203f04_final_key

203f04_final_key - \t, / Chemistry 203 Lg (Fall 2004) FINAL...

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Unformatted text preview: \t, / Chemistry 203 Lg (Fall 2004) FINAL EXAM Last Name:_‘:*_74__ Tuesday Dec. 14, 2004 First Name: 8:00 a.m.—10:00 a.m. USC I'D. # f, _r+ Professor Charles E. McKenna Professor Amy M. Barrios Please do not open this exam until you are told to do so. Write legibly to avoid confusion. GOOD LUCK ! ! I will observe the rules of Academic integrity while taking this exam. .9 ,x 5’ .5 in»: A» tea-M“ W— Studen} $1 gnature (1‘ 35,3 (1) (4 pts total) List four ethical issues discussed in class related to AIDS, drug development or therapy: (3) AW]; fibpw ds‘smmd W: 12:13; 25‘ wk? $.3ng iii/1W1: W leNZ 0’) E‘S'S‘M‘ diswswg gal/liar m Hu— rmm’w. Wflwflplfl lndUcUI Animals MW} (e) Wis/Em” Ywfifi mh‘m Cpl/‘fidwfiflfliy a? is? Wallis digit/i'mmh'm (game ilk» wi’w ifin POSHWt Edward“ {Emmi 33w HW 'i‘fifi! W Minva “56165320 Msi'lilg mmiah‘tg + abh'w. H W (d) VL’AMWfim MAME? $360pr 33w? jauflh'v‘c galaaiaw {ll pmh‘enhc :‘m elm/15 mm W ‘ ‘fi i ' V . s Wm M '20:» mm meran km" Ll; 1/"?in CIRCLE THE MOST NEARLY CORRECT ANSWER FOR EACH QUESTION. (4 Pts.) (2) Which COVALENT bond below will be the most POLAR? — Na+Cl‘ — H—H — C—F — C—S (3) Since 1987, according to Dr. Khalsa, the total number of new anti-HIV drugs approved by the FDA has been: _ 34 - ilk 6.23% — > 100 (4) A serious side—effect of AZT is: ( frw’NEuropathy 3 -— Lymphoma — Lipodystrophy — Loss of short—term memory (5) Per Dr. Khalsa, film /”‘"’w W . . ( — ‘_I‘-Iighly Ac_t1ve Ant1—Retrov1ral Thelng — Human Anti-AIDS Retroviral Therapy — Honduran—American AIDS Research Training — Humans Against Animal Research on Toxicity (6) Dr. Khalsa emphasized that the rate of progression to AIDS can be predicted by a patient’s: — CD4 (T—cell) count (lower count, longer progression) _ CWLDsgunLLhighercouanhonerflogression) ii: <Vira1 load (higher count, faster progression D — Age at HIV infection (7) The amino acid sequence of a protein is: - Secondary structure - Tertiary structure — Quaternary structure (8) The picture shown illustrates: - ELISA test results (bands = antibodies) __ Viral Load test resyltflands = yiralQM)\ C Western Blot test results (bands = viral proteinsD — Western Blot test results (bands 2 viral RNA) (9) Suppose among 100,000 persons, 500 are HIV+. If a person takes an “AIDS” test that is 995% accurate (0.5% false positives) and gets a positive result, the chance of this person really being positive is about: - 0.5% —— 9% _ —— 99% (10) In the picture shown, “E” represents: — Chymotrypsin ‘ l I ‘ 3 — HIV Integrase W MOI WW II W W" m — HIV Reverse transcriptase //« ejm@ eeaa Ammmmwmmam géfir“??? (11) The primary source of “R & E” research funding to universities in the biosciences and medicine is: — Large drug companies — Small start-up companies W (—. National Instltutes of Health (NIH) fix -— National Science Foundations (NSF) (12) A double-blind clinical trial is one in which: M — Physicians and subjects all know who got drug, who got p ace 0 —— Only subjects know who got drug, who got placebo — Only physicians know who got drug, who got placebo (13) AIDS—linked diseases (opportunistic infections) include: — Varicella é Cytomegalovirus including CMV-retinitib —- Osteoporosis — All of the above (14) The most efficient path for HIV transmission: — Kissing (mouth to mouth) - Needle stick (infected blood in syringe) (5* Blood transfusio.n~(infected 1310? M - Air mist (coughing and sneezing) (15) The structure shown below is: a; — Penicillin —- 3TC, an NRTI — Indinavir, a protease inhibitor —— Nevirapine, an NNRTI (16) Once symptoms appear and an AIDS diagnosis is made, the average life left to the untreated patient is: ~ A few weeks I'm Qut 18 months } — 7-10 years — More than 20 years (17) Key difference in going from Phase I to Phase II clinical trials of an AIDS drug is: — Phase 11, looking for toxicity — Phase I, larger patient base — Phase I is usually a single-blind study /’ .rrm Q Phase II, looking for efficacy) ——.._.__. (18) Drug resistance by the HIV virus is due to: M ,____.,._._ {m Random challgss in th. LQW -— Random changes in the viral RNA sugar (ribose)—phosphate backbone —- Random changes in the drug structure caused by viral enzymes — Random changes in the host cell DNA genome (19) The compound shown is an example of a drug first discovered by: — The impetus given to anti—viral research in the 1990s 0 II — Random screening of many compounds R/C\NH W______.i__’ 6’ Serendipity (chance disggygfl/ — Analogy with the structure of another AIDS drug (20) Anthrax is: — Caused by a virus — A new disease first appearing in 2001 * Higflw (- Caused by a bacieriury ‘\._‘ M, —— (21) As we make an HIV test more sensitive, we get: - Fewer false positives / /~’—""‘~'T"~"\ C Fewer false negatives ; — Both fewer false positives and false negatives — Both more false positives and false negatives (2'21 “Sulfa” antibiotics form a class of drug that act by: E Mimicking a natural bacterial compound (antimetabolite, PABAD — Blocking DNA synthesis by bacteria — Inactivating a bacterial enzyme for cell wall synthesis — Punching a “hole” in bacterial membranes (23) A drug taken orally, to be effective, must: — Be readily absorbed by the gastrointestinal tract — Resist stomach acid — l3£only slowly broken down in the liver All of the above are true (24) The ELISA test for HIV involves three steps: a) A colorless compound converted by an enzyme into a yellow product is added. b) An enzyme linked to an antigen specific for human antibody is added. c) Patient’s anti—HIV p24 antibody (blood sample) binds to immobilized HIV p24. The correct sequence is: — CBA \ - BCA — ABC — CAB (25) A cell membrane: — Has a polar hydrophilic interior -— Is a barrier to all non-polar molecules -— Always freely passes ions like Na” or Cl E” I Has a hydrophilic surface j “W -H__~‘_.‘_’/ (26) HIV is termed a “retrovirus” because: — it “retro-fits” into the enzyme active site —— it incorporates the host’s DNAinLQfiRNAMNV‘ “\ (— its genetic RNA is transcribed “backwards” to DNA — it was discovered using retro-grade analysis (27) A series of drug analogs X, Y and Z showed partition coefficient (P) values of: X = 10; Y = 1; Z = 0.1. The effective concentrations (C) for activity were, X = 0.01; Y = 1; Z = 100. This result shows that: — a more hydrophilic analog has more activity .M fl‘ a more hydrophobic anglgghas more ~— ‘ hydrophobicity of the drugs does not effect their activity —- a plot of log (1/C) vs. log P will have a negative slope (28) A company makes a new AIDS drug carelessly, specifying that the average amount p. of drug/pill is 100.0 mg with a standard deviation 0 = 57 mg. It is known that increasing the normal dose by 100% causes fatal side effects. In a clinical trial where only 1,000 patients take this drug once, how many are likely to be killed? (See “Z table”, last page.) -— ~500 ,A pm—N w? — <5 - 110116 (29) A sample of 26 patients receiving a drug shows a 5% decrease in average viral load (control 2 200) with sample standard deviation = 20.5. The probability that the decrease is NOT “real” is about: — 99% — 5% f... G 1%)“ — 0.5% (3 ) AIDS as a disease in the USA was first recognized in the: “M ____ ,/ — early 70’s — early 60’s — early 50’s (31) In the diagram of HIV shown: —— C 2 viral RNA, D = target cell receptors r/r— w ' \ C — B 2 viral RNA, C = viral enzymes \\3. \ maw...-_.. '\—_ «a, _-.,.._,_.____.#-__.a-_ — D 2 protein envelope, A = viral RNA —— A = cell wall, E = viral enzymes (32) In the reaction: H2 -) H '+ H' — The enthalpy is positive, the entropy is negative 6 The enthalpy is positive, the entropy is positive \‘ — The enthalpy is negative, the entropy is positive — The enthalpy is negative, the entropy is negative Note: enthalpy 2 AH entropy = AS (33) éwmggdated by: fl Pharmacological effectgfi — . Chemical structure - Site of action - Target system (34) A drug has LD50 = 0.001 g and effective dose ED50 = 0.0000001 g. Its therapeutic index is: — 0.1 -— 10 — 0.0001 (35) A drug has LDSO = 0.1 mg/Kg in human beings. Assume an average weight of 60 Kg. An « accidental dose of 25 mg (about 1/10 the size of one aspirin tablet) will be fatal to: Q > 1/2 the people dosed ) —— Exactly 1/2 the people dosed —- < 1/2 the people dosed — None of the people dosed (36) “pH” is defined as: — grams HJr per liter of water ‘ 10” WEIELWBIEL 911i: 7/ “FEMS the 10% — acidic if its value is above 7 in water 10 (37) An amino acid has equilibria in water (R = CH3): + + .. swam-00,11 = "HR—603 + H‘ + .. "’ v Hart—011m W 4- H At pH = 7, the average total charge of the amino acid is: ":1.-- (QWQ/ — —1 — —2 (38) y The drug shown is:. A? G (39) Heroin, a prodrug of morphine/r "5 Morphine Ecstasy (MDMA) Cocaine The secondary immune response: Is complete within minutes of an infection Helps us fight a disease for the first time All olfuthe above—are true Which of the diseases listed below is NOT caused by a virus? AIDS he ~ - —~—‘A—--\ Malaria: Polio Hepatitis 11 mph-4 (2)1)!“ =10 dig/lakes possible what we call “Being imrriunegto—a disease we—alreadfiad“ (41) What does a catalyst such as an enzyme do? — Decreases the free energy of a reaction C: Decreases the activation energy of a reaction > — Increases the activation energy of a reaction — None of the above (42) If the influenza season in 2004—2005 is like the influenza epidemic of 1918-1919: -— The mortality rate would be 100% —- There would be ve ' .Europe.~*% ,,,,, _____m 1/( H. /-’—’ A “ ’ pattern of mortality would be observed (young children, young Mum Q~.M_.___gl_d_er people‘viould all be at risk) // — The current stock of flu vaccine would be enough to protect everyone in the US (43) In reversible, non-competitive enzyme inhibition: — Inhibitor binds to the enzyme only in the active site, preventing substrate from binding — Inhibitor covalently bonds to the enzyme away from the active site — An increagWWsult in a decrease in rate of the reaction (inhibitor binds to the active site and also away fW (44) The drug Practolol (on the right) contains: — An amide and a secondary amine H — A benzene ring and an ether —— A chiral carbon and an alcohol _7\ —- All of the above/" “T O (45) Which NEUTRAL compound is NOT stable according to valence rules? — LiH — BH3 — H20 (46) The molecular shape of a boron atom with 3 things bound to it (for example, BF3) can best be described as: — ramidal — Trigonal Planar ’\3 (47) Tetrahedral Linear Which ion has an octet of electrons in its outer shell? :flflli’: Q My; — F“ (48) Ar“ Which definition below is INCORRECT? ydrophllic 2 water avouiin/g‘l (49) Non—polar covalent bond : bond between two atoms of the same element Electronegative = element that readin accepts an electron Chiral = a compound not superimposable on its mirror image Which metal is the most electropositive and will react the most violently with water? Li Na (50) What are the criteria for obtaining a patent on an invention? Invention must be non-obvious but need not have utility Invention must be not be previously copyrighted or trademarked Invention must be useful, but could be obvious (we Invention must be useful and non-glyng 13 BONUS QUESTIONS (i) Possible 4 points. An enzyme has Km = 0.1 M and Vm = 10 rnin‘1 for a substrate S. Construct (just sketch freehand) a Michelis—Menten plot (V vs. S) that defines Km (put in x—axis and y—axis scale) and Vm/2 graphically. Sketch the corresponding Lineweaver—Burk plot, defining l/Km and l/Vm graphically. ,. \{v V m s k); ~ - - h i _ __ _ I 2 / ! ' \rm {2- // ,// x l ,i Q / / W (VV‘ 9‘- . . , , _ - V/ // «=- g‘ / W“ ; / lbw?" l / \l ,// (ii) . . Enzyme active site Possnble 4 pomts As a medicinal chemist, you are asked to design a drug to bind in the active site of the enzyme shown below. Name at least two kinds of interactions you could use (2 points) and name at least two specific functional groups that would provide the desired interactions (2 points). W = hydrophobic group l'n’fflrfldlvfls ‘- Functional 3mm“ '. H ~ W4 3 x (doubt l'am'u Cm”? ’d’lmaL} :1me Van dermal: L‘vydwfiw'é “Mew mam, male}: 144%?) av. 14 120nm ring ...
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This note was uploaded on 07/22/2008 for the course CHEM 203Lxg taught by Professor Mc kenna during the Fall '07 term at USC.

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203f04_final_key - \t, / Chemistry 203 Lg (Fall 2004) FINAL...

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