, Zarfl and colleagues simulated accumulation in cells of a group of antibacterial sulfonamides based on various assumptions about the permeating capability of the anionic species of the compounds (402).…”

Influence of Triphenylphosphonium (TPP) Cation Hydrophobization with Phospholipids on Cellular Toxicity and Mitochondrial Selectivity

“…The underlying mechanisms by which mitochondriotropic low-molecular weight molecules target mitochondria have been exhaustively discussed earlier by Horobin et al [26] In brief, the main mechanism by which the CTPP-PE conjugates selectively target mitochondria is attributed to the hydrophobic surface and the positive delocalized charge of the TPP cation, which facilitate its movement through the phospholipid bilayers without requiring a transporter, followed by its accumulation into mitochondria driven by the large mitochondrial membrane potential (150-180 mV, negatively inside). In addition, we presume that the hydrophobicity of the two long fatty acid hydrocarbon chains in CTPP-PE may contribute to lowering its activation energy to pass through the cells membrane, thus facilitating its uptake [19].…”