Synthesis, Surface Active Properties and Cytotoxicity of Sodium &lt;i&gt;N&lt;/i&gt;-Acyl Prolines

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

doi:10.5650/jos.ess15077

Cited by 8 publications

(4 citation statements)

References 38 publications

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“…Much attention has been paid by the industry to these surfactants because of their unique safety and performance, and some commodities to the formula of infant care and cosmetics have been commercialized. For example, Sreenu et al studied the synthesis, surface activity, and cytotoxicity of sodium N-acylproline 9) . Madhumanchi et al studied the synthesis and surface and biological properties of sodium Most studies on surfactant/protein systems have focused on the interaction between bovine serum albumin (BSA) and common surfactants, such as sodium dodecyl sulfate (SDS) , cetylmethylammonium chloride, and cetylmethylammonium bromide 21−26) .…”

Section: Introductionmentioning

confidence: 99%

Contrastive Study of the Foaming Properties of N-Acyl Amino Acid Surfactants with Bovine Serum Albumin and Gelatin

et al. 2021

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N-acyl-isoleucine 10) . The surface and antibacterial properties of N-palmitoyl amino acid surfactants were studied by Sreenu et al. 11) . Dianrui Zhang et al. studied the environmental properties of lauryl glutamate and the properties of gel foam 12) . Most current research on N-acyl amino acid surfactants focused on synthesis, environmental response, surface activity, interfacial property 13) , toxicology 14) , and antibacterial activity.Surfactant/protein mixtures have been widely used in detergents, cosmetics, food, and pharmaceutical fields. The interaction between surfactants and proteins has attracted much attention in the past decades. Surfactants can stabilize or alter the structure of proteins 15,16) . Therefore, surfactants have attracted much attention in the cosmetics, medicine, and food fields. Such as Alzheimer s disease, that is related with starch fibrous denatured protein aggregation 17,18) . In the food field, the mixtures of protein and surfactant are usually used as emulsifier 19) and foam stabilizer 20) .

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Section: Introductionmentioning

confidence: 99%

Contrastive Study of the Foaming Properties of N-Acyl Amino Acid Surfactants with Bovine Serum Albumin and Gelatin

et al. 2021

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“…The newly produced NAAs in this reaction system are amphiphilic and can provide a membrane compartment for early protocells. NAAs have been widely studied as a kind of amino acid surfactant, and numerous aspects have been investigated, including surface activity, [25] interfacial properties, [26] antibacterial properties, [27] and foam properties [28] . However, NAA, as an original amphiphilic substance, can form vesicles alone, and its effect on fatty acid vesicles has rarely been studied.…”

Section: Resultsmentioning

confidence: 99%

“…Chemistry-A European Journal investigated, including surface activity, [25] interfacial properties, [26] antibacterial properties, [27] and foam properties. [28] However, NAA, as an original amphiphilic substance, can form vesicles alone, and its effect on fatty acid vesicles has rarely been studied.…”

Section: The Ability Of N-decanoyl Phenylalanine (Da-phe) To Self-ass...mentioning

confidence: 99%

Protocell Self‐Assembly Driven by Sodium Trimetaphosphate

Chen

Yan

Chi

et al. 2023

Chemistry A European J

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The co‐evolution of peptide formation and membrane self‐assembly is considered an essential step in the origin of life. However, more research is required on both processes, particularly on the interaction between prebiotic simple fatty‐acid membranes and peptide synthesis. In this study, the sodium trimetaphosphate (P3m)‐activated peptide formation reaction of phenylalanine (Phe) in an alkaline decanoic acid‐decanol vesicle system was systematically investigated. The experimental results showed that peptide formation could competitively occur with N‐acyl amino acid (NAA) formation. NAA formation did not follow the traditional P3m‐activated peptide formation reaction involving the intermediate cyclic acylphosphoramidate (CAPA). Decanoic acid was activated by P3m to form a mixed anhydride, which then reacted with an amino acid to form the amide NAA. As a kind of membrane‐forming amphiphile, NAA can form vesicles independently and reduce the critical vesicle concentration of the fatty‐acid vesicles. Moreover, 11 other representative amino acids, namely alanine (Ala), aspartic acid (Asp), glutamic acid (Glu), glycine (Gly), isoleucine (Ile), leucine (Leu), proline (Pro), serine (Ser), threonine (Thr), valine (Val), and arginine (Arg), were selected for investigation. All of them reacted with decanoic acid to form NAA via the activation effect of P3m. The abovementioned mechanism involving P3m‐activated carboxylic acid has not been reported in the literature. Our experimental results indicate that the participation of decanoic acid in the P3m activation‐based peptide formation reaction system plays a significant role in the emergence of functionalized protocells. The P3m activation effect can provide diversified raw membrane materials to form and stabilize protocell membranes; moreover, the small peptides, such as Phe‐Leu, formed in the same reaction system can induce the amplification of primitive cells. This implies that synergistic symbiosis between membrane and peptide can be realized via the P3m activation effect.

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“…Derivatives of N-acyl taurines, N-acyl taurates (NATs), possess excellent properties of detergency and stability over the whole pH range in aqueous solution. [21][22][23] Owing to the variety of available fatty acids, the functionality of NATs may be modified to suit different purposes. Recently, we discovered a novel application of NATs as absorption enhancers, demonstrating improvement of the intestinal absorption of alendronate, a water-soluble and poorly absorbed drug.…”

Section: )mentioning

confidence: 99%

Improvement of the Solubility and Intestinal Absorption of Curcumin by <i>N</i>-Acyl Taurates and Elucidation of the Absorption-Enhancing Mechanisms

Kawamura

Sato

et al. 2017

Biological & Pharmaceutical Bulletin

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In this study, the effects of N-acyl taurates (NATs) on the intestinal absorption of curcumin (CUR), a water-insoluble and poorly absorbed compound, were examined in rats. Sodium methyl lauroyl taurate (LMT) and sodium methyl cocoyl taurate (CMT) were the most effective in increasing the solubility and intestinal absorption of CUR. The intestinal membrane toxicity of the NATs was also evaluated by measuring the activity of lactate dehydrogenase (LDH), a toxicity marker. NATs did not increase the activity of LDH, suggesting that they may be safely administered orally. We further elucidated the absorption-enhancing mechanisms of NATs by using Caco-2 cells. In cellular transport studies, LMT and CMT reduced the transepithelial electrical resistance value of Caco-2 cells and increased the transport of 5(6)-carboxyfluorescein and CUR. Hence, the intestinal absorption enhancement by LMT and CMT was attributed to the synergistic effect of higher solubility and greater permeability of the cell layer towards CUR in the presence of the surfactants. In summary, co-administration of CUR with either LMT or CMT is a simple and effective method to enhance oral delivery of CUR.

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

Cited by 8 publications

References 38 publications

Contrastive Study of the Foaming Properties of N-Acyl Amino Acid Surfactants with Bovine Serum Albumin and Gelatin

Contrastive Study of the Foaming Properties of N-Acyl Amino Acid Surfactants with Bovine Serum Albumin and Gelatin

Protocell Self‐Assembly Driven by Sodium Trimetaphosphate

Improvement of the Solubility and Intestinal Absorption of Curcumin by <i>N</i>-Acyl Taurates and Elucidation of the Absorption-Enhancing Mechanisms

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