BIOCOMPATIBLE SURFACTANTS AND IONIC LIQUIDS
Group Leader: Aurora Pinazo
Chemistry is currently facing one of the greatest challenges in its history. Environmental concern and regulatory pressure have provided the driving force to try to replace petrochemical-based compounds with those based on naturally occurring renewable sources. Addressing this challenge involves investigating for how renewable resources can be used in the synthesis of new biocompatible compounds.
Since it is well known that surface-active compounds can adversely affect the aquatic environment, there is a clear trend to move towards non-toxic biodegradable renewable raw materials as building blocks for the synthesis of non-polluting biocompatible surface-active compounds. Our group conducts a comprehensive research on novel surfactants and ionic liquids derived from natural renewable sources like amino acids and natural oils. The goal is to develop biocompatible compounds with low toxicity and high biodegradability. Surfactants and ionic liquids with these properties would fulfill the requirements of industries in the food, cosmetics and pharmaceutical field.
RESEARCH LINES
- Synthesis of new biocompatible surfactants and ionic liquids derived from amino acids.
- Study of their adsorption at interfaces and self-aggregation behavior.
- Study of the interaction with biological membranes.
- Study of their antimicrobial activity, toxicity and biodegradation.
Liquid crystals of biocompatible amino acid based surfactants and ionic liquids
Antimicrobial effect of biocompatible amino acid based surfactants on E. coli bacteria
Scientific staff
Aurora Pinazo
Tenured Scientist
aurora.pinazo@iqac.csic.es
Mª Teresa García
Tenured Scientist
teresa.garcia@iqac.csic.es
Lourdes Pérez
Tenured Scientist
lourdes.perez@iqac.csic.es
Full list of publications
Lab people
Zakaria Hafidi
Postdoctoral Researcher
zakaria.hafidi@iqac.csic.es
Juan José González
Research assistant
juanjose.gonzalez@iqac.csic.es
Elena Bautista
Research support technician
- Arginine Gemini-Based Surfactants for Antimicrobial and Antibiofilm Applications: Molecular Interactions, Skin-Related Anti-Enzymatic Activity and Cytotoxicity-
Sousa, F.F.O.D., Pinazo, A., Hafidi, Z., García, M.T., Bautista, E., Moran, M.D.C., Pérez, L.
Molecules, 28 (18), art. no. 6570, 2023.
- Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles Formulation-
Hafidi, Z., Pérez, L., El Achouri, M., Pons, R.
Pharmaceutics, 15 (7), art. no. 1856, 2023.
- Cholinium-Based Ionic Liquids as Promising Antimicrobial Agents in Pharmaceutical Applications: Surface Activity, Antibacterial Activity and Ecotoxicological Profile- María Teresa García, Elena Bautista,Ana de la Fuente and Lourdes PérezPharmaceutics 2023, 15(7), 1806
- Skin repairing potential of ellagic acid-loaded zein nanoparticles: Chemical and biopharmaceutical characterization, enzymatic inhibition and cytotoxicity over keratinocytes-
Tavares, W.D.S., Martin Pastor, M., Pérez, L., Morán, M.D.C., Sousa, F.F.O.D.
Journal of Molecular Liquids, 384, 2023
- Ceratonia siliqua L. Pod Extract: From Phytochemical Characterization to Liposomal Formulation and Evaluation of Behaviour in Cells-
De Luca, M., Tuberoso, C.I.G., Pons, R., García, M.T., Morán, M.D.C., Martelli, G., Vassallo, A., Caddeo, C.
Antioxidants, 12 (6), art. no. 1209, 2023.
- Phenolic Fingerprint, Bioactivity and Nanoformulation of Prunus spinosa L. Fruit Extract for Skin Delivery-
De Luca, M., Tuberoso, C.I.G., Pons, R., García, M.T., Morán, M.D.C., Ferino, G., Vassallo, A., Martelli, G., Caddeo, C.
Pharmaceutics, 15 (4), art. no. 1063, 2023
- Zein Nanoparticles Containing Arginine-Based Surfactants: Physicochemical Characterization and Effect on the Biological Properties-
Pérez, L., Sentís, A., Hafidi, Z., Pinazo, A., García, M.T., Martín-Pastor, M., de Sousa, F.F.O.
International Journal of Molecular Sciences, 24 (3), art. no. 2568, 2023.
- Zein Nanoparticles Containing Arginine-Phenylalanine-Based Surfactants: Stability, Antimicrobial and Hemolytic Activity-
Perez, L., Hafidi, Z., Pinazo, A., García, M.T., Martín-Pastor, M., Sousa, F.F.O.D.
Nanomaterials, 13 (1), art. no. 200, 2023.
- Cationic Surfactants Based on Arginine-Phenylalanine and Arginine-Tryptophan: Synthesis, Aggregation Behavior, Antimicrobial Activity, and Biodegradation-
Lourdes Pérez, María Teresa García, Aurora Pinazo, Edgar Pérez-Matas, Zakaria Hafidi and Elena Bautista
Pharmaceutics 2022, 14(12), 2602
- Biological, toxicological and molecular docking evaluations of isoxazoline-thiazolidine-2,4-dione analogues as new class of anti-hyperglycemic agents-
Fettach, S., Thari, F.Z., Hafidi, Z., Karrouchi, K., Bouathmany, K., Cherrah, Y., El Achouri, M., Benbacer, L., El Mzibri, M., Sefrioui, H., Bougrin, K., Faouzi, M.E.A.
Journal of Biomolecular Structure and Dynamics, 41 (3), pp. 1072-1084. 2023
- Arginine-phenylalanine and arginine-tryptophan-based surfactants as new biocompatible antifungal agents and their synergistic effect with Amphotericin B against fluconazole-resistant Candida strains-
Serpa Sampaio Moreno, L., Nobre Junior, H.V., Ramos da Silva, A., Aires do Nascimento, F.B.S., Rocha da Silva, C., de Andrade Neto, J.B., Cavalcanti, B.C., Odorico de Moraes, M., Pinazo, A., Pérez, L.
Colloids and Surfaces B: Biointerfaces, 207, art. no. 112017, 2021
- Green cationic arginine surfactants: Influence of the polar head cationic character on the self-aggregation and biological properties-
Pérez, L., Pons, R., Oliveira de Sousa, F.F., Morán, M.D.C., Ramos da Silva, A., Pinazo, A
Journal of Molecular Liquids, 339, art. no. 116819, . 2021
- Antifungal activity of amino-alcohols based cationic surfactants and in silico, homology modeling, docking and molecular dynamics studies against lanosterol 14-α-demethylase enzyme-
Hafidi, Z., El achouri, M., O.Sousa, F.F., Pérez, L.
Journal of Biomolecular Structure and Dynamics, 2021
- Interaction of cationic surfactants with DPPC membranes: effect of a novel N α-benzoylated arginine-based compound-
Hermet, M., Elisa Fait, M., Vazquez, R.F., Mate, S., Daza Millone, M.A., Elena Vela, M., García, M.T., Morcelle, S.R., Bakas, L.
Amino Acids, 53 (4), pp. 609-619. 2021
- Development of anacardic acid-loaded zein nanoparticles: Physical chemical characterization, stability and antimicrobial improvement-
Araujo, J.T.C.D., Martin-Pastor, M., Pérez, L., Pinazo, A., Sousa, F.F.O.D.
Journal of Molecular Liquids, 332, art. no. 115808, 2021
- Aggregation behavior, antibacterial activity and biocompatibility of catanionic assemblies based on amino acid‐derived surfactants-
Pérez, L., Pinazo, A., Morán, M.C., Pons, R.
International Journal of Molecular Sciences, 21 (23), art. no. 8912, pp. 1-23. 2020
- Catanionic mixtures of surface-active ionic liquids and N-lauroyl sarcosinate: Surface adsorption, aggregation behavior and microbial toxicity-
Garcia, M.T., Ribosa, I., Gonzalez, J.J., Comelles, F.
Journal of Molecular Liquids, 318, art. no. 114040, 2020
- Antifungal and antiprotozoal green amino acid-based rhamnolipids: Mode of action, antibiofilm efficiency and selective activity against resistant Candida spp. strains and Acanthamoeba castellanii-
da Silva, A., Nobre, H., Sampaio, L., Nascimento, B.D., da Silva, C., de Andrade Neto, J.B., Manresa, Á., Pinazo, A., Cavalcanti, B., de Moraes, M.O., Ruiz-Trillo, I., Antó, M., Morán, C., Pérez, L.
Colloids and Surfaces B: Biointerfaces, 193, art. no. 111148, 2020
- Biocompatible catanionic vesicles from arginine-based surfactants: A new strategy to tune the antimicrobial activity and cytotoxicity of vesicular systems-
Pinazo, A., Pons, R., Marqués, A., Farfan, M., da Silva, A., Perez, L.
Pharmaceutics, 12 (9), art. no. 857, pp. 1-24. 2020
- Protein expression knockdown in cancer cells induced by a gemini cationic lipid nanovector with histidine-based polar heads-
Sánchez-Arribas, N., Martínez-Negro, M., Villar, E.M., Pérez, L., Barcina, J.O., Aicart, E., Taboada, P., Guerrero-Martínez, A., Junquera, E.
Pharmaceutics, 12 (9), art. no. 791, pp. 1-22. 2020
- Biocompatible Nanovector of siRNA Consisting of Arginine-Based Cationic Lipid for Gene Knockdown in Cancer Cells-
Sánchez-Arribas, N., Martínez-Negro, M., Villar, E.M., Pérez, L., Aicart, E., Taboada, P., Guerrero-Martínez, A., Junquera, E.
ACS applied materials & interfaces, 12 (31), pp. 34536-34547. 2020
- Surface activity, self-aggregation and antimicrobial activity of catanionicmixtures of surface active imidazolium- or pyridinium-based ionicliquids and sodium bis(2-ethylhexyl) sulfosuccionate-
M. Teresa Garcia, Isabel Ribosa, Juan José González, Francesc Comelles
Journal of Molecular Liquids 303, 2020, 112637
- Rhamnolipids functionalized with basic amino acids: Synthesis, aggregation behavior, antibacterial activity and biodegradation studies-
Ramos da Silva, A., Manresa, M.Á., Pinazo, A., García, M.T., Pérez, L.
Colloids and Surfaces B: Biointerfaces, 181, pp. 234-243. 2019
- Gemini histidine based surfactants: Characterization; surface properties and biological activity-
Pinazo, A., Pons, R., Bustelo, M., Manresa, M.Á., Morán, C., Raluy, M., Pérez, L.
Journal of Molecular Liquids, 289, art. no. 111156, 2019
- Synthesis, self-assembly, bacterial and fungal toxicity, and preliminary biodegradation studies of a series of L-phenylalanine-derived surface-active ionic liquids-
Illia V. Kapitanov, Andrew Jordan, Yevgen Karpichev, Marcel Spulak, Lourdes Perez, Andrew Kellett, Klaus Kümmerer and Nicholas Gathergood
Green Chem. 2019
- Biodegradability and aquatic toxicity of new cleavable betainate cationic oligomeric surfactants-
M. Teresa Garcia, Isabel Ribosa, Iwona Kowalczyk, Marta Pakiet and Bogumil Brycki
Journal of Hazardous Materials 371 (2019) 108–114
- Green Catanionic Gemini Surfactant–Lichenysin Mixture: Improved Surface, Antimicrobial, and Physiological Properties.-
Ruiz A., A. Pinazo, L. Pérez, A. Manresa, A. Marquez
ACS Appl. Mater. Interfaces, 2017, 9, 22121-22131.
- Monocatenary histidine-based surfactants: Role of the alkyl chain length in antimicrobial activity and their selectivity over red blood cells-
Bustelo, M; Pinazo, A.; Manresa, M.A.; Vinardell, M.P.; Pérez, L.
Colloids Surf A, 2017, 532, 501-509.
- Pharmaceutical versatility of cationic niosomes derived from amino acid-based surfactants: Skin penetration behavior and controlled drug release.-
Muzzalupo, L. Pérez, A. Pinazo, L. Tavano
Int J Pharm., 2017, 529, 245-252.
- Protein-repellent and antimicrobial nanoparticle coatings from hyaluronic acid and a lysine-derived biocompatible surfactant-
Bračič, M., Fras-Zemljič, L.,Pérez, L.,Kogej, K.,Stana-Kleinschek, K.,Kargl, R., Mohan, T.
J Mater Chem B. 2017, 5, 3888-3897.
- Hydrophilicity and flexibility of the spacer as critical parameters on the aggregation behavior of long alkyl chain cationic gemini surfactants in aqueous solution.-
M.T. Garcia; O. Kaczerewska; I. Ribosa; B. Brycki; P. Materna; M. Drgas.
J Molec Liquids. 2017, .230, 453 - 460.
- Micellization and Antimicrobial Properties of Surface-Active Ionic Liquids Containing Cleavable Carbonate Linkages-
M.Teresa Garcia; Isabel Ribosa; Lourdes Perez; Angeles Manresa; Francesc Comelles..
Langmuir. 2017, 33 -26, 6511 - 6520.
- New cationic vesicles prepared with double chain surfactants from arginine: Role of the hydrophobic group on the antimicrobial activity and cytotoxicity.-
Pinazo, A; Petrizelli, V; Bustelo, M; Pons, R; Vinardell, M P; Mitjans, M; Manresa, A; Perez, L
Colloids Surf B Biointerfaces, 2016, 141, 19-27
- Amino acid-based surfactants: New antimicrobial agents-
Pinazo, A.; Manresa, M. A.; Marques, A. M.; Pérez, L.
Adv Colloid Interface Sci. 2016, 228, 17-39
- Biodegradability and aquatic toxicity of quaternary ammonium-based gemini surfactants: Effect of the spacer on their ecological properties.-
M.T. Garcia; O. Kaczerewska; I. Ribosa; B. Brycki; P. Materna; M. Drgas.
Chemosphere. 2016, 154, 155 - 160.
- Cationic vesicles based on biocompatible diacyl glycerol-arginine surfactants: Physicochemical properties, antimicrobial activity, encapsulation efficiency and drug release-
LTavano, A. Pinazo, M. Abo-Riya, M.R. Infante, M.A, Manresa, Pérez L.
Colloids Surf B Biointerfaces. 2014,120, 160-167.
- Self-assembly and antimicrobial activity of long-chain amide-functionalized ionic liquids in aqueous solution.-
M.T. Garcia; I. Ribosa; L. Perez; A. Manresa; F. Comelles.
Colloids Surf B Biointerfaces. 2014, 123, 318 - 325.
- Amino Acid Based Surfactants: An Overview-
Pérez, A. Pinazo, R. Pons, M.R. Infante
Adv Colloid Interface Sci. 2014, 205, 134-135.
- Role of aggregate size in the hemolytic and antimicrobial activity of colloidal solutions based on single and gemini surfactants from arginine-
Tavano, M.R. Infante, M. Abo Riya, A. Pinazo, M.P. Vinardell, M. Mitjans, M.A. Manresa, L. Perez
Soft Matter, 2013, 9, 306-319.
- Mixed Monolayer of DPPC and Lysine-Based Cationic Surfactants: An Investigation into the Antimicrobial Activity-
Colomer, L. Pérez, R. Pons, M.R. Infante, D. Perez-Clos, A. Manresa, M.J. Espuny, A. Pinazo
Langmuir, 2013, 29, 7912-7921.
- A new generation of aprotic yet Brønsted acidic imidazolium salts: effect of ester/amide groups in the C-2, C-4 and C-5 on antimicrobial toxicity and biodegradation.-
R.G. Gore, L. Myles, M. Spulak, I. Beadham, M.T. Garcia, S.J. Connon, N. Gathergood.
Green Chemistry. 2013, 15, 2747 - 2760.
- Aggregation behavior and antimicrobial activity of ester-functionalized imidazolium- and pyrdinium based ionic liquids in aqueous solution.-
M.T.Garcia , I. Ribosa, L. Perez, A. Manresa, F. Comelles.
Langmuir. 2013, 29, 2536 -2545.
- Antimicrobial toxicity studies of ionic liquids leading to a "hit" MRSA selective antibacterial imidazolium salt.-
Coleman; M. Spulak; M.T. Garcia; N. Gathergood.
Green Chemistry. 2012, 14, 1350 - 1356.
- Interaction of Nonionic Surfactants and Hydrophilic Ionic Liquids in Aqueous Solutions: Can Short Ionic Liquids Be More than a Solvent?.-
Comelles; I. Ribosa; J.J. González; M.T. Garcia.
Langmuir. 2012, 28, 14522 - 14530.
- Self-aggregation and antimicrobial activity of imidazolium and pyridinium based ionic liquids in aqueous solution.-
Cornellas, L. Pérez, F. Comelles, I. Ribosa, A. Manresa; M.T. García.
J Colloid Interface Sci. 2011, 355, 164 - 171.
- Adsorption of polyphenols in wastewater by organo-bentonites-
A.Marsal, E. Bautista, I. Ribosa, R. Pons, M.T. García
Applied Clay Science 44 (2009) 151 – 155
- Cationic gemini surfactants containing an O-substituted spacer and hydroxyethyl moiety in the polar heads: Self-assembly, biodegradability and aquatic toxicity-
O.Kaczerewska; B. Brycki; I. Ribosa; F. Comelles; M.T. Garcia.
J Industrial Engineer Chem. 2018, 59, 141-148
