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| Keywords: Drug-heme interaction.png en Top row Binding of chloroquine CQ to the 001 and 100 faces of hemozoin HZ Left Electrostatic interactions between CQ and HZ at the 001 face including base-acid N CH2CH3 2-H+ ¦-O2C acceptor-donor ring N ¦H-C H CH- acceptor-donor quinoline Cl ¦H3C- and proton donor-p acceptor exocyclic N-H ¦H2C CH Center CQ intercalated within groove delineated by dashed green line on surface of 001 face viewed edge-on along the a-crystal axis Binding of CQ to the 100 face of HZ Central row Binding of halofantrine HF to the 001 and 010 faces of HZ Left top Molecular structure of HF The double-arrow denotes the separation between the tertiary N and the OH group Left bottom Cyclic heme dimer in crystal structure of HZ where the double-arrow denotes the separation between the propionic acid group and the Fe carboxylate carbonyl group Center binding of HF to the 001 face of HZ viewed face-on HF is too bulky to be intercalated within a groove on the 001 face as is CQ Nevertheless HF forms strong interactions with the 001 surface; the OH group of HF is hydrogen bonded to the Fe-carboxylate carbonyl O atom and the tertiary N-H+ group is H-bonded to the CO2- group of HZ Note HF can bind to the 100 face of HZ in an arrangement akin to that of CQ to the 100 face of HZ see top row right Bottom row Binding of HF-heme coordination complex to the 010 face of hemozoin Left Molecular structure of the HF-ferriprotoporphyrin IX coordination complex K A de Villiers H M Marques T J Egan J Inorg Biochem 2008 102 1660 Right Binding of the HF-Heme complex to the 010 face of hemozoin where the HF moiety of the complex emerges from the crystal face The 010 face is viewed edge-on along the c-axis Note that the quinoline methanols such as quinine and mefloquine also form coordination complexes with ferriproto-porphyrin IX according to Egan and coworkers Thus such quinoline-heme complexes can also be adsorbed onto the 010 face Note that the red violet and blue arrows drawn above the drug-hemozoin arrangements and on the crystal faces shown in central row right designate attachment of the particular antimalarial drug to the 001 100 and 010 faces respectively and subsequent inhibition Original work by Leslie Leiserowitz and Isabelle Weissbuch Leslie Leiserowitz and Isabelle Weissbuch PermissionOTRS 2009022010051995 Leslie Leiserowitz Chloroquine | ||||
