Interaction of Chlorpromazine and Trifluoperazine with Anionic Sodium Dodecyl Sulfate (SDS) Micelles: Electronic Absorption and Fluorescence Studies

Caetano, Wilker; Tabak, Marcel

doi:10.1006/jcis.2000.6720

Cited by 137 publications

(75 citation statements)

References 45 publications

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“…Thus, those interactions of DTAB with BPB which result to red shift, can be attributed to the hydrophobic interactions between them. The red shift has been previously reported for other compounds upon going from polar to apolar solvents 29 and upon going from the aqueous solution to the more hydrophobic micellar environment. 30 Thermodynamic parameters of this interaction are given in Table 7.…”

Section: Methodssupporting

confidence: 74%

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Study of Kinetics of Bromophenol Blue Fading in the Presence of SDS, DTAB and Triton X-100 by Classical Model

2004

Bulletin of the Korean Chemical Society

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In this paper, kinetics of reaction between Bromophenol blue (BPB) and OH − , called fading, has been studied through a spectrophotometric method in the presence of nonionic Triton X-100 (TX-100), anionic sodium dodecyl sulfate (SDS) and cationic dodecyl trimethylammonium bromide (DTAB) surfactants. The influence of changes in the surfactant concentration on the observed rate constant was investigated. The results are treated quantitatively by pseudophase ion-exchange (PPIE) model and a new simple model called "classical model". The binding constants of BPB molecules to the micelles and free molecules of surfactants, their stoichiometric ratios and thermodynamic parameters of binding have been evaluated. It was found that SDS has nearly no effect on the fading rate up to 10 mM, whereas TX-100 and DTAB interact with BPB which reduce the reaction rate. By the use of fading reaction of BPB, the binding constants of SDS molecules to TX-100 micelles and their Langmuir and Freundlich adsorption isotherms were obtained and when mixtures of DTAB and TX-100 were used, no interaction was observed between these two surfactants.

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Section: Methodssupporting

confidence: 74%

“…For interaction of SDS with TX-100 (here abbreviated as TX)we can write: (29) (30) (31) substituting equation (31) for (30) we have: . Those sc points which are obtained from the intersection of Samiey equations for adjacent regions, are shown in a box.…”

Section: Proof Of Adjacent Regions By Destructive Interaction With Sumentioning

confidence: 99%

Study of Kinetics of Bromophenol Blue Fading in the Presence of SDS, DTAB and Triton X-100 by Classical Model

2004

Bulletin of the Korean Chemical Society

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“…12,13 The apparent pK a changes of the drugs induced by the micelles were observed to be consistent with a strong interaction. The binding constants (K b ) showed a significant hydrophobic contribution modulated by electrostatic interactions of the positively charged drug with the micelle headgroup.…”

Section: Introductionmentioning

confidence: 62%

“…The special characteristics of the drugs binding to anionic sodium dodecyl sulfate (SDS) monomers and/ or micellar aggregates were also focused. 13 K b values are higher than 5 × 10 3 M -1 for both SDS concentration ranges, at low surfactant concentrations and up to 1-2 mM (drug interaction with surfactant monomers and formation of nonmicellar aggregates) and for more concentrated solutions (in the presence of premicellar and/or micellar aggregates).…”

Section: Introductionmentioning

confidence: 86%

Interaction of Phenothiazine Compounds with Zwitterionic Lysophosphatidylcholine Micelles: Small Angle X-ray Scattering, Electronic Absorption Spectroscopy, and Theoretical Calculations

Barbosa¹,

Caetano²,

Itri³

et al. 2006

J. Phys. Chem. B

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In this work, small-angle X-ray scattering (SAXS) studies on the interaction of the phenothiazine cationic compounds trifluoperazine (TFP, 2-10 mM) and chlorpromazine (CPZ, 2-10 mM) with micelles of the zwitterionic surfactant L-R-lysophosphatidylcholine (LPC, 30 mM), at pHs 4.0 and 7.0, are reported. The SAXS results demonstrate that, upon addition of both phenothiazines, the LPC micelle of prolate ellipsoidal shape changes into a cylindrically shaped micelle, increasing its axial ratio from 1.6 ( 0.1 (in the absence of drug) to 2.5 ( 0.1 (for 5 and 10 mM of phenothiazine). Such an effect is accompanied by a shrinking of the paraffinic shortest semiaxis from 22.5 ( 0.3 to 20.0 ( 0.5 Å. Besides, a significant increase in polar shell electron density from 0.39(1) to 0.45(1) e/Å 3 is observed, consistent with cylinder-like aggregate geometry. Moreover, an increase of the phenothiazine concentration induces the appearance of a repulsive interference function over the SAXS curve of zwitterionic micelles, which is typical of interaction between surfacecharged micelles. Such a finding provides evidence that the positively charged phenothiazine molecule must be accommodated near the hydrophobic/hydrophilic inner micellar interface in such a way that a net surface charge is altered with respect to the original overall neutral zwitterionic micelle. Such phenothiazine location is favored by both electrostatic and hydrophobic contributions, giving rise to binding constant values, obtained from electronic absorption results, that are quite larger compared to their binding to another zwitterionic surfactant, 3-(N-hexadecyl-N,N-dimethylammonio)propanesulfonate (HPS) (Caetano, W., et al. J. Colloid Int. Sci. 2003, 260, 414-422). Comparisons are made by means of theoretical calculations of the surfactant headgroup dipole moments for monomers of LPC and HPS. The theoretical results show that the dipole moment in LPC is almost perpendicular to the methylene chain, while a significant contribution along the methylene chain occurs for HPS. Besides, evidence is presented for extensive delocalization of the charges in the headgroups, which could be also relevant for the binding of the drugs.

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“…The red shift has been previously reported for other compounds upon going from polar to apolar solvents, as a result of hydrophobic interaction. [22][23][24] It seems that TX-100 molecules decrease dielectric constant of the MG + micro-environment. According to Hughs-Ingold rules for nucleophilic substitution reactions, 25,26 formation of the neutral carbinol base from two oppositely charged reactants is more favorable in lower dielectric constant media and thus with increase in TX-100 concentration, the rate of MG + fading increases in the first region.…”

Section: Resultsmentioning

confidence: 99%

Kinetics Study of Malachite Green Fading in the Presence of TX-100, DTAB and SDS

2009

Bulletin of the Korean Chemical Society

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The rate constants of alkaline fading of malachite green (MG + ) was measured in the presence of nonionic (TX-100), cationic (DTAB) and anionic (SDS) surfactants. This reaction was studied under pseudo-first-order conditions at 283∼303 K. The rate of fading reaction showed noticeable dependence on the electrical charge of the used surfactants. It was observed that the reaction rate constants were increased in the presence of TX-100 and DTAB and decreased in the presence of SDS. According to Hughs-Ingold rules for nucleophilic substitution reactions, the electric charge of MG/surfactant compound along with decrease in dielectric constant of MG + micro-environment in this compound varies the rate of fading reaction. Binding constants of surfactant molecules to MG + were calculated using cooperativity, pseudo-phase ion exchange and classical models and the related thermodynamic parameters were obtained by classical model. The results show that the binding of MG + to TX-100 is exothermic and binding of MG + to DTAB and SDS in some concentration ranges of the used surfactants is endothermic and in the other ones is exothermic.

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Interaction of Chlorpromazine and Trifluoperazine with Anionic Sodium Dodecyl Sulfate (SDS) Micelles: Electronic Absorption and Fluorescence Studies

Cited by 137 publications

References 45 publications

Study of Kinetics of Bromophenol Blue Fading in the Presence of SDS, DTAB and Triton X-100 by Classical Model

Study of Kinetics of Bromophenol Blue Fading in the Presence of SDS, DTAB and Triton X-100 by Classical Model

Interaction of Phenothiazine Compounds with Zwitterionic Lysophosphatidylcholine Micelles: Small Angle X-ray Scattering, Electronic Absorption Spectroscopy, and Theoretical Calculations

Kinetics Study of Malachite Green Fading in the Presence of TX-100, DTAB and SDS

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