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)
Introduction to Chemistry 32B - Spring 2009
Preliminary Syllabus (PLEASE COPY DOWN)
Week of
(Mon) 1/26
Page No. in Text
704-719
(Wed) 1/28
70-83
269-282
Chapter, WS, & Lab
Topics
29
Nutrition and digestion
lab check in, Safety contract
Safety video worksheet
3
10
Chemical bonds (Review)
Organic Chemistry
Updated Syllabus
Text: General, Organic and Biochemistry, Bettelheim, Brown and March, 7th ed. 2004,
Thomson-Brookes/Cole:
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)
My Expectations of You
Introduction to Chemistry 32B - Spring 2009
1. 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
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
BACKGROUND
Marine Natural Products
What We Study . . .
Where & Why . . .
SOURCES FOR CHEMICALLY PROLIFIC
SIMPLE MARINE ORGANISMS
BACKGROUND
Percent of bioactive ‘Hits” against the NCI-60 cell line(s)
434
18,293
6,540
1871
Why, Marine Natural Products
8,246
-Bioactive Hit Rate (NCI 60 cell line)
-Structural Diversity
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
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.
Over-Arching Goals
1. Discover Structurally distinct Novel Chemistry
(e.g. psymberin)
2. Identify & Develop biologically active Marine Natural Products
Bengamide B
3. Locate the Mechanism of Action
LAF 289
(Phase II)
Approach to Achieve Objectives
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
Disk Diffusion Soft Agar Colony Formation Assay
Paclitaxel (Taxol)
= extract/compound
fijianolide B
Valeriote, F.; Grieshaber, C. K.; Media, J.; et al. J. Exp. Ther. Oncol. 2002, 2, 228-236.
Pharmakokinetic Analysis of
Fijianolide B
1.E+06
Conc. (ng/ml)
1.E+05
1.E+04
1.E+03
1.E+02
0
200
400
600
800
1000
1200
1400
1600
Time (Minutes)
Pharmacokinetic analysis of 2 in HCT-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.
Tumor Weight (mg)
In vivo Evaluation of Fijianolide B
1100
1000
900
800
700
600
500
400
300
200
100
0
0
2
4
6
8
10 12 14 16 18 20 22 24 26 28
Days after tumor inoculation
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.
General, Organic, and
Biochemistry, 8e
Bettelheim, Brown
Campbell, & Farrell