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Research Article

Design, synthesis, spectroscopic characterization, in-vitro antibacterial evaluation and in-silico analysis of polycaprolactone containing chitosan-quercetin microspheres

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Pages 7084-7103 | Received 23 Sep 2021, Accepted 14 Aug 2022, Published online: 07 Sep 2022

References

  • AL-Hussaini, S. M., Al-Ghanimi, A. A. K., & Kadhim, H. (2018). Preparation of nanohybrid antibiotic from levofloxacin and determination its inhibitory efficacy against Staphylococcus aureus isolated from diabetic foot ulcer. Scientific Journal of Medical Research, 02(05), 29–35. https://doi.org/10.37623/SJMR.2018.2507
  • Al-Jumaili, M. H. A., Siddique, F., Abul Qais, F., Hashem, H. E., Chtita, S., Rani, A., Uzair, M., & Almzaien, K. A. (2021). Analysis and prediction pathways of natural products and their cytotoxicity against HeLa cell line protein using docking, molecular dynamics and ADMET. Journal of Biomolecular Structure and Dynamics, 1–13. https://doi.org/10.1080/07391102.2021.2011785
  • Archana, D., Dutta, J., & Dutta, P. (2013). Evaluation of chitosan nano dressing for wound healing: Characterization, in-vitro and in vivo studies. International Journal of Biological Macromolecules, 57, 193–203. https://doi.org/10.1016/j.ijbiomac.2013.03.002
  • Aziz, H., Saeed, A., Jabeen, F., Wadood, A., Rehman, A. U., Majid, M., & Haq, I. U. (2019). Synthesis, characterization and in-vitro antioxidant assay of 4-(benzylideneamino)-5-pentadecyl-2H-1, 2, 4-triazol-3 (4H)-ones. Journal of the Iranian Chemical Society, 16(10), 2143–2157. https://doi.org/10.1007/s13738-019-01686-3
  • Aziz, H., Saeed, A., Khan, M. A., Afridi, S., Jabeen, F., & Hashim, M. (2020). Novel N‐acyl‐1H‐imidazole‐1‐carbothioamides: Design, synthesis, biological and computational studies. J Chemistry Biodiversity, 17(3), e1900509.
  • Bazzaz, B. S. F. (2018). In-vitro evaluation of antibacterial activity of verbascoside, lemon verbena extract and caffeine in combination with gentamicin against drug-resistant Staphylococcus aureus and Escherichia coli clinical isolates. Avicenna Journal of Phytomedicine, 8(3), 246.
  • Chai, J.-D., & Head-Gordon, M. (2008). Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections. Physical Chemistry Chemical Physics : PCCP, 10(44), 6615–6620. https://doi.org/10.1039/b810189b
  • Chaudhari, G. M., & Mahajan, R. T. (2015). Bioprospecting of Terminalia arjuna stem bark and its flavonoids for antimicrobial and anti-biofilm potential. Journal of Chemical Pharmaceutical Research, 7(12), 834–841.
  • Childers, M. C., & Daggett, V. (2018). Validating molecular dynamics simulations against experimental observables in light of underlying conformational ensembles. The Journal of Physical Chemistry. B, 122(26), 6673–6689. https://doi.org/10.1021/acs.jpcb.8b02144
  • Cho, S., Hiott, L. M., Barrett, J. B., McMillan, E. A., House, S. L., Humayoun, S. B., Adams, E. S., Jackson, C. R., & Frye, J. G. (2018). Prevalence and characterization of Escherichia coli isolated from the Upper Oconee Watershed in Northeast Georgia. PloS One, 13(5), e0197005. https://doi.org/10.1371/journal.pone.0197005
  • Croxen, M. A., Law, R. J., Scholz, R., Keeney, K. M., Wlodarska, M., & Finlay, B. B. (2013). Recent advances in understanding enteric pathogenic Escherichia coli. Clinical Microbiology Reviews, 26(4), 822–880. https://doi.org/10.1128/CMR.00022-13
  • da Costa Júnior, S. D. (2018). Antibacterial and antibiofilm activities of quercetin against clinical isolates of Staphyloccocus aureus and Staphylococcus saprophyticus with resistance profile. J International Journal of Environment, Agriculture, 3(5), 266213.
  • Danley, D. E., Baima, E. T., Mansour, M., Fennell, K. F., Chrunyk, B. A., Mueller, J. P., Liu, S., & Qiu, X. (2015). Discovery and structural characterization of an allosteric inhibitor of bacterial cis‐prenyltransferase. Protein Science : A Publication of the Protein Society, 24(1), 20–26. https://doi.org/10.1002/pro.2579
  • de Queiroz Antonino, R., Lia Fook, B., de Oliveira Lima, V., de Farias Rached, R., Lima, E., da Silva Lima, R., Peniche Covas, C., & Lia Fook, M. (2017). Preparation and characterization of chitosan obtained from shells of shrimp (Litopenaeus vannamei Boone). Marine Drugs, 15(5), 141. https://doi.org/10.3390/md15050141
  • Diao, Y., Yu, X., Zhang, C., & Jing, Y. (2020). Quercetin-grafted chitosan prepared by free radical grafting: Characterization and evaluation of antioxidant and antibacterial properties. Journal of Food Science and Technology, 57(6), 2259–2268. https://doi.org/10.1007/s13197-020-04263-2
  • Divya, K., Vijayan, S., George, T. K., & Jisha, M. S. (2017). Antimicrobial properties of chitosan nanoparticles: Mode of action and factors affecting activity. Fibers and Polymers, 18(2), 221–230. https://doi.org/10.1007/s12221-017-6690-1
  • Doblack, B. N., Allis, T., & Dávila, L. (2014). Novel 3D/VR interactive environment for MD simulations, visualization and analysis. JoVE (Journal of Visualized Experiments), 94, e51384.
  • Feng, C., Li, J., Kong, M., Liu, Y., Cheng, X. J., Li, Y., Park, H. J., & Chen, X. G. (2015). Surface charge effect on mucoadhesion of chitosan based nanogels for local anti-colorectal cancer drug delivery. Colloids and Surfaces. B, Biointerfaces, 128, 439–447. https://doi.org/10.1016/j.colsurfb.2015.02.042
  • Gellatly, S. L., & Hancock, R. E. (2013). Pseudomonas aeruginosa: New insights into pathogenesis and host defenses. Pathogens and Disease, 67(3), 159–173. https://doi.org/10.1111/2049-632X.12033
  • Grimme, S., Antony, J., Ehrlich, S., & Krieg, H. (2010). A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. The Journal of Chemical Physics, 132(15), 154104. https://doi.org/10.1063/1.3382344
  • Hao, J., Guo, B., Yu, S., Zhang, W., Zhang, D., Wang, J., & Wang, Y. (2017). Encapsulation of the flavonoid quercetin with chitosan-coated nano-liposomes. LWT - Food Science and Technology, 85, 37–44. https://doi.org/10.1016/j.lwt.2017.06.048
  • Jin, L., Ding, Y., Feng, M., & Cao, Q. (2016). Preparation oral levofloxacin colon-specific microspheres delivery: In-vitro and in vivo studies. Journal of Drug Delivery. 23(3), 982–988. https://doi.org/10.3109/10717544.2014.926429
  • Kant, K., Rawat, R., Bhati, V., Bhosale, S., Sharma, D., Banerjee, S., & Kumar, A. (2021). Computational identification of natural product leads that inhibit mast cell chymase: An exclusive plausible treatment for Japanese encephalitis. Journal of Biomolecular Structure & Dynamics, 39(4), 1203–1212. https://doi.org/10.1080/07391102.2020.1726820
  • Kumar, S., Saini, V., Maurya, I. K., Sindhu, J., Kumari, M., Kataria, R., & Kumar, V. (2018). Design, synthesis, DFT, docking studies and ADME prediction of some new coumarinyl linked pyrazolylthiazoles: Potential standalone or adjuvant antimicrobial agents. PloS One, 13(4), e0196016. https://doi.org/10.1371/journal.pone.0196016
  • Kumar, M., & Sharma, H. K. (2018). Formulation and evaluation of doxorubicin containing nanogels for delivery to cancer cells. Journal of Drug Delivery and Therapeutics, 8(5), 178–183. https://doi.org/10.22270/jddt.v8i5.1890
  • Kuula, L. S. M., Viljemaa, K. M., Backman, J. T., & Blom, M. (2019). Fluoroquinolone-related adverse events resulting in health service use and costs: A systematic review. Plos One, 14(4), e0216029. https://doi.org/10.1371/journal.pone.0216029
  • Lee, J., Cheng, X., Swails, J. M., Yeom, M. S., Eastman, P. K., Lemkul, J. A., Wei, S., Buckner, J., Jeong, J. C., Qi, Y., Jo, S., Pande, V. S., Case, D. A., Brooks, C. L., MacKerell, A. D., Klauda, J. B., & Im, W. (2016). CHARMM-GUI input generator for NAMD, GROMACS, AMBER, OpenMM, and CHARMM/OpenMM simulations using the CHARMM36 additive force field. Journal of Chemical Theory and Computation, 12(1), 405–413. https://doi.org/10.1021/acs.jctc.5b00935
  • Li, X., Ho, B., & Zhang, Y. (2016). Selective aerobic oxidation of furfural to maleic anhydride with heterogeneous Mo–V–O catalysts. Green Chemistry, 18(10), 2976–2980. https://doi.org/10.1039/C6GC00508J
  • Li, F., Jin, H., Xiao, J., Yin, X., Liu, X., Li, D., & Huang, Q. (2018). The simultaneous loading of catechin and quercetin on chitosan-based nanoparticles as effective antioxidant and antibacterial agent. Food Research International (Ottawa, Ont.), 111, 351–360. https://doi.org/10.1016/j.foodres.2018.05.038
  • Li, F., Jin, H., Xiao, J., Yin, X., Liu, X., Li, D., & Huang, Q. (2018). The simultaneous loading of catechin and quercetin on chitosan-based nanoparticles as effective antioxidant and antibacterial agent. Food Research International (Ottawa, Ont.), 111, 351–360. https://doi.org/10.1016/j.foodres.2018.05.038
  • Lin, Y., Zhang, Y., Liu, S., Ye, D., Chen, L., Huang, N., Zeng, W., Liao, W., Zhan, Y., Zhou, T., & Cao, J. (2021). Quercetin rejuvenates sensitization of colistin-resistant Escherichia coli and Klebsiella pneumoniae clinical isolates to Colistin. Frontiers in Chemistry, 9, 795150. https://doi.org/10.3389/fchem.2021.795150
  • López-López, M., Fernández-Delgado, A., Moyá, M., Blanco-Arévalo, D., Carrera, C., de la Haba, R., Ventosa, A., Bernal, E., & López-Cornejo, P. (2019). Optimized preparation of levofloxacin loaded polymeric nanoparticles. Pharmaceutics, 11(2), 57. https://doi.org/10.3390/pharmaceutics11020057
  • Ma, J.-J., Yu, Y.-G., Yin, S.-W., Tang, C.-H., & Yang, X.-Q. (2018). Cellular uptake and intracellular antioxidant activity of zein/chitosan nanoparticles incorporated with quercetin. Journal of Agricultural and Food Chemistry, 66(48), 12783–12793. https://doi.org/10.1021/acs.jafc.8b04571
  • Mu, Y., Fu, Y., Li, J., Yu, X., Li, Y., Wang, Y., Wu, X., Zhang, K., Kong, M., Feng, C., & Chen, X. (2019). Multifunctional quercetin conjugated chitosan nano-micelles with P-gp inhibition and permeation enhancement of anticancer drug. Carbohydrate Polymers, 203, 10–18. https://doi.org/10.1016/j.carbpol.2018.09.020
  • Natarajan, V., Krithica, N., Madhan, B., & Sehgal, P. K. (2011). Formulation and evaluation of quercetin polycaprolactone microspheres for the treatment of rheumatoid arthritis. Journal of Pharmaceutical Sciences, 100(1), 195–205. https://doi.org/10.1002/jps.22266
  • Ouassaf, M., Belaidi, S., Chtita, S., Lanez, T., Abul Qais, F., & Md Amiruddin, H. (2021)., Combined molecular docking and dynamics simulations studies of natural compounds as potent inhibitors against SARS-CoV-2 main protease. Journal of Biomolecular Structure and Dynamics, 39, 1–10. https://doi.org/10.1080/07391102.2021.1957712
  • Packialakshmi, P., Gobinath, P., Ali, D., Alarifi, S., Alsaiari, N., Idhayadhulla, A., & Surendrakumar, R. (2021). Synthesis and characterization of a minophosphonate containing chitosan polymer derivatives: Investigations of cytotoxic activity and in silico study of SARS-CoV-19. Polymers, 13(7), 1046. https://doi.org/10.3390/polym13071046
  • Pahal, V., Devi, U., & Dadhich, K. (2018). Quercetin, a secondary metabolite present in methanolic extract of Calendula officinalis, is a potent inhibitor of peptide deformylase, undecaprenyl pyrophosphate synthase and DNA primase enzymes of S. aureus: An in-vitro and in silico res. MOJ Drug Design Development Therapy, 2(4), 216–225.
  • Pal, A., & Tripathi, A. (2019). Quercetin potentiates meropenem activity among pathogenic carbapenem-resistant Pseudomonas aeruginosa and Acinetobacter baumannii. Journal of Applied Microbiology, 127(4), 1038–1047. https://doi.org/10.1111/jam.14388
  • Parhi, B., Bharatiya, D., & Swain, S. K. (2020). Application of quercetin flavonoid based hybrid nanocomposites: A review. Saudi Pharmaceutical Journal : SPJ : The Official Publication of the Saudi Pharmaceutical Society, 28(12), 1719–1732.
  • Raut, A. V., Satvekar, R. K., Rohiwal, S. S., Tiwari, A. P., Gnanamani, A., Pushpavanam, S., Nanaware, S. G., & Pawar, S. H. (2016). In-vitro biocompatibility and antimicrobial activity of chitin monomer obtain from hollow fiber membrane. Designed Monomers and Polymers, 19(5), 445–455. https://doi.org/10.1080/15685551.2016.1169379
  • Rawat, R., & Verma, S. (2020). An exclusive computational insight toward molecular mechanism of MMV007571, a multitarget inhibitor of Plasmodium falciparum. Journal of Biomolecular Structure & Dynamics, 38(18), 5362–5373. Dynamics https://doi.org/10.1080/07391102.2019.1700165
  • Rawat, R., & Verma, S. (2021). High-throughput virtual screening approach involving pharmacophore mapping, ADME filtering, molecular docking and MM-GBSA to identify new dual target inhibitors of Pf DHODH and Pf Cytbc1 complex to combat drug resistant malaria. Journal of Biomolecular Structure & Dynamics, 39(14), 5148–5159. https://doi.org/10.1080/07391102.2020.1784288
  • Sambandam, B. (2016). Extraction and isolation of flavonoid quercetin from the leaves of Trigonella foenum-graecum and their anti-oxidant activity. International Journal of Pharmacy and Pharmaceutical Sciences, 8(6), 120–124.
  • Sharma, V., & Janmeda, P. (2017). Extraction, isolation and identification of flavonoid from Euphorbia neriifolia leaves. Arabian Journal of Chemistry, 10(4), 509–514. https://doi.org/10.1016/j.arabjc.2014.08.019
  • Singh, S. P., Konwarh, R., Konwar, B. K., & Karak, N. (2013). Molecular docking studies on analogues of quercetin with D-alanine: D-alanine ligase of Helicobacter pylori. Medicinal Chemistry Research, 22(5), 2139–2150. https://doi.org/10.1007/s00044-012-0207-7
  • Sirin, S., Kumar, R., Martinez, C., Karmilowicz, M. J., Ghosh, P., Abramov, Y. A., Martin, V., & Sherman, W. (2014). A computational approach to enzyme design: Predicting ω-aminotransferase catalytic activity using docking and MM-GBSA scoring. Journal of Chemical Information and Modeling, 54(8), 2334–2346. https://doi.org/10.1021/ci5002185
  • Tomasi, J., Mennucci, B., & Cammi, R. (2005). Quantum mechanical continuum solvation models. Chemical Reviews, 105(8), 2999–3093. https://doi.org/10.1021/cr9904009
  • Tong, S. Y. C., Davis, J. S., Eichenberger, E., Holland, T. L., & Fowler, V. G. (2015). Staphylococcus aureus infections: Epidemiology, pathophysiology, clinical manifestations, and management. Clinical Microbiology Reviews, 28(3), 603–661. https://doi.org/10.1128/CMR.00134-14
  • Tribble, D. R. (2017). Antibiotic therapy for acute watery diarrhea and dysentery. Military Medicine, 182(S2), 17–25. https://doi.org/10.7205/MILMED-D-17-00068
  • Tzankova, V., Aluani, D., Kondeva-Burdina, M., Yordanov, Y., Odzhakov, F., Apostolov, A., & Yoncheva, K. (2017). Hepatoprotective and antioxidant activity of quercetin loaded chitosan/alginate particles in-vitro and in vivo in a model of paracetamol-induced toxicity. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 92, 569–579. https://doi.org/10.1016/j.biopha.2017.05.008
  • Vila, J., Sáez-López, E., Johnson, J. R., Römling, U., Dobrindt, U., Cantón, R., Giske, C. G., Naas, T., Carattoli, A., Martínez-Medina, M., Bosch, J., Retamar, P., Rodríguez-Baño, J., Baquero, F., & Soto, S. M. (2016). Escherichia coli: An old friend with new tidings. FEMS Microbiology Reviews, 40(4), 437–463. https://doi.org/10.1093/femsre/fuw005
  • Weigend, F., & Ahlrichs, R. (2005). Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy. Physical Chemistry Chemical Physics : PCCP, 7(18), 3297–3305. https://doi.org/10.1039/b508541a
  • Wizard, P. P. (2011). Epik version 2.2, Impact version 5.7, Prime version 3. Schrödinger, LLC.
  • Zaboon, M., Saleh, A., & Al-Lami, H. (2019). Comparative cytotoxicity and genotoxicity assessments of chitosan amino acid derivative nanoparticles toward human breast cancer cell lines. Egyptian Journal of Chemistry, 62(11), 2061–2075. https://doi.org/10.21608/ejchem.2019.10806.1708
  • Zhang, N., Bi, F., Xu, F., Yong, H., Bao, Y., Jin, C., & Liu, J. (2020). Structure and functional properties of active packaging films prepared by incorporating different flavonols into chitosan based matrix. International Journal of Biological Macromolecules, 165(Pt A), 625–634. https://doi.org/10.1016/j.ijbiomac.2020.09.209

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