ArticlePharmaceutics2011
Fliposomes: pH-Sensitive Liposomes Containing a trans-2-morpholinocyclohexanol-Based Lipid That Performs a Conformational Flip and Triggers an Instant Cargo Release in Acidic Medium.
Article in Pharmaceutics, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
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.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
11 citing papers in PubMed, 51 citations in OpenAlex.
- Exploring and Re-Assessing Reverse Anomeric Effect in 2-Iminoaldoses Derived from Mono- and Polynuclear Aromatic Aldehydes.Molecules (Basel, Switzerland) · 2024Article
- A True Reverse Anomeric Effect Does Exist After All: A Hydrogen Bonding Stereocontrolling Effect in 2-Iminoaldoses.The Journal of organic chemistry · 2024Article
- Key Design Features of Lipid Nanoparticles and Electrostatic Charge-Based Lipid Nanoparticle Targeting.Pharmaceutics · 2023Review
- pH-Sensitive Liposomes with Embedded 3-(isobutylamino)cholan-24-oic Acid: What Is the Possible Mechanism of Fast Cargo Release?Membranes · 2023Article
- Imidazole-Based pH-Sensitive Convertible Liposomes for Anticancer Drug Delivery.Pharmaceuticals (Basel, Switzerland) · 2022Article
- 2,3-Dimethoxy-2,3-dimethyl-1,4-dioxane as a useful precursor to 2,3-dimethylene-1,4-dioxane for [4+2] cycloaddition reaction.RSC advances · 2021Article
- Pharmaceutical Applications of Molecular Tweezers, Clefts and Clips.Molecules (Basel, Switzerland) · 2019Review
- Lipid-Coated, pH-Sensitive Magnesium Phosphate Particles for Intracellular Protein Delivery.Pharmaceutical research · 2019Article
- Modification of fliposomes with a polycation can enhance the control of pH-induced release.International journal of nanomedicine · 2019Article
- Stimuli-responsive liposomes for drug delivery.Wiley interdisciplinary reviews. Nanomedicine and nanobiotechnology · 2017Review
- Remarkable functions ofBeilstein journal of organic chemistry · 2017Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Incorporation of a pH-sensitive conformational switch into a lipid structure enables a drastic conformational flip upon protonation that disrupts the liposome membrane and causes rapid release of cargo specifically in areas of increased acidity. pH-sensitive liposomes containing the amphiphile (1) with trans-2-morpholinocyclohexanol conformational switch, a phospholipid, and a PEG-lipid conjugate were constructed and characterized. The optimized composition-1/POPC/PEG-ceramide (50/45/5)-could be stored at 4 °C and pH 7.4 for up to 1.5 years, and was stable in blood serum in vitro after 48 h at 37 °C. Liposomes loaded with ANTS/DPX or methotrexate demonstrated an unusually quick content release (in a few seconds) at pH below 5.5, which was independent of inter-liposome contact. The pH-titration curve for the liposome leakage paralleled the curve for the acid-induced conformational flip of 1 studied by 1H-NMR. Freeze-fracture electron microscopy images showed budding and division of the bilayer at pH 5.5. A plausible mechanism of pH-sensitivity involves an acid-triggered conformational flip of 1, shortening of lipid tails, and membrane perturbations, which cause the content leakage. The methotrexate-loaded liposomes demonstrated much higher cytotoxicity in HeLa cells than the free drug indicating that they can serve as viable drug delivery systems.
Identifiers
What OpenQuestion holds
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.