Caffeic and 3-(3,4-dihydroxyphenyl)glyceric acid derivatives as antimicrobial agent: biological evaluation and molecular docking studies

References

• J.L. Ríos and M.C. Recio, Medicinal plants and antimicrobial activity, J. Ethnopharmacol. 100 (2005), pp. 80–84. doi:https://doi.org/10.1016/j.jep.2005.04.025.
   PubMed Web of Science ®Google Scholar
• S. Dresler, G. Szymczak, and M. Wójcik, Comparison of some secondary metabolite content in the seventeen species of the Boraginaceae family, Pharm. Biol. 55 (2017), pp. 691–695. doi:https://doi.org/10.1080/13880209.2016.1265986.
   PubMedGoogle Scholar
• R.A. Ynalvez, K.L. Compean, and A. Addo-Mensah, Qualitative determination of the secondary metabolites and evaluation of the antimicrobial activity of leaf extracts from different plant families (Boraginaceae, Fabaceae, Lamiacea Lauraceae) against microorganisms of clinical importance, J. Pharm. Res. Int. 23 (2018), pp. 1–12. doi:https://doi.org/10.9734/JPRI/2018/41205.
   Google Scholar
• M. Merlani, V. Barbakadze, L. Amiranashvili, L. Gogilashvili, E. Yannakopoulou, K. Papadopoulos, and B. Chankvetadze, Enantioselective synthesis and antioxidant activity of 3-(3,4-dihydroxyphenyl)-glyceric acid - Basic monomeric moiety of a biologically active polyether from Symphytum asperum and S. caucasicum, Chirality 22 (2010), pp. 717–725. doi:https://doi.org/10.1002/chir.20823.
   PubMed Web of Science ®Google Scholar
• S. Shrotriya, G. Deep, K. Ramasamy, K. Raina, V. Barbakadze, M. Merlani, L. Gogilashvili, L. Amiranashvili, K. Mulkijanyan, K. Papadopoulos, C. Agarwal, and R. Agarwal, Poly[3-(3, 4-dihydroxyphenyl)glyceric acid] from Comfrey exerts anti-cancer efficacy against human prostate cancer via targeting androgen receptor, cell cycle arrest and apoptosis, Carcinogenesis 33 (2012), pp. 1572–1580. doi:https://doi.org/10.1093/carcin/bgs202.
   PubMedGoogle Scholar
• M. Merlani, V. Barbakadze, L. Amiranashvili, L. Gogilashvili, V. Poroikov, A. Petrou, A. Geronikaki, A. Ciric, J. Glamoclijad, and M. Sokovic, New caffeic acid derivatives as antimicrobial agents: Design, synthesis, evaluation and docking, Curr. Top. Med. Chem. 19 (2019), pp. 292–304. doi:https://doi.org/10.2174/1568026619666190122152957.
   PubMedGoogle Scholar
• M. Merlani, D.M. Scheibel, V. Barbakadze, L. Gogilashvili, L. Amiranashvili, A. Geronikaki, V. Catania, D. Schillaci, G. Gallo, and I. Gitsov, Enzymatic synthesis and antimicrobial activity of oligomer analogues of medicinal biopolymers from comfrey and their species of the Boraginaceae family, Pharmaceutics 14 (2022), pp. 115. doi:https://doi.org/10.3390/pharmaceutics14010115.
   PubMedGoogle Scholar
• V. Barbakadze, E. Kemertelidze, K. Mulkijanyan, A. van den Berg, C. Beukelman, E. van den Worm, H. Quarles van Ufford, and A. Usov, Antioxidant and anticomplementary activity of poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Symphytum asperum and S. caucasicum, Pharm. Chem. J. 41 (2007), pp. 14–16. doi:https://doi.org/10.1007/s11094-007-0004-7.
   Google Scholar
• C.M. Barthomeuf, E. Debiton, V.V. Barbakadze, and E.P Kemertelidze, Evaluation of the dietetic and therapeutic potential of a high molecular weight hydroxicinnamate-derived polymer from Symphytum asperum Lepech. Regarding its antioxidant, antilipoperoxidant, antiinflammatory, and cytotoxic properties, J. Agric. Food Chem. 49 (2001), pp. 3942–3946. doi:https://doi.org/10.1021/jf010189d.
   PubMedGoogle Scholar
• V. Barbakadze, K. Mulkijanyan, L. Gogilashvili, L. Amiranashvili, M. Merlani, Z. Novikova, and M. Sulakvelidze, Allantoin- and pyrrolizidine alkaloids-free wound healing compositions from Symphytum asperum, Bull. Georgian Natl. Acad. Sci. 3 (2009), pp. 159–164.
   Google Scholar
• K. Mulkijanyan, V. Barbakadze, Z. Novikova, M. Sulakvelidze, L. ogilashvili, L. Amiranashvili, and M. Merlani, Burn healing compositions from Caucasian species of comfrey (Symphytum L.), Bull. Georgian Natl. Acad. Sci. 3 (2009), pp. 114–117.
   Google Scholar
• M. Merlani, Y. Koyama, H. Sato, L. Geng, V. Barbakadze, B. Chankvetadze, and T. Nakano, Ring-opening polymerization of a 2,3-disubstituted oxirane leading to a polyether having a carbonyl–aromatic π-stacked structure, Polym. Chem. 6 (2015), pp. 1932–1936. doi:https://doi.org/10.1039/C4PY01711K.
   Google Scholar
• M. Merlani, V. Barbakadze, L. Amiranashvili, L. Gogilashvili, and K. Mulkijanyan, Synthesis of some caffeic and 2,3-dihydroxy-3-(3,4-dihydroxyphenyl)propanoic acids amides, Bull. Georgian Natl. Acad. Sci. 5 (2011), pp. 107–111.
   Google Scholar
• V. Kartsev, B. Lichitsky, A. Geronikaki, A. Petrou, M. Smiljkovic, M. Kostic, O. Radanovic, and M. Soković, Design, synthesis and antimicrobial activity of usnic acid derivatives, Med. Chem. Comm. 9 (2018), pp. 870–882. doi:https://doi.org/10.1039/C8MD00076J.
   Google Scholar
• S. Simakov, V. Kartsev, A. Petrou, I. Nicolaou, A. Geronikaki, M. Ivanov, M. Kostic, J. Glamoˇclija, M. Sokovic, D. Talea, and I.S. Vizirianakis, 4-(Indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole acylamines as novel antimicrobial agents: Synthesis, in silico and in vitro evaluation, Pharmaceuticals 14 (2021), pp. 1096–1125. doi:https://doi.org/10.3390/ph14111096.
   Web of Science ®Google Scholar
• Clinical and Laboratory Standards Institute, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard, 8th ed., CLSI publication M07-A8, Clinical and Laboratory Standards Institute, Wayne, PA, 2009.
   Google Scholar
• V. Horishny, V. Kartsev, V. Matiychuk, A. Geronikaki, A. Anthi, P. Pogodin, V. Poroikov, M. Ivanov, M. Kostic, M. Soković, and P. Eleftheriou, 3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine derivatives as antimicrobial agents: Synthesis, computational and biological evaluation, Pharmaceuticals (Basel) 13 (2020), pp. 229. doi:https://doi.org/10.3390/ph13090229.
   Google Scholar
• A. Geronikaki, M. Fesatidou, V. Kartsev, and F. Macaev, Synthesis and biological evaluation of potent antifungal agents, Curr. Top. Med. Chem. 13 (2013), pp. 2684–2733. doi:https://doi.org/10.2174/15680266113136660195.
   PubMedGoogle Scholar
• R. Huey, G.M. Morris, A.J. Olson, and D.S. Goodsell, A semiempirical free energy force field with charge-based desolvation, J. Comp. Chem. 28 (2007), pp. 1145–1152. doi:https://doi.org/10.1002/jcc.20634.
   PubMed Web of Science ®Google Scholar
• A. Geronikaki, A. Petrou, V. Kartsev, P. Eleftheriou, R. Boga, B. Bartolo, E. Crespan, G. Franco, and G. Maga, Molecular docking, design, synthesis and biological evaluation of novel 2,3-aryl-thiazolidin-4-ones as potent NNRTIs, SAR QSAR Environ. Res. 10 (2019), pp. 697–714. doi:https://doi.org/10.1080/1062936X.2019.1653364.
   Google Scholar
• M. Saxena, S. Nandi, and A.K. Saxena, QSAR and molecular docking studies of lethal factor protease inhibitors against Bacillus anthracis, SAR QSAR Environ. Res. 10 (2019), pp. 715–731. doi:https://doi.org/10.1080/1062936X.2019.1658219.
   Google Scholar
• M.-T. Le, T.T. Mai, P.N.H. Huynh, T.-D. Tran, K.-M. Thai, and Q.-T. Nguyen, Structure-based discovery of interleukin-33 inhibitors: A pharmacophore modelling, molecular docking, and molecular dynamics simulation approach, SAR QSAR Environ. Res. 12 (2020), pp. 883–904. doi:https://doi.org/10.1080/1062936X.2020.1837239.
   Google Scholar
• M. Arora, S. Choudhary, and O. Silakari, In silico guided designing of 4-(1H-benzo[d]imidazol-2-yl)phenol-basedmutual-prodrugs of NSAIDs: Synthesis and biological evaluation, SAR QSAR Environ. Res. 10 (2020), pp. 761–784. doi:https://doi.org/10.1080/1062936X.2020.1810117.
   Google Scholar
• Z. Kalaki and M. Asadollahi-Baboli, Molecular docking-based classification and systematic QSAR analysis of indoles as Pim kinase inhibitors, SAR QSAR Environ. Res. 5 (2020), pp. 399–419. doi:https://doi.org/10.1080/1062936X.2020.1751277.
   Google Scholar