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Design and Synthesis of Novel Coumarin Derivatives as Quorum Sensing Inhibitors & Performing Click Chemistry Involving Lysozyme Protein and a Novel Synthetic Fluorecent Compound

Mansoori, Sirwan | 2019

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  1. Type of Document: M.Sc. Thesis
  2. Language: Farsi
  3. Document No: 51962 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Kalhor, Hamid Reza
  7. Abstract:
  8. Quorum Sensing is a cell-to-cell communication pr°Cess depending on cell concentration. Communication among bacterial cells °Ccurs through small molecular signals called autoinducers. The consequences of quorum sensing include the activation of pathogenic properties and activation of the gene for biofilm formation. Biofilms are aggregations of bacteria that adhere to surfaces through extracellular polymeric substances. Bacteria in the biofilm phase are much more resistant to antimicrobial agents than their free-swimming counterparts (i.e. the bacteria in planktonic form). In this study, first a series of coumarin derivatives were synthesized; but due to low solubility of the synthesized compounds in water, the biological assay was not performed. To solve the solubility problem, bioinformatics tools including molecular d°Cking, molecular dynamics, and DFT quantum calculations were used to design and synthesize the best compounds that interacted with LasR protein. The structures of the synthesized derivatives were confirmed by FT-IR spectroscopy, NMR spectroscopy, and crystallography. Finaly the quorum sensing inhibiting properties of some of synthesized compounds were examined against pseudomonas aeruginosa bacterium.In another study, a click chemistry reaction was examined for protein labeling. Click chemistry is a powerful tool for modification of DNA, proteins, and fluorescent labeling of biomolecule. Click chemistry is chosen as a bi°Conjugation reaction among various organic reactions due to its multiple advantages. In this study, a new fluorescent compound carboxy rhodamine, which containes a triple bond and azido acetic acid, was synthesized and the functional groups were identified by FT-IR. Moreover, the fluorescent compound was covalently attached to Hen Egg White (HEW) Lysozyme containing azido group using the Cu(I) catalyst and copper nan°Catalyst at room temperature. The click chemistry products was identified using SDS-PAGE
  9. Keywords:
  10. Quorum Sensing ; Biofilm ; Coumarin ; Simulation ; Click Chemistry ; Label ; Bioorthogonal Chemistry

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