{"id":{"repo_id":"brock","oai_identifier":"oai:brocku.scholaris.ca:10464/15612"},"canonical_url":"https://search.dev.ndltd.org/etd/brock/oai:brocku.scholaris.ca:10464/15612","repository":{"repo_id":"brock","name":"Brock University","base_url":"https://brocku.scholaris.ca/server/oai/request"},"display":{"title":"(A). Regulation of B-/Z-DNA transition in modified oligonucleotides; (B). Synthesis of cationic BODIPY analogues for antimicrobial and anticancer applications","abstract":"A. In this work, LNA-dG was incorporated into d(CG)6 sequence in a site-specific manner through the phosphoramidite chemistry-based solid phase synthesis to investigate the impact of this modification on the B→Z-DNA transition. Circular dichroism study showed that the incorporation of a single LNA-dG unit into d(CG)6 at internal positions virtually suppressed Z-DNA formation at 4 M NaCl concentration, whereas the presence of single LNA-dG unit towards the terminal ends showed only partially inhibition of B→Z-DNA transition. To further understand the influence of chemical modification on B→Z-DNA transition, modification at C8-position on LNA-dG residue was explored. Towards this goal, compounds such as 8-bromo-5′-dimethoxytrityl-N-dimethylformamidine-(2′-O,4′-C-methylene)-guanosine-3′-O-(2-cyanoethyl)-N,N-diisopropy phosphoramidite and 8-bromo-2′-deoxy-5′-O-dimethoxy-N-[(dimethylamino)methylene]-2′-fluoroguanosine-3′-O-(2-cyanoethyl)-N,N-diisopropyl phosphoramidite were synthesized. B. In this study, N,N,N-trimethyl-2-(4,4-difluoro-2,6-diiodo-4-bora-3a,4a-diaza-s-indacen-8-yl) ethylammonium iodide 111 was successfully synthesized. Singlet oxygen generation experiments suggested that BODIPY 111 is ~2.5 times more efficient with respect to Rose Bengal (RB) in generating singlet oxygen. However, based on the cell-culture experiment, BODIPY 111 treated culture plates showed only slight reduction in CFUs compared to Rose Bengal and control plates. BODIPY compounds 107 (iodinated-fluoro-BODIPY), 130 (brominated-fluoro-BODIPY) and 110 (brominated-meso-dimethylamine-fluoro-BODIPY) showed excellent stability both in dark and in light conditions and were found to be very efficient in generating singlet oxygen when compared to RB.","abstract_html":"A. In this work, LNA-dG was incorporated into d(CG)6 sequence in a site-specific manner through the phosphoramidite chemistry-based solid phase synthesis to investigate the impact of this modification on the B→Z-DNA transition. Circular dichroism study showed that the incorporation of a single LNA-dG unit into d(CG)6 at internal positions virtually suppressed Z-DNA formation at 4 M NaCl concentration, whereas the presence of single LNA-dG unit towards the terminal ends showed only partially inhibition of B→Z-DNA transition. To further understand the influence of chemical modification on B→Z-DNA transition, modification at C8-position on LNA-dG residue was explored. Towards this goal, compounds such as 8-bromo-5′-dimethoxytrityl-N-dimethylformamidine-(2′-O,4′-C-methylene)-guanosine-3′-O-(2-cyanoethyl)-N,N-diisopropy phosphoramidite and 8-bromo-2′-deoxy-5′-O-dimethoxy-N-[(dimethylamino)methylene]-2′-fluoroguanosine-3′-O-(2-cyanoethyl)-N,N-diisopropyl phosphoramidite were synthesized. B. In this study, N,N,N-trimethyl-2-(4,4-difluoro-2,6-diiodo-4-bora-3a,4a-diaza-s-indacen-8-yl) ethylammonium iodide 111 was successfully synthesized. Singlet oxygen generation experiments suggested that BODIPY 111 is ~2.5 times more efficient with respect to Rose Bengal (RB) in generating singlet oxygen. However, based on the cell-culture experiment, BODIPY 111 treated culture plates showed only slight reduction in CFUs compared to Rose Bengal and control plates. BODIPY compounds 107 (iodinated-fluoro-BODIPY), 130 (brominated-fluoro-BODIPY) and 110 (brominated-meso-dimethylamine-fluoro-BODIPY) showed excellent stability both in dark and in light conditions and were found to be very efficient in generating singlet oxygen when compared to RB.","abstract_has_math":false,"creators":["Joshi, Dhruval Kumar"],"institution":"Brock University","degree_name":"Ph.D. Biotechnology","degree_level":"Doctoral","degree_discipline":"Faculty of Mathematics and Science","degree_department":"Centre for Biotechnology","school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2022,"date_issued":"2022-02-18T19:41:30Z","date_published":"2022-02-18T19:41:30Z","updated_at":"2026-07-24T01:22:58Z","subjects":["Nucleic acids, B-DNA, Z-DNA, BODIPY, Photosensitizers"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/10464/15612","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.department","label":"Department","values":["Centre for Biotechnology"]},{"key":"dc:creator","label":"Author","values":["Joshi, Dhruval Kumar"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2022-02-18T19:41:30Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2022-02-18T19:41:30Z"]},{"key":"dc:date.issued","label":"Date","values":["2022-02-18T19:41:30Z"]},{"key":"dc:type","label":"Dc Type","values":["Electronic Thesis or Dissertation"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Faculty of Mathematics and Science"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Doctoral"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D. Biotechnology"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["Brock University"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Nucleic acids, B-DNA, Z-DNA, BODIPY, Photosensitizers"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/10464/15612"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["A. In this work, LNA-dG was incorporated into d(CG)6 sequence in a site-specific manner through the phosphoramidite chemistry-based solid phase synthesis to investigate the impact of this modification on the B→Z-DNA transition. Circular dichroism study showed that the incorporation of a single LNA-dG unit into d(CG)6 at internal positions virtually suppressed Z-DNA formation at 4 M NaCl concentration, whereas the presence of single LNA-dG unit towards the terminal ends showed only partially inhibition of B→Z-DNA transition. To further understand the influence of chemical modification on B→Z-DNA transition, modification at C8-position on LNA-dG residue was explored. Towards this goal, compounds such as 8-bromo-5′-dimethoxytrityl-N-dimethylformamidine-(2′-O,4′-C-methylene)-guanosine-3′-O-(2-cyanoethyl)-N,N-diisopropy phosphoramidite and 8-bromo-2′-deoxy-5′-O-dimethoxy-N-[(dimethylamino)methylene]-2′-fluoroguanosine-3′-O-(2-cyanoethyl)-N,N-diisopropyl phosphoramidite were synthesized. B. In this study, N,N,N-trimethyl-2-(4,4-difluoro-2,6-diiodo-4-bora-3a,4a-diaza-s-indacen-8-yl) ethylammonium iodide 111 was successfully synthesized. Singlet oxygen generation experiments suggested that BODIPY 111 is ~2.5 times more efficient with respect to Rose Bengal (RB) in generating singlet oxygen. However, based on the cell-culture experiment, BODIPY 111 treated culture plates showed only slight reduction in CFUs compared to Rose Bengal and control plates. BODIPY compounds 107 (iodinated-fluoro-BODIPY), 130 (brominated-fluoro-BODIPY) and 110 (brominated-meso-dimethylamine-fluoro-BODIPY) showed excellent stability both in dark and in light conditions and were found to be very efficient in generating singlet oxygen when compared to RB."]},{"key":"dc:title","label":"Title","values":["(A). Regulation of B-/Z-DNA transition in modified oligonucleotides; (B). Synthesis of cationic BODIPY analogues for antimicrobial and anticancer applications"]}]}],"canonical_facts":{"dc:contributor.department":["Centre for Biotechnology"],"dc:creator":["Joshi, Dhruval Kumar"],"dc:date.accessioned":["2022-02-18T19:41:30Z"],"dc:date.available":["2022-02-18T19:41:30Z"],"dc:date.issued":["2022-02-18T19:41:30Z"],"dc:description.abstract":["A. In this work, LNA-dG was incorporated into d(CG)6 sequence in a site-specific manner through the phosphoramidite chemistry-based solid phase synthesis to investigate the impact of this modification on the B→Z-DNA transition. Circular dichroism study showed that the incorporation of a single LNA-dG unit into d(CG)6 at internal positions virtually suppressed Z-DNA formation at 4 M NaCl concentration, whereas the presence of single LNA-dG unit towards the terminal ends showed only partially inhibition of B→Z-DNA transition. To further understand the influence of chemical modification on B→Z-DNA transition, modification at C8-position on LNA-dG residue was explored. Towards this goal, compounds such as 8-bromo-5′-dimethoxytrityl-N-dimethylformamidine-(2′-O,4′-C-methylene)-guanosine-3′-O-(2-cyanoethyl)-N,N-diisopropy phosphoramidite and 8-bromo-2′-deoxy-5′-O-dimethoxy-N-[(dimethylamino)methylene]-2′-fluoroguanosine-3′-O-(2-cyanoethyl)-N,N-diisopropyl phosphoramidite were synthesized. B. In this study, N,N,N-trimethyl-2-(4,4-difluoro-2,6-diiodo-4-bora-3a,4a-diaza-s-indacen-8-yl) ethylammonium iodide 111 was successfully synthesized. Singlet oxygen generation experiments suggested that BODIPY 111 is ~2.5 times more efficient with respect to Rose Bengal (RB) in generating singlet oxygen. However, based on the cell-culture experiment, BODIPY 111 treated culture plates showed only slight reduction in CFUs compared to Rose Bengal and control plates. BODIPY compounds 107 (iodinated-fluoro-BODIPY), 130 (brominated-fluoro-BODIPY) and 110 (brominated-meso-dimethylamine-fluoro-BODIPY) showed excellent stability both in dark and in light conditions and were found to be very efficient in generating singlet oxygen when compared to RB."],"dc:identifier.uri":["http://hdl.handle.net/10464/15612"],"dc:language.iso":["eng"],"dc:subject":["Nucleic acids, B-DNA, Z-DNA, BODIPY, Photosensitizers"],"dc:title":["(A). Regulation of B-/Z-DNA transition in modified oligonucleotides; (B). Synthesis of cationic BODIPY analogues for antimicrobial and anticancer applications"],"dc:type":["Electronic Thesis or Dissertation"],"thesis:degree_discipline":["Faculty of Mathematics and Science"],"thesis:degree_level":["Doctoral"],"thesis:degree_name":["Ph.D. Biotechnology"],"thesis:institution_name":["Brock University"]},"updated_at":"2026-07-24T01:22:58Z"}