203f02_final_key

203f02_final_key - Chemistry 203 Lg(Fall 2002 FINAL EXAM...

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Unformatted text preview: Chemistry 203 Lg (Fall 2002) FINAL EXAM Last Name: \I f" Thurs. Dec. 12, 2002 First Name: 8:00 a.m.-10:00 a.m. Social Security # Professor 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! ! Maximum Question # Points Score _— __- I will observe the rules of Academic integrity while taking this exam. 1. i 3 L14? Student gnature CIRCLE THE MOST NEARLY CORRECT ANSWER FOR EACH QUESTION. (4 Pts.) (1) Since 1995, according to Dr. Khalsa, on average the number of new anti-HIV drugs approved by by the FDA per year has been: 0— 1 2-3 5-10 > 20 A serious side-effect of some recent AIDS drugs (protease inhibitors) is: Lymphoma Skin allergy Loss of short-term memory Lipodystrophy Per Dr. Khalsa, HAART stands for: Highly Active Anti-Retroviral Therapy Human Anti-AIDS Retroviral Therapy Honduran-American AIDS Research Training Humans Against Animal Research on Toxicity Dr. Khalsa emphasized that the time to progression to AIDS can be predicted by a patient’s: CD4 (T-cell) count (higher count, longer progression) CD4 (T-cell) count (lower count, longer progression) Age at HIV infection Viral load (lower count, faster progression) In the USA, among young people, the number of HIV-positives who do not know their status (never tested) is about: 5% 10% 33-50% 95% (6) (8) The ELISA “AIDS test” detects: An HIV antigen An antibody to HIV HIV RNA HIV DNA The picture shown illustrates: ELISA test results (bands = antibodies) Viral Load test result (bands = viral DNA) Western Blot test results (bands = viral proteins) Western Blot test results bands = viral RNA) Suppose among 100,000 persons, 1,000 are HIV+. One takes an “AIDS” test that is 99% accurate (1% false positives) and gets a positive result. The chance this person is really positive is about: 1 % 5% 50% 99% AZT as a single drug is still used : To protect an unborn child from HIV transmission if the mother is HIV+ Widely in most US. AIDS clinics To treat many cancers To treat herpes infections In the picture shown, “B” represents: Chymotrypsin W; I‘__‘° HIV Integrase 7‘ mm-w...“ HIV R tr ' t HIV 150:2: mp 9 ° 9 5 Ammmh—umwum (11) New anti-AIDS drug therapy under active development aims at: Blocking synthesis of the virus cell wall Blocking fusion of the virus to its target cell Blocking integration of viral genes into the host cell genome Both of the above An IND: Approves use of a new drug in the clinic Is not always required by FDA for clinical trials of a new drug Summarizes chemical, biological, toxicological and pharmacological data of a drug candidate for clinical trials Is an approval for manufacture given by a drug company Which clinical trial is usually non-blind (subjects know what the drug is and who is getting it): Phase I Phase II Phase III Both Phases II and III A Phase III trial may require: 100-300 healthy volunteers to verify drug safety 100-300 patients to verify drug effectiveness 1,000-3,000 healthy volunteers to verify drug safety LOGO-3,000 patients to verify drug effectiveness To be considered “HIV-free,” a person who has a known risk factor should: Have two negative HIV tests over a period of 6 months Should have one negative HIV test Should have three negative HIV tests separated by one week each Should have two or more HIV tests on the same day (16) A patent is NOT: Published after issue, until it first expires @ A right to use an invention — Invalid 5 years after it is issued — Invalidated if the discovery was made public before the patent is filed (17) Drug resistance by the HIV virus is due to : —— Random changes in the viral RNA sugar (ribose)-phosphate backbone @ Random changes in the viral RNA genome — Random changes in the host cell DNA genome — Random changes in the drug structure caused by viral enzymes HIV causes collapse of the immune system by attacking: Antibodies T4 helper cells, which coordinate the immune response Phagocytes — Antibody-producing B cells (19) The compound shown is an example of a drug first discovered by: — The impetus given to anti-viral research in the 19905 andom screening of many compounds , erendipity (chance discovery) Computer design based on target enzyme structure (20) In the list below, the newest type of AIDS drug used in the clinic (Dr. Khalsa) is: — NRTIs — NNRTIs PIs NtRTIs (22) Anthrax is A new disease first appearing in 2001 Caused by a Virus Caused by a bacterium Highly contagious In a bond-breaking process like: H—H —> 2H The reaction happens more slowly at higher temperatures The product (2H atoms) is more stable than the starting material (H2) Energy must be supplied Energy is released Comparing structural vs. globular proteins: structural proteins: Have more diverse, non-repeating primary and secondary structures Are water—soluble 6 Are found in human hair, wool and silk Are typically catalysts (25) Protein folding in water solutions: Places non-polar groups in the interior of the protein Places polar and charged groups in the interior of the protein Determines the primary structure of the protein Places non-polar groups on the surface of the protein Applying the Octet Rule and using the periodic table info (last page), in the nitro group shown to the right: Nitrogen has formal charge +1, oxygen A has +1, oxygen B has —1 Nitrogen has formal charge 0, oxygens A, B have formal charge 0 Nitrogen has formal charge +1, oxygen A has 0, oxygen B has —1 Nitrogen has formal charge —1, oxygens A, B have formal charge +1 3b; A _N . .‘o: B (26) The picture shows, within a protein: — A Van der Waals (weak like-like) bond formation within a protein — Formation of a Ser—Ser peptide bond within a protein — Base pairing in DNA 0 Formation of a covalent Cys-Cys bond within a protein (27) A severe worldwide epidemic that decreased the average US life expectancy in 1919— 1920 was caused by : Q Influenza — Bubonic Plague — Cholera — Smallpox 2 The drug molecule shown is: fifiontosil (sulfa prodrug) ~ 0 _ Sulfanilamide (sulfa drug) Hat—QM NQ§_NHZ — Salvarsan (anti-syphilis drug) 0 NH — L-DOPA (for Parkinson’s disease) 2 (29) Neutral water has a pH value of: (30) Which compound is the least polar: — CH3OH — NH3 — HF Carbon has atomic weight 12.01 and hydrogen, 1.00 The molecular weight of (C2H4): 28 grams 13 grams/mole 28 moles/ gram 28 grams/mole I find a new way of making someone else’s patented drug. I can obtain: A use patent A composition of matter patent A process patent All of the above Two amino acids X and Y are joined together via a —C(O)NH— bond to make a new compound X-Y. This compound is: o Ser-Gly HzN-(IJI-KHD-OH 9 9H2 Phe-Lys ”ZN—3:30” 3:: Cys-Asp Q $32 Tyr-Arg X Y The drug shown, MDMA (known as ‘ecstasy’) does NOT contain which group? amine O ether > ketone CHSN O benzene Immunity to an infectious disease is provided by the: Primary immune response Secondary immune repsonse T8 cells (killer T cells) Red blood cells (erythrocytes) (37) A drug taken orally, to be effective, must: Be absorbed by the gastrointestinal tract Decompose rapidly at low pH Be very rapidly excreted via the kidney Be very rapidly broken down in the liver A fly-by-night company makes a new AIDS drug cheaply, but weighs its doses sloppily, specifying that the average amount it of drug/pill is 1,000 mg with a standard deviation 0 = 500 mg. It is known that double the normal dose causes fatal side effects. If 10,000 patients take this drug once, how many are likely to be killed? (See “Z” table, last page): None 2-3 200-250 ~5,000 In a drug trial, the control group showed a viral load of 400.0 (= pt) and the group treated with a new drug showed a viral load of 397.4. “N” = 16, sample std. dev. “s” = 4. The chance that this slight decrease is real, based on the “t” table (See “t” table, last page) is: 5% 1% 97.5% 99% HIV stands for: Human immunoabsorbent virus Health impairing virus Highly immunogenic virus Human immunodeficiency virus Triple-combination therapy vs. HIV (AIDS): Can reduce virus levels by about one “log” Can reduce virus levels by about two “logs” Can reduce virus levels by about three “logs” Can cure HIV infections after 24—36 months of uninterrupted treatment 9 (41) The first step in HIV infection of a cell: — HIV RT copies Viral RNA to DNA — HIV integrase inserts viral DNA in to host cell DNA — Host cell synthesizes viral RNA and viral proteins 0 HIV gp120 recognizes host cell CD4 protein (42) For the RNA sequence 5 ’—C—U-—A—G—3 ’, the complementary DNA sequence 5 ’ —Y—Z—W—3 ’ is: —‘ 5’—C—T—A—G—3’ — 5’—G—A—U—C—3’ — 5’—G—A—T—C—3’ — 5’—C—U—A—G—3’ (43) Aspirin has the following drug effect(s) : — Analgesic — Antipyretic — ‘. Prevents heart attacks (anticoagulent) ()All of the above (44) A small amount of a drug is added to an enzyme, and we analyze the effect using kinetics (Michaelis-Menten or Lineweaver-Burk plot). me increases, Km is unchanged. This suggests that the drug inhibits the enzyme: if) Reversibly and non-competitively, or irreversibly — Irreversibly — Reversibly and competitively — Reversibly and non-competitively (45) The most expensive part of drug development — Chemical synthesis — Pharmacology — nimal testing for toxic effects “,1; A uman clinical trials ’ 10 (46) To design a more effective drug, the chemist may change the parent drug structure’s - Size - Shape - Polarity a All of the above (47) Key criterion/criteria for a patentable invention: — Novel — Useful — Novel and useful Single inventor (48) Imagine a drug, RNH2 which is a white powder; R is a non-polar group. I put 100 mL of neutral water and 100 mL of hexane in a flask, add the drug and shake. I separate the water A and hexane B phases. Now I add fresh hexane C to A and (fresh water + HCl), D to B, shake both, and re-separate all four phases. I should now find my drug in which phase? — A — B — C 9 D (49) The term “molar” (M) refers to: — Large tooth used for chewing — Spanish word for dark pigmentation on the skin am An Avogadro number (6.02 x 1023) of molecules —/ The number of moles of a compound dissolved in a liter of water (50) The active form of AZT is — AZT monophosphate 3 AZTdiphosphate 4 2 AZT triphosphate I i — As taken in the pill (nucleoside) 11 DOUBLE BONUS QUESTION (i) a) For up to 2 points, give two examples of ethical dilemmas posed by the phenomenon of AIDS ‘2“ 1‘33 W i 3 k Ks} b) For up to 2 points, name the co-discovcrers of HIV/AIDS (ii) For up to 4 points, give either the generic or the trademark name of four different AIDS anti-HIV drugs currently used in the clinic (except AZT); or else draw the structure of fly m drug correctly. lekfll Patccmaoe perms a! m. standard normal dismbuuon AREA TD RIGHT Z SCORE m.au l.lfl§ 6.81 H.02 H.025 H.03 a.flk U.fl5 U.U& U.fl7 U.UB U.U9 H.1U u.11 U.12 H.13 n.1u U.15 0.16 0.17 n.1e H.19 U.ZU fl.21 v.22 u.23 F.2h H.25 ¢.26 H.27 0.26 0.29 n.561fia 2.57553 2.32636 2.u5376 1.96Bflfl 1.58a79 1.75369 1.6hb85 1.55L77 1.47579 1-hfl507 1.3aa76 1.25155 1.22653 1.17h99 1.12639 1.fl8032 1.8}6h3 H.99hus H.95h17 H.91537 H.5779fi B.eb1sz 0.5fl6h2 H.77z19 H.73555 n.7u630 H.67uu9 8.6h335 B.61281 H.5826h H.55338 Reference Page (Please Detach) Mu maul-Ina Note that in this equation we are taking ‘ Tum ".5 Nmmm calm: Io! In. I dutnbuuon 26 Fm Inger um: o! n max I as a 1 score and us. I». snndud normal tame Simplified Periodic Table IA! 29m [In 133 318: IISZ 2776 2015 1571 Ian 2u7 IM 2% 1w) 2“ 1833 , 2m IBM 733 115 1m1 luv 1|79 \TIl 2.!60 1m! 2M5 17m Zlm 17w 21x 11w zno 17M Zlm 17m LEE 1ns 2am In! La» l7l7 1074 1n4 * 1&3 I7n 2a; In! zap 1705 ZCEJG 17m 1 2052 1m! - 10w 1699 HMS A:- Alu 10 IN nqm X’ as ‘x-bar’, the sample mean value. 14 ...
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