203f03_final_key

203f03_final_key - ‘ Chemistry 203 Lg (Fall 2003) FINAL...

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Unformatted text preview: ‘ Chemistry 203 Lg (Fall 2003) FINAL EXAM Last Name: PM (34/6 December 11, 2003; 8:00 — 10:00 AM First Name: g l & ,_———-——-‘_ Social Security # T.A:CL1.VC€ZA 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 Points Student Signature CIRCLE THE MOST NEARLY CORRECT ANSWER FOR EACH QUESTION. (4 Pts.) (1) According to Dr. Khalsa, HIV has been traced back to: Congo, 1959 — New York, 1980’s — Canada, 1990’s —— London, 1970’s I? (2) A serious side—effect of some recent AIDS drugs (protease inhibitors) is: — Rashes — Bone tumors 9 Dangerously high cholesterol levels — Loss of short—term memory (3) HAART currently involves treating HIV infection using: — Two different protease inhibitors — Four drugs from different classes, used one—at-a—time (sequentially) Q One drug from each drug class (at least three) — 4-5 drugs from the same drug class (4) Dr. Khalsa emphasized that the time to progression to AIDS can be predicted by a patient’s: — CD4 (T—cell) count (lower count, longer progression) Q7 CD4 (T-cell) count (higher count, longer progression) — Viral load (lower count, faster progression) — Weight (thinner, faster progression) (5) Which statement related to HIV drug resistance is true? — HIV has a mutation rate of 1 — 3% per DNA copy — Omitting a few drug doses in combination therapy (10 — 20%) has no significant effect on treatment success 0 Drug resistance can be transmitted from one infected person to another — Degree of resistance to anti—HIV drugs per viral mutation is the same for all known drugs (6) — Viral load test result (bands = viral DNA) - ELISA test results (bands = antibodies) — Western Blot test results bands 2 viral RNA) — ‘ Western Blot test results (bands = viral proteins) (7) (8) (10) The picture shown illustrates: Cocaine hydrochloride is heated with a basic salt to form crack cocaine and sodium chloride. This makes a form of the drug that is more water soluble This makes a more hydrophobic (lipophilic) form of the drug This makes a form of the drug that will resist extraction into ether or hexane This makes a form of the drug that is less volatile An IND: Is not required by FDA for clinical trials of a new drug Approves use of a new drug in the clinic Is an approval for manufacture given by a drug company Summarizes chemical, biological, toxicological and pharmacological data of a drug candidate for clinical trials Which clinical trial is usually non—blind (subjects know what the drug is and who is getting it): Phase 11 Phase I Both Phases II and 111 Phase III A drug with an acidic group having a pKa of 4 Will have a + charge at pH 7 Will have a — charge at pH 7 Will have no charge at pH 7 Will not react with ammonia, NH3 (pKa of protonated form is 9) (9 (12) 9 (14) Q Zfi 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 The figure shows: . . . . o 0 ConverSIOn of pemcrllin prodrug to \C_: a X." 51 . a, s m V . . fi/ - s u. 1V 2 ————‘> act e form by an en yme $ij I} ml? min. Conversion of sulfa prodrug to active ° ‘W ‘w form by an enzyme Inactivation of penicillin by a resistance enzyme Inactivation of sulfanilide by a resistance enzyme Which step is NOT involved in an ELIZA AIDS test? An enzyme linked to an antigen specific for human antibody is added A colorless compound converted by an enzyme into a yellow product is added Infected patient’s p24 antibody (blood sample) binds to immobilized p24 Infected patient’s HIV DNA is amplified using the PCR technique The drug structure shown is: Ew—o—fi—O—Nw O Procaine, an anesthetic A nucleoside RT inhibitor An antibiotic A drug used to treat sleeping sickness The main problem facing drug therapy for HIV infection in the USA is: Drug resistance caused by rapid mutation of the virus No 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 (16) Saquinivir is also called Invirase. Indinavir is also called Crixivan. Ritonavir is also called Norvir. Why the dual names for these AIDS drugs? 0 One is a company trademark, the other is generic — One is for patients, the other for doctors. — Companies and FDA couldn’t agree on names — Different drug companies use different trademark names for the same drug (17) Consider a population that is known to have a rate of 2HIV+ /500 persons. The population is tested, using a test that gives .8% false positives, but detects all true positives. l omeone tests positive, the odds of being positive are about: ( f 1/3 — 2/3 — 1/250 — 3/250 (18) The compound shown is: H2N H — A naturally occurring amino acid a An effective drug vs. sleeping sickness that also removes facial hair — A toxic drug vs. sleeping sickness — A new AIDS drug (19) The picture illustrates: (20) Copying of HIV RNA into DNA in the cell Entry of HIV into a cell Assembly of an HIV virion (virus particle) Synthesis of HIV enzyme proteins in the cell The structure shown is: RU—486 A protease inhibitor Nevirapine (NNRTI) Not an AIDS drug — it is used against osteoporosis As we make an HIV test more sensitive, we get: Fewer false positives Fewer false negatives Both fewer false positives and false negatives Both more false positives and false negatives ‘ (22) Salvarsan was discovered by: — Gallo in the 1980’s — Fleming in the 1920’s @ Ehrlich in the 1900’s — Sheehan in the 1950’s (23) The primary source of “R & E” research funding to universities in the biosciences and medicine is: - Small start—up companies — Large drug companies — National Science Foundations (NSF) @ National Institutes of Health (NIH) (24) The key role of HIV in destroying the immune system seems to be: — HIV attacks Tm,r cells, impairing both Tkiller cell and B cell (antibody) production — HIV attacks B cells (antibody production) —— HIV kills liver cells 0 HIV attacks Thelper cells, impairing both Thelper cell and B cell (antibody) production 25) AIDS—linked disease (opportunistic infections) include: 9 Pneumocystis (pneumonia) — Gonorrhea — Yellow fever — Malaria (26) A patent is, once issued, is typically good: — Indefinitely — Until the death of the inventor 0 For roughly 15 years — For one year __————_————l (27) Hydrogen molecule (H—H) has a bond formation energy of —104 kcal/mole, and fluorine molecule (F-F), —38 kcal/mole. In the reaction: H2 + F2 -) 2HF, the AH is —130 kcal/mol. To convert 2H—F to 2H- + 2F- will require: — -71 kcal/mol — -272 kcal/mol — +71 kcal/mol @ +272 kcal/mol (28) An example of an amino acid having a polar side chain is: — Alanine —- Glycine — Valine < l Serine (29) A peptide with 9 units (nonapeptide), assuming any of the naturally occurring amino acids can occur at any position in the peptide, can have how many isomers? — 9 — 20 _ 920 o (30) The total number of chiral centers in the amino acid shown is: oHo ARLOH NH 2 WNF-‘O E) A (31) A small amount of a drug is added to an enzyme, and we analyze the effect using kinetics (Lineweaver—Burk plot). Vmax is unchanged but Km is increased. This suggests that the drug inhibits this enzyme: 9 Reversibly and competitively — Reversibly and non—competitively — Not at all —— Irreversibly (32) The weakest secondary type of bond found in proteins is: — Hydrogen bond 0 Van de Waals (like—like) bond — Covalent S-S bond — Ionic bond (33) A drug taken orally, to be effective, must: — Resist being absorbed by the gastrointestinal tract Q Resist stomach acid — Be rapidly decomposed by stomach acid — Be quickly broken down in the liver (34) Pharmacodynamics is concerned with: — Drug bioavailability — Drug metabolism — Drug distribution in tissues 9 Clinical response to a drug 35 Anthrax presents a biodefense hazard because: — There is no single—use vaccine that provides >99% protection — It is highly contagious — It does not form endospores like other bacteria — There is no known effective antibiotic (36) Nitrogen has atomic weight 14.00. The molecular weight of (N2) is: — 14 grams — 14 moles/ gram a 28 grams/ mole — 28 moles/ gram ( CH3CH20H is — Ethanol, active ingredient in booze — Methanol, a toxic alcohol — Methane (natural gas) — Isopropanol (rubbing alcohol) The amino acid sequence of a protein is defined as its @ Primary structure — Secondary structure — Tertiary structure — Alpha helical structure (39) In a large group of 1,000 HIV+ people, the average viral load was 200 (u) with a standard deviation (0) i 20. Use the table on the next page to estimate the probability of a patient having a viral load of a or higher. Answer: p: 1 0.005 ‘3’” Q 0.04 —— 0.16 — >0.29 (40) 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 / _ 0 1 —2 years 10 (41) ) Table 11.2 Percentage points 01 the standard normal distribution AREA TU RIGHT z SCDRE g‘gg b.86165 [LUIS 2.57563 (3431 2.32636 Luz 2.115376 u,a25 1.96Bflfl Lu: 1.35879 gm. 1.75369 1 5.05 1.6Lb85 (Lee 1.551.77 0.07 1.h7579 9.08 1.kfl5fl7 0.09 1.3hfl76 5.10 1.23155 U.11 1.22653 n.12 1.17h99 $.13 1.12639 (1.11. LUBUSZ 9.15 1.!36b3 G.16 9.99hh6 3.17 H.95417 $.13 H.915}? H.19 H.57795 H.25 B.8h162 9.21 0.8U6h2 U.22 H.77219 H.23 0.73865 [3.21. 12.7%” $.25 H.67hh9 U.26 $.6h335 H.27 H.61ZB1 $.28 9.5828L 8.29 H.55336 HIV stands for: Hepatic infective virus Health impairing Virus Human immunodeficiency virus Highly immunogenic virus A catalyst does what? Lowers reaction activation energy Increases reaction entropy Lowers total reaction energy Raises reaction activation energy Are- tabulated The most efficient path for HIV transmission: Needle stick (infected blood in syringe) Kissing (mouth to mouth) Air mist (coughing and sneezing) Blood transfusion (infected blood) 11 (47) When aspirin tablets decompose in the bottle, one product is: Acetic acid Morphine Acetic anydride Benzene Which disease is NOT caused by a virus: Hepatitis Genital warts Tuberculosis Small pox The valence of carbon is: 1 2 3 4 The structure shown below is: NH. acre-4,», 04,50,“ A protease inhibitor AZT LSD Aspirin 12 (48) In the picture of double-stranded DNA, circle the stronger of two possible base-recognition interactions (boxed) involving hydrogen bonds. (49) The drug action of AZT against HIV-infected cells is due to: — Inactivating RT, the enzyme needed for viral DNA replication — Blocking incorporation of viral DNA into host cell DNA —, _ Non—competitively inhibiting viral RT binding of DNA “T \ — Blocking viral DNA replication by preventing further addition of bases to viral DNA (50) Satisfying the octet rule, in the compound CH3CONH2 — The O atom has one nonbonding pair of electrons The N atom has one nonbonding pair of electrons — The O atom has a + charge, the N atom has a — charge — There are no double bonds Simplified Periodic Table 6 1 C N 12.0” It“? a I: I. I7 II Si Cl At am “A” 19.9.! DOUBLE BONUS QUESTION (8 pts) (a) Define “bisphosphonate” 0/7 ...
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203f03_final_key - ‘ Chemistry 203 Lg (Fall 2003) FINAL...

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