Review
Surface active drugs: self-association and interaction with membranes and surfactants. Physicochemical and biological aspects

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Abstract

Many pharmacologically active compounds are of amphiphilic (or hydrophobic) nature. As a result, they tend to self-associate and to interact with biological membranes. This review focuses on the self-aggregation properties of drugs, as well as on their interaction with membranes. It is seen that drug–membrane interactions are analogous to the interactions between membranes and classical detergents. Phenomena such as shape changes, vesiculation, membrane disruption, and solubilization have been observed. At the molecular level, these events seem to be modulated by lipid flip-flop and formation of non-bilayer phases. The modulation of physicochemical properties of drugs by self-association and membrane binding is discussed. Pathological consequences of drug–membrane interaction are described. The mechanisms of drug solubilization by surfactants are reviewed from the physicochemical point of view and in relation to drug carrying and absorption by the organism.

Keywords

Surface active drug
Drug self-association
Drug–membrane interaction
Drug–surfactant interaction
Membrane solubilization
Drug delivery

Abbreviations

AmB, amphotericin B
BS, bile salt
CAD, cationic amphiphilic drug
CD, circular dichroism
cmc, critical micellar concentration
CPZ, chlorpromazine
DBC, dibucaine
DOC, deoxycholate
DSC, differential scanning calorimetry
EPR, electron paramagnetic resonance
GI, gastrointestinal
HHB, hydrophilic–hydrophobic balance
LA, local anesthetic
Lyso PC, lysophosphatidylcholine
MM, mixed micelle
NMR, nuclear magnetic resonance
P, partition coefficient
PC, phosphatidylcholine
PEG, polyethylene glycol
PM, polymeric micelle
POE, polyoxyethylene
RBC, red blood cell
RES, reticuloendothelial system
SDS, sodium dodecyl sulfate
TFP, trifluoperazine
TI, therapeutic index
TTC, tetracaine

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