Switchable Lipids: Conformational Change for Fast pH‐Triggered Cytoplasmic Delivery

Viricel, Warren; Mbarek, Amira; Leblond, Jeanne

doi:10.1002/ange.201504661

Cited by 18 publications

(8 citation statements)

References 59 publications

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“…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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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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“…All solvents were dried and degassed before used, and commercially available reagents were used without further purification. 2,6-Dibromo-4-methoxypyridine [ 36 , 37 ], 2,6-dibromo- N , N -dimethylpyridin-4-amine [ 38 , 39 ] and 6-( tert -butyl)-9H-pyrido[2,3-b]indole [ 40 ] were prepared using methods reported in literature. All reactions were conducted under N 2 atmosphere and monitored by precoated TLC plates (0.20 nm with fluorescent indicator F254).…”

Section: Methodsmentioning

confidence: 99%

Probing Electron Excitation Characters of Carboline-Based Bis-Tridentate Ir(III) Complexes

et al. 2021

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In this work, we report a series of bis-tridentate Ir(III) metal complexes, comprising a dianionic pyrazole-pyridine-phenyl tridentate chelate and a monoanionic chelate bearing a peripheral carbene and carboline coordination fragment that is linked to the central phenyl group. All these Ir(III) complexes were synthesized with an efficient one-pot and two-step method, and their emission hue was fine-tuned by variation of the substituent at the central coordination entity (i.e., pyridinyl and phenyl group) of each of the tridentate chelates. Their photophysical and electrochemical properties, thermal stabilities and electroluminescence performances are examined and discussed comprehensively. The doped devices based on [Ir(cbF)(phyz1)] (Cb1) and [Ir(cbB)(phyz1)] (Cb4) give a maximum external quantum efficiency (current efficiency) of 16.6% (55.2 cd/A) and 13.9% (43.8 cd/A), respectively. The relatively high electroluminescence efficiencies indicate that bis-tridentate Ir(III) complexes are promising candidates for OLED applications.

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“…The methodologies and modifications used for liposomes can also be applied to porphysomes to tune their stability and biological behavior. Triggered release conditions for liposomes induce triggers such as pH [48, 373] , biodegradability [374] , biomolecules [375] , and thermal sensitivity [376, 377] .…”

Section: Theranostic Nanomaterialsmentioning

confidence: 99%

Advanced Functional Nanomaterials for Theranostics

Huang

Lovell

2016

Adv Funct Materials

209

135

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Nanoscale materials have been explored extensively as agents for therapeutic and diagnostic (i.e. theranostic) applications. Research efforts have shifted from exploring new materials in vitro to designing materials that function in more relevant animal disease models, thereby increasing potential for clinical translation. Current interests include non-invasive imaging of diseases, biomarkers and targeted delivery of therapeutic drugs. Here, we discuss some general design considerations of advanced theranostic materials and challenges of their use, from both diagnostic and therapeutic perspectives. Common classes of nanoscale biomaterials, including magnetic nanoparticles, quantum dots, upconversion nanoparticles, mesoporous silica nanoparticles, carbon-based nanoparticles and organic dye-based nanoparticles, have demonstrated potential for both diagnosis and therapy. Variations such as size control and surface modifications can modulate biocompatibility and interactions with target tissues. The needs for improved disease detection and enhanced chemotherapeutic treatments, together with realistic considerations for clinically translatable nanomaterials will be key driving factors for theranostic agent research in the near future.

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Switchable Lipids: Conformational Change for Fast pH‐Triggered Cytoplasmic Delivery

Cited by 18 publications

References 59 publications

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

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

Probing Electron Excitation Characters of Carboline-Based Bis-Tridentate Ir(III) Complexes

Advanced Functional Nanomaterials for Theranostics

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