scholarly journals Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups

2019 ◽  
Vol 15 ◽  
pp. 1515-1520 ◽  
Author(s):  
Sean H Kennedy ◽  
Makafui Gasonoo ◽  
Douglas A Klumpp
Keyword(s):  
Cyclization Product ◽  
Ionizable Groups

A substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization in the Brønsted superacid CF3SO3H, the substrate undergoes two types of reactions. In the presence of only the superacid, the highly ionized intermediate(s) provide a double cyclization product having two pyrido[1,2-a]indole rings. With added benzene, an arylation product is obtained. A mechanism is proposed involving tetra-, penta-, or hexacationic species.

BODIPY Fluorophores for Membrane Potential Imaging

2019 ◽  
Author(s):  
Jenna Franke ◽  
Benjamin Raliski ◽  
Steven Boggess ◽  
Divya Natesan ◽  
Evan Koretsky ◽  
...  
Keyword(s):  
Mammalian Cells ◽  
Water Solubility ◽  
Water Soluble ◽  
Voltage Sensitivity ◽  
Chemical Transformations ◽  
Direct Modification ◽  
Biological Compatibility ◽  
Meso Position ◽  
Ionizable Groups ◽  
Boron Center

Fluorophores based on the BODIPY scaffold are prized for their tunable excitation and emission profiles, mild syntheses, and biological compatibility. Improving the water-solubility of BODIPY dyes remains an outstanding challenge. The development of water-soluble BODIPY dyes usually involves direct modification of the BODIPY fluorophore core with ionizable groups or substitution at the boron center. While these strategies are effective for the generation of water-soluble fluorophores, they are challenging to implement when developing BODIPY-based indicators: direct modification of BODIPY core can disrupt the electronics of the dye, complicating the design of functional indicators; and substitution at the boron center often renders the resultant BODIPY incompatible with the chemical transformations required to generate fluorescent sensors. In this study, we show that BODIPYs bearing a sulfonated aromatic group at the meso position provide a general solution for water-soluble BODIPYs. We outline the route to a suite of 5 new sulfonated BODIPYs with 2,6-disubstitution patterns spanning a range of electron-donating and -withdrawing propensities. To highlight the utility of these new, sulfonated BODIPYs, we further functionalize them to access 13 new, BODIPY-based voltage-sensitive fluorophores. The most sensitive of these BODIPY VF dyes displays a 48% ΔF/F per 100 mV in mammalian cells. Two additional BODIPY VFs show good voltage sensitivity (≥24% ΔF/F) and excellent brightness in cells. These compounds can report on action potential dynamics in both mammalian neurons and human stem cell-derived cardiomyocytes. Accessing a range of substituents in the context of a water soluble BODIPY fluorophore provides opportunities to tune the electronic properties of water-soluble BODIPY dyes for functional indicators.

scholarly journals Emulsion Formation and Stabilizing Properties of Olive Oil Cake Crude Extracts

Processes ◽  
2021 ◽  
Vol 9 (4) ◽  
pp. 633
Author(s):  
Firdaous Fainassi ◽  
Noamane Taarji ◽  
Fatiha Benkhalti ◽  
Abdellatif Hafidi ◽  
Marcos A. Neves ◽  
...  
Keyword(s):  
Olive Oil ◽  
Ethanol Extract ◽  
Active Components ◽  
Oil In Water ◽  
Surface Active ◽  
Ph Conditions ◽  
Oil Water ◽  
Surface Active Compounds ◽  
Ionizable Groups ◽  
Emulsifying Ability

The surface-active and emulsifying properties of crude aqueous ethanolic extracts from untreated olive oil cake (OOC) were investigated. OOC extracts contained important concentrations of surface-active components including proteins, saponins and polyphenols (1.2–2.8%, 7.8–9.5% and 0.7–4.5% (w/w), respectively) and reduced the interfacial tension by up to 46% (14.0 ± 0.2 mN m−1) at the oil–water interface. The emulsifying ability of OOC extracts was not correlated, however, with their interfacial activity or surface-active composition. Eighty percent aqueous ethanol extract produced the most stable oil-in-water (O/W) emulsions by high-pressure homogenization. The emulsions had average volume mean droplet diameters of approximately 0.4 µm and negative ζ-potentials of about -45 mV, and were stable for up to 1 month of storage at 5, 25 and 50 °C. They were sensitive, however, to acidic pH conditions (<5) and NaCl addition (≥25 mM), indicating that the main stabilization mechanism is electrostatic due to the presence of surface-active compounds with ionizable groups, such as saponins.

scholarly journals The effect of heme-linked ionizable groups on cyanide binding to methemoglobin.

1986 ◽  
Vol 261 (23) ◽  
pp. 10576-10581
Author(s):  
F J Vega-Catalan ◽  
O J Odeyemi ◽  
K O Okonjo
Keyword(s):  
Cyanide Binding ◽  
Ionizable Groups

scholarly journals Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarbonyl-N-Propargylanilines

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3366
Author(s):  
Antonio Arcadi ◽  
Andrea Calcaterra ◽  
Giancarlo Fabrizi ◽  
Andrea Fochetti ◽  
Antonella Goggiamani ◽  
...  
Keyword(s):  
Building Blocks ◽  
Fine Tuning ◽  
Para Position ◽  
Cyclization Product ◽  
Synthetic Route ◽  
Substituted Anilines ◽  
Novel Approach ◽  
High Yields

An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of N-ethoxycarbonyl protected-N-propargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-endo cyclization product in good to high yields. In the presence of N-ethoxycarbonyl-N-propargyl-meta-substituted anilines, the regiodivergent cyclization at the ortho-/para-position is achieved by the means of catalyst fine tuning.

scholarly journals Purification and Identification of the Essential Ionizable Groups of Honeybee, Apis mellifera L., Trehalase

2001 ◽  
Vol 65 (12) ◽  
pp. 2657-2665 ◽  
Author(s):  
Jin-Ha LEE ◽  
Masahisa TSUJI ◽  
Mitsuru NAKAMURA ◽  
Mamoru NISHIMOTO ◽  
Masayuki OKUYAMA ◽  
...  
Keyword(s):  
Apis Mellifera ◽  
Ionizable Groups

scholarly journals Hydrogen-ion titration studies on erythrocyte membranes

1976 ◽  
Vol 156 (1) ◽  
pp. 159-165 ◽  
Author(s):  
C Hallam ◽  
J M Wrigglesworth
Keyword(s):  
Membrane Structure ◽  
Plasma Membranes ◽  
Sodium Dodecyl ◽  
Spectrophotometric Assay ◽  
Hydrogen Ion ◽  
Erythrocyte Membranes ◽  
Chemical Treatments ◽  
Before And After ◽  
Selective Chemical ◽  
Ionizable Groups

1. H+ titration was used to detect the presence of ionizable groups on human erythrocyte plasma membranes. Between pH2.9 and 11.3, two significant peaks of H+ association/dissociation occur in the differential from of the titration curve, one at pH3. 1. And the other at pH10.3. 2. After disruption of membrane structure by exposure to high pH or by the addition of sodium dodecyl sulphate, maxima of H+ association/dissociation were seen at pH3.1,4.3,6.5,10.3 and 10.7. 3. Spectrophotometric assay and selective chemical treatments were used to identify several of the titratable residues. 4. The degree of eleectrostatic interaction between titratable charged groups was investigated by comparing the titration characteristics of the membranes before and after modification of membrane structure.

scholarly journals A summary of the measured pKvalues of the ionizable groups in folded proteins

2008 ◽  
pp. NA-NA ◽  
Author(s):  
Gerald R. Grimsley ◽  
J. Martin Scholtz ◽  
C. Nick Pace
Keyword(s):  
Folded Proteins ◽  
Ionizable Groups

Swelling Process and Order-Disorder Transition of Hydrogel Containing Hydrophobic Ionizable Groups

1995 ◽  
Vol 28 (13) ◽  
pp. 4583-4586 ◽  
Author(s):  
Makoto Uchida ◽  
Miyuki Kurosawa ◽  
Yoshihito Osada
Keyword(s):  
Disorder Transition ◽  
Ionizable Groups
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