203f00final - Chemistry 203 Lg(Fall 2000 FINAL Last Name...

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Unformatted text preview: Chemistry 203 Lg (Fall 2000) FINAL Last Name: DEC. 12, 2000; 11:00 AM—1200 PM First Name: PROF. CHARLES E. MCKENNA T.A: INITIAL OF LAST NAME Please do not open this exam until you are told to do so. Write legibly to avoid confusion. GOOD LUCK ! ! _ f '- Quest10n# Points ' Grader ‘ x’ 7 -" y A TOTAL -- CIRCLE THE MOST NEARLY CORRECT ANSWER FOR EACH QUESTIONS. (4 Pts.) 1 At a pH of 2, water is: Acidic — Neutral — Basic — Freezing solid 2) 4 CH3CHZOH is: — Ethanol, active ingredient of booze — Methanol, a toxic alcohol — Methane (natural gas) — Isopropanol (rubbing alcohol) (3) The drawback of the original penicillin is: — Mg part of it can be modified without loss of drug activity — Very narrow antibacterial spectrum — Highly toxic fi None of the above (4) Oxygen has atomic weight 15.999 and hydrogen, 1.00. The molecular weight of (H20) is: — 18 molecules — 19 grams 18 moles/ gram § 18 grams/mole (5) The key role of HIV in destroying the immune system seems to be: 0 HIV attacks Thelper cells, impairing both Tkiller cell and B cell (antibody) production — HIV damages the spleen — HIV attacks B cells (antibody production) — HIV kills red blood cells (6) AIDS—linked diseases (opportunistic infections) include: — Osteoporosis — Rhinovirus (cold virus) — ,, Smallpox ’ Kaposi’s sarcoma (a cancer) (7) In order to design a more effective drug, we might consider changing the parent drug structure’s — Size — Shape ~ Polarity (7d of the above (8) Key differences in going from Phase I 9 Phase II clinical trials of an AIDS drug is: — Phase 1, larger patient base Phase II, looking for toxicity § Phase II, looking for efficacy — Phase I, looking for efficacy (9) A recommended procedure for HIV- testing to avoid false positives is: — Initial Western Blot @ nitial ELISA, then if positive, repeat; then if still positive Western Blot — ELISA only — Western Blot; then if positive, ELISA (10) The active form of AZT is: As taken in the pill (nucleoside) AZT monophosphate AZT diphosphate a AZT triphosphate (11) “Triple—combination” or drug cocktail chemotherapy vs. HIV (AIDS): — Is about as effective as one—drug therapy Cannot reduce virus levels by more than about one “log” (power of ten) Can reduce viral load in a patient to virtually undetectable level Completely eradicates HIV after 24 months of treatment (12) Saquinivir is also called Invirase. Indinavir is also called Crixivan. Ritonavir is also called Norvir. Why the dual names for these AIDS drugs? —— One is for patients, the other for doctors. ~ Companies and FDA couldn’t agree on names — Drug companies use multiple names to confuse the consumer a One is a company trademark, the other is generic (13) Typical drugs cross cell membranes in their form and bind to their enzyme target in their form. f ,, Ionized, non—ionized —— Non—ionized, ionized — + charged, — charged — Stable, unstable (14) A prodrug; — Is typically a highly polar form of a less actual drug — Is an active form that is converted into a non—active form in the body — Is typically an ionic form of a non—polar actual drug Is typically an inactive form of a drug, converted internally into the active form (15) Factors that should be taken into account when calculating the dose of a drug include: — Gender — Body weight — Wax Age — If) All of the above , «all (16) A drug company gets an IND approval from its new drug from the FDA. It is now: — Ready to start Phase II clinical trials fl Ready to start Phase I clinical trials — Ready to start toxicology studies in an animal model — Ready to sell the drug on the market (17) For the DNA sequence 5’—G—A—C—T—3’, the complementary 5’—X—Y—Z—W—3’ is: — —5’ —T—C—G—A’ —3’ ‘“ ' —5’ —A—G—T—C’ —3’ — ~5’ —A—C—G—T’ —3’ — —5’ —A—G—U—C’ —3’ (18) In small clinical trials of drugs A and B with the same number of patients, the difference between the means for drug and placebo groups was the same. However, the data for A gave a bigger ‘t” value than the data for B at the .05 probability level. This could be explained by: C/ Smaller spread (std. deviation) in data for drug A — Smaller spread (std.deviation) in data for drug B — More degrees of freedom in trial of drug A — Drug B has a more significant effect than drug A (19) The compound shown below contains: — Both an ether and an amine group —, Both a ketone and an ester group @ Both an amine and an acid group -— Both an alkene and an alcohol group (20) Key criterion/criteria for a patentable invention: — Novel — Useful a Novel and useful — Single inventor (21) Which one of the following amino acids is chiral H -—-OH H\\\\“" (22) T e weakest secondary type of bond found in proteins is: an der Waals (like—like bond) (25) Hydrogen bond Ionic bond Covalent S—S bond Comparing structural vs. globular proteins: globular proteins Are not water-soluble Never have diverse secondary structures Are typically catalysts Are found in human hair, wool and silk “Sulfa” antibiotics form a class of drug that act by: locking DNA synthesis by bacteria imicking a natural bacterial compound (antimetabolite, PABA) Punching a “hole” in bacterial membranes Inactivating a bacterial enzyme for cell wall synthesis l (I) o 0=T-—O 0 OH ‘f T 0:7—0 0 OH ‘1’ c O=I"-—-O 0 OH ‘I’ A O=T-O 0 OH w 3' and ’ gure above shows: DNA — curare — nevirapine —-" RNA (26/) The secondary immune response: — I I Makes possible what we call ‘being immune’ to a disease we already had — Helps us fight a disease for the first time — ls slower in reacting to infection than the primary immune response — All of the above are true In creating an ‘AIDS vaccine’ it is true that: Vaccine may not give long—term immunity due to virus mutation — Attenuated virus in vaccine is very unlikely to revert and cause the disease — An effective vaccine should be available in 1—2 years — Vaccinated people are likely to test ‘HIV-negative’ (28) The genetic code is based on a 3—base triplet, like A—A—A etc. Suppose the code were based on only 4 bases, then the maximum total number of codes is: (Remember, there are four bases: A, T, C, G): — 4 — 16 — 64 a 256 (29) “AIDS” stands for: — Acute Immune Deficiency Syndrome acquired Immune Deficiency Syndrome A uto Immune Deficiency Syndrome — Acquired Internal Disease from Sexual contact (30) In the reaction: CH3 CH3 + l/ } @l/ “C1 N —-——-—> H-N + c? \ \ l A ‘ 3 = a drug, HCl is the acid, A is the base — A is the acid, HCl is the base — B is the base, Cl is the acid 4 Both HCl and A are acids (31) A “single blind” study of a new drug means that: — Subjects but not doctors know who is receiving drug or placebo — Neither subjects nor doctors know who is receiving drug or placebo — “Both doctors and subjects know who is receiving drug or placebo 6/ Doctors but not subjects know who is receiving drug or placebo (32) An enzyme catalyzes break—down of proteins by cleaving the peptide CO-NH bond. The mechanism has several steps, one of which is shown in the figure below. According to the Figure the role of Ser OH group in this step is: — Form a hydrogen bond to the peptide NH group — Act as an acid to transfer a proton to the peptide — Act as a base to remove a proton from HIS, activating it @ Directly attack the peptide C=O bond (33) Drugs are mainly deactivated in the: — Kidney — Pancreas Blood Liver (34) Applying the Octet Rule for bonding, a correct structure is: 10 (35) (37) The formal charges in the molecule to the right are: 0+ C— O- O— C+ O— 0 zero C zero 0 zero 0+ C zero O+ The ELISA test detects: AIDS HIV viral DNA An antibody to p24, and HIV viral protein P24, an HIV viral protein The current number of people worldwide infected with HIV is about: _ 500,000 a 43,000,000 — 1,000,000,000 _ 1,500,000 (38) The picture shows t ._ ”V M.\ I . .- ‘ - :.., . 1. ‘h ' j», r.‘ - ,s t f i Y "um 'V'.‘\ 'N‘ v g; o c? . I i ‘ O ‘0 2:2; ’ 3 O I) ., .’ 'N. 1 . «3:9 Q: Q; s 5 o o u 1 ' 4-1 {‘7 m; 4? 7: .41.: 7; P” ,I’ a ELISA test results, dark = positive — Viral load test results, dark = positive — ELISA test results, light = positive — Western Blot test result, light = positive (39) The structure shows test results for: _. mi I " flaww P. z , , Wixf ._ “Wm em ‘ EU. 41.5 717ng 3‘ pr 3‘ 1,; 7' , v n‘e' "a — ELISA (tubes/dark bands = positive) a Western Blot (tubes/dark bands = positive) Western Blot (clear tubes = positive) — Viral DNA (clear tubes = positive) (40) Consider a population that is known to have a rate of 2HIV+ / 1000 persons. \The odds of being positive are about: L 1/500 1/ 100 — 1/5000 — 1/250 (41) See #40: The population is tested, using a test that gives 1% false positives, but detects all true positives. If someone tes’tpositive, the odds of being positive are now about: — 1/500 1/1 1 w 2 7' I Z [3 a J — \ I 0 4— .. — 1/6 7% / 7/ W l f “ - 5/6 /’L- - G (42) In #41 above, suppose it was found that the true rate of HIV+ incidence in the population was only 2/ 10,000. If someone tests positive, the odd of being positive are now: — About the same V 6 About 10X lower 7/ WI/ _ About 2% lower / fl [04¢ L 1 A, 57) — Slightly higher , r . /. 1 ‘ v/M a, ‘1 ,1 Z 3 > ,, ," a (43) The viral load test: I W :59 5 —/ Measures p24 levels (if? Measures viral RNA (or DNA) — Does not indicate response to anti—AIDS drugs — Is much less sensitive than the ELISA test (44) Current types of HIV drugs include: — Nucleoside RT inhibitors (NRTIs) 13 — Non—nucleoside RT inhibitors (NNRTIs) ——m \ Protease inhibitors \ — i All of the above (45) One statement is not true: — Pharmacokinetics studies are of drug uptake and elimination in the body — In any reaction, the change of energy = +energy(all bonds broken)—energy(all bonds made) a Ala—Leu—Gly defines the primary structure. of a small oligonucleotide — In a reaction A + B -) C + energy, Where k: rate constant and energy = AH, an added catalyst will increase k but not affect AH (46) The first anti—viral drugs were identified in the: ~ 1900’s — 1940’s 0 1980’s 1990’s (47) The picture illustrates: — Entry of HIV into a cell — Copying of HIV RNA into DNA in the cell Synthesis of HIV enzyme proteins in the cell Assembly of an HIV virion (virus particle) The structure shown (3TC) is most similar to: AZT A protease inhibitor — Nevirapine (NNRI) — Is not an AIDS drug — it is used against osteoporosis (49 AZT acts by: — Damaging Viral DNA — Blocking the enzyme responsible for making viral DNA — Blocking out Viral protease — Preventing the virus from entering the cell _..9 Dr. Khalsa told us that in the USA, HIV is currently spreading most rapidly: I In women — In heterosexual men — In hemophiliacs — In persons over the age of 80 15 BONUS QUESTION (+4 pts) Identify Tamiflu, a new anti—flu drug, by either its manufacturer o_r its site of action (how it inhibits the virus) g its structure. 16 ...
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