Thermodynamics of Micellization of Cholic Acid Based Facial Amphiphiles Carrying Three Permanent Ionic Head Groups

Willemen, Hendra M.; Marcelis, and Antonius T. M.; Sudhölter, Ernst J. R.

doi:10.1021/la0267443

Cited by 13 publications

(9 citation statements)

References 28 publications

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“…The general trend in this work is a continuous decrease in CMC with the increase in the hydrophobic chain as shown in Fig. 2 Scheme 1 Structures and abbreviations of sulfo-propane betaines and sulfo-butane betaines the longer hydrophilic chain length will be more flexible and the hydrophilic groups will be easier to move into the same average chemical environment easily [17]. Amphoteric surfactants have both positive and negative ions on the hydrophilic groups, the charges can be distributed better over the micellar surface, therefore the hydrophilic groups may attract each other as much as possible.…”

Section: Thermodynamics Of Micellizationmentioning

confidence: 75%

Thermodynamics of Micellization of Sulfobetaine Surfactants in Aqueous Solution

Cheng

Ji-jun

et al. 2012

J Surfact & Detergents

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The thermodynamics of micellization of the sulfobetaine (SB) amphoteric surfactants, that is N‐alkyl‐N,N‐dimethyl‐3‐ammonio‐1‐propanesulfonate and N‐alkyl‐N,Nd‐imethyl‐3‐ammonio‐1‐butanesulfonate (the carbon atom number of the alkyl chain is 12, 14 and 16 respectively) in aqueous solution, have been studied by surface tension measurements with the temperature range from 298.15 to 318.15 K. The critical micelle concentrations (CMC) of SB n‐3 and SB n‐4 surfactants were determined from the drop‐volume methods at different temperatures. The obtained results indicated that the values of critical micelle concentration strongly depended on the surfactants species and temperatures. Thermodynamic parameters (Gmic∘, Hmic∘ and Smic∘) of the micelle formation were determined. The micellization was found to be enthalpy‐driven at lower temperatures, while this process was entropy‐driven at higher temperatures. The enthalpy–entropy compensation were also investigated. The compensation temperature Tc and Hmic⃰ decreased, while Smic⃰ increased with the increase in the hydrophobic chain length.

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Section: Thermodynamics Of Micellizationmentioning

confidence: 75%

Thermodynamics of Micellization of Sulfobetaine Surfactants in Aqueous Solution

Cheng

Ji-jun

et al. 2012

J Surfact & Detergents

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“…Over the last few decades, researchers have worked on the synthesis and studies of cationic bile acid derivatives owing to their wide range of applications as cancerostatic, cholesterol dissolution agents, gallstone dissolution enhancers, and DNA transfection agents. − Moreover, these derivatives were found to be potent antibacterial agents in biomedical applications. , Many reports are available on the synthesis of cationic bile salts through ether, ester, and amide linkages in both facial and side chain of the bile acids and the level of difficulty varies widely in these syntheses. − In most of the cases, bile salts has been synthesized with a cationic group at the side chain by introducing a bis (amine) through amide conjugation chemistry and converting the second amine to a quaternary ammonium salt. , On the other hand, Maitra and co-workers has reported cationic bile salts without amide linkage at the side chain and studied their aggregation and gelation behavior . Recently, Galantini and co-workers has reported the self-assembly of a tryptophan and phenylalanine substituted bile acids …”

Section: Introductionmentioning

confidence: 99%

Hierarchical Self-Assembly of Bile-Acid-Derived Dicationic Amphiphiles and Their Toxicity Assessment on Microbial and Mammalian Systems

Muthukumarasamyvel

Raju

Chandirasekar

et al. 2016

ACS Appl. Mater. Interfaces

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A thiol-yne click chemistry approach was adopted for the first time to prepare highly water-soluble bile acid derived dicationic amphiphiles. The synthesized amphiphiles dicationic cysteamine conjugated cholic acid (DCaC), dicationic cysteamine conjugated deoxycholic acid (DCaDC), and dicationic cysteamine conjugated lithocholic acid (DCaLC) exhibited hierarchically self-assembled microstructures at various concentrations in an aqueous medium. Interestingly at below critical micellar concentration (CMC) the amphiphiles showed distinct fractal patterns such as fractal grass, microdendrites and fern leaf like fractals for DCaC, DCaDC and DCaLC respectively. The fractal dimension (Df) analysis indicated that the formation of fractal like aggregates is a diffusion limited aggregation (DLA) process. The preliminary aggregation studies such as determination of CMC, fluorescence quenching, wettability and contact angle measurements were elaborately investigated. The morphology of the aggregates were analyzed by SEM and OPM techniques. Further, we demonstrated the antimicrobial and hemolytic activity for the cationic amphiphiles. DCaC had potent antimicrobial activity and showed no toxicity on human RBCs indicating that DCaC could be used in biomedical applications, in addition to their industrial and laboratory applications such as detergency, surface cleaning, and disinfection agent.

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“…It is important to ascertain how progressive increases in the number of headgroups influence the thermodynamics of micelle formation and govern the stability and spontaneity of formation of the resulting aggregates. Toward this end, the calorimetric titration method has been employed for the determination of cmc and enthalpy of micellization (Δ H m ) of a number of surfactants. − However, no such investigation has been undertaken to examine the above-mentioned multiheaded surfactants. Herein, we report the results of our studies on the thermodynamics of aggregation of multiheaded surfactants bearing single, double, and triple trimethylammonium headgroups.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamics of Micellization of Multiheaded Single-Chain Cationic Surfactants

Bhattacharya

Haldar

2004

Langmuir

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The energetics of micelle formation of three single-chain cationic surfactants bearing single (h = 1), double (h = 2), and triple (h = 3) trimethylammonium [(+)N(CH(3))(3)] headgroups have been investigated by microcalorimetry. The results were compared with the microcalorimetric data obtained from well-known cationic surfactant, cetyl trimethylammonium bromide (CTAB), bearing a single chain and single headgroup. The critical micellar concentrations (cmc's) and the degrees of counterion dissociation (alpha) of micelles of these surfactants were also determined by conductometry. The cmc and the alpha values increased with the increase in the number of headgroups of the surfactant. The relationship between the cmc of the surfactant in solution and its free energy of micellization (DeltaG(m)) was derived for each surfactant. Exothermic enthalpies of micellization (DeltaH(m)) and positive entropies of micellization (DeltaS(m)) were observed for all the surfactants. Negative DeltaH(m) values increased from CTAB to h = 1 to h = 2 and decreased for h = 3 whereas DeltaS(m) values decreased with increase in the number of headgroups. The DeltaG(m) values progressively became less negative with the increase in the number of headgroups. This implies that micelle formation becomes progressively less favorable as more headgroups are incorporated in the surfactant. From the steady-state fluorescence measurements using pyrene as a probe, the micropolarities sensed by the probe inside various micelles were determined. These studies suggest that the micelles are more hydrated with multiheaded surfactants and the micropolarity of micelles increases with the increase in the number of headgroups.

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Thermodynamics of Micellization of Cholic Acid Based Facial Amphiphiles Carrying Three Permanent Ionic Head Groups

Cited by 13 publications

References 28 publications

Thermodynamics of Micellization of Sulfobetaine Surfactants in Aqueous Solution

Thermodynamics of Micellization of Sulfobetaine Surfactants in Aqueous Solution

Hierarchical Self-Assembly of Bile-Acid-Derived Dicationic Amphiphiles and Their Toxicity Assessment on Microbial and Mammalian Systems

Thermodynamics of Micellization of Multiheaded Single-Chain Cationic Surfactants

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