Acid-sensitive liposome has drawn much interest as drug and gene carriers that release payloads specifically at the low-pH target sites, such as in solid tumors, tissues with inflammation, and ischemia sites. Also, it helps drug/gene to escape endosome trapping and followed lysosome degradation.
The goal of this thesis research is to develop novel trans-2-aminocyclohexanols based lipids and their liposome that can be switched by mildly acidic pH. NMR study · show that in certain acidic medium, the amine group on cyclohexane will attract proton and form hydrogen bond with the neighboring -OH. This change will force the bonds switch to from equatorial conformation to axial conformation. This conformational change is transmitted by the structure of the molecular, and induces consequently dramatic conformational change of the two long lipid tails. Fluorescence leakage assay was conducted on liposomes that encapsulated with ANTs/DPX fluorescence dyes. For certain special designed cyclohexane compounds, the pH triggered lipid conformation change will rupture liposome membrane, release the encapsulated content, and thus help them escape lysosome degradation. This would in tum improve the efficiency of liposome drug delivery and gene transfection.
Luciferase gene transfection was conducted on B16F10 cultured cells. The lipoplex comprising trans-2-aminocyclohexanollipid 1 significantly enhanced the Luciferase gene expression. The gene transfection efficiency correlated well with the pH-triggered membrane-rupture in the trans-aminocyclohexanol-based lipoplexes.
","abstract_html":"<p>Acid-sensitive liposome has drawn much interest as drug and gene carriers that release payloads specifically at the low-pH target sites, such as in solid tumors, tissues with inflammation, and ischemia sites. Also, it helps drug/gene to escape endosome trapping and followed lysosome degradation.</p> <p>The goal of this thesis research is to develop novel trans-2-aminocyclohexanols based lipids and their liposome that can be switched by mildly acidic pH. NMR study · show that in certain acidic medium, the amine group on cyclohexane will attract proton and form hydrogen bond with the neighboring -OH. This change will force the bonds switch to from equatorial conformation to axial conformation. This conformational change is transmitted by the structure of the molecular, and induces consequently dramatic conformational change of the two long lipid tails. Fluorescence leakage assay was conducted on liposomes that encapsulated with ANTs/DPX fluorescence dyes. For certain special designed cyclohexane compounds, the pH triggered lipid conformation change will rupture liposome membrane, release the encapsulated content, and thus help them escape lysosome degradation. This would in tum improve the efficiency of liposome drug delivery and gene transfection.</p> <p>Luciferase gene transfection was conducted on B16F10 cultured cells. The lipoplex comprising trans-2-aminocyclohexanollipid 1 significantly enhanced the Luciferase gene expression. The gene transfection efficiency correlated well with the pH-triggered membrane-rupture in the trans-aminocyclohexanol-based lipoplexes.</p>","abstract_has_math":false,"creators":["Zhang, Ningrong"],"institution":null,"degree_name":"Master of Science (M.S.)","degree_level":"Thesis - Pacific Access Restricted","degree_discipline":"Pharmaceutical and Chemical Sciences","degree_department":null,"school":null,"contributors":["Xin Guo"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2007,"date_issued":"2007-01-01T08:00:00Z","date_published":"2007-01-01T08:00:00Z","updated_at":"2026-07-24T05:36:35Z","subjects":["Drug carriers (Pharmacy)","Liposomes","Medicinal and Pharmaceutical Chemistry","Medicine and Health Sciences","Pharmacy and Pharmaceutical Sciences"],"languages":[],"rights":[],"rights_urls":["http://rightsstatements.org/vocab/InC/1.0/"],"identifier_entries":[]},"links":{"outbound_url":"https://scholarlycommons.pacific.edu/uop_etds/681","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Xin Guo"]},{"key":"dc:creator","label":"Author","values":["Zhang, Ningrong"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2007-01-01T08:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Pharmaceutical and Chemical Sciences"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis - Pacific Access Restricted"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (M.S.)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Drug carriers (Pharmacy)","Liposomes","Medicinal and Pharmaceutical Chemistry","Medicine and Health Sciences","Pharmacy and Pharmaceutical Sciences"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:rights","label":"Dc Rights","values":["http://rightsstatements.org/vocab/InC/1.0/"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://scholarlycommons.pacific.edu/uop_etds/681"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Acid-sensitive liposome has drawn much interest as drug and gene carriers that release payloads specifically at the low-pH target sites, such as in solid tumors, tissues with inflammation, and ischemia sites. Also, it helps drug/gene to escape endosome trapping and followed lysosome degradation.
The goal of this thesis research is to develop novel trans-2-aminocyclohexanols based lipids and their liposome that can be switched by mildly acidic pH. NMR study · show that in certain acidic medium, the amine group on cyclohexane will attract proton and form hydrogen bond with the neighboring -OH. This change will force the bonds switch to from equatorial conformation to axial conformation. This conformational change is transmitted by the structure of the molecular, and induces consequently dramatic conformational change of the two long lipid tails. Fluorescence leakage assay was conducted on liposomes that encapsulated with ANTs/DPX fluorescence dyes. For certain special designed cyclohexane compounds, the pH triggered lipid conformation change will rupture liposome membrane, release the encapsulated content, and thus help them escape lysosome degradation. This would in tum improve the efficiency of liposome drug delivery and gene transfection.
Luciferase gene transfection was conducted on B16F10 cultured cells. The lipoplex comprising trans-2-aminocyclohexanollipid 1 significantly enhanced the Luciferase gene expression. The gene transfection efficiency correlated well with the pH-triggered membrane-rupture in the trans-aminocyclohexanol-based lipoplexes.
"]},{"key":"dc:source","label":"Dc Source","values":["107"]},{"key":"dc:title","label":"Title","values":["Trans-2-aminocyclohexanol as a pH-sensitive conformation switch in liposomes"]}]}],"canonical_facts":{"dc:contributor":["Xin Guo"],"dc:creator":["Zhang, Ningrong"],"dc:date.available":["2007-01-01T08:00:00Z"],"dc:description.abstract":["Acid-sensitive liposome has drawn much interest as drug and gene carriers that release payloads specifically at the low-pH target sites, such as in solid tumors, tissues with inflammation, and ischemia sites. Also, it helps drug/gene to escape endosome trapping and followed lysosome degradation.
The goal of this thesis research is to develop novel trans-2-aminocyclohexanols based lipids and their liposome that can be switched by mildly acidic pH. NMR study · show that in certain acidic medium, the amine group on cyclohexane will attract proton and form hydrogen bond with the neighboring -OH. This change will force the bonds switch to from equatorial conformation to axial conformation. This conformational change is transmitted by the structure of the molecular, and induces consequently dramatic conformational change of the two long lipid tails. Fluorescence leakage assay was conducted on liposomes that encapsulated with ANTs/DPX fluorescence dyes. For certain special designed cyclohexane compounds, the pH triggered lipid conformation change will rupture liposome membrane, release the encapsulated content, and thus help them escape lysosome degradation. This would in tum improve the efficiency of liposome drug delivery and gene transfection.
Luciferase gene transfection was conducted on B16F10 cultured cells. The lipoplex comprising trans-2-aminocyclohexanollipid 1 significantly enhanced the Luciferase gene expression. The gene transfection efficiency correlated well with the pH-triggered membrane-rupture in the trans-aminocyclohexanol-based lipoplexes.
"],"dc:identifier":["https://scholarlycommons.pacific.edu/uop_etds/681"],"dc:rights":["http://rightsstatements.org/vocab/InC/1.0/"],"dc:source":["107"],"dc:subject":["Drug carriers (Pharmacy)","Liposomes","Medicinal and Pharmaceutical Chemistry","Medicine and Health Sciences","Pharmacy and Pharmaceutical Sciences"],"dc:title":["Trans-2-aminocyclohexanol as a pH-sensitive conformation switch in liposomes"],"thesis:degree_discipline":["Pharmaceutical and Chemical Sciences"],"thesis:degree_level":["Thesis - Pacific Access Restricted"],"thesis:degree_name":["Master of Science (M.S.)"]},"updated_at":"2026-07-24T05:36:35Z"}