Deficiency. - Night blindness - Dry, rough skin - Decreased resistance to infection - Faulty tooth development - Slower bone growth

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1 MEDCHEM 562 Fall 2013 Vitamin Problem Set 1: 1) Complete the table: Vitamin A D Physiological Function / Therapeutic Uses - Vision - Promotion of cell differentiation - Inhibition of cell proliferation - Carotenoid antioxidant/free radical scavenger activity - Acne - Psoriasis - Calcium homeostasis - Modulation of cell proliferation and differentiation - Used for prevention of metabolic bone disease in renal failure Deficiency States - Night blindness - Dry, rough skin - Decreased resistance to infection - Faulty tooth development - Slower bone growth - steomalacia - Rickets in children Toxicities - Hydrocephalus - Vomiting - Hypercalcemia - Brittle bones - Fatigue - Malaise - Headache - Rough skin - Increased risk of fractures - Calcification of soft tissues Daily Value 5,000 IU 400 IU Upper Limit 10,000 IU 4,000 IU E - Antioxidant/ free radical scavenger - Slowing of Alzheimer s disease progression - Protection against eye and lung damage in premature infants - Neuromuscular abnormalities - Myopathies - Hemolytic anemia in infants - Adverse bleeding effect (rare) - Exacerbated bleeding when given with warfarin 30 mg (30IU) 1,000 mg K - Gla protein formation - Blood clotting - Artery calcification inhibition - Bone metabolism - Spontaneous hemorrhaging (usually in neonates) - Allergic reactions 80 μg none 2) Complete the metabolic pathway shown below:

2 Retinyl esters (all trans retinyl palmitate) Retinoid isomerohydrolase 11-cis retinol LRAT REH psin RetSDR AKR1B1 AKR1B10 Retinol all-trans retinaldehyde ADHs (RDH10, RDH4) 11-cis-retinal dehydrogenase hv ALDH1a2 (RALDH2) 11-cis retinal psin Rhodopsin all-trans-retinoic acid CYP26A1 CYP26B1 CYP26C1 all-trans-4-oxo retinoic acid and other retinoid acid metabolites Note: for the retinol to retinal and retinal to retinoic acid pathways it is sufficient to know that ADH and ALDH enzymes, respectively, catalyze these reactions. a) Which fat-soluble vitamin is this pathway related to? Vitamin A. b) Which sense (hearing, sight, smell, taste, or touch) does the pathway play a role in? Name a symptom associated with a deficiency in the vitamin in part A and the sense affected by this pathway? Sight. Night blindness. c) ATRA binds to which heterodimeric receptor to control growth and development? RAR/RXR.

3 3) Acitretin is a vitamin A related drug. The structure is shown below: H a) What is the half-life of the Acitretin? 2 days. b) Acitretin can be converted to what other drug in patients who consume large amounts of alcohol. What is this drug? Draw the structure of this drug. What is its half-life? Etretinate. 3 month half-life. c) How can the drug in part b be converted back to acitretin? Hydrolysis of the ester. 4) The structure of β-carotene is shown below: a) β-carotene is cleaved to yield how many moles of retinal? Circle the portion(s) that is important for Vitamin A activity. Indicate on the structure where the bond cleavage takes place.

4 2 moles of retinal. Circled β-ionone rings. Cleavage at C15-C15. b) A patient is worried about hypervitaminosis A because he/she eats a diet high in carrots. Should he/she be concerned by vitamin A produced by the cleavage of β-carotene (found in carrots)? Why or why not? No, he/she should not because conversion of the carotenoids to form retinal is inefficient as conversion decreases when body stores of vitamin A are high. The patient might experience yellowing of skin, but no negative symptoms associated with high levels of vitamin A. 5) Question 5 H H CYP2R1 or CYP27A1 Location: Liver CYP27B1 Location: Kidney H H H H Name: Cholecalciferol 25-hydroxy vitamin D3 or Calcidiol 1,25-dihydroxy vitamin D3 or Calcitriol a) Cholecalciferol is shown on the far left. Which fat-soluble vitamin is this? Vitamin D3. b) Cholecalciferol is hydroxylated twice by P450 to yield the active form of this vitamin. i. Draw in the hydroxyl groups on the structures above in each step. ii. Indicate which CYP carries out each hydroxylation and the location (which organ) it takes place in. iii. Finally, provide a name for each molecule (there are multiple names for each!). 6) Vitamin D and parathyroid hormone (PTH) have important roles in metabolic bone disease.

5 a) Metabolic bone disease typically happens as a result of failure in which organ? Kidney. b) Metabolic bone disease is associated with deficiency of which mineral in the bones? Calcium, Ca 2+. c) Describe how PTH interacts with bones, the failed organ in part a, and the mineral in part b. Provide reasoning for how this can cause metabolic bone disease. PTH is released when serum calcium concentrations fall below acceptable levels (~1.2 mm). PTH signals to the bone to release calcium into the circulation, to the kidney to reabsorb more calcium from the tubules and toexpress more renal CYP27B1. The resulting increased formation of calcitriol by the kidney causes more calcium to be absorbed from the gut. If these effects of PTH in the kidney and bone are insufficient to maintain calcium levels (for example in renal failure), excessive bone resorption occurs because bone represents the largest stores of calcium in the body. The latter effect is termed metabolic bone disease. d) What can be prescribed to patients to help patients who have failure in the organ from part a? Calcitriol (1,25DHCC), which provides the active hormone directly as Rocaltrol or the generic products. 7) Menadione is shown below: a) Menadione is also known as vitamin K3. b) Is menadione active? If so, identify the portions that contribute to its activity. If not, what modification needs to be done for it become active?

6 Menadione itself is inactive. The modification needed is a geranylgeranyl side chain at C3 (shown by red arrow above). The circled methyl group and the 1,4-napthoquinone ring are necessary for anti-hemorrhagic activity. 8) What is a potential health risk associated with prescribing warfarin at high doses? How does this occur? Which enzyme does warfarin inhibit to accomplish its therapeutic effect? Excessive bleeding. This is due to excessively diminished production of several vitamin K-dependent clotting factors. Warfarin inhibits VKRC1 as shown in the diagram below. 9) A patient who recently finished taking his/her prescription of antibiotics might be expected to have lower amounts of gut bacteria. Which specific vitamin s production can be altered by changes in gut flora? Is this vitamin active or inactive? Based on your previous answer, would the vitamin production increase or decrease as a result? Vitamin K2 is produced by anaerobic bacteria in the lower gut. Vitamin K2 is active. Vitamin production would decrease as a result of lower bacteria levels in the gut. 10) Identify two structural features of vitamin E that are essential for its biological activity.

7 The chromanol ring contains a phenolic hydroxyl group at 6-position that can donate a hydrogen atom (H ) to reduce free radicals. The hydrophobic side-chain aids in penetration of biological membranes. 11) α-tocopherol is the most important form of vitamin E. ne electron oxidation of α-tocopherol leads to resonance stabilization of the radical shown below: a) The radical can interact with which vitamin to regenerate Vitamin E? b) Vitamin C. c) Show diagrammatically how this occurs: d) Donation of H (given off in the one electron oxidation mentioned above) can neutralize what type of radical discussed in class? Lipid peroxyl radicals, shown overleaf.

8 Below, R is the lipid peroxyl radical, which recombines with H. 12) Some multiple-choice questions below. nly one answer is correct. Copper and zinc intake would be important for high activity of what important enzyme that helps protect against free radical damage? a) superoxide dismutase b) glutathione reductase c) peroxidase d) catalase Riboflavin helps to reduce the damage caused by free radical reactions because; a) glutathione peroxidase requires NADPH, b) glutathione reductase requires NADPH, c) glutathione peroxidase requires FAD, d) glutathione reductase requires FAD. Selenium has an important antioxidant role because it is a constituent of: a) glucose-6-phosphate dehydrogenase, b) superoxide dismutase, c) glutathione reductase, d) glutathione peroxidase.

9 13) Identify the three major (general) causes of vitamin deficiency and give a specific example of a group of people at risk for each one. 1) Inadequate intake: Alcoholics, poor, elderly, dieters 2) Increased needs: Infants, pregnant women, patients recovering from surgery, infection 3) Poor absorption: People with: GI disorders, specific GI surgeries (gallbladder removal, gastric bypass), cystic fibrosis, severe diarrhea, drug-induced vitamin deficiencies due to long term antibiotic, cholestyramine or mineral oil use

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