Synthesis and Properties of a Novel Class of Gemini Pyridinium Surfactants

Zhou, Limei; Jiang, Xiaohui; Li, Yintao; Chen, Zhi; Hu, Xingqi

doi:10.1021/la701154w

Cited by 122 publications

(108 citation statements)

References 26 publications

(38 reference statements)

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“…Among the surfactants, Gemini surfactants especially attract scientists' attention [37,38,[46][47][48][49][50][51][52] It is also known that one of the most important processes leading to micellar effects on reactions is the solubilization of solutes in micellar phase [53]. In this study, both Mn(III) catalysts and substrate PNPP are less water-soluble, so the introduction of cationic surfactants benefit an increase in local concentration of catalyst and PNPP molecules in a small volume inside micelle aggregates.…”

Section: Impact Of Various Surfactant Micelles On the Catalytic Hydromentioning

confidence: 93%

Hydrolysis kinetics of p-nitrophenylpicolinate catalyzed by schiff base Mn(III) complexes in Gemini 16-2-16 micellar solutiony

Jiang

Zhang

et al. 2009

Open Chemistry

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Cl under a comparable condition, which confirmed that an open active centre is essential for modulating the activities of the two enzyme mimics. Moreover, under the conditions employed, hydrolytic rates of PNPP induced by these Mn(III) complexes were faster in Gemini 16-2-16 micelles than that in the micellar solution of cetyltrimethylammonium bromide (CTAB), a conventional analogue of Gemini 16-2-16.

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Section: Impact Of Various Surfactant Micelles On the Catalytic Hydromentioning

confidence: 93%

Hydrolysis kinetics of p-nitrophenylpicolinate catalyzed by schiff base Mn(III) complexes in Gemini 16-2-16 micellar solutiony

Jiang

Zhang

et al. 2009

Open Chemistry

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“…The spectral data of one representative monocationic surfactant, 1-(4 0 -hexadecyloxy benzyl)-3-methyl imidazolium bromide [C 16 …”

Section: Spectral Datamentioning

confidence: 99%

“…Baltazar et al [9] first reported synthesis and evaluation of surface properties of some dicationic imidazolium-based surfactant. A novel class of pyridinium-based gemini surfactants have also been synthesized and evaluated for their surface properties [15,16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of new imidazolium‐based aromatic ether functionalized cationic mono and gemini surfactants

Sadula

Reddy

Kanjilal

2011

Eur. J. Lipid Sci. Technol.

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Synthesis of a novel series of imidazolium-based surfactants, [(ROArCH 2 MIm)Br] with aromatic ether functionalized hydrophobic tail of varying chain lengths and also their gemini counterparts were conducted in the present work. Synthesis involves initial conversion of 4-hydroxy benzoic acid to its methyl ester followed by its O-alkylation with long chain fatty alcohols, which was subsequently reduced and brominated to get 4-alkyloxy benzyl bromide. For the synthesis of monocationic surfactant, 4-alkyloxy benzyl bromide is quaternized with N-methylimidazole. Gemini surfactants are synthesized by initial coupling of imidazole to 4-alkyloxy benzyl bromide followed by its quaternization with dibromoalkane. The surface properties of all the synthesized surfactants were determined using surface tensiometry. Within the same homologous series, expected decrease in critical micelle concentration (cmc) with the increase in hydrophobicity was observed for shorter chain homologs. However, the deviation in cmc value from regularity was observed when the number of carbon atoms in the hydrophobic chain exceeded a certain number. The cmc values of the geminis were found to be remarkably low compared to their monomeric counterparts.

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“…Gemini amphiphiles are the class of compound with twin hydrophobic tails linked with hydrophilic head with or without spacer [10]. Gemini amphiphiles are more beneficial as compared to single tailed ionic amphiphiles, because of their high surface activity, low critical micelle concentration [11], better solubilizing ability and greater ability to form stable structures with globular proteins [12,13]. In the recent instance, the interaction of globular protein with single tailed and Gemini amphiphiles had been investigated by the different research groups [14][15][16][17].…”

Section: Introduction Bioactive Peptidesmentioning

confidence: 99%

Comparison of Physicochemical Studies of Single Tailed and Gemini Cyclohexanoxy Carbonyl Pyridinium Cationic Amphiphiles

Aggarwal¹

2017

J Proteomics Bioinform

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In the present research work, the physicochemical studies of surface active Cyclohexanoxy carbonyl Pyridinium single tailed and Gemini amphiphiles had been compared. Thermal stability, size of aggregates in aqueous system and interaction with a globular protein, Bovine Serum Albumin (BSA), was done by using TGA analysis, DLS, UV-visible, steady-state fluorescence and synchronous fluorescence and TEM respectively. On the basis of the experiments, it had been concluded that the Gemini amphiphile possessed less cytotoxicity, high thermally stability, form small sized compact aggregates and stable complex with BSA. The results have further been supported by higher value of Stern-Volmer quenching constant (K SV ) and a higher binding constants for Gemini amphiphiles as compared to single tailed amphiphiles. Moreover, on the basis of synchronous fluorescence spectra and UV spectra, it has been concluded that both the amphiphiles mainly interact with tryptophan residues. The less cytotoxicity values and stabilization of secondary structure of BSA in low concentration of ionic liquids implies that these ionic liquids can replaced the conventional surfactants in the detergent industries and used as a potential vehicles for the drug and gene delivery.the change in the wavelength of emission maximum (λ max ) and intensity parameters found to be sensitive to protein conformation and can be used to investigate the interactions between BSA and ionic liquids. DLS and TEM studies are used to see the change in conformation of the amphiphiles in the presence of BSA. Materials and Methods MaterialsGemini Amphiphiles (GA) and Single Tailed amphiphiles (ST) ( Figure 1) were synthesized in our lab by an earlier reported procedure [18,19]. Bovine Serum Albumin (BSA) (MW=66 kDa) was purchased from Central drug house (New Delhi, India) and was used as received. 0.01 M buffer, pH 7.2, was made from 0.01 M KH 2 PO 4 and 0.01 M sodium hydroxide. Potassium dihydrogen phosphate and sodium hydroxide were purchased from Merck, India. Millipore water was used in all experiments. Thermal gravimetric analysisThermal stability of both the amphiphiles had been investigated by Perkin Elmer Pyris 1 Thermal Gravimetric Analyzer (TGA). Both the samples were completely dried by rotatory vaccum pump. Both the samples were added in to the aluminum pans under the inert atmosphere at a heating rate of 10°C/min. Dynamic Light Scattering (DLS)The size of the studied cationic amphiphiles has been measured by the Zetasizer Nano ZS (Malvern Instrument Ltd.) UK. The inbuilt peltier device controls the temperature with an accuracy of ±0.1 K. The 1.0 mM aqueous solution of both amphiphiles has been filtered through 0.45 μM pore sized filter before measurement. CytotoxicityThe cytotoxicity of, 1.0 mM aqueous solution, both synthesized amphiphiles was carried out on C 6 glioma (cancerous brain cell line, passage number 65) by using MTT assay to calculate the IC 50 value of both the synthesized ionic liquids. Cells were seeded at a density of 10 × 10 3 cells/m...

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Synthesis and Properties of a Novel Class of Gemini Pyridinium Surfactants

Cited by 122 publications

References 26 publications

Hydrolysis kinetics of p-nitrophenylpicolinate catalyzed by schiff base Mn(III) complexes in Gemini 16-2-16 micellar solutiony

Hydrolysis kinetics of p-nitrophenylpicolinate catalyzed by schiff base Mn(III) complexes in Gemini 16-2-16 micellar solutiony

Synthesis and evaluation of new imidazolium‐based aromatic ether functionalized cationic mono and gemini surfactants

Comparison of Physicochemical Studies of Single Tailed and Gemini Cyclohexanoxy Carbonyl Pyridinium Cationic Amphiphiles

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