chm115_lecture20 - Chemistry 115 Lecture 20 Outline...

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Chemistry 115 Lecture 20 Outline Molecular Shape and Drug Discovery Molecular Shape Drug discovery process Shape of drug molecules/polymorphism Curing Cancer Recitation: Molecular Shapes Organic Compounds HW9 due Wed 3/30 at 11pm
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3-D Molecular Shape and Vision Rhodopsin is responsible for vision. Rhodopsin consists of 11- cis -retinal covalently bonded to a large protein. Note how 11- cis -retinal “fits” into the protein to allow it to bond.
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3-D Molecular Shape and Vision When light strikes the molecule, the shape will change via a rotation around the 11-12 bond.
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3-D Molecular Shape and Vision When the shape changes, the molecule no longer “fits” with the protein, and they separate. This change in shape and separation from the protein contributes to the electrical signal that travels through your neurons as “vision.”
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Molecular Shape and Drugs Molecular shape affects the interaction of drugs in your body In order to develop useful drugs, chemists at pharmaceutical companies: synthesize different potential drugs Work to understand the drug targets (proteins) Use chemical knowledge to find protein/drug interactions. Let’s start with a disease example, Malaria:
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Malaria Malaria is caused by parasitic protozoa (genus: Plasmodium) and is transferred to humans by mosquitoes Symptoms: VERY high fever (107°!), nausea, delirium There are an estimated 100 – 200 MILLION cases of malaria worldwide each year (80% are in Africa) 1 – 1.5 millions deaths per year Used to treat syphilis prior to antibiotics.
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Peruvian Indians used bark from the Cinchona tree (found in the Andes) to treat fever; it also was found to cure malaria Europeans started harvesting Cinchona bark (almost to extinction) and sending it back to Europe The active ingredient in the Cinchona bark is quinine, isolated in 1820 Quinine cures malaria by killing the parasite (it binds to proteins in the body that the parasites need). Treatment of Malaria: Quinine
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Interesting Facts about Quinine The British Army developed tonic water in order to get their soldiers to take quinine to fight malaria (it’s not known who was the first to add gin) Although quinine can be obtained from tree bark, it was first synthesized artificially in 1944 by RB Woodward and W Doering (not a coincidence that it was during WWII – natural supplies were cut off)
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as quinine Aspirin – salicylic acid (not aspirin) was obtained by chewing on Willow bark. Alfred Bayer in Germany discovered that the acetyl ester was more effective for pain relief, and called it “aspirin” (the trademark was lost when the US seized all domestic German assets after WWI) Mold in a petri dish led to the discovery of penicillin Taxol is an anti-cancer drug that is obtained from the bark of Yew trees Countless potential drugs are isolated from plants, algae, and even things like sea sponges. In all these cases, the general approach is
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This note was uploaded on 04/09/2011 for the course CHM 115 taught by Professor Towns during the Spring '08 term at Purdue University-West Lafayette.

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chm115_lecture20 - Chemistry 115 Lecture 20 Outline...

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