Theoretical Electrochemical Study and Calculation of Free Energies of Electron Transfer in B-Cyclodextrins/Fullerenes C60 Nanostructure Complexes
DOI:
https://doi.org/10.52547.jcc.5.1.3Keywords:
Fullerenes, β–Cyclodextrins, The electron transfer energies, Rate constants, Marcus theoryAbstract
Cyclodextrin is a cyclic molecule that contains the three essential six, seven, and eight glucose molecules, called by the names ?, ?, and ?-cyclodextrin, individually. Cyclodextrins compounds are thought to be completely polar as a result of the hydroxyl groups present in glucose moieties. Secondary C2-hydroxyl groups of glucose units are found on the secondary face, while the C6-hydroxyl type groups are located on the primary face because these are related to the primary face of the incomplete cone. The C1 group, a glucoside oxygen ring, and another ring of C-H groups make up the inside of the cyclodextrin cone, making it rather nonpolar. Hydrophobic fullerenes compounds Cn [n= 60, 70, 76, 82, and 86] have been chosen for the guest molecules and different parameters like first to fourth free activations, the kinetic rate constant, the energies of electron transfer (ket(n)), and ?G#et(n) where (n=1-4), were calculated and discussed in detail. All the computed results showed the best coherence with the Marcus theory. Different analyses suggested that free energy is lowered due to an efficient electron transfer, which begins with the first step (the first of the four activate free energy values).
References
“Co-Delivery of Letrozole and Cyclophosphamide via Folic Acid-Decorated Nanoniosomes for Breast Cancer Therapy: Synergic Effect, Augmentation of Cytotoxicity,” mdpi.com, Accessed: Jan. 12, 2023. [Online]. Available: https://www.mdpi.com/1416182
C. Muankaew and T. Loftsson, “Cyclodextrin-Based Formulations: A Non-Invasive Platform for Targeted Drug Delivery,” Basic Clin Pharmacol Toxicol, vol. 122, no. 1, pp. 46–55, Jan. 2018, doi: 10.1111/BCPT.12917.
“In vitro cytotoxicity and anti-cancer drug release behavior of methionine-coated magnetite nanoparticles as carriers,” Springer, Accessed: Jan. 12, 2023. [Online]. Available: https://link.springer.com/article/10.1007/s12032-022-01838-1
B. Farasati Far, S. Asadi, M. R. Naimi-Jamal, W. Kamal Abdelbasset, and A. Aghajani Shahrivar, “Insights into the interaction of azinphos-methyl with bovine serum albumin: experimental and molecular docking studies,” J Biomol Struct Dyn, 2021, doi: 10.1080/07391102.2021.1968954.
M. A. Przybyla, G. Yilmaz, and C. Remzi Becer, “Natural cyclodextrins and their derivatives for polymer synthesis,” Polym Chem, vol. 11, no. 48, pp. 7582–7602, Dec. 2020, doi: 10.1039/D0PY01464H.
S. Choudhary, L. Gupta, S. Rani, K. Dave, and U. Gupta, “Impact of Dendrimers on Solubility of Hydrophobic Drug Molecules,” Front Pharmacol, vol. 8, no. MAY, May 2017, doi: 10.3389/FPHAR.2017.00261.
A. Celebioglu and T. Uyar, “Hydrocortisone/cyclodextrin complex electrospun nanofibers for a fast-dissolving oral drug delivery system,” RSC Med Chem, vol. 11, no. 2, pp. 245–258, Feb. 2020, doi: 10.1039/C9MD00390H.
Y. A. Choi et al., “Methyl-B-cyclodextrin inhibits cell growth and cell cycle arrest via a prostaglandin E(2) independent pathway,” Experimental & Molecular Medicine 2004 36:1, vol. 36, no. 1, pp. 78–84, Feb. 2004, doi: 10.1038/emm.2004.11.
A. Stasilowicz et al., “The Inclusion of Tolfenamic Acid into Cyclodextrins Stimulated by Microenvironmental pH Modification as a Way to Increase the Anti-Migraine Effect,” J Pain Res, vol. 14, p. 981, 2021, doi: 10.2147/JPR.S295795.
P. Berben et al., “Linking the concentrations of itraconazole and 2-hydroxypropyl-B-cyclodextrin in human intestinal fluids after oral intake of Sporanox,” European Journal of Pharmaceutics and Biopharmaceutics, vol. 132, pp. 231–236, Nov. 2018, doi: 10.1016/J.EJPB.2018.06.025.
Y. Xu et al., “Chloramphenicol/sulfobutyl ether-B-cyclodextrin complexes in an ophthalmic delivery system: prolonged residence time and enhanced bioavailability in the conjunctival sac,” Expert Opin Drug Deliv, vol. 16, no. 6, pp. 657–666, Jun. 2019, doi: 10.1080/17425247.2019.1609447.
S. S. Braga, “Cyclodextrins: Emerging Medicines of the New Millennium,” Biomolecules, vol. 9, no. 12, 2019, doi: 10.3390/BIOM9120801.
M. H. Asim et al., “Thiolated cyclodextrins: Mucoadhesive and permeation enhancing excipients for ocular drug delivery,” Int J Pharm, vol. 599, p. 120451, Apr. 2021, doi: 10.1016/J.IJPHARM.2021.120451.
P. C. S. Costa, J. S. Evangelista, I. Leal, and P. C. M. L. Miranda, “Chemical Graph Theory for Property Modeling in QSAR and QSPR—Charming QSAR & QSPR,” Mathematics 2021, Vol. 9, Page 60, vol. 9, no. 1, p. 60, Dec. 2020, doi: 10.3390/MATH9010060.
“Plant-based synthesis of cerium oxide nanoparticles as a drug delivery system in improving the anticancer effects of free temozolomide in glioblastoma (U87) cells,” Elsevier, Accessed: Jan. 12, 2023. [Online]. Available: https://www.sciencedirect.com/science/article/pii/S0272884222023574
F. Eshrati Yeganeh, A. Eshrati Yeganeh, M. Fatemizadeh, B. Farasati Far, S. Quazi, and M. Safdar, “In vitro cytotoxicity and anti-cancer drug release behavior of methionine-coated magnetite nanoparticles as carriers,” Medical Oncology, vol. 39, no. 12, Dec. 2022, doi: 10.1007/S12032-022-01838-1.
F. Ban, K. Dalal, H. Li, E. LeBlanc, P. S. Rennie, and A. Cherkasov, “Best Practices of Computer-Aided Drug Discovery: Lessons Learned from the Development of a Preclinical Candidate for Prostate Cancer with a New Mechanism of Action,” J Chem Inf Model, vol. 57, no. 5, pp. 1018–1028, May 2017, doi: 10.1021/ACS.JCIM.7B00137.
E. Karooby, N. G.-O. Engineering, and undefined 2019, “Potential applications of nanoshell bow-tie antennas for biological imaging and hyperthermia therapy,” spiedigitallibrary.org, Accessed: Jan. 12, 2023. [Online]. Available: https://www.spiedigitallibrary.org/journals/Optical-Engineering/volume-58/issue-6/065102/Potential-applications-of-nanoshell-bow-tie-antennas-for-biological-imaging/10.1117/1.OE.58.6.065102.short
I. Hdoufane, D. Ounaissi, A. Dermoune, and D. Cherqaoui, “Development of QSAR models using singular value decomposition method: A case study for predicting anti-hiv-1 and anti-HCV biological activities,” Biointerface Res Appl Chem, vol. 12, no. 3, pp. 3090–3105, 2022, doi: 10.33263/BRIAC123.30903105.
H. Shen, “The compressive mechanical properties of Cn (n=20, 60, 80, 180) and endohedral M@C60 (M=Na, Al, Fe) fullerene molecules,” Mol Phys, vol. 105, no. 17–18, pp. 2405–2409, Sep. 2007, doi: 10.1080/00268970701679467.
F. Lu, E. A. Neal, and T. Nakanishi, “Self-Assembled and Nonassembled Alkylated-Fullerene Materials,” Acc Chem Res, vol. 52, no. 7, pp. 1834–1843, Jul. 2019, doi: 10.1021/ACS.ACCOUNTS.9B00217.
L. Kavan, L. Dunsch, and H. Kataura, “Electrochemical tuning of electronic structure of carbon nanotubes and fullerene peapods,” Carbon N Y, vol. 42, no. 5–6, pp. 1011–1019, Jan. 2004, doi: 10.1016/J.CARBON.2003.12.024.
H. Chadli, F. Fergani, and A. Rahmani, “Structural and Vibrational Properties of C60 and C70 Fullerenes Encapsulating Carbon Nanotubes,” Fullerenes and Relative Materials - Properties and Applications, Apr. 2018, doi: 10.5772/INTECHOPEN.71246.
R. E. Haufler et al., “Efficient production of C60 (buckminsterfullerene), C60H36, and the solvated buckide ion,” Journal of Physical Chemistry, vol. 94, no. 24, pp. 8634–8636, 2002, doi: 10.1021/J100387A005.
P. A. Maggard, X. Cheng, S. Deng, and M. H. Whangbo, “Physical Properties of Molecules and Condensed Materials Governed by Onsite Repulsion, Spin-Orbit Coupling and Polarizability of Their Constituent Atoms,” Molecules, vol. 25, no. 4, Feb. 2020, doi: 10.3390/MOLECULES25040867.
R. Otero, A. L. Vázquez de Parga, and J. M. Gallego, “Electronic, structural and chemical effects of charge-transfer at organic/inorganic interfaces,” Surf Sci Rep, vol. 72, no. 3, pp. 105–145, Jul. 2017, doi: 10.1016/J.SURFREP.2017.03.001.
R. L. Purchase and H. J. M. De Groot, “Biosolar cells: Global artificial photosynthesis needs responsive matrices with quantum coherent kinetic control for high yield,” Interface Focus, vol. 5, no. 3. The Royal Society, pp. 1–16, 2015. doi: 10.1098/rsfs.2015.0014.
R. A. Voloshin, M. V. Rodionova, S. K. Zharmukhamedov, H. J. M. Hou, J.-R. Shen, and S. I. Allakhverdiev, “Components of Natural Photosynthetic Apparatus in Solar Cells,” in Applied Photosynthesis - New Progress, IntechOpen, 2016. doi: 10.5772/62238.
S. J. Huang and Y. T. Hsu, “Faithful derivation of symmetry indicators: A case study for topological superconductors with time-reversal and inversion symmetries,” Phys Rev Res, vol. 3, no. 1, p. 013243, Mar. 2021, doi: 10.1103/PHYSREVRESEARCH.3.013243/FIGURES/9/MEDIUM.
X. Chen et al., “Disrupted Brain Connectivity Networks in Aphasia Revealed by Resting-State fMRI,” Front Aging Neurosci, vol. 0, p. 658, 2021, doi: 10.3389/FNAGI.2021.666301.
L. Wang, X. Xue, X. Zhou, Z. Wang, and R. Liu, “Analyzing the topology characteristic and effectiveness of the China city network:,” https://doi.org/10.1177/2399808320983011, Jan. 2021, doi: 10.1177/2399808320983011.
A. A. Taherpour, D. Narian, and A. Taherpour, “Structural relationships and theoretical study of the free energies of electron transfer, electrochemical properties, and electron transfer kinetic of cephalosporin antibiotics derivatives with fullerenes in nanostructure of [R]•Cn (R = cefadroxil, cefepime, cephalexin, cefotaxime, cefoperazone and ceftriaxone) supramolecular complexes,” J Nanostructure Chem, vol. 5, no. 2, pp. 153–167, Jun. 2015, doi: 10.1007/S40097-014-0146-6.
A. A. Taherpour and M. Maleki-Noureini, “Free energies of electron transfer, electron transfer kinetic theoretical and quantitative structural relationships and electrochemical properties studies of gadolinium nitride cluster fullerenes Gd 3N@C n in [X-UT-Y][Gd 3N@C n](n = 80, 82, 84, 86 and 88) supramolecular complexes,” Fullerenes Nanotubes and Carbon Nanostructures, vol. 21, no. 6, pp. 485–502, Jan. 2013, doi: 10.1080/1536383X.2011.629761.
H. R. A. El-Mageed, F. M. Mustafa, and M. K. Abdel-Latif, “Boron nitride nanoclusters, nanoparticles and nanotubes as a drug carrier for isoniazid anti-tuberculosis drug, computational chemistry approaches,” https://doi.org/10.1080/07391102.2020.1814871, vol. 40, no. 1, pp. 226–235, 2020, doi: 10.1080/07391102.2020.1814871.
B. Farasati Far, M. R. Naimi-Jamal, M. Jahanbakhshi, H. T. Mohammed, U. S. Altimari, and J. Ansari, “Poly(3-thienylboronic acid) coated magnetic nanoparticles as a magnetic solid-phase adsorbent for extraction of methamphetamine from urine samples,” J Dispers Sci Technol, 2022, doi: 10.1080/01932691.2022.2124169.
B. Farasati Far et al., “Metronidazole, acyclovir and tetrahydrobiopterin may be promising to treat COVID-19 patients, through interaction with interleukin-12,” J Biomol Struct Dyn, 2022, doi: 10.1080/07391102.2022.2064917.
C. A. Celaya, J. Muñiz, and L. E. Sansores, “New nanostructures of carbon: Quasi-fullerenes Cn-q (n = 20, 42, 48, 60),” Comput Theor Chem, vol. 1117, pp. 20–29, Oct. 2017, doi: 10.1016/j.comptc.2017.07.013.
C. Bannwarth, S. Ehlert, and S. Grimme, “GFN2-xTB - An Accurate and Broadly Parametrized Self-Consistent Tight-Binding Quantum Chemical Method with Multipole Electrostatics and Density-Dependent Dispersion Contributions,” J Chem Theory Comput, vol. 15, no. 3, pp. 1652–1671, Mar. 2019, doi: 10.1021/ACS.JCTC.8B01176/SUPPL_FILE/CT8B01176_SI_002.ZIP.
R. A. Marcus, “On the Theory of Oxidation-Reduction Reactions Involving Electron Transfer. I,” J Chem Phys, vol. 24, no. 5, pp. 966–978, May 1956, doi: 10.1063/1.1742723.
T. Avat Arman and A. R. Shafaati, “Theoretical study of structural relationships and electrochemical properties of [DNA-nucleotide bases]@ Cn complexes,” Oriental Journal of Chemistry, vol. 27, no. 3, pp. 823–833, 2011.
B. F. Far, K. Vakili, M. Fathi, S. Yaghoobpoor, M. Bhia, and M. R. N. Jamal, “The role of microRNA-21 (miR-21) in pathogenesis, diagnosis, and prognosis of gastrointestinal cancers: A review,” Life Sci, p. 121340, Dec. 2022, doi: 10.1016/J.LFS.2022.121340.
B. F. Far, S. Asadi, … M. N.-J.-J. of, and undefined 2021, “Insights into the interaction of azinphos-methyl with bovine serum albumin: Experimental and molecular docking studies,” Taylor & Francis, Accessed: Jan. 12, 2023. [Online]. Available: https://www.tandfonline.com/doi/abs/10.1080/07391102.2021.1968954
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