Synthesis of Three Novel Anionic Gemini Surfactants and Comparative Studies of Their Assemble Behavior in the Presence of Bovine Serum Albumin

Abstract

Three novel anionic sulfonate gemini surfactants, sodium 4,4'-(10,19-dioxo-9,11,18,20-tetraazaoctacosane-9,20-diyl) dibenzenesulfonate (Surfactant I), sodium 4,4'-(12,21-dioxo-11,13,20,22-tetraazadotriacontane-11,22-diyl) dibenzenesulfonate (Surfactant II), and sodium 4,4'-(14,23-dioxo-13,15,22,24-tetraazahezatriacontane-13,24-diyl) dibenzenesulfonate (Surfactant III), with different lengths of hydrophobic tail have been synthesized, and their assembly behavior in the presence of bovine serum albumin (BSA) has been studied using spectral methods and molecular modeling methods at physiological pH and 298 K. Critical micelle concentrations (CMCs) of the three surfactants have been determined by surface tension measurements. Despite the obvious decrease of CMC with the increase of tail length, fluorescence spectra have shown much closer CAC in the presence of BSA. Surfactant II shows the highest CAC of 3.19 × 10(-5) mol L(-1) compared with the other two. The polarity of the microenvironment in BSA-surfactant systems has been investigated using pyrene as the probe. In addition, far-UV CD spectra studied the change of the secondary structure content of BSA caused by the three surfactants. The features of the assembly behavior were discussed by three concentration regions. Surfactant II could unfold the protein much more efficiently than the other two surfactants at low concentration, but at high concentration, the change of the secondary structure and the formation of hydrophobic microenvironment show a direct relationship to the length of the hydrophobic tail with the increase of the surfactant concentration.

Conformational alterations induced by novel green 16-E2-16 gemini surfactant in xanthine oxidase: Biophysical insights from tensiometry, spectroscopy, microscopy and molecular modeling

“…Therefore, it seems appropriate to study 16-E2-16 + xanthine oxidase interactions. Moreover, as most of the surfactants (both conventional and gemini surfactants) have the ability to alter/denature proteins [1][2][3][4][5][6][7][21][22][23][24][25][26][27][28][29][30][31][32], therefore, 16-E2-16 gemini surfactant too is expected to influence the conformation of xanthine oxidase.…”

Novel Synthesis of Anionic Gemini Surfactants from 1, 4-Diol as a Key Block Material

“…SO 4 , and concentrated. The concentrated residue was subjected to column chromatography on silica, eluting with hexane/ AcOEt 10:1 , to obtain the dicyano derivative, 12, 0.240 g, yield 24 . A stirred mixture of 12 0.166 g, 0.4 mmol and 75 H 2 SO 4 5 mL was heated to 150 for 6 h. The resulting dark mixture was poured onto crushed ice, the pH was adjusted to 1, and the product was extracted into ether, dried over Na 2 SO 4 , and concentrated.…”

Effect of Polar Organic Solvents on Self‐Aggregation of Some Cationic Monomeric and Dimeric Surfactants

“…A large number of studies have been dedicated to the development of gemini surfactants as they have a number of exclusive properties in contrast to conventional single-chain surfactants [8,9]. In general, Gemini surfactants have much lower CMC values, higher surface & Kallol K. Ghosh kallolkghosh@yahoo.com 1 activity, lower Krafft temperatures, interesting visco-elasticity properties and better lime-soap dissolving properties, and they are often better moistening agents [10][11][12][13][14].…”