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University of California Los Angeles HIV Virology Medical Chemistry Paper

University of California Los Angeles HIV Virology Medical Chemistry Paper

Question Description

The following questions are based on topics we covered in class as well as published manuscripts. I have included the pdf copies of the manuscripts that will be important to answer these questions. However, I encourage you to refer to additional literature to come up with possible answers. You may include scheme(s) and/or figure(s) to illustrate a particular point. Please follow the recommended word limits (including the figure captions). Also, note that your answers will be checked for plagiarism

Question 1. As I mentioned during the class, HIV-1 protease is an important drug target. Refer to this review – Konvalinka et al., Virology 2015 (Fig. 5, pages 408-409). Explain the strategies used by HIV-1 to evade clinically used protease inhibitors. Explain how and why these strategies are effective when interactions between the synthetic drugs and protease are always much stronger than that of interactions between protease and its natural substrate. (500 words; 15 points)

Question 2. Not many small therapeutic molecules have been on the cover of TIME magazine. However, Gleevec (Imatinib; Novartis) has had this honor on May 2001. See this web-article to gain more information about Gleevec – https://www.nature.com/scitable/topicpage/gleevec-the- breakthrough-in-cancer-treatment-565/. Using this and other literature, explain why Gleevec – a tyrosine kinase inhibitor – has been such a trendsetter as a kinase inhibitor. (500 words; 15 points)

Question 3. Consider following two compounds – estradiol and raloxifene – that interact with estrogen receptor, a GPCR (see the figure below – binding site residues and interactions are

depicted in blue). Note that estradiol is an agonist, whereas raloxifene acts as an antagonist of estrogen receptor. Explain why Tamoxifen and its metabolite can, therefore, act as an antagonist and agonist of the same estrogen receptor, respectively. (400 words; 10 points)

Question 4. As we discussed in class, Aspirin inhibits cyclooxygenase-1 (COX-1) by irreversibly acetylating a serine residue at position 529. It is also well-known that residue 523, an isoleucine – is a part of active site of COX-1. In its isoform, COX-2, this residue is a valine. Explain how this information can be used to design a molecule that can selectively bind to COX-2. (300 words; 10 points)

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