ArticleBioconjugate chemistry2015
A clickable and photocleavable lipid analogue for cell membrane delivery and release.
Article in Bioconjugate chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
7 citing papers in PubMed.
- Fluorescent Labeling Methods for Brain Structure Research.Molecules (Basel, Switzerland) · 2026Review
- Hybrid bilayer membranes as platforms for biomimicry and catalysis.Nature reviews. Chemistry · 2022Review
- Ultrasound-Triggered Delivery of Iproplatin from Microbubble-Conjugated Liposomes.ChemistryOpen · 2021Article
- UVA-Triggered Drug Release and Photo-Protection of Skin.Frontiers in cell and developmental biology · 2021Review
- Application and design of esterase-responsive nanoparticles for cancer therapy.Drug delivery · 2019Review
- Impacting Pancreatic Cancer Therapy in HeterotypicNano letters · 2019Article
- Artificial Membrane Fusion Triggered by Strain-Promoted Alkyne-Azide Cycloaddition.Bioconjugate chemistry · 2017Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
For drug delivery purposes, the ability to conveniently attach a targeting moiety that will deliver drugs to cells and then enable controlled release of the active molecule after localization is desirable. Toward this end, we designed and synthesized clickable and photocleavable lipid analogue 1 to maximize the efficiency of bioconjugation and triggered release. This compound contains a dibenzocyclooctyne group for bioorthogonal derivatization linked via a photocleavable 2-nitrobenzyl moiety at the headgroup of a synthetic lipid backbone for targeting to cell membranes. To assess delivery and release using this system, we report fluorescence-based assays for liposomal modification and photocleavage in solution as well as through surface immobilization to demonstrate successful liposome functionalization and photoinduced release. In addition, fluorophore delivery to and release from live cells was confirmed and characterized using fluorescence microscopy and flow cytometry analysis in which 1 was delivered to cells, derivatized, and photocleaved. Finally, drug delivery studies were performed using an azide-tagged analogue of camptothecin, a potent anticancer drug that is challenging to deliver due to poor solubility. In this case, the ester attachment of the azide tag acted as a caging group for release by intracellular esterases rather than through photocleavage. This resulted in a dose-dependent response in the presence of liposomes containing delivery agent 1, confirming the ability of this compound to stimulate delivery to the cytoplasm of cells.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.