This thesis describes the isolation, structure elucidation, and synthesis of natural products from marine cyanobacteria. A crude extract from a cyanobacterium collected in Curacao showed selective affinity for the dopamine D5 receptor in a screen against a panel of CNS receptors. Due to the high similarity of the D5 and D1 receptor, to date there are no known ligands that differentiate them. Attempts to purify the compound responsible for this affinity led to the isolation of the known compound caylobolide A. A second extract from a cyanobacterium collected in Panama underwent bioassay-guided fractionation and yielded the novel compound naranjamide, which showed activity against P. falciparum the protozoa responsible for malaria. Syntheses of naranjamide and its nonmethylated analog were attempted in order to verify the proposed structure and stereochemistry, as well as determine its mechanism of action.
","abstract_html":"<p>This thesis describes the isolation, structure elucidation, and synthesis of natural products from marine cyanobacteria. A crude extract from a cyanobacterium collected in Curacao showed selective affinity for the dopamine D<sub>5</sub> receptor in a screen against a panel of CNS receptors. Due to the high similarity of the D<sub>5</sub> and D<sub>1</sub> receptor, to date there are no known ligands that differentiate them. Attempts to purify the compound responsible for this affinity led to the isolation of the known compound caylobolide A. A second extract from a cyanobacterium collected in Panama underwent bioassay-guided fractionation and yielded the novel compound naranjamide, which showed activity against <em>P. falciparum</em> the protozoa responsible for malaria. Syntheses of naranjamide and its nonmethylated analog were attempted in order to verify the proposed structure and stereochemistry, as well as determine its mechanism of action.</p>","abstract_has_math":false,"creators":["Solomon, Keren"],"institution":null,"degree_name":"MS","degree_level":"Immediate Access","degree_discipline":"Medicinal Chemistry","degree_department":null,"school":null,"contributors":["Kevin Tidgewell","Aleem Gangjee","Marc Harrold","Jelena Janjic"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2020,"date_issued":"2020-08-08T07:00:00Z","date_published":"2020-08-08T07:00:00Z","updated_at":"2026-07-24T02:10:58Z","subjects":["medicinal chemistry","organic chemistry","cyanobacteria","synthesis","CNS","malaria","analytical chemistry","Marine Biology","Medicinal Chemistry and Pharmaceutics","Medicinal-Pharmaceutical Chemistry","Pharmacology"],"languages":["English"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://dsc.duq.edu/etd/1918","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Kevin Tidgewell","Aleem Gangjee","Marc Harrold","Jelena Janjic"]},{"key":"dc:creator","label":"Author","values":["Solomon, Keren"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2020-08-01T07:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Medicinal Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Immediate Access"]},{"key":"thesis:degree_name","label":"Degree Name","values":["MS"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["medicinal chemistry","organic chemistry","cyanobacteria","synthesis","CNS","malaria","analytical chemistry","Marine Biology","Medicinal Chemistry and Pharmaceutics","Medicinal-Pharmaceutical Chemistry","Pharmacology"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["English"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://dsc.duq.edu/etd/1918"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["This thesis describes the isolation, structure elucidation, and synthesis of natural products from marine cyanobacteria. A crude extract from a cyanobacterium collected in Curacao showed selective affinity for the dopamine D5 receptor in a screen against a panel of CNS receptors. Due to the high similarity of the D5 and D1 receptor, to date there are no known ligands that differentiate them. Attempts to purify the compound responsible for this affinity led to the isolation of the known compound caylobolide A. A second extract from a cyanobacterium collected in Panama underwent bioassay-guided fractionation and yielded the novel compound naranjamide, which showed activity against P. falciparum the protozoa responsible for malaria. Syntheses of naranjamide and its nonmethylated analog were attempted in order to verify the proposed structure and stereochemistry, as well as determine its mechanism of action.
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