Molecular Spectroscopic (FTIR and UV-Vis) Analysis and In Vitro Antibacterial Investigation of a Deep Eutectic Solvent of N,N-Dimethyl Urea-Citric Acid
Abstract
The intriguing pursuit of environmentally friendly solvents with tailored properties for diverse applications is a focal point of numerous studies, encompassing precursor selection, thorough characterization, and the exploration of potential applications. The study aims to assess the physicochemical properties and antimicrobial activity of deep eutectic solvents (DES) produced from N,N-dimethyl urea (DMU) and citric acid (CA), highlighting differences from their individual precursors. Various mass ratio variations of (DMU, solid) and (CA, solid) (DMU:CA = 1.0:1.0; 1.0:1.5; 1.0:2.0; 2.0: 1.0; 1.5:1.0) have been tested to make DES solvents through the melt process. Both types of blends generally melt at a temperature of 80°C. The overall liquid resulting from the melting of solids was generally clear in color. Molecular analysis using an infrared spectrophotometer showed some insignificant shifts from one product to another, compared with DMU and CA as precursors. Likewise, analysis using a UV–Vis spectrophotometer, when the entire sample was dissolved in demineralized water (2 mg/mL), showed no difference in the spectrum. In addition, functional group analysis using a spectrophotometer showed some minor changes, mainly shifts in peaks due to changes in the DMU:CA ratio. This may be due to the interaction of the hydrogen donor and the hydrogen acceptor in DES. All samples showed absorption peaks in the ultraviolet region of 202-210 nm. The resulting DES application showed growth inhibitory activity for Staphylococcus aureus and Escherichia coli bacteria in all products produced. The same analysis of the two types of precursors used showed that only CA had activity, but DMU did not have similar activity.
References
Akbar, N., N. A. Khan, T. Ibrahim, M. Khamis, A. S. Khan, A. M. Alharbi, H. Alfahemi, and R. Siddiqui (2023). Antimicrobial Activity of Novel Deep Eutectic Solvents. Scientia Pharmaceutica, 91(1); 9
Al-Akayleh, F., R. Khalid, D. Hawash, E. Al-Kaissi, I. Al-Adham, N. Al-Muhtaseb, N. Jaber, M. Al Remawi, and P. Collier (2022). Antimicrobial Potential of Natural Deep Eutectic Solvents. Letters in Applied Microbiology, 75(3); 607–615
Azmi, N. A. N., A. Elgharbawy, H. M. Salleh, and A. Hayyan (2021). Evaluation of the Antimicrobial Performance of Menthol and Menthol-Based Deep Eutectic Solvents As Potential Future Antibiotic. In E3S Web of Conferences, volume 287. EDP Sciences, page 02010
Bafti, B. and H. Khabazzadeh (2014). Dimethylurea/citric Acid As a Highly Efficient Deep Eutectic Solvent for the Multi-Component Reactions. Journal of Chemical Sciences, 126; 881–887
Burel, C., A. Kala, and L. Purevdorj-Gage (2021). Impact of pH on Citric Acid Antimicrobial Activity against Gram-Negative Bacteria. Letters in Applied Microbiology, 72(3); 332–340
Chen, J., M. C. Ali, R. Liu, J. C. Munyemana, Z. Li, H. Zhai, and H. Qiu (2020). Basic Deep Eutectic Solvents As Reactant, Template and Solvents for Ultra-Fast Preparation of Transition Metal Oxide Nanomaterials. Chinese Chemical Letters, 31(6); 1584–1587
Cruz, H., N. Jordão, and L. C. Branco (2017). Deep Eutectic Solvents (DESs) As Low-Cost and Green Electrolytes for Electrochromic Devices. Green Chemistry, 19(7); 1653–1658
Długosz, O. (2023). Natural Deep Eutectic Solvents in the Synthesis of Inorganic Nanoparticles. Materials, 16(2); 627
Garcia-Arguelles, S., M. C. Serrano, M. C. Gutierrez, M. L. Ferrer, L. Yuste, F. Rojo, and F. del Monte (2013). Deep Eutectic Solvent-Assisted Synthesis of Biodegradable Polyesters with Antibacterial Properties. Langmuir, 29(30); 9525–9534
Gu, T., M. Zhang, J. Chen, and H. Qiu (2015). A Novel Green Approach for the Chemical Modification of Silica Particles Based on Deep Eutectic Solvents. Chemical Communications, 51(48); 9825–9828
Inayat, S., S. R. Ahmad, S. J. Awan, and N. Muhammad (2023). Antimicrobial, Antioxidant, and Toxicity Assessment of Ammonium-Based Deep Eutectic Solvents with Formic Acid and Butyric Acid Hydrogen Bond Donors. Journal of Molecular Liquids, 388; 122735
Kaur, G., N. Singh, A. Rajor, and J. P. Kushwaha (2021). Deep Eutectic Solvent Functionalized Rice Husk Ash for Effective Adsorption of Ofloxacin from Aqueous Environment. Journal of Contaminant Hydrology, 242; 103847
Kumar, N., P. D. Muley, D. Boldor, G. G. Coty IV, and J. G. Lynam (2019). Pretreatment of Waste Biomass in Deep Eutectic Solvents: Conductive Heating Versus Microwave Heating. Industrial Crops and Products, 142; 111865
Li, X. S., J. Z. Xue, Y. Qi, I. Muhammad, H. Wang, X. Y. Li, Y. J. Luo, D. M. Zhu, Y. H. Gao, and L. C. Kong (2023). Citric Acid Confers Broad Antibiotic Tolerance through Alteration of Bacterial Metabolism and Oxidative Stress. International Journal of Molecular Sciences, 24(10); 9089
Mai-Prochnow, A., M. Clauson, J. Hong, and A. B. Murphy (2016). Gram Positive and Gram Negative Bacteria Differ in their Sensitivity to Cold Plasma. Scientific Reports, 6(1); 38610
Ogita, A., K. I. Fujita, and T. Tanaka (2009). Salinomycin and Citric Acid in Combination Demonstrate Bactericidal Activity against Gram-Negative Bacteria. Annals of Microbiology, 59; 611–614
Radošević, K., I. Čanak, M. Panić, K. Markov, M. C. Bubalo, J. Frece, V. G. Srček, and I. R. Redovniković (2018). Antimicrobial, Cytotoxic and Antioxidative Evaluation of Natural Deep Eutectic Solvents. Environmental Science and Pollution Research, 25; 14188–14196
Rafiq, S., N. Muhammad, F. Rehman, M. Irfan, S. U. Zaman, F. Jamil, S. Saqib, A. Mukhtar, K. S. Khoo, and M. Mubashir (2022). Surface Tuning of Silica by Deep Eutectic Solvent to Synthesize Biomass Derived Based Membranes for Gas Separation to Enhance the Circular Bioeconomy. Fuel, 310; 122355
Richter, J. and M. Ruck (2019). Synthesis and Dissolution of Metal Oxides in Ionic Liquids and Deep Eutectic Solvents. Molecules, 25(1); 78
Silva, J. M., E. Silva, R. L. Reis, and A. R. C. Duarte (2019). A Closer Look in the Antimicrobial Properties of Deep Eutectic Solvents Based on Fatty Acids. Sustainable Chemistry and Pharmacy, 14; 100192
Smith, E. L., A. P. Abbott, and K. S. Ryder (2014). Deep Eutectic Solvents (DESs) and their Applications. Chemical Reviews, 114(21); 11060–11082
Strauss, V., H. Wang, S. Delacroix, M. Ledendecker, and P. Wessig (2020). Carbon Nanodots Revised: The Thermal Citric Acid/urea Reaction. Chemical Science, 11(31); 8256–8266
Su, L.-C., Z. Xie, Y. Zhang, K. T. Nguyen, and J. Yang (2014). Study on the Antimicrobial Properties of Citrate-Based Biodegradable Polymers. Frontiers in Bioengineering and Biotechnology, 2; 23
Tang, B., H. E. Park, and K. H. Row (2014). Preparation of Chlorocholine Chloride/urea Deep Eutectic Solvent-Modified Silica and an Examination of the Ion Exchange Properties of Modified Silica As a Lewis Adduct. Analytical and Bioanalytical Chemistry, 406; 4309–4313
Wikene, K. O., H. V. Rukke, E. Bruzell, and H. H. Tønnesen (2017). Investigation of the Antimicrobial Effect of Natural Deep Eutectic Solvents (NADES) As Solvents in Antimicrobial Photodynamic Therapy. Journal of Photochemistry and Photobiology B: Biology, 171; 27–33
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