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Introduction to Chemistry 32B Spring 2009

Introduction to Chemistry 32B Spring 2009. Instructor: Dr. Tyler Johnson email: tjohnson@sjcc.edu Office Hours: Wednesday 12:15-1:15pm S-205 Text: General, Organic and Biochemistry, Bettelheim, Brown and March, 7 th ed. 2004, Thomson-Brookes/Cole: (a) workshop Workbook,

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Introduction to Chemistry 32B Spring 2009

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  1. Introduction to Chemistry 32B Spring 2009 Instructor: Dr. Tyler Johnson email: tjohnson@sjcc.edu Office Hours: Wednesday 12:15-1:15pm S-205 Text: General, Organic and Biochemistry, Bettelheim, Brown and March, 7th ed. 2004, Thomson-Brookes/Cole: (a) workshop Workbook, (b) Chime molecular modeling exercises (c) Laboratory manual - purchased in the campus bookstore (in separate shrink wrap) Lecture: M/W: 10:45-12:10pm in S-205 Laboratory: M: 12:40-3:45pm in S-201 (computer) or S-211 (wet lab)

  2. Introduction to Chemistry 32B - Spring 2009 Preliminary Syllabus (PLEASE COPY DOWN) Week of Page No. in Text Chapter, WS, & Lab Topics (Mon) 1/26 704-719 29 Nutrition and digestion lab check in, Safety contract Safety video worksheet (Wed) 1/28 70-83 3 Chemical bonds (Review) 269-282 10 Organic Chemistry Updated Syllabus Text: General, Organic and Biochemistry, Bettelheim, Brown and March, 7th ed. 2004, Thomson-Brookes/Cole:

  3. Introduction to Chemistry 32B - Spring 2009 • First Assignment • Required Questionnaire: Please fill out: . . . Pass to the front • 1. Name? 2. MAJOR? 3. Why are you taking Chem 32B? 4. What are your career goals? 5. What do you hope to learn from this course? 6. Your email, (please print) • 10 bonus points if you email me your email by Monday 2/2/09: tjohnson@sjcc.edu • Just title it “Hi-my email” so I have it on file . . .

  4. My Expectations of YouIntroduction to Chemistry 32B - Spring 2009 • Read the chapter before lecture 2. DO ALL THE ASSIGNED HOMEWORK PROBLEMS - Understand 3. Do not wait until last minute to Study (Unlike BIO, O-Chem cannot be crammed the night before) 4. Plan to set aside, min 3-4 hrs/ day reading the chapter, answering Homework Qs Most test Qs -- from H-work directly or very similar and Lecture Problems 5. O-Chem not terribly difficult . . .really . . . It just takes a lot of time to master, unlike most science classes 6. GET SERIOUS, Just study (3-4hrs/day) and you should be fine

  5. A COMPREHENSIVE REINVESTIGATION INTO THE BIOACTIVE SECONDARY METABOLITES OF AN INDO-PACIFIC MARINE SPONGE:Cacospongia mycofijiensis A dissertation submitted in partial satisfaction of the requirements for the degree of DOCTOR OF PHILOSOPHY in CHEMICAL OCEANOGRAPHY by Tyler A. Johnson November 2008

  6. BACKGROUND Marine Natural Products What We Study . . . Where & Why . . .

  7. SOURCES FOR CHEMICALLY PROLIFIC SIMPLE MARINE ORGANISMS

  8. Percent of bioactive ‘Hits” against the NCI-60 cell line(s) 434 18,293 6,540 1871 8,246 -Bioactive Hit Rate (NCI 60 cell line) Recreated from Munro, M. H. G. et al.,J. Biotechnol.1999, 70, 15-25. Recreated from Feher and Schmidt J. Chem. Inf. Comput. Sci. 2003, 43: 218-227 BACKGROUND Why, Marine Natural Products -Structural Diversity

  9. Why Sponges? Percent of marine natural products reported by phylum1 (1) Harvey, A. L. Advances in drug discovery techniques; John Wiley & Sons: Chichester , NY, 1998.

  10. 2. Identify & Develop biologically active Marine Natural Products Bengamide B LAF 289 (Phase II) 3. Locate the Mechanism of Action Over-Arching Goals • Discover Structurally distinct Novel Chemistry • (e.g. psymberin)

  11. Discovery (3-5 years) Discovery (3-5 years) Collection  Extraction  (Bioassay/Analytical)  Purification HPLC • Structure Elucidation NMR, MS  In vitro Map Coll Site/ Obs.Chem. GPS 1,4 1, 2 3 Development Preclinical (In Vivo) evaluation  Clinical Evaluation (6 years) 1/5000 Approach to Achieve Objectives

  12. Disk Diffusion Soft Agar Colony Formation Assay fijianolide B Paclitaxel (Taxol) = extract/compound Valeriote, F.; Grieshaber, C. K.; Media, J.; et al. J. Exp. Ther. Oncol. 2002, 2, 228-236.

  13. Pharmakokinetic Analysis of Fijianolide B Pharmacokinetic analysis of 2 inHCT-116 tumor-bearing SCID mice. The observed concentration of 2 in the plasma (●) and HCT-116 tumor (■) over a 24h period (1440 minutes). At 24h concentration of 2: plasma = 0.2 ug/mL, tumor = 2.8 ug/mg. Johnson, T. A.; Tenney, K.; Cichewicz, R. H.; Morinaka, B. I.; White, K. N.; Amagata, T.; Subramanian, B.; Media, J.; Mooberry, S. L.; Valeriote, F. A.; Crews, P. J. Med. Chem. 2007, 50, 3795-3803.

  14. In vivo Evaluation of Fijianolide B In vivo assessment of 2 using HCT-116 tumor-bearing SCID mice. The average tumor weight measured per day after daily inoculation of 2 for 5 days: 25 mg/kg/day (■), 12.5 mg/kg/day (▲), and control (♦). NOTES: + preclinical in vivo of 2 -Launch Phase I clinical trial . . Johnson, T. A.; Tenney, K.; Cichewicz, R. H.; Morinaka, B. I.; White, K. N.; Amagata, T.; Subramanian, B.; Media, J.; Mooberry, S. L.; Valeriote, F. A.; Crews, P. J. Med. Chem. 2007, 50, 3795-3803.

  15. General, Organic, and Biochemistry, 8e Bettelheim, Brown Campbell, & Farrell

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