Synthesis, characterization, and antibacterial activity of a novel hybrid material layered double hydroxide doped by diaminododecylphosphonic acid
DOI:
https://doi.org/10.3329/bjp.v19i4.79648Keywords:
Layered double hydroxide, Zn/Al-DADPHA, Antibacterial activity, Molecular docking, DFT, molecular dynamics simulationAbstract
A novel hybrid material Zn/Al-diaminododecylphosphonic acid (DADPHA) layered double hydroxide (LDH) was synthesized and characterized for its structural, electronic, and antibacterial properties. X-ray diffraction confirmed DADPHA intercalation, increasing basal spacing from 7.55 to 7.95 angstrom. The crystallite size of Zn/Al-DADPHA (11.10 nm) was smaller than that of Zn/Al-SO₄ LDH (16.70 nm), indicating modification. FTIR confirmed phosphonic acid functional groups, while SEM revealed a morphological shift from hexagonal platelets to aggregated structures. Zn/Al-DADPHA exhibited significant antibacterial activity, with inhibition zones of 25.6 mm (Escherichia coli), 10.9 mm (Pseudomonas aeruginosa), 30.2 mm (Staphylococcus aureus), and 25.5 mm (Bacillus cereus). Molecular docking revealed strong ligand-protein interactions (-7.1 to -9.4 kcal/mol). DFT calculations showed a HOMO-LUMO gap of 4.82 eV, confirming electronic stability. MD simulations over 100 ns indicated complex stability with RMSD below 2.5 angstrom. These findings highlight the potential of Zn/Al-DADPHA LDH for biomedical and antimicrobial applications.
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Al-Fakeh MS, Alazmi MS, El-Ghoul Y. Preparation and characterization of nano-sized CO (II), CU (II), MN (II) and NI (II) coordination PAA/alginate biopolymers and study of their biological and anticancer performance. Crystals. 2023; 13: 1148.
Almalki AJ, Ibrahim TS, Elhady SS, Hegazy WA, Darwish KM. Computational and biological evaluation of β-adrenoreceptor blockers as promising bacterial anti-virulence agents. Pharmaceuticals 2022; 15: 110.
Almeida MO, Barros DA, Araujo SC, Faria SH, Maltarollo VG, Honorio KM. Study on molecular structure, spectroscopic properties (FTIR and UV–Vis), NBO, QTAIM, HOMO-LUMO energies and docking studies of 5-fluorouracil, a substance used to treat cancer. Spectrochim Acta Part A Mol Biomol Spectrosc. 2017; 184: 169-76.
Arribat M, Cavelier F, Remond E. Phosphorus-containing amino acids with a P–C bond in the side chain or a P–O, P–S or P–N bond: From synthesis to applications. RSC Adv. 2020; 10: 6678-724.
Cao Y, Zheng D, Zhang F, Pan J, Lin C. Layered double hydro-xide (LDH) for multi-functionalized corrosion protection of metals: A review. J Mater Sci Technol. 2022; 102: 232-63.
Chen Q, Yu Y, Li J, Nan H, Luo S, Jia C, Deng P, Zhong S, Tian X. Recent progress in layered double hydroxide‐based electrocatalyst for hydrogen evolution reaction. Chem Electro Chem. 2022; 9: e202101387.
Donadio G, Mensitieri F, Santoro V, Parisi V, Bellone ML, De Tommasi N, Izzo V, Dal Piaz F. Interactions with microbial proteins driving the antibacterial activity of flavonoids. Pharmaceutics. 2021; 13: 660.
Dubnova L, Daňhel R, Meinhardova V, Korolova V, Smolakova L, Kondratowicz T, Kikhtyanin O, Capek L. Reconstruction of the ZnAl mixed oxides into the layered double hydroxide catalysts active in the aldol condensation of furfural: The role of ZnO particles. Front Chem. 2022; 9: 803764.
Ebrahimian J, Khayatkashani M, Soltani N, Yousif QA, Salavati-Niasari M. Catechin mediated green synthesis of Au nanoparticles: Experimental and theoretical approaches to the determination HOMO-LUMO energy gap and reactivity indexes for the (+)-epicatechin (2S, 3S). Arabian J Chem. 2022; 15: 103758.
Jiang W, Faid AY, Gomes BF, Galkina I, Xia L, Lobo CMS, Desmau M, Borowski P, Hartmann H, Maljusch A. Composition‐dependent morphology, structure, and catalytical performance of nickel–iron layered double hydroxide as highly‐efficient and stable anode catalyst in anion exchange membrane water electrolysis. Adv Funct Mater. 2022; 32: 2203520.
Kaboudin B, Daliri P, Faghih S, Esfandiari H. Hydroxy-and amino-phosphonates and bisphosphonates: Synthetic methods and their biological applications. Front Chem. 2022; 10: 890696.
Kadari M, Kaid Mh, Ben Ali M, Villemin D. The intercalation of Zn/Al-HDL by the diaminododecylphosphonic acid: Synthesis and properties of adsorption of basic fuchsine. J Chinese Adv Mater Soc. 2016; 4: 148-57.
Kim TH, Lee GJ, Kang JH, Kim HJ, Kim Ti, Oh JM. Anticancer drug‐incorporated layered double hydroxide nanohybrids and their enhanced anticancer therapeutic efficacy in combination cancer treatment. Biomed Res Int. 2014; 2014: 193401.
Kumar G, Engle K. Natural products acting against S. aureus through membrane and cell wall disruption. Nat Prod Rep. 2023; 40: 1608-46.
Liu K, Kokubo H. Exploring the stability of ligand binding modes to proteins by molecular dynamics simulations: A cross-docking study. J Chem Inf Model. 2017; 57: 2514-22.
Liu X, Wu Y, Zhao X, Wang Z. Fabrication and applications of bioactive chitosan-based organic-inorganic hybrid materials: A review. Carbohydr Polym. 2021; 267: 118179.
Mallakpour S, Radfar Z, Hussain CM. Current advances on polymer-layered double hydroxides/metal oxides nanocomposites and bionanocomposites: Fabrications and applications in the textile industry and nanofibers. Appl Clay Sci. 2021; 206: 106054.
Manzoor S, Ahmed A, Moin ST. Iron coordination to pyochelin siderophore influences dynamics of FptA receptor from Pseudomonas aeruginosa: A molecular dynamics simulation study. Biometals. 2021; 34: 1099-119.
Mishra G, Dash B, Pandey S, Mohanty PP. Antibacterial actions of silver nanoparticles incorporated Zn–Al layered double hydroxide and its spinel. J Environ Chem Eng. 2013; 1: 1124-30.
Miyata S. The syntheses of hydrotalcite-like compounds and their structures and physico-chemical properties - I: The systems Mg2+-Al3+-NO3−, Mg2+-Al3+-Cl−, Mg2+-Al3+-ClO4−, Ni 2+-Al3+-Cl− and Zn2+-Al3+-Cl−. Clays Clay Miner. 1975; 23: 369-75.
Modi SK, Gaur S, Sengupta M, Singh MS. Mechanistic insights into nanoparticle surface-bacterial membrane interactions in overcoming antibiotic resistance. Front Microbiol. 2023; 14: 1135579.
Nassarawa SS, Nayik GA, Gupta SD, Areche FO, Jagdale YD, Ansari MJ, Hemeg HA, Al-Farga A, Alotaibi SS. Chemical aspects of polyphenol-protein interactions and their antibacterial activity. Crit Rev Food Sci Nutr. 2023; 63: 9482-505.
Nava-Andrade K, Carbajal-Arizaga G, Obregon S, Rodriguez-Gonzalez V. Layered double hydroxides and related hybrid materials for removal of pharmaceutical pollutants from water. J Environ Manage. 2021; 288: 112399.
Obalova L, Karaskova K, Jiratova K, Kovanda F. Effect of potassium in calcined Co–Mn–Al layered double hydroxide on the catalytic decomposition of N2O. Appl Catal B Environ. 2009; 90: 132-40.
Ouazene M, Kaid Mh, Ilikti H, Villemin D. Solvent extraction of samarium (III) by diaminododecylphosphonic acid followed by UV/Vis spectroscopy using arsenazo III. Phys Chem Liquids. 2016; 54: 552-62.
Rashad MM, El-Sayed IE, Galhoum AA, Abdeen MM, Mira HI, Elshehy EA, Zhang S, Lu X, Xin J, Guibal E. Synthesis of α-aminophosphonate based sorbents–Influence of inserted groups (carboxylic vs. amine) on uranyl sorption. Chem Eng J. 2021; 421: 127830.
Rezaei FY, Pircheraghi G, Nikbin VS. Antibacterial activity, cell wall damage, and cytotoxicity of zinc oxide nanospheres, nanorods, and nanoflowers. ACS Appl Nano Mater. 2024; 7: 15242-54.
Roy S, Sarkhel S, Bisht D, Hanumantharao SN, Rao S, Jaiswal A. Antimicrobial mechanisms of biomaterials: From macro to nano. Biomater Sci. 2022; 10: 4392-423.
Saidin S, Jumat MA, Amin NAA, Al-Hammadi ASS. Organic and inorganic antibacterial approaches in combating bacterial infection for biomedical application. Mater Sci Eng C. 2021; 118: 111382.
Sharma A, Kumari S, Sharma S, Singh T, Kumar S, Thakur A, Bhatia S, Sharma A. Layered double hydroxides: An insight into the role of hydrotalcite-type anionic clays in energy and environmental applications with current progress and recent prospects. Mater Today Sustain. 2023; 22: 100399.
Shirin VA, Sankar R, Johnson AP, Gangadharappa H, Pramod K. Advanced drug delivery applications of layered double hydroxide. J Control Release. 2021; 330: 398-426.
Si Z, Hou Z, Vikhe YS, Thappeta KRV, Marimuthu K, De PP, Ng OT, Li P, Zhu Y, Pethe K. Antimicrobial effect of a novel chitosan derivative and its synergistic effect with antibiotics. ACS Appl Mater Interfaces. 2021; 13: 3237-45.
Soleymani M, Kabirifard H, Hekmati M, Esmaeili A, Veisi H. In situ bio-inspired fabrication of Ag nanoparticles on Matricaria chamomilla extract modified Cu-Al-Zn LDH as a beneficial antimicrobial agent. Inorg Chem Commun. 2024; 160: 111998.
Stamate AE, Pavel OD, Zavoianu R, Birjega R, Neubauer K, Koeckritz A, Marcu IC. Study of the catalytic properties of MgNi (Cu) Al LDH in the one-pot cascade oxidation-Knoevenagel condensation reaction. Mol Catal. 2023; 537: 112968.
Sultana S, Hossain MA, Biswas S, Saleh MA, Ali F, Kawsar SM. Chemical reactivity, molecular electrostatic potential, FTIR, NMR, in vitro, and in silico studies of mannopyranoside derivatives: 3-Nitrobenzoylation leads to improve anti-microbial activity. Chem Phys Impact. 2024; 9: 100692.
Theiss FL, Ayoko GA, Frost RL. Synthesis of layered double hydroxides containing Mg2+, Zn2+, Ca2+ and Al3+ layer cations by co-precipitation methods: A review. Appl Surf Sci. 2016; 383: 200-13.
Vejzovic D, Piller P, Cordfunke RA, Drijfhout JW, Eisenberg T, Lohner K, Malanovic N. Where electrostatics matter: Bacterial surface neutralization and membrane disruption by antimicrobial peptides SAAP-148 and OP-145. Biomolecules 2022; 12: 1252.
Wang M, Chen Y, Yu Z, Hou Y, Jiang R, Li S, Chen J, Tang W, Pang H, Xie W. Unraveling the π-interaction of NiFe-based metal–organic frameworks with enhanced oxygen evolution: Optimizing electronic structure and facilitating electron transfer modulation. J Colloid Interface Sci. 2023; 640: 1-14.
Wei C, Yan X, Zhou Y, Xu W, Gan Y, Zhang Y, Zhang N. Morphological control of layered double hydroxides prepared by co-precipitation method. Crystals 2022; 12: 1713.
Zavoianu R, Mihaila SD, Cojocaru B, Tudorache M, Parvulescu VI, Pavel OD, Oikonomopoulos S, Jacobsen EE. An advanced approach for MgZnAl-LDH catalysts synthesis used in Claisen-Schmidt condensation. Catalysts 2022; 12: 759.
Zhang J, Su P, Chen H, Qiao M, Yang B, Zhao X. Impact of reactive oxygen species on cell activity and structural integrity of Gram-positive and Gram-negative bacteria in electrochemical disinfection system. Chem Eng J. 2023; 451: 138879.
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Copyright (c) 2025 Djamila Ikhou, Farouk Boudou, Hanane Ziani, M'hamed Kaid, Didier Villemein
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