A ratiometric solvent polarity sensing Schiff base molecule for estimating the interfacial polarity of versatile amphiphilic self-assemblies

Majumder, Rini; Sarkar, Yeasmin; Das, Sanju; Jewrajka, Suresh K.; Ray, Ambarish; Parui, Partha Pratim

doi:10.1039/c6an00582a

Cited by 13 publications

(15 citation statements)

References 38 publications

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“…Tahara and co-workers have established a heterodyne-detected electronic sum frequency generation (HD-ESFG) spectroscopic method to estimate the self-assembled system-induced acid/base p K a shift and have monitored the interfacial pH values. , It has been identified that the interfacial pH is substantially altered from the bulk pH. Recently, we have introduced a new interfacial pH/polarity monitoring method for biologically important micelles and vesicles by utilizing interface-interacting pH/polarity-detecting probes. − The estimated values of the pH/polarity differences between the bulk phase and the interface are observed to be similar to that obtained from the HD-ESFG method. Most importantly, the inherent simplicity of our detection technique can be highly effective for monitoring the shape- and structure-dependent manipulation of the pH/polarity at the complex biological membrane interfaces.…”

Section: Introductionmentioning

confidence: 99%

Detection of Curvature-Radius-Dependent Interfacial pH/Polarity for Amphiphilic Self-Assemblies: Positive versus Negative Curvature

et al. 2017

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It is possible that a defined curvature at the membrane interface controls its pH/polarity to exhibit specific bioactivity. By utilizing an interface-interacting spiro-rhodamine pH probe and the Schiff base polarity probe, we have shown that the pH deviation from the bulk phase to the interface (ΔpH)/interfacial dielectric constant (κ(i)) for amphiphilic self-assemblies can be regulated by the curvature geometry (positive/negative) and its radius. According to H NMR and fluorescence anisotropy investigations, the probes selectively interact with an anionic interfacial Stern layer. The ΔpH/κ(i) values for the Stern layer are estimated by UV-vis absorption and fluorescence studies. For the anionic sodium bis-2-ethylhexyl-sulfosuccinate (AOT) inverted micellar (IM) negative interface, the highly restricted water and proton penetration into the Stern layer owing to tight surfactant packing or a reduced water-exposed headgroup area may be responsible for the much lower ΔpH ≈ -0.45 and κ(i) ≈ 28 in comparison to ∼-2.35 and ∼44, respectively, for the anionic sodium dodecyl sulfate (SDS) micellar positive interface with a close similar Stern layer. With increasing AOT IM water-pool radius (1.7-9.5 nm) or [water]/[AOT] ratio ( w) (8.0-43.0), the ΔpH and κ(i) increase maximally up to ∼-1.22 and ∼45, respectively, due to a greater water-exposed headgroup area. However, the unchanged ΔpH ≈ -0.65 and κ(i) ≈ 53.0 within radii ∼3.5-8.0 nm for the positive interface of a mixed Triton X-100 (TX-100)/SDS (4:1) micelle justify its packing flexibility. Interestingly, the continuously increasing ΔpH trend for IM up to its largest possible water-pool radius of ∼9.5 nm may rationalize the increase in ΔpH (∼-1.4 to -1.6) with the change in the curvature radii (∼15 to 50 nm) for sodium 1,2-dimyristoyl- sn-glycero-3-phosphorylglycerol (DMPG)/1,2-dimyristoyl- sn-glycero-3-phosphocholine (DMPC) (2:1) large unilamellar vesicles (LUV) owing to its negative interface. Whereas, similar to the micellar positive interface, the unchanged ΔpH at the positive LUV interface was confirmed by fluorescence microscopic studies with giant unilamellar vesicles of identical lipids composition. The present study offers a unique and simple method of monitoring the curvature-radius-dependent interfacial pH/polarity for biologically related membranes.

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Section: Introductionmentioning

confidence: 99%

Detection of Curvature-Radius-Dependent Interfacial pH/Polarity for Amphiphilic Self-Assemblies: Positive versus Negative Curvature

et al. 2017

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“…S13†). 29 The dielectric constant of the buffer solution was adjusted to 44–45 with addition of 58% (w/w) ethanol at pH 2.0–6.5,30 where the δ value was estimated to be ∼0.7 (Fig. 2C and D, gray and black curves).…”

Section: Resultsmentioning

confidence: 99%

“…A spiro-rhodamine-glucose molecule (RHG)45 and a Schiff-base molecule (PMP)46 were prepared according to earlier procedures. Briefly, spiro-rhodamine 6G hydrazide was prepared by the reaction of rhodamine 6G hydrochloride with hydrazine in ethanol.…”

Section: Methodsmentioning

confidence: 99%

“…The UV-vis absorption spectra of PMP were measured in the presence and absence of DOPC/DOPE/CL (2 : 1 : 1), DOPC/DOPE (2 : 1), DOPC, or DOPG LUVs (total lipid, 3 mM) and LUVs of lipids from the mitochondrial membranes in 10 mM HEPES buffer, pH 6.5. The dielectric constant ( D ) at the LUV interface was estimated using the following relation as reported previously 29 ε 420 D / ε 420 8.0 = 0.42 × D – 1.8 …”

Section: Methodsmentioning

confidence: 99%

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Determination of proton concentration at cardiolipin-containing membrane interfaces and its relation with the peroxidase activity of cytochromec

et al. 2019

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“…where log k, p refer to the analyte retention factor, the compound polarity, respectively. (log k) 0 and are the constants related to the stationary phase, is the polarity of mobile phase [27,28,30].…”

Section: Calculation Of the Polarity Of Target Compoundsmentioning

confidence: 99%

Rapid enrichment and separation of two novel minor phenols from Malus hupehensis utilizing liquid–liquid extraction with three‐phase solvent system and high‐speed counter‐current chromatography based on the polarity parameter

Cai

Xiao

Tang

et al. 2021

J of Separation Science

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For a rapid enrichment and separation of minor components from Malus hupehensis, the selection of suitable solvent system is the great challenge for liquid-liquid extraction with a three-phase solvent system and high-speed counter-current chromatography. According to the concept of "like dissolves like," the similarity of the average polarity between solvent system and target compounds was the significant characteristic of liquid-liquid extraction with a three-phase solvent system and high-speed counter-current chromatography separation. The polarity parameter model provides a way to calculate the polarity of unknown compounds. Under the guidance of the polarity, an efficient enrichment and separation approach was established through liquid-liquid extraction and high-speed counter-current chromatography with solvent systems composed of n-hexane-ethyl acetate-acetonitrile-water (5:3:5:7, v/v), n-hexane-ethyl acetate-methanol-water (1:2:1:2, v/v), respectively. Thus, the total content of minor compounds was increased from 2.6% to 17.2%, and two novel compounds (6ťť-O-coumaroyl-2ť-O-glucopyranosylphloretin and 3ťťť-methoxy-6ťť-O-feruloy-2ť-glucopyranosylphloretin) were obtained. The discovery of the new dihydrochalcones expanded the structural diversity of compounds produced by the genus Malus. The experimental results demonstrated that compound polarity can be described by the polarity parameter model and is an important reference for investigating optimum solvent systems for liquid-liquid extraction with a three-phase solvent system and high-speed counter-current chromatography.

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A ratiometric solvent polarity sensing Schiff base molecule for estimating the interfacial polarity of versatile amphiphilic self-assemblies

Cited by 13 publications

References 38 publications

Detection of Curvature-Radius-Dependent Interfacial pH/Polarity for Amphiphilic Self-Assemblies: Positive versus Negative Curvature

Detection of Curvature-Radius-Dependent Interfacial pH/Polarity for Amphiphilic Self-Assemblies: Positive versus Negative Curvature

Determination of proton concentration at cardiolipin-containing membrane interfaces and its relation with the peroxidase activity of cytochromec

Rapid enrichment and separation of two novel minor phenols from Malus hupehensis utilizing liquid–liquid extraction with three‐phase solvent system and high‐speed counter‐current chromatography based on the polarity parameter

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