59
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Computational choreography: dissecting the dance of hydrogen bonding and π–π stacking in the fluorescence discrimination mechanism of ciprofloxacin with supramolecular assembly

, ORCID Icon, ORCID Icon, , , ORCID Icon & show all
Received 06 Dec 2023, Accepted 06 Mar 2024, Published online: 18 Mar 2024

References

  • Ball, P. (1986). Ciprofloxacin: An overview of adverse experiences. The Journal of Antimicrobial Chemotherapy, 18 (Suppl. D), 187–193. https://doi.org/10.1093/jac/18.sd.187
  • Bhatt, K. D., Makwana, B. A., Vyas, D. J., Mishra, D. R., & Jain, V. K. (2014). Selective recognition by novel calix system: ICT based chemosensor for metal ions. Journal of Luminescence, 146, 450–457. https://doi.org/10.1016/j.jlumin.2013.10.004
  • Boraste, D. R., Chakraborty, G., Ray, A. K., Shankarling, G. S., & Pal, H. (2018). Supramolecular host-guest interaction of antibiotic drug ciprofloxacin with cucurbit[7]uril macrocycle: Modulations in photophysical properties and enhanced photostability. Journal of Photochemistry and Photobiology A: Chemistry, 358, 26–37. https://doi.org/10.1016/j.jphotochem.2018.02.037
  • Bowers, K. J., Chow, E., Xu, H., Dror, R. O., Eastwood, M. P., Gregersen, B. A., Klepeis, J. L., Kolossvary, I., Moraes, M. A., & Sacerdoti, F. D. (2006). Scalable algorithms for molecular dynamics simulations on commodity clusters. In: Proceedings of the 2006 ACM/IEEE Conference on Supercomputing, pp. 84-es. https://doi.org/10.1145/1188455.1188544
  • Desai, A. L., Bhatt, K., Modi, K. M., Patel, N. P., Panchal, M., Kongor, A., Patel, C. N., & Liška, A. (2022). Calix[4]pyrrole based scrupulous probe for track on of tryptophan: Host-guest interaction, in silico modeling and molecular docking insights. Chemical Physics, 554, 111426. https://doi.org/10.1016/j.chemphys.2021.111426
  • Dunnington, B. D., & Schmidt, J. R. (2012). Generalization of natural bond orbital analysis to periodic systems: Applications to solids and surfaces via plane-wave density functional theory. Journal of Chemical Theory and Computation, 8(6), 1902–1911. https://doi.org/10.1021/ct300002t
  • Efferth, T., Xu, A.-L., & Lee, D. Y. W. (2019). Combining the wisdoms of traditional medicine with cutting-edge science and technology at the forefront of medical sciences. Phytomedicine: International Journal of Phytotherapy and Phytopharmacology, 64, 153078. https://doi.org/10.1016/j.phymed.2019.153078
  • El-Shamy, N. T., Alkaoud, A. M., Hussein, R. K., Ibrahim, M. A., Alhamzani, A. G., & Abou-Krisha, M. M. (2022). DFT, ADMET and molecular docking investigations for the antimicrobial activity of 6,6′-diamino-1,1′,3,3′-tetramethyl-5,5′-(4-chlorobenzylidene)bis[pyrimidine-2,4(1H,3H)-dione]. Molecules (Basel, Switzerland), 27(3), 620. https://doi.org/10.3390/molecules27030620
  • El-Sheshtawy, H. S., Chatterjee, S., Assaf, K. I., Shinde, M. N., Nau, W. M., & Mohanty, J. (2018). A supramolecular approach for enhanced antibacterial activity and extended shelf-life of fluoroquinolone drugs with cucurbit[7]uril. Scientific Reports, 8(1), 13925. https://doi.org/10.1038/s41598-018-32312-6
  • Fleming, A. (1941). Penicillin. British Medical Journal, 2(4210), 386–386. https://doi.org/10.1136/bmj.2.4210.386
  • Friesner, R. A., Murphy, R. B., Repasky, M. P., Frye, L. L., Greenwood, J. R., Halgren, T. A., Sanschagrin, P. C., & Mainz, D. T. (2006). Extra precision glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein − ligand complexes. Journal of Medicinal Chemistry, 49(21), 6177–6196. https://doi.org/10.1021/jm051256o
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., & Petersson, G. (2009). Gaussian 09, Revision D. 01, Gaussian, Inc. See Also: URL: http://www. Gaussian. Com
  • Holzgrabe, U., & Branch, S. K. (1994). 1H,19F and13C NMR spectral data of fifteen gyrase inhibitors and some metabolites. Magnetic Resonance in Chemistry, 32(3), 192–196. https://doi.org/10.1002/mrc.1260320313
  • Hooper, D. C., Wolfson, J. S., Ng, E. Y., & Swartz, M. N. (1987). Mechanisms of action of and resistance to ciprofloxacin. The American Journal of Medicine, 82(4A), 12–20.
  • Khan, M. S. A., & Ahmad, I. (2019). Herbal medicine: Current trends and future prospects. In New look to phytomedicine (pp. 3–13). Elsevier.
  • Krošl, I., Otković, E., Nikšić-Franjić, I., Colasson, B., Reinaud, O., Višnjevac, A., & Piantanida, I. (2022). Impact of positive charge and ring-size on the interactions of calixarenes with DNA, RNA and nucleotides. New Journal of Chemistry, 46(15), 6860–6869. https://doi.org/10.1039/D2NJ00061J
  • Li, B., Lei, Q., Wang, F., Zhao, D., Deng, Y., Yang, L., Fan, L., & Zhang, Z. (2021). A stable cationic Cd (II) coordination network as bifunctional chemosensor with high sensitively and selectively detection of antibiotics and Cr (VI) anions in water. Journal of Solid State Chemistry, 298, 122117. https://doi.org/10.1016/j.jssc.2021.122117
  • Makwana, B. A., Vyas, D. J., Bhatt, K. D., & Jain, V. K. (2017). Selective sensing of copper (II) and leucine using fluorescent turn on – off mechanism from calix[4]resorcinarene modified gold nanoparticles. Sensors and Actuators B: Chemical, 240, 278–287. https://doi.org/10.1016/j.snb.2016.08.128
  • Miettinen, M., & Khan, S. A. (2022). Pharmaceutical pollution: A weakly regulated global environmental risk. Review of European, Comparative & International Environmental Law, 31(1), 75–88. https://doi.org/10.1111/reel.12422
  • Mishra, D. R., Darjee, S. M., Bhatt, K. D., Modi, K. M., & Jain, V. K. (2015). Calix protected gold nanobeacon as turn-off fluorescent sensor for phenylalanine. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 82(3-4), 425–436. https://doi.org/10.1007/s10847-015-0509-8
  • Mohan, B., Modi, K., Parikh, J., Ma, S., Kumar, S., Kumar Manar, K., Sun, F., You, H., & Ren, P. (2022). Efficacy of 2-nitrobenzylidene-hydrazine-based selective and rapid sensor for Cu2+ ions, histidine, and tyrosine: Spectral and computational study. Journal of Photochemistry and Photobiology A: Chemistry, 422, 113557. https://doi.org/10.1016/j.jphotochem.2021.113557
  • Nikolova, S., Milusheva, M., Gledacheva, V., Feizi-Dehnayebi, M., Kaynarova, L., Georgieva, D., Delchev, V., Stefanova, I., Tumbarski, Y., Mihaylova, R., Cherneva, E., Stoencheva, S., & Todorova, M. (2023). Drug-delivery silver nanoparticles: A new perspective for phenindione as an anticoagulant. Biomedicines, 11(8), 2201. https://doi.org/10.3390/biomedicines11082201
  • Pal, T., Mathai, T., & Mukherji, S. (2023). Colorimetric chemosensor for rapid detection of fluoroquinolone load in environmental water bodies, urine, and counterfeit drug testing. Biosensors and Bioelectronics: X, 14, 100384. https://doi.org/10.1016/j.biosx.2023.100384
  • Patel, P., & Sharma, S. (2017). Intermolecular interactions behavior of terpinolene with some halobenzenes: A thermophysical, acoustical, spectral and DFT study. Journal of Molecular Liquids, 244, 549–583. https://doi.org/10.1016/j.molliq.2017.07.028
  • Raouf Bhat, A., Ud Din Parray, M., Imtiyaz, K., Moshahid Alam Rizvi, M., & Patel, R. (2024). Interaction and antibacterial activity of ciprofloxacin with choline based ionic liquid and CTAB: A comparative spectroscopic study. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 309, 123770. https://doi.org/10.1016/j.saa.2023.123770
  • Rawat, V., Baheti, A., Tiwari, O. S., & Vigalok, A. (2023). Carbazole-fused calixarene cavities: Single and mixed AIEgen systems for NO detection. Chemical Communications (Cambridge, England), 59(37), 5543–5546. https://doi.org/10.1039/D3CC01181J
  • Reed, A. E., Weinstock, R. B., & Weinhold, F. (1985). Natural population analysis. Journal of Chemical Physics, 83, 735–746. https://doi.org/10.1063/1.449486
  • Sahoo, S., Chakraborti, C. K., Mishra, S. C., Nanda, U. N., & Naik, S. (2011). FTIR and XRD investigations of some fluoroquinolones.
  • Sayin, S. (2022). A highly selective fluorescence probe for Co2+ or Cu2+ detection based on a new tetraquinoline-substituted calix[4]arene derivative. Tetrahedron, 122, 132960. https://doi.org/10.1016/j.tet.2022.132960
  • Schuchardt, K. L., Didier, B. T., Elsethagen, T., Sun, L., Gurumoorthi, V., Chase, J., Li, J., & Windus, T. L. (2007). Basis Set Exchange: A community database for computational sciences. Journal of Chemical Information and Modeling, 47(3), 1045–1052. https://doi.org/10.1021/ci600510j
  • Seeger, Z. L., & Izgorodina, E. I. (2020). A systematic study of DFT performance for geometry optimizations of ionic liquid clusters. Journal of Chemical Theory and Computation, 16(10), 6735–6753. https://doi.org/10.1021/acs.jctc.0c00549
  • Siddiquee, A., Parray, Z., Anand, A., Tasneem, S., Hasan, N., Alamier, W. M., Ageeli, A. A., Wani, F. A., Singh, P., & Patel, R. (2023). Binding study of antibacterial drug ciprofloxacin with imidazolium-based ionic liquids having different halide anions: A spectroscopic and density functional theory analysis. ACS Omega, 8(45), 42699–42710. https://doi.org/10.1021/acsomega.3c05100
  • Siddiquee, M., Patel, R., Saraswat, J., Khatoon, B. S., Ud Din Parray, M., Wani, F. A., Khan, M. R., & Busquets, R. (2021). Interfacial and antibacterial properties of imidazolium based ionic liquids having different counterions with ciprofloxacin. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 629, 127474. https://doi.org/10.1016/j.colsurfa.2021.127474
  • Uttam, B., Polepalli, S., & Rao, C. P. (2023). Synthetic strategies for the functionalization of upper or lower rim of supramolecular calix [4] arene platform. Arkivoc, 2022(6), 254–279. https://doi.org/10.24820/ark.5550190.p011.939
  • Vagadiya, N., Odedara, M., Joshi, A., Manhas, A., & Mukherjee, N. (2022). Recent advances in fluorescent chemosensors for aromatic amino acids detection. In K. Mukherjee, R. K. Layek, & D. De (Eds.), Tailored functional materials: Select proceedings of MMETFP 2021 (pp. 221–232). Springer. https://doi.org/10.1007/978-981-19-2572-6_17
  • Xu, W., Feng, H., Zhao, W., Huang, C., Redshaw, C., Tao, Z., & Xiao, X. (2020). Amino acid recognition by a fluorescent chemosensor based on cucurbit[8]uril and acridine hydrochloride. Analytica Chimica Acta, 1135, 142–149. https://doi.org/10.1016/j.aca.2020.09.028
  • Yang, S., Gu, L., Wu, F., Dai, X., Xu, F., Li, Q., Fang, X., Yu, S., & Ding, C.-F. (2022). The chirality determination of amino acids by forming complexes with cyclodextrins and metal ions using ion mobility spectrometry, and a DFT calculation. Talanta, 243, 123363. https://doi.org/10.1016/j.talanta.2022.123363
  • Zhao, X., Hu, Z., Yang, X., Cai, X., Wang, Z., & Xie, X. (2019). Noncovalent interactions between fluoroquinolone antibiotics with dissolved organic matter: A 1H NMR binding site study and multi-spectroscopic methods. Environmental Pollution (Barking, Essex: 1987), 248, 815–822. https://doi.org/10.1016/j.envpol.2019.02.077

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.