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Textbook Chem Bio - Chem 1AA3

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Pippa Lock

Chem 1AA3 Chemical Biology Queen Pheromone Blocks Aversive Learning In Young Worker Bees  Vergoz et al. Science (2007) 317:384-386  Queen mandibular pheromone (QMP) o Causes young workers to feed and groom her o Suppresses new queens, controls colony behaviour Biology of Brainwashing Bees  QMP contains homovanillyl alcohol (HVA) o HVA suppresses bad memories, but not good ones  Biological Role: o Mitigates unpleasant side effects of QMP  Significance o HVA lowers [dopamine] o Dopamine is associated with learning  Therapeutic Potential o High [dopamine] in some psychoses & schizophrenia o HVA-like molecules could be treatments BUT o Need high specificity  Attention deficit disorder & Parkinson’s disease are linked to low [dopamine]  Global suppression of [dopamine], or suppression in the wrong parts of the brain, could have undesired side effects  Key Concepts o Queen bees control worker bees memories using HVA o Help understanding human learning o Develop new therapeutics The Chemical Biology of Brainwashing Bees  How do we go from a biological phenomenon to the development of a new therapeutic agent?  1 new drug requires ~5000 failed compounds  Improving synthesis & accelerating assays facilitates drug discovery High-Throughput Screening  High-Throughput Screening (HTS_ o Fast way to assay for a complex biological response  2 Components: 1. A fast assay 2. Massively parallel assays  Instead of doing experiments on live bees, use dopamine-producing bee neural cells growing in cell culture  A fast, color-producing dopamine assay already exists  96 well microliter plates allow 96 simultaneous assays  Grow bee neural cells in wells of plates  Test for dopamine production  Some wells are used for standards and controls, others are for test compounds Chem 1AA3  Screening must be able to test thousands of compounds per day, therefore it must be automated using robots and microtiter plates  Grow neural cell cultures in 96-well plates, measure [dopamine] in response to test compounds  Key Concepts o High throughput assays that replicate complex biological phenomena o Require many compounds o Use microtiter plates o Highly automated  I Clicker Aromaticity (26)  One of the most notable features of HVA is that it is an aromatic compound, like benzene  Benzene looks like “cyclohexatriene” but does not behave like an alkene  Aromatic systems are very stable, less reactive than alkenes Chem 1AA3 Recognizing Aromatic Compounds:  Cyclic  Planar  All sp in ring o All the atoms (C, N, O) in the aromatic ring system are sp hybridized  Conjugation o Often see a pattern of alternating single & double bonds in line drawings o Not always completely followed for herteroaromatics or ions  Huckel 4n+2 rule o Aromatic systems have (4n + 2) π electrons, n = 0, 1, 2, 3 o A π electrons is an electron engages
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