Non-covalent interactions involving π-π stacking play an essential role in self-assembly and molecular recognition processes such as protein folding and DNA/RNA-protein selective recognition. The knowledge gained from these studies could provide insight into possible site recognition complexes, inhibiting or mimicking protein-protein or protein-DNA interactions. Based on molecular modeling as well as HOMO and LUMO energies, several chromophores were selected with a variety of ∆ε values (∆ε= |εHOMO,NAcTrp – εLUMO,chromophores|), high and low, to establish a correlating trend with the modeling and experimental data. The corresponding Pt(dien) compounds were synthesized and their ability to stack to N-acetyl tryptophan was evaluated by fluorescence quench experiments. Attaching a strong electron donating/withdrawing group or extending the π system of pyridine or thiazole by means of a benzene ring (quinoline and benzothiazole) was found to enhance the π-π interaction with N-acetyl tryptophan.
","abstract_html":"<p>Non-covalent interactions involving π-π stacking play an essential role in self-assembly and molecular recognition processes such as protein folding and DNA/RNA-protein selective recognition. The knowledge gained from these studies could provide insight into possible site recognition complexes, inhibiting or mimicking protein-protein or protein-DNA interactions. Based on molecular modeling as well as HOMO and LUMO energies, several chromophores were selected with a variety of ∆ε values (∆ε= |εHOMO,NAcTrp – εLUMO,chromophores|), high and low, to establish a correlating trend with the modeling and experimental data. The corresponding Pt(dien) compounds were synthesized and their ability to stack to N-acetyl tryptophan was evaluated by fluorescence quench experiments. Attaching a strong electron donating/withdrawing group or extending the π system of pyridine or thiazole by means of a benzene ring (quinoline and benzothiazole) was found to enhance the π-π interaction with N-acetyl tryptophan.</p>","abstract_has_math":false,"creators":["Bate, Aaron"],"institution":null,"degree_name":"Master of Science","degree_level":"Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Dr. Nicholas Farrell"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2009,"date_issued":"2009-01-01T08:00:00Z","date_published":"2009-01-01T08:00:00Z","updated_at":"2026-07-24T05:53:18Z","subjects":["Chemistry","Physical Sciences and Mathematics"],"languages":[],"rights":["© The Author"],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["https://scholarscompass.vcu.edu/etd/29"],"render_values":[{"text":"https://scholarscompass.vcu.edu/etd/29","href":"https://scholarscompass.vcu.edu/etd/29","code":true}]}]},"links":{"outbound_url":"https://doi.org/10.25772/E68W-ZM15","outbound_label":"DOI","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Dr. Nicholas Farrell"]},{"key":"dc:creator","label":"Author","values":["Bate, Aaron"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2014-12-11T08:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry","Physical Sciences and Mathematics"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:rights","label":"Dc Rights","values":["© The Author"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://doi.org/10.25772/E68W-ZM15","https://scholarscompass.vcu.edu/etd/29"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Non-covalent interactions involving π-π stacking play an essential role in self-assembly and molecular recognition processes such as protein folding and DNA/RNA-protein selective recognition. The knowledge gained from these studies could provide insight into possible site recognition complexes, inhibiting or mimicking protein-protein or protein-DNA interactions. Based on molecular modeling as well as HOMO and LUMO energies, several chromophores were selected with a variety of ∆ε values (∆ε= |εHOMO,NAcTrp – εLUMO,chromophores|), high and low, to establish a correlating trend with the modeling and experimental data. The corresponding Pt(dien) compounds were synthesized and their ability to stack to N-acetyl tryptophan was evaluated by fluorescence quench experiments. Attaching a strong electron donating/withdrawing group or extending the π system of pyridine or thiazole by means of a benzene ring (quinoline and benzothiazole) was found to enhance the π-π interaction with N-acetyl tryptophan.
"]},{"key":"dc:title","label":"Title","values":["NONCOVALENT INTERACTION OF PLATINUM PLANAR AMINE COMPOUNDS WITH TRYPTOPHAN: A STRATEGY TO INTERFERE WITH P53-MDM2 INTERACTIONS AND TARGETING RETROVIRAL ZN FINGER-DNA INTERACTION (HIV NCP7)"]}]}],"canonical_facts":{"dc:contributor":["Dr. Nicholas Farrell"],"dc:creator":["Bate, Aaron"],"dc:date.available":["2014-12-11T08:00:00Z"],"dc:description.abstract":["Non-covalent interactions involving π-π stacking play an essential role in self-assembly and molecular recognition processes such as protein folding and DNA/RNA-protein selective recognition. The knowledge gained from these studies could provide insight into possible site recognition complexes, inhibiting or mimicking protein-protein or protein-DNA interactions. Based on molecular modeling as well as HOMO and LUMO energies, several chromophores were selected with a variety of ∆ε values (∆ε= |εHOMO,NAcTrp – εLUMO,chromophores|), high and low, to establish a correlating trend with the modeling and experimental data. The corresponding Pt(dien) compounds were synthesized and their ability to stack to N-acetyl tryptophan was evaluated by fluorescence quench experiments. Attaching a strong electron donating/withdrawing group or extending the π system of pyridine or thiazole by means of a benzene ring (quinoline and benzothiazole) was found to enhance the π-π interaction with N-acetyl tryptophan.
"],"dc:identifier":["https://doi.org/10.25772/E68W-ZM15","https://scholarscompass.vcu.edu/etd/29"],"dc:rights":["© The Author"],"dc:subject":["Chemistry","Physical Sciences and Mathematics"],"dc:title":["NONCOVALENT INTERACTION OF PLATINUM PLANAR AMINE COMPOUNDS WITH TRYPTOPHAN: A STRATEGY TO INTERFERE WITH P53-MDM2 INTERACTIONS AND TARGETING RETROVIRAL ZN FINGER-DNA INTERACTION (HIV NCP7)"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Thesis"],"thesis:degree_name":["Master of Science"]},"updated_at":"2026-07-24T05:53:18Z"}