scholarly journals Aggregation Behavior, Antibacterial Activity and Biocompatibility of Catanionic Assemblies Based on Amino Acid-Derived Surfactants

2020 ◽  
Vol 21 (23) ◽  
pp. 8912
Author(s):  
Lourdes Pérez ◽  
Aurora Pinazo ◽  
M. C. Morán ◽  
Ramon Pons
Keyword(s):  
Antibacterial Activity ◽  
Amino Acid ◽  
Surface Activity ◽  
Cationic Surfactant ◽  
Anionic Surfactant ◽  
High Surface ◽  
Critical Aggregation Concentration ◽  
Medium Size ◽  
Catanionic Vesicles ◽  
Catanionic Mixtures

The surface activity, aggregates morphology, size and charge characteristics of binary catanionic mixtures containing a cationic amino acid-derived surfactant N(π), N(τ)-bis(methyl)-L-Histidine tetradecyl amide (DMHNHC14) and an anionic surfactant (the lysine-based surfactant Nα-lauroyl-Nεacetyl lysine (C12C3L) or sodium myristate) were investigated for the first time. The cationic surfactant has an acid proton which shows a strong pKa shift irrespective of aggregation. The resulting catanionic mixtures exhibited high surface activity and low critical aggregation concentration as compared with the pure constituents. Catanionic vesicles based on DMHNHC14/sodium myristate showed a monodisperse population of medium-size aggregates and good storage stability. According to Small-Angle X-Ray Scattering (SAXS), the characteristics of the bilayers did not depend strongly on the system composition for the positively charged vesicles. Negatively charged vesicles (cationic surfactant:myristate ratio below 1:2) had similar bilayer composition but tended to aggregate. The DMHNHC14-rich vesicles exhibited good antibacterial activity against Gram-positive bacteria and their bactericidal effectivity declined with the decrease of the cationic surfactant content in the mixtures. The hemolytic activity and cytotoxicity of these catanionic formulations against non-tumoral (3T3, HaCaT) and tumoral (HeLa, A431) cell lines also improved by increasing the ratio of cationic surfactant in the mixture. These results indicate that the biological activity of these systems is mainly governed by the cationic charge density, which can be modulated by changing the cationic/anionic surfactant ratio in the mixtures. Remarkably, the incorporation of cholesterol in those catanionic vesicles reduces their cytotoxicity and increases the safety of future biomedical applications of these systems.

Rheology of wormlike micelles in aqueous systems of a mixed amino acid-based anionic surfactant and cationic surfactant

2009 ◽  
Vol 287 (11) ◽  
pp. 1305-1315 ◽  
Author(s):  
Rekha Goswami Shrestha ◽  
Lok Kumar Shrestha ◽  
Kenji Aramaki
Keyword(s):  
Amino Acid ◽  
Cationic Surfactant ◽  
Anionic Surfactant ◽  
Wormlike Micelles ◽  
Aqueous Systems

scholarly journals Biocompatible Catanionic Vesicles from Arginine-Based Surfactants: A New Strategy to Tune the Antimicrobial Activity and Cytotoxicity of Vesicular Systems

Pharmaceutics ◽  
2020 ◽  
Vol 12 (9) ◽  
pp. 857
Author(s):  
Aurora Pinazo ◽  
Ramon Pons ◽  
Ana Marqués ◽  
Maribel Farfan ◽  
Anderson da Silva ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Charge Density ◽  
Hemolytic Activity ◽  
Colloidal Stability ◽  
Low Cost ◽  
Critical Aggregation Concentration ◽  
Medium Size ◽  
Colloidal Systems ◽  
Single Chain ◽  
Catanionic Vesicles

Their stability and low cost make catanionic vesicles suitable for application as drug delivery systems. In this work we prepared catanionic vesicles using biocompatible surfactants: two cationic arginine-based surfactants (the monocatenary Nα-lauroyl-arginine methyl ester—LAM and the gemini Nα,Nϖ-bis(Nα-lauroylarginine) α, ϖ-propylendiamide—C3(CA)2) and three anionic amphiphiles (the single chain sodium dodecanoate, sodium myristate, and the double chain 8-SH). The critical aggregation concentration, colloidal stability, size, and charge density of these systems were comprehensively studied for the first time. These catanionic vesicles, which form spontaneously after mixing two aqueous solutions of oppositely charged surfactants, exhibited a monodisperse population of medium-size aggregates and good stability. The antimicrobial and hemolytic activity of the vesicles can be modulated by changing the cationic/anionic surfactant ratio. Vesicles with a positive charge efficiently killed Gram-negative and Gram-positive bacteria as well as yeasts; the antibacterial activity declined with the decrease of the cationic charge density. The catanionic systems also effectively eradicated MRSA (Methicillin-resistant Staphylococcus Aureus) and Pseudomonas aeruginosa biofilms. Interestingly, the incorporation of cholesterol in the catanionic mixtures improved the stability of these colloidal systems and considerably reduced their cytotoxicity without affecting their antimicrobial activity. Additionally, these catanionic vesicles showed good DNA affinity. Their antimicrobial efficiency and low hemolytic activity render these catanionic vesicles very promising candidates for biomedical applications.

Study on the properties and self-assembly of fatty alcohol ether carboxylic ester anionic surfactant and cationic surfactant in a mixed system

2019 ◽  
Vol 43 (31) ◽  
pp. 12494-12502
Author(s):  
Zhifang Wu ◽  
Yunling Li ◽  
Jun Li ◽  
Mengwei Wang ◽  
Zhifei Wang
Keyword(s):  
Surface Activity ◽  
Cationic Surfactant ◽  
Fatty Alcohol ◽  
Anionic Surfactant ◽  
Self Assembly ◽  
Mixed System ◽  
Carboxylic Ester ◽  
System A ◽  
System P

Mixed system A12–14EC9E-Na/DEQ exhibits excellent surface activity, application properties, and interesting self-assembly behaviors.

Fluoroquinolone-3-carboxamide Amino Acid Conjugates: Synthesis, Antibacterial Properties And Molecular Modeling Studies

2020 ◽  
Vol 17 (1) ◽  
pp. 71-84
Author(s):  
Riham M. Bokhtia ◽  
Siva S. Panda ◽  
Adel S. Girgis ◽  
Hitesh H. Honkanadavar ◽  
Tarek S. Ibrahim ◽  
...  
Keyword(s):  
Experimental Data ◽  
Antibacterial Activity ◽  
Amino Acid ◽  
Bacterial Infections ◽  
Antibacterial Agents ◽  
Antibacterial Properties ◽  
Computational Studies ◽  
Protecting Group ◽  
Amino Acid Conjugates ◽  
Molecular Modeling Studies

Background: Bacterial infections are considered as one of the major global health threats, so it is very essential to design and develop new antibacterial agents to overcome the drawbacks of existing antibacterial agents. Method: The aim of this work is to synthesize a series of new fluoroquinolone-3-carboxamide amino acid conjugates by molecular hybridization. We utilized benzotriazole chemistry to synthesize the desired hybrid conjugates. Result: All the conjugates were synthesized in good yields, characterized, evaluated for their antibacterial activity. The compounds were screened for their antibacterial activity using methods adapted from the Clinical and Laboratory Standards Institute. Synthesized conjugates were tested for activity against medically relevant pathogens; Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27856) Staphylococcus aureus (ATCC 25923) and Enterococcus faecalis (ATCC 19433). Conclusion: The observed antibacterial experimental data indicates the selectivity of our synthesized conjugates against E.Coli. The protecting group on amino acids decreases the antibacterial activity. The synthesized conjugates are non-toxic to the normal cell lines. The experimental data were supported by computational studies.

scholarly journals Biological and Physico-Chemical Characteristics of Arginine-Rich Peptide Gemini Surfactants with Lysine and Cystine Spacers

2021 ◽  
Vol 22 (7) ◽  
pp. 3299
Author(s):  
Damian Neubauer ◽  
Maciej Jaśkiewicz ◽  
Marta Bauer ◽  
Agata Olejniczak-Kęder ◽  
Emilia Sikorska ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Amino Acid ◽  
Cationic Surfactants ◽  
Antimicrobial Agents ◽  
Gemini Surfactants ◽  
Antimicrobial Activities ◽  
Critical Aggregation Concentration ◽  
Cytotoxic Activities ◽  
Candida Sp ◽  
Enhanced Selectivity

Ultrashort cationic lipopeptides (USCLs) and gemini cationic surfactants are classes of potent antimicrobials. Our recent study has shown that the branching and shortening of the fatty acids chains with the simultaneous addition of a hydrophobic N-terminal amino acid in USCLs result in compounds with enhanced selectivity. Here, this approach was introduced into arginine-rich gemini cationic surfactants. L-cystine diamide and L-lysine amide linkers were used as spacers. Antimicrobial activity against planktonic and biofilm cultures of ESKAPE (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter spp.) strains and Candida sp. as well as hemolytic and cytotoxic activities were examined. Moreover, antimicrobial activity in the presence of human serum and the ability to form micelles were evaluated. Membrane permeabilization study, serum stability assay, and molecular dynamics were performed. Generally, critical aggregation concentration was linearly correlated with hydrophobicity. Gemini surfactants were more active than the parent USCLs, and they turned out to be selective antimicrobial agents with relatively low hemolytic and cytotoxic activities. Geminis with the L-cystine diamide spacer seem to be less cytotoxic than their L-lysine amide counterparts, but they exhibited lower antibiofilm and antimicrobial activities in serum. In some cases, geminis with branched fatty acid chains and N-terminal hydrophobic amino acid resides exhibited enhanced selectivity to pathogens over human cells.

scholarly journals Controlling Antibacterial Activity Exclusively with Visible Light: Introducing a Tetra‐ortho‐Chloro‐Azobenzene Amino Acid

2021 ◽  
Author(s):  
Xavier Just-Baringo ◽  
Alejandro Yeste-Vázquez ◽  
Javier Moreno-Morales ◽  
Clara Ballesté-Delpierre ◽  
Jordi Vila ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Amino Acid ◽  
Visible Light

scholarly journals Effects of Synthetic Procedures and Postsynthesis Incubation pH on Size, Shape, and Antibacterial Activity of Copper (I) Oxide Nanoparticles

2020 ◽  
Vol 2020 ◽  
pp. 1-10
Author(s):  
Vinh Tien Nguyen ◽  
Khanh Son Trinh
Keyword(s):  
Antibacterial Activity ◽  
High Surface ◽  
Size Variation ◽  
Reaction Rates ◽  
Bacterial Suspension ◽  
Oxide Nanoparticles ◽  
Surface Charges ◽  
Fast Reaction ◽  
Sem Images ◽  
Etching Effect

Copper (I) oxide nanoparticles (Cu2O NP) were synthesized by reducing CuSO4 with glucose in the presence of polyvinyl alcohol as a capping agent. We used three different synthetic procedures with a fast reaction (procedure 1p), a fast-then-slow reaction (procedure 2p), and a slow-then-fast reaction (procedure 3p). The reaction rates were controlled by changing the temperature and the speed of adding reagents. The synthesized Cu2O NP were subsequently incubated for 24 h in a pH 6 solution (Cu2O NP6) or a pH 8 solution (Cu2O NP8) at 5°C. XRD and SEM images analysis revealed that the 1p procedure produced smaller NP, while the 2p procedure produced larger but more uniform NP. The 3p procedure produced the largest NP with a higher size variation. The 24-hour acidic postsynthesis incubation resulted in an etching effect, which reduced the size and size variation of Cu2O NP6. To evaluate the antibacterial activity, E. coli suspensions were mixed with the obtained Cu2O NP (32, 96, or 160 ppm) for different time intervals (1 or 24 h) and then grown on Petri dishes at 37°C for 24 h. Higher doses, smaller sizes of Cu2O NP, and longer contact times with the bacterial suspension resulted in higher inactivation efficiencies. Cu2O NP6 showed higher antibacterial effects at low doses, possibly due to the etching effect and the positive surface charge. Increasing the Cu2O doses from 32 to 96 and 160 ppm noticeably increased the antibacterial effect of the Cu2O NP8, but not significantly for Cu2O NP6. We suggested that the Cu2O NP6 suffered from agglomeration at high doses due to their high surface activity and low surface charges.

scholarly journals SYNTHESIS AND ANTIMICROBIAL EVALUATION OF QUINAZOLINONE PEPTIDE DERIVATIVES

2017 ◽  
Vol 10 (16) ◽  
pp. 7 ◽  
Author(s):  
Bhupinder Kapoor ◽  
Arshid Nabi ◽  
Reena Gupta ◽  
Mukta Gupta
Keyword(s):  
Antibacterial Activity ◽  
Amino Acid ◽  
Antimicrobial Agents ◽  
Methyl Esters ◽  
Standard Drug ◽  
Amino Acid Peptide ◽  
Chemical Structures ◽  
1H Nuclear Magnetic Resonance ◽  
Peptide Derivatives ◽  
Derivatives Of

  Objective: The increased microbial resistance against commercially available drugs initiated the development of novel and safe antimicrobial agents in last few decades. In this view, a series of amino acid/dipeptide derivatives of quinazolin-3(4H)-one was synthesized and was evaluated for their antimicrobial potential.Method: Synthesis of amino acid/peptide derivatives were carried out by coupling 5-(2-(2-chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-hydroxy benzoic acid with amino acid/dipeptide methyl esters in the presence of dicyclohexylcarbodiimide and N-methylmorpholine. The chemical structures of synthesized compounds were characterized by 1H nuclear magnetic resonance and infrared spectroscopy and were screened for antibacterial activity by disc diffusion method.Results: All the synthesized derivatives exhibited moderate to significant antibacterial activity against both Gram-positive and Gram-negative bacteria. The potency of compound 5d was comparable to standard drug ciprofloxacin in all the strains of bacteria used. The compound 5a was found to be more active against Streptococcus pyogenes and Staphylococcus aureus while compound 5c against Pseudomonas aeruginosa and Escherichia coli. Conclusion: Peptide derivatives of quinazolinone are promising antimicrobial agent and can be used for the synthesis of other novel compounds.

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