DFT/NBO Analysis of Interaction between 4-hydroxycoumarin and Single Walled Carbon Nanotubes in Pistachio
محورهای موضوعی : Nanobiotechnology
Azar Bagheri
1
(Department of Chemistry, Central Tehran Branch, Islamic Azad University, Tehran, Iran)
کلید واژه: Density functional theory (DFT), single-walled carbon nanotubes, Energetic materials, 3-acetyl-6-methyl -4-hydroxy- Coumarin,
چکیده مقاله :
Fruits, vegetables, oils, coffee, nuts, and tea contain coumarin. The scientific attraction of coumarins is attributed to their pharmacological activity. In this study, density functional theory (DFT) calculations were performed in the B3LYP/6-31G(d) level of theory to evaluate the potentialities of single-walled carbon nanotubes (SWCNT) as a carrier for 3-acetyl-6-methyl-4-hydroxy-coumarin. The natural bond orbital (NBO) analysis suggested that the functionalized nanotube plays the role of an electron donor and 3-acetyl-6-methyl -4-hydroxy- coumarin molecule acts as an electron acceptor at the SWCNT -coumarin complex. Variations of density and dipole moment values of coumarin after interaction were studied. Also, the frontier orbital energies, HOMO-LUMO gap, chemical hardness (η), electrophilicity index (ω), charge transferred (ΔNmax) and chemical potential (μ) were computed. Pure coumarin is less conductive and smoother than SWCNT -coumarin. Our results show efficient coumarin loading with the interaction energy of -1.19 eV. NBO analysis shows that the occupied orbitals in the coumarin and the unoccupied orbitals in the nanotube overlap.
Alasalvar C, & Bolling BW (2015) Review of nut phytochemicals, fat-soluble bioactives, antioxidant components and health effects. British Journal of Nutrition, 113, 68-78.
Alasalvar C, Pelvan E (2011) Fat-soluble bioactives in nuts. European Journal of Lipid Science and Technology. 113, 943-949.
Alasalvar C, Shahidi F (2009) Natural antioxidants in tree nuts. European Journal of Lipid Science and Technology 111(11), 1056 - 1062
Arriagada DC, Escobar NV, Ortega, DE (2018) Fedoped Graphene nanosheet as an adsorption platform of harmful gas molecules (CO, CO2, SO2 and H2S), and the coadsorption in O2 environments. Applied Surface Science, 427, 227- 236.
Balasubramanian K, Burghard M (2006) Biosensors based on carbon nanotubes Analytical and bioanalytical chemistry 385, 452-468.
Becke ADJ (1993) Density-functional thermochemistry. III. The role of exact exchange. Chemical Physic.98, 5648-5653.
Bhagat K, Bhagat J, Gupta MK, Singh JV, Gulati HK, Singh A, Kaur K, Kaur G, Sharma S, Rana A, Singh H, Sharma S, Singh Bedi PM (2019) Design, Synthesis, Antimicrobial Evaluation, and Molecular Modeling Studies of Novel Indolinedione –Coumarin Molecular Hybrids. American Chemical Society Omega. 4(5), 8720 -8730.
Cheniany M, Ebrahimzadeh H, Vahdati K, Preece J, Masoudinejad A, Mirmasoumi M (2013) Content of different groups of phenolic compounds in microshoots of Juglans regia
cultivars and studies on antioxidant activity. Acta Physiologia Plantarum. 35:443–450
Ewend MG, Brem S, Gilbert M, Goodkin R, Penar PL, Varia M, Cush S, Carey LA (2007) Treatment of single brain metastasis with resection, intracavity carmustine polymer wafers, and radiation therapy is safe and provides excellent local control. Clinical Cancer Research 13, 3637-3641.
Fernández Izquierdo ME, Quesada Granados J, Villalón Mir M, López Martinez MC,(2000) Comparison of methods for determining coumarins in distilled beverages. Food Chemistry, 70, 251–258.
Ferrone V, Genovese S, Carlucci M, Tiecco M, Germani R, Preziuso F, Epifano F, Carlucci G, Taddeo VA (2018) A green deep eutectic solvent dispersive liquid-liquid micro-extraction (DES-DLLME) for the UHPLC-PDA determination of oxyprenylated phenylpropanoids in olive, soy, peanuts, corn, and sunflower oil. Food Chemistry 245, 578–585.
Frisch M, Trucks G, Schlegel H, Scuseria G, Cheeseman J, Scalmani G, Barone V, Mennucci B, Petersson G, Gaussian (2016) Inc., Wallingford CT.
Huang H, Yuan Q, Shah JS, Misra RDK (2011) A new family of folate-decorated and carbon nanotube- mediated drug delivery system: Synthesis and drug delivery response. Advanced drug delivery reviews, 63, 1332-1339.
Iijima S, Ichihashi T, Nature (1993) Single-shell carbon nanotubes of 1-nm diameter. Nature, 363, 603-605.
Jahanbani R, Ghaffari SM, Salami M, Vahdati K, Sepehri H, Namazi Sarvestani N, Sheibani N, Moosavi-Movahedi AA (2016) Antioxidant and anticancer activities of walnut (Juglans regia L.) protein hydrolysates using different proteases. Plant Foods and Human Nutrition. 71: 402-409.
Jahanbani R, Ghaffari SM, Vahdati K, Salami M, Khalesi MR, Sheibani N, Moosavi-Movahedi AA (2018) Kinetics study of protein hydrolysis and inhibition of angiotensin converting enzyme by peptides hydrolysate extracted from walnut. International Journal of Peptide Research Therapeutic. 24(1):77-85.
Khorram R, Raissi H, Morsali A (2017) Assessment of solvent effects on the interaction of Carmustine drug with the pristine and COOH-functionalized single-walled carbon nanotubes: a DFT perspective. Journal of Molecular Liquid. 240, 87–97.
Lacy A (2005) Studies on Coumarins and Coumarin-Related Compounds to Determine their Therapeutic Role in the Treatment of Cancer. Current Pharmaceutical. Design. 10, 3797–3811.
O’Boyle N (2013) GaussSum 3.0, GaussSum Inc., (Cambridge, UK).
Pantarotto D, Singh R, McCarthy D, Erhardt M, Briand JP, Prato M, Kostarelos K, Bianco A (2004) Functionalized carbon nanotubes for plasmid DNA gene delivery Angewandte Chemie. 116, 5354-5358.
Pereira TM, Franco DP, Vitorio F, Kummerle AE (2018) Coumarin Compounds in Medicinal Chemistry: Some Important Examples from the Last Years. Current Topics In Medicinal Chemistry. 18(2), 124 -148
Romier B, Schneider YJ, Larondelle Y, During A (2009) Dietary polyphenols canmodulate the intestinal inflammatory response. Nutrition Reviews. 67, 363–378.
Saikia N, Deka RC (2010) Theoretical study on pyrazinamide adsorption onto covalently functionalized (5,5) metallic single-walled carbon nanotube. Chemical Physic Letters 500, 65–70.
Sanches K, Dias RVR, Silva DA, Fossey MA, Caruso ÍP, De Souza FP, De Oliveira LC, De Melo FA (2019) Grb2 dimer interacts with Coumarin through SH2 domains: A combined experimental and molecular modeling study. Heliyon. 5, 2869-2882
Sandhu S, Bansal Y, Silakari O, Bansal G (2014) Coumarin hybrids as novel therapeutic agents. Bioorganic & Medicinal Chemistry. 22(15), 3806 -3814.
Sanghavi BJ, Mobin SM, Mathur P, Lahiri GK, Srivastava AK (2013) The design, fabrication, and applications of flexible biosensing devices. Biosensors and Bioelectronics 124, 33-39.
Sharifkhah M, Bakhshi D, Pourghayoumi M, Abdi S, Hokmabadi H (2020) Effect of Pollination Time on Yield and Antioxidant Properties of Some Pistachio Cultivars. International Journal of Horticultural Science and Technology. 1:7(1), 51-8.
Tiwari A, Mishra AK, Kobayashi H, Turner AP (2012) Intelligent nanomaterials. John Wiley &Sons 585-625
Wang BS, Yoong SL, Jagusiak A, Panczyk T, Ho HK, Ang WH, Pastorin G (2013) Carbon nanotubes for delivery of small molecule drugs. Advanced Drug Delivery Review 65, 1964-2015.
Witaicenis A, Luchini AC, Hiruma-Lima CA, Felisbino SL , Garrido-Mesa N ,Utrilla P, Gálvez J, Di Stasi LC ( 2012) Suppression of TNBS-induced colitis inrats by 4-methylesculetin, a natural coumarin: comparison with prednisoloneand sulphasalazine. Chemico-Biological Interactions. 195, 76–85.
