Synthesis and Surface-Active Properties of Sodium N-Acylphenylalanines and Their Cytotoxicity

Sreenu, Madhumanchi; Sujitha, Pombala; Kumar, C. Ganesh

doi:10.1021/ie503764v

Cited by 18 publications

(7 citation statements)

References 44 publications

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“…This trend is reverse to the conventional surfactants and this erratic behavior is unknown to us. This behavior was not found in case of pure and mixture of N-acyl phenylalanines and isoleucines head groups 17,24,30 .…”

Section: Surface Tensionmentioning

confidence: 78%

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Synthesis, Surface Active Properties and Cytotoxicity of Sodium N-Acyl Prolines

2015

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Section: Surface Tensionmentioning

confidence: 78%

“…The cytotoxicity of the sodium N-acyl prolines was assessed by using the MTT assay according to reported method 29,30 .…”

Section: In Vitro Cytotoxicity Of Sodium N-acyl Prolinesmentioning

confidence: 99%

Synthesis, Surface Active Properties and Cytotoxicity of Sodium N-Acyl Prolines

2015

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“…The sodium salts of N-acyl phenylalanines and N-acyl isoleucines prepared from fatty acid mixtures obtained from coconut, palm, palm kernel, jathropa, karanja, Sterculia foetida, castor, and high oleic sunflower oils exhibited superior surface active properties like surface tension, CMC, calcium tolerance, wetting power, foaming, and emulsion stability compared to reference surfactant sodium lauryl sulphate (SLS) [12,29]. Except for the N-acylphenylalaninate from coconut oil, all the other N-acyl phenylalanines showed promising cytotoxicity against human cancer cell lines [12].…”

Section: Single-chain Surfactantsmentioning

confidence: 99%

“…Amino acid surfactants (AAS) are biocompatible and biodegradable surfactants obtained by condensation of natural amino acids with fatty acids (or their derivatives) of oleochemical source [5,9,10]. Hydrolysis of triglycerides from animal fat or vegetable oils furnishes a wide variety of saturated and unsaturated fatty acids with straight hydrocarbon chains and an even number of carbon atoms due to their biosynthetic route [3,11,12]. The use of non-edible waste cooking oils is also a viable alternative, and further contributes to reduce the environmental burden [13].…”

Section: Introductionmentioning

confidence: 99%

Amino Acid-Based Surfactants for Biomedical Applications

Pinheiro¹,

Faustino²

2017

Application and Characterization of Surfactants

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The growing demand for surfactants worldwide has a profound impact on the environment and public health. The quest for environmentally friendly "green" surfactants has driven research toward bio-based surfactants from renewable sources with improved performances and low toxicity. Amino acid-based surfactants (AAS) are a promising class of biocompatible and biodegradable surfactants for biomedical applications due to their improved safety profiles that meet the requirements of both physiological and ecological compatibility. Natural amino acids are chiral compounds and important raw materials for production of AAS. The amino acid pool allows the synthesis of multifunctional surfactants with chiral properties that can be tailored for specific technological and/or biomedical applications. The nature of the amino acid residue, the chirality, and the ability for hydrogen bond formation strongly influences the surface active properties and self-assembly behavior of AAS. This review summarizes recent developments in AAS structure-property relationships providing valuable information for modulation of the surface active and biological properties of AAS to meet specific biomedical applications. The interaction of AAS with biointerfaces and biological molecules is also addressed concerning cellular toxicity and potential therapeutic applications of AAS as antimicrobial agents, drug delivery vehicles, and a promising alternative to viral vectors in gene therapy.

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“…Micelle radii were also found to scale linearly with the solution's specific optical rotation values (Covington & Polavarapu, ; Vijay, Baskar, Mandal, & Polavarapu, ). The synthesis and surface‐active properties of sodium N ‐acylphenylalanine surfactants prepared from natural oils (Sreenu, Prasad, Sujitha, & Kumar, ) and anionic phenylalanine‐glycerol ether surfactants have also been reported (Varka, Coutouli‐Argyropoulou, Infante, & Pegiadou, ). Finally, cationic phenylalanine‐based surfactants have been found to interact with model membranes and to have antimicrobial activity (Joondan, Jhaumeer‐Laulloo, & Caumul, ).…”

Section: Introductionmentioning

confidence: 99%

Nuclear Magnetic Resonance Investigation of the Effect of pH on Micelle Formation by the Amino Acid‐Based Surfactant Undecyl l‐Phenylalaninate

Rothbauer

Rutter

Reuter-Seng

et al. 2018

J Surfact & Detergents

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Micelle formation by the anionic amino acidbased surfactant undecyl L-phenylalaninate (und-Phe) was investigated as a function of pH in solutions containing either Na + , L-arginine, L-lysine, or L-ornithine counterions. In each mixture, the surfactant's critical micelle concentration (CMC) was the lowest at low pH and increased as solutions became more basic. Below pH 9, surfactant solutions containing L-arginine and L-lysine had lower CMC than the corresponding solutions with Na + counterions. Nuclear magnetic resonance (NMR) diffusometry and dynamic light scattering studies revealed that und-Phe micelles with Na + counterions had hydrodynamic radii of approximately 15 Å throughout the investigated pH range. Furthermore, L-arginine, L-lysine, and L-ornithine were found to bind most strongly to the micelles below pH 9 when the counterions were cationic. Above pH 9, the counterions became zwitterionic and dissociated from the micelle surface. In und-Phe/L-arginine solution, counterion dissociation was accompanied by a decrease in the hydrodynamic radius of the micelle. However, in experiments with L-lysine and L-ornithine, micelle radii remained the same at low pH when counterions were bound and at high pH when they were not. This result suggested that Larginine is attached perpendicular to the micelle surface through its guanidinium functional group with the remainder of the molecule extending into solution. Contrastingly, L-lysine and L-ornithine likely bind parallel to the micelle surface with their two amine functional groups interacting with different surfactant monomers. This model was consistent with the results from two-dimensional ROESY (rotating frame Overhauser enhancement spectroscopy) NMR experiments. Two-dimensional NMR also showed that in und-Phe micelles, the aromatic rings on the phenylalanine headgroups were rotated toward the hydrocarbon core of micelle. KeywordsAmino acid surfactant Á Micelle Á Counterion Á NMR J Surfact Deterg (2018) 21: 139-153. Abbreviations CE capillary electrophoresis CMC critical micelle concentration DLS dynamic light scattering HPLC high-performance liquid chromatography NMR nuclear magnetic resonance NOESY nuclear Overhauser effect spectroscopy ROESY rotating frame Overhauser enhancement spectroscopy TMS tetramethylsilane und-Leu undecylenyl L-leucine und-Phe L-undecyl phenylalaninateFig. 1 Structures of (a) L-undecyl phenylalaninate, (b) L-arginine, (c) L-lysine, and (d) L-ornithine. Atom labels are used to assign the twodimensional NMR spectra. Cationic forms of the amino acid counterions found in solution below pH 9.0 are shown 140 J Surfact Deterg J Surfact Deterg (2018) 21: 139-153 141 J Surfact Deterg J Surfact Deterg (2018) 21: 139-153

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Synthesis and Surface-Active Properties of Sodium N-Acylphenylalanines and Their Cytotoxicity

Cited by 18 publications

References 44 publications

Synthesis, Surface Active Properties and Cytotoxicity of Sodium <i>N</i>-Acyl Prolines

Synthesis, Surface Active Properties and Cytotoxicity of Sodium <i>N</i>-Acyl Prolines

Amino Acid-Based Surfactants for Biomedical Applications

Nuclear Magnetic Resonance Investigation of the Effect of pH on Micelle Formation by the Amino Acid‐Based Surfactant Undecyl l‐Phenylalaninate

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