Given the surface structure of a typical bile salt below, do you expect Cholesty

Question

Given the surface structure of a typical bile salt below, do you expect Cholestyramine resin to have a surface chemistry similar to resin I or resin II? Explain

Modern statin drugs (Lovastatin, Lipitor, Crestor, etc.) are used to lower serum cholesterol levels by inhibiting a key liver enzyme responsible for cholesterol biosynthesis. Before 3. Modern sta levels by inhibi ese drugs were developed, an ion exchange resin, Cholestyramine, was used therapeuti ealy to lower cholesterol levels. A patient would actually drink a solution of little plastic these drugs were devel heads coated with charged groups and counter ions (yum!). The therapy works because Ie converts some of the cholesterol into bile salts, which are used in the small intestine to the liver, in addition to synthesizing cholesterol, pulls cholesterol out of the bloodstream. It converts some o help with digestion. since the Most of the bile salts are reabsorbed in the intestine and reused. But, ioce the bile salts are ionic, they bind to the resin (little insoluble plastic beads) and are excreted instead of being reabsorbed. The resin essentially gives the bile salt, derived from cholesterol, a one way ticket out of the body. The liver then takes more cholesterol out of the blood to replace the bile salt. Given the structure of a typical bile salt below, do you expect Cholestyramine resin to e a surface chemistry similar to resin I or resin II? Explain. CH, H,C CH3 CH3 H,C CH3 NH CH2 C-o CH3 CH3 Ho HO Glycocholate, a typical bile salt derived from cholesterol Cholesterol CH3 H2 -C-N-CH, C CH, Resin II Resin I

Explanation / Answer

Resin II

Bile salts are typically negatively charged and can be sequestered by ion exchange resins which harbour a potential positive core with a negative ion that can be displaced (a phenomenon seen in anion exchange chromatography). In resin II you can see that it contains a positively charged core (which function as binding sites for anion) and chloride ion for displacement. The exchange of anions is dependent on electronegativities of ions. The ion with highest electronegativity will displace corresponding ion of lower negativity. Here, in this resin oxygen of bile salt has more electronegativity than chloride ion.

[n resin I, the location of charges is totally opposite. Even if sodium ion is lost, oxygen - oxygen ions can not bind to each other because of same electronegativity or charge.]

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