pH-Sensitive liposomes with embedded 3,7-diazabicyclo[3.3.1]nonane derivative

Veremeeva, Polina N.; Grishina, I. A.; Лаптева, В. Л.; Yaroslavov, Alexander A.; Sybachin, Andrey V.; Palyulin, V. A.; Зефиров, Н. С.

doi:10.1016/j.mencom.2014.04.008

Cited by 25 publications

(10 citation statements)

References 15 publications

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“…Furthermore, the conformational switch of the polar groups forced the lipid tails to a mirror switch from equatorial to axial conformation, resulting in the destabilization of the LP membrane. Veremeeva et al [128] described the synthesis of a similar molecule with two long alkyl substituents and a chair-boat conformation at pH > 7, which was inserted into phosphotidylcholine-LPS. Below pH 7.0, protonation of nitrogen atoms led to a different orientation of the two alkyl chains, so that the molecule changed its conformation from chair-boat to chair-chair.…”

Section: Conformationally Switchable Lps and Fliposomesmentioning

confidence: 99%

Stimulus-responsive liposomes for biomedical applications

Antoniou

Giofrè

Seneci

et al. 2021

Drug Discovery Today

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Liposomes are amphipathic lipidic supramolecular aggregates able to encapsulate and carry molecules of both hydrophilic and hydrophobic nature. They have been widely used as in vivo drug delivery systems since long due to their favorable features, such as synthetic flexibility, biodegradability, biocompatibility, low immunogenicity, and negligible toxicity. In recent years, the possibility to introduce chemical modifications on liposomes has paved the way to smart liposome-based drug delivery systems characterized by even more tunable and disease-directed features. In this review, the different types of chemical modifications introduced so far have been highlighted, with a particular focus on internal stimuli-responsive liposomes and pro-drug activation.

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Section: Conformationally Switchable Lps and Fliposomesmentioning

confidence: 99%

Stimulus-responsive liposomes for biomedical applications

Antoniou

Giofrè

Seneci

et al. 2021

Drug Discovery Today

View full text Add to dashboard Cite

show abstract

“…This move changes dramatically their ability to interact with another molecule or ion, or to pack into lipid bilayers (depending on the nature of R). The moieties of trans ‐3,4‐bis(acyloxy)‐piperidine, trans ‐4‐amino‐3‐piperidinol, 3,7‐diazabicyclo[3.3.1]nonan‐9‐one, arylamide‐substituted diphenylacetylene, trans ‐4,5‐dihydroxyhexahydropyridazine, di(methoxyphenyl)pyridine and substituted amides, and other more complex molecular devices were also suggested recently as new pH sensitive bases for analogous applications.…”

Section: Introductionmentioning

confidence: 99%

Trans‐2‐Aminocyclohexanol derivatives as pH‐triggered conformational switches

Samoshin

Zheng

Liu

2017

J of Physical Organic Chem

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A series of trans-2-aminocyclohexanol derivatives have been explored as powerful conformational pH triggers. On protonation of the amino group, a conformer with equatorial position of ammonio and hydroxy groups becomes predominant because of an intramolecular hydrogen bond and electrostatic interactions. The energy of these interactions was estimated to be above 10 kJ/mol and in some models exceeded 20 kJ/mol (strong enough to twist a ring in tert-butyl derivatives). As a result of this conformational flip, all other substituents are forced to change their orientation. If the substituents are designed to perform certain geometry-dependent functions, for example, as cation chelators or as lipid tails, such acid-induced transition may be used to control the corresponding molecular properties. The pH sensitivity of conformational equilibria was explored by 1 H nuclear magnetic resonance spectroscopy (NMR), and the titration curves were used for estimation of the pK a values of protonated compounds that varied from 2.6 to 8.5 (in d 4 -methanol) depending on the structure of amino group. Thus, trans-2-aminocyclohexanols can be also used as conformational pH indicators in organic solvents.

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“…In other examples, the sensing unit has been incorporated into lipid structures to drive release based on conformational changes triggered by molecular recognition events. Zefirov and co‐workers developed bispidinone‐based lipid switches that respond to copper and acid by interconverting from chair–boat form ( 4 a ) to chair–chair ( 4 b ) upon ion complexation (Scheme ). Of note in this case is that the hydrophobic chains appear to converge upon switching, which differs from the divergence of the chains in other examples we have discussed.…”

Section: Lipid Switches Triggered By Molecular Recognitionmentioning

confidence: 99%

Lipid Switches: Stimuli‐Responsive Liposomes through Conformational Isomerism Driven by Molecular Recognition

Lou

Zhang

Best

2018

Chemistry A European J

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Advancements in the field of liposomal drug carriers have culminated in greatly improved delivery properties. An important aspect of this work entails development of designer liposomes for release of contents triggered by environmental changes. The majority of these systems are driven by chemical reactions in the presence of different stimuli. However, a promising new paradigm instead focuses on molecular recognition events as the impetus for content release. In certain cases, these platforms exploit synthetic lipid switches designed to undergo conformational changes upon binding to target ions or molecules that perturb membrane assembly, thereby triggering cargo release. Examples of this approach reported thus far showcase how rational design of lipid switches can result in dramatic changes in lipid assembly properties. These strategies show great promise for opening up new pathophysiological stimuli that can be harnessed for programmed content release in drug delivery applications.

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pH-Sensitive liposomes with embedded 3,7-diazabicyclo[3.3.1]nonane derivative

Cited by 25 publications

References 15 publications

Stimulus-responsive liposomes for biomedical applications

Stimulus-responsive liposomes for biomedical applications

Trans‐2‐Aminocyclohexanol derivatives as pH‐triggered conformational switches

Lipid Switches: Stimuli‐Responsive Liposomes through Conformational Isomerism Driven by Molecular Recognition

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