203final99 - LASTN{HAM CHEMISTRY 203 Lg(Fall-99 FINAL...

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Unformatted text preview: LASTN ; {HAM CHEMISTRY 203 Lg (Fall-99) FINAL EXAM :7 ”J FIR T NAME: I: '1 DEC. 16, 1999 2:00 pm-4:00 pm / so IAL SECURITY #..0..’..0..:4.‘<:49..0 PROF. CHARLES E. MCKENNA ""' /’ T.A: &; . (i; 114 Ir 5 4 / INITIAL OF LAST NAME Please do not open this exam until you are told to do so. GOOD LUCK ! ! prf ac:final99:"'0203L999 final CIRCLE THE MOST NEARLY CORRECT ANSWER FOR EACH QUESTION (4 PTS). 1. A body fluid has a [H”] (conc.of H*) = 10‘8 M. Its pH is: -6 -7 ® -10 2. A cell membrane typically - is a barrier to all non-polar molecules - has a polar hydrophilic interior Gas a hydrophilic surface — always freely passes ions like Na+ or Cl— 3. CHsCHZOH is: @n01, active ingredient of booze — methanol, a toxic alcohol — methane (natural gas) — isopropanol (rubbing alcohol) 4. The drawback of the original penicillin is: - very narrow antibacterial spectrum. —m part of it can be modified without loss of drug activity. @ne of the above - highly toxic. 5. Comparing viruses, bacteria: Cbgcteria are usually larger and more complex — antibiotics are effective against both - only bacteria cause epidemics — Viruses have thicker cell walls 6. HIV is termed a “retrovirus” because: - it incorporates the host’s DNA into its RNA @genetic RNA is transcribed “backwards” to DNA - it was discovered using retro-grade analysis - it “retro-fits” into the enzyme active site 7. Oxygen has atomic weight 16.00. The molecular weight of (02) is: - 16 grams — l6 moles/gram Cams/mole - 32 moles/gram 8. The key role of HIV in destroying the immune system seems to be: - HIV attacks Tm,“ cells, impairing both Tkiller cell and B cell (antibody) production. @ attacks Thelper cells, impairing both Tkiller cell and B cell (antibody) production. - HIV kills red blood cells. - HIV attacks B cells (antibody production). 9. AIDS-linked diseases (opportunistic infections) include: - herpes simplex — pneumocystis (pneumonia) - , .ingles a of the above 10. A patent is: — a right to use an invention. — license to use an invention — a onopoly on use of an invention. - all of the above. 11. i find a new method for making someone else’s patented drug. I can obtain: - a composition of matter patent. @process patent. - a use patent. - none of the above. 12. An example of a basic compound is: - ‘ - - -NH3 — R-COZH - HCl 13. The first step in HIV infection of a cell: — HIV RT copies viral RNA to DNA - HIV integrase inserts viral DNA into host cell DNA - V protease slices viral polyprotein into functional enzyme fragments gp120 surface protein recognizes host CD-4 membrane protein 14. The molecule shown is: HOCH, H ,-~“‘ H 1N >\COOH - thymidine, a nucleoside @rine, an amino acid — adenine, a DNA purine —— sequanavir, a protease inhibitor 15. For the DNA sequence 5’—A—G—C—T—3’, the complementary sequence 5'—X—Y—Z—W—3' is: - 5’—T—C—G—A‘—3 ’ A—G—C—T—3’ — 5’—A—G—G—C—3’ — 5’—A—G—C—U—3’ 16. HIV replicates: fl expressing its genes in the host cell genome, using the cell’s biochemical machinery - by expressing its genes separately from the host cell genome, using the cell’s biochemical machinery - by expressing its genes independently of the host cell genome, using viral biochemical machinery — outside the host cell 17. After infection with HIV, without treatment the time for progression to disease symptoms is usually. about: — 1-2 years — more than 20 years — a few months 18. Proteins consist of: - nucleosides linked by phosphate bonds @ more or more amino acids linked by peptide bonds — fewer than 5 amino acids linked by peptide bonds — nucleic acids linked by amide bonds 19. An enzyme protein in an aqueous environment (e.g., blood): — stretches out into a linear structure ads to move its hydrophobic R groups into its interior, while placing its ionic and polar groups on or near its surface - folds to move its ionic and polar groups into its interior, while placing its hydrophobic R groups on or near its surface — shows no preference in placing its R, ionic and polar groups 20. A small amount of a drug is added to an enzyme, and we analyze the effect using kinetics (Lineweaver—Burk plot). Vmax increases, Km is unchanged. This suggests that the drug inhibits the enzyme; / “’fi KC @versibly and non-competitively, or irreversibly M} Q — not at all — irreversibly but not non-competively , — reversibly and competitively lb 21. Once symptoms appear and an AIDS diagnosis is made, the average life left to an untreated patient is about: - a few months — 7-10 years — more than 20 years ( 1—2 years > 22. For acetic acid shown below, draw in all covalent bonds (use single lines) and unshared electrons (use double dots). Be sure your structure obeys the octet rule! 23. A drug taken orally, to be effective, should: - resist stomach acid - be readily absorbed by the gastrointestinal tract - be only slowly broken down in the liver of the above are true 24. In order to design a more effective drug, we might consider changing the parent drug structure’s - size - shape - olarity @of the above 25. For very large ranges of “P” vs. “C” data in phamacodynamics studies of a certain drug, we obtain the equation the log (l/C) = 2.1 log P — 0.2 log (P2) + 0.5 The equation predicts that a plot of log(1/C) vs. log P will: - be linear, positive slope - be linear, negative slope '2 bell—shaped curve, with both + and — slopes — be a hyperbola 26. A fly-by night company makes a new AIDS drug sloppily, specifying that the average amount (x) of drug/pill 1s 39.0 mg with a standard deviation (x): +10 mg. It 18 known that d__ouble the normal dose causes fatal side effects. 1&1? 0004000 patients take this drug once, how many3 are jl$<ely to be killed? (see “Z table” next page) [Recallz Z=(x-u)/cs]z ’ C If X Z "‘ //0 —none Fm" W x $le F 5.440,) __ fl/Oaaoof) : j—? 6 - about 2,400 X /0 27. A fimpany gets 1ND approval for its hot new drug from the FDA - r dy to start Phase I clinical trials - ready to start toxicology studies in an animal model - ready to sell the drug on the market - ready to start Phase HI clinical trials 28. Key difference in going from Phase I - Phase II clinical trials of an AIDS drug is: - Phase I, larger patient base - Phase II lookin for toxicity - Phase II, looking for efficacy - Phase I in usually a single—blind study Table 11.1 Area under the Standard Normal Curve Z .00 U .saaaw 1 .u6017 2 .h2u7a 3 .36289 G h .th58 8.5 .JBasa 3-6 .27u25 9-7 .2h196 8-8 .21186 0.9 .18h86 1.a .15555 1-1 .13557 1-2 .1159? 1 3 .Bessa 1-“ .BBG76 1-5 .flesei -6 .asuau .7 .Guu57 -6 .a3593 1-9 .a2572 2.8 .a2275 2-1 .a17ee -2 .a1390 .3 .a1u72 .0 .uaaza -5 .uaszi .6 .aauss 7 .aa3u7 8 .aazss 9 .aaie7 G .80135 1 .uaa97 2 .aausa 3 .Baeua h .awasu 5 .GGBZ) 6 .aaa15 7 .00011 2 .aa 7 9 . was .U1 .agsar .aseza .h1683 -.37523 .Jauga .zasns .27u93 .23355 .2B897 .16131 .15625 .13350 .1131b .u951n .07927 .asssz .as37a .auses .a3515 .azeav .u2222 .B1?h3 .81355 .B1aau .aa79a .ZBSBQ .aaus; .92335 .aazae .Ga181 .Bfi131 .Gflflgu .amnss .anauv .aez32 .uaazz .aaa1s .BGG1B .aaanv .aauas .GZ .LQZBZ .hSZZh .h129a .37Ab8 .3372a .3015) .2676) .23576 .2fl611 .17579 .15386 .13136 .1112} .893h2 .67780 .B6h26 .65262 .au272 .B3L35 .B27h3 .B2169 .017BU .u1321 .G1B17 .BB776 .aasa7 .BBLLB .BGJZS .BBZLG .Ga175 .aaizs .BBB9B .GBBEL .BBBhS .GBE31 .azazz .GGB1S .09919 .0989? .GGUUL .GJ .aeeas .hheze .LB9GS .37G7B .3336U .29606 .26h35 .23270 .2832? .17619 .15158 .1292b .10935 .39176 .57636 .863B1 .05155 .Bh182 .B3362 .B2680 .02118 .01659 .0128? .DB99B .BB755 .GB57U .BBQZ? .0031? .3823} .90169 .00122 .BBUB? .2936? .GBBLJ .BBB3U .BBBZ1 .BBG1L .99818 .BGUGE .BBBBA -M‘IIM 1 .0h .LBLBS .thI} .QBS17 .3669} .3299? .29h6fl .261fl9 .22965 .ZBBQS .17361 .1b91? .1271h .1M7h9 .69812 .27h93 .fl6178 .GSUSU .UL093 .B3288 .02619 .BZGEB .B1fi1fl .fl1255 .flfigfih .UB73h .UMSSA .flGh15 .GEJM? .GBZZS .Ufi1fiu .Ufl118 .GWGBS .BUUEB .UGBQZ .GGUZ? .BBUZM .UGB1L .GMUGQ .UMUGE .GBHBL .GS .aeaas .thJB .hfl129 .36317 .32636 .29116 .25785 .2266} .19766 .17166 .1h686 .1250? .1B565 .B5851 .3735} .06BS7 .Uh9b7 .BLBZS .83216 .82559 .BZB1B .u157n .01222 .M6939 .MG71A .60539 .GBLB) .BBZgfi .63219 .UM159 .BB11L .BBBBZ .ZBBSB .GGBLB .BBGZB .EBB19 .BEH13 .UBGMG .GBUES .UBGBL .06 .L76B6 .u3saa .397L3 .359h2 .J2276 .28774 .25h63 .2236} .19L89 .1685} .1AL57 .12382 .1018} .80691 .3721b .fl5938 .Gbflbfi .fl3928 .EJ1LL .UZSBB .U197B .fl1539 .51191 .UB91L .UWSGS .Ufifiz} .UM391 .UBZB? .BB212 .MUISu .MM111 .BBB79 .BBBSB .BBBJ9 .GBZZ? .BBB19 .wa15 .MBMUQ .MGGUE .anuu .G? .93 .09 .h721fl .h6612 .h6h1h .03251 .AZBSB .h2h65 .39358 .3897h .38591 .35569 .3519? .SLBZ? .31918 .}1561 .3128? .28b3b .28596 .27?GG .251b3 .ZQBZS .2h51B .22fl65 .217?B .21476 .19215 .189b3 .1867} .1660? .1635h .161fl9 .1L231 .1LBH? .13786 .121GB .119BB .117G2 .1BZBQ .1GU27 .8985} .8853h .U5379 .U8226 .07878 .fifigbb .06811 .BSBZl .957B5 .35592 .Bh7h6 .UbELB .Bh551 .83836 .B375h .0367} .8387b .UBBBS .02938 .BZth .32385 .6233B .fl1923 .B1876 .U1831 .M1SGW .H1LH}. .U1b2fi .0116“ .M113H .M11U1 .BMBBg .HGDGG .UUBhZ .UU676 .BMGS? .GUEB? .GBSG? .wuugu .BULBB .UU379 .UMJEB .0035? .GEZBB .MGZ?2 .GGZSA .BBZBS .UB199 .BB19} .091“? .Bfllhh .MH1I? .UM1B7 .MMth .MU1MM .BBU76 .HM67h .MUB71 .HGBSh .UMBSZ .GGGSU .GBUJB .89936 .UWBJS .UGGZB .GMBZS .BBBZL .BBU18 .GMH1? .MEU17 .UMGIZ .BMG12 .BMM11 .MUBQH .UUGUH .MUMUH .UUMGS .UUMUG .UUUUU .MUUBL .UMMUJ .MMUM) a. AW“...- . «mum. m 29. In two clinical trials A and B, A uses 50 patients, B uses 5 patients. We are looking for the / statistical significance of a certain toxic side effect that appears in a few patients in both WW / use the fata from B instead of A, we: (Hint: see table on next page.) W rease the value of “t”, the test statistic for a given “level of significance” of a result — decrease the value of “t”, the test statistic for a given “level of significance” of a result - don’t change the value of “t”, the test statistic for a given “level of significance” of a result - increase the degrees of freedom associated with our result 30. AIDS as a disease in the USA was first recognized in the: - early 50’s - early 60’s - earl 70’s ~ early 80’ 31. HIV stands for: @an immunodeficiency virus - health impairing virus - highly immunogenic virus - none of the above 32. The most efficient path for HIV transmission: @d transfusions (infected blood). — heterosexual intercourse (infected partner) - air mist (coughing or sneezing) - kissing (mouth to mouth). 33. A recommended procedure for HIV- testing to avoid false positives is: - initial Western Blot. - initial ELISA. @ISA; repeat; then if still positive, Western Blot. - Western Blot; repeat; then if still positive, ELISA. 34. The ELISA test for HIV involves three steps: A. patient’s anti—HIV p24 antibody (blood sample) binds to immobilized HIV p24 B. An enzyme linked to an antigen specific for human antibody is added. C. A colorless compound converted by this enzyme into a yellow product is added. The correct order of steps is: Tablo11.5 Percentage points for the tdistribution Area Area to the right Degrees of freedom. P 0.005 1 63.657 2 9.925 3 5.841 4 4.604 5 4. 2 6 3. O7 7 3.499 8 3.355 9 3.250 10 3.169 11 3.106 12 3.055 13 3.012 14 2.977 15 2.947 16 2.921 17 2,898 18 2.878 19 2.861 20 2.845 21 2.831 22 2.819 23 2.807 24 2.797 25 2.787 26 2,779 27 2.771 28 2.763 29 2.756 30 2.750 40 2.704 60 2.660 For larger values of u treat t as a z score and use the standard normal table. 10 35. Total cost of bringing a new AIDS drug to market, including development is about: - $2.5 M - $ on ~ $250,000 36. Key criterion/criteria for a patentable invention: - novel - usefu — single inventor 37. The key problem in distributing modern drugs to AIDS patients in many “third world” countries is: - lack of local drug manufacturing facilities — shortage of physicians to write prescriptions - lack of drug patent protection in those countries 'of licensing patented drugs 38. After exposure to HIV, taking AZT immediately on a daily basis for several months: — will delay AIDS for 5 - 10 years - will prevent getting AIDS provide protection against getting AIDS in a fe_w cases — has no benefit in preventing AIDS 39. What is a “mole”? — subterranean burrowing animal — individual within an intelligence agency who secretly works for a foreign agency ‘vogadro number (6.02 x 1023) of molecules — twice the number of molecules in 12.0 g of carbon 40. The drug action of AZT is due to: . inactivating RT, the enzyme eeded for viral DNA replication 69 stopping viral DNA redidation by preventing further addition of bases to new DNA strands. - incorporation of viral DNA into host cell DNA. — it§ blocking competitively inhibiting HIV protease ll 41. The active form of AZT is: - AZT monophosphate - AZT diphosphate @phosphate - as taken in the pill (nucleoside). 42. An unexpected (Khalsa) side effect of protease inhibitors is: fat deposits and high cholesterol. - baldness. - mental disorders - gum disease 43. The best current anti-HIV (AIDS) drug strategy (“HAART”): - one drug from each drug class (at least two) - two drugs from the same drug class. — three drugs from the same drug class. @g from each drug class ( at least three). 44. “Gene therapy”of AIDS could involve: — repairing “sick” genes — is a current basis of AIDS treatment - is about to emerge as a key new therapy @ently is only a conceptual therapy that may be years in the future 45. One statement is not true: - CH3C(=O)CH3 is a ketone - CHsNI-I2 is an amine - Glu—Lys—Gly defines the primary structure of a small peptide reaction A + B -> C + energy, where k = rate constant and energy = AH, an added catalyst will decrease k and increase AH O H‘N CH3 46. The AIDS drug structure shown is a //J\ l O N - rotease inhibitor HOW - nu eoside RT inhibitor .— — non-nucleoside RT inhibitor d4T (stavudine) — all of the above Zerit 12 47. Abacavl'r is also called Ziagen. Why the dual names for this AIDS drug? - ' is a company trademark, the other is generic - drug companies use multiple names to confuse the consumer - companies and FDA couldn’t agree on names. - one is for patients, the other for doctors. 48. HIV“viral loa ”: - measures capacity of virus to withstand mutations - measures anti-HIV antibody in the blood -ures amount of virus RNA in the blood — measures a drug’s breadth of action against different viruses 49. A drug that decreases “viral load” by “3 logs” has decreased the amount of Vvirus by 1 - 3 - 10 3O - LL 5 I The main problem facing drug therapy for HIV infection in the USA is.‘ a; resistance caused by rapid mutation of the virus - less than 2 lead compounds have entered clinical trials in the past two years - there are no rational targets for viral drug design - there are only 2 classes of AIDS drugs currently available 13 BONUS QUESTIONS (@4 pts): B 1. If an HIV test gives 1/25 false positives and the known rate of HIV infection among UCLA students is l/ 100, what are the odds that a UCLA student who tests positive ONCE is really HIV positive? Explain. (M 3W 9/ WWIHH \ L; W Lam/4a (/érX/{é 5 j 0 M W i a‘ g B2. Give two examples of ethical problems unique to the phenomenon of AIDS, & discuss BRIEFLY. fl w 373M; W15 0K> 14 ...
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