395
Views
6
CrossRef citations to date
0
Altmetric
Research Articles

New imino-methoxy derivatives: design, synthesis, characterization, antimicrobial activity, DNA interaction and molecular docking studies

ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon
Pages 11082-11094 | Received 26 Mar 2021, Accepted 10 Jul 2021, Published online: 06 Aug 2021

References

  • Adımcılar, V., Çeşme, M., Şenel, P., Danış, İ., Ünal, D., & Gölcü, A. (2021). Comparative study of cytotoxic activities, DNA binding and molecular docking interactions of anticancer agent epirubicin and its novel copper complex. Journal of Molecular Structure, 1232, 130072. https://doi.org/10.1016/j.molstruc.2021.130072
  • Allan, J. R., Gardner, A. R., McCloy, B., & Smith, W. E. (1992). Structural and thermal studies of the chloro complexes of cobalt, nickel and copper with 2,6-diaminopyridine and an assessment of their suitability as anti-static additives for polyethylene. Thermochimica Acta, 208(C), 125–131. https://doi.org/10.1016/0040-6031(92)80158-S
  • Ameen, D., & Snape, T. J. (2013). Chiral 1,1-diaryl compounds as important pharmacophores. In MedChemComm (Vol. 4, No. 6, pp. 893–907). The Royal Society of Chemistry. https://doi.org/10.1039/c3md00088e
  • Ashton, M. J., Ashford, A., Loveless, A. H., Riddell, D., Salmon, J., & Stevenson, G. V. (1984). Heterocyclic analogues of chlorcyclizine with potent hypolipidemic activity. Journal of Medicinal Chemistry, 27(10), 1245–1253. https://doi.org/10.1021/jm00376a002
  • Balouiri, M., Sadiki, M., & Ibnsouda, S. K. (2016). Methods for in vitro evaluating antimicrobial activity: A review. Journal of Pharmaceutical Analysis, 6(2), 71–79. https://doi.org/10.1016/j.jpha.2015.11.005
  • Bauer, A. W., Kirby, W. M., Sherris, J. C., & Turck, M. (1966). Antibiotic susceptibility testing by a standardized single disk method. American Journal of Clinical Pathology, 45(4), 493–496. https://doi.org/10.1093/ajcp/45.4_ts.493
  • Bradshaw, L. J. (1992). Laboratory microbiology. Acta Crystallographica Section A: Foundations and Advances 4, 435.
  • C.L.S.I. (2012). Performance standards for antimicrobial disk susceptibility tests approved standard. In CLSI document M02-A11 (Vol. 950, 7th ed.). Clinical and Laboratory Standards Institute.
  • Cardellicchio, C., Capozzi, M. A. M., & Naso, F. (2010). The Betti base: The awakening of a sleeping beauty. In Tetrahedron asymmetry. (Vol. 21, No. 5, pp. 507–517). Pergamon. https://doi.org/10.1016/j.tetasy.2010.03.020
  • Dahm, R. (2005). Friedrich Miescher and the discovery of DNA. Developmental Biology, 278(2), 274–288. https://doi.org/10.1016/j.ydbio.2004.11.028
  • Dallakyan, S., & Olson, A. J. (2015). Small-molecule library screening by docking with PyRx. In J. E. Hempel, C. H. Williams, & C. C. Hong (Eds.), Methods in molecular biology (Vol. 1263, No. January, pp. 243–250). Springer. https://doi.org/10.1007/978-1-4939-2269-7_19
  • Di Santo, R., Tafi, A., Costi, R., Botta, M., Artico, M., Corelli, F., Forte, M., Caporuscio, F., Angiolella, L., & Palamara, A. T. (2005). Antifungal agents. 11. N-substituted derivatives of 1-[(aryl)(4-aryl-1H-pyrrol-3-yl)methyl]-1H-imidazole: Synthesis, anti-Candida activity, and QSAR studies. Journal of Medicinal Chemistry, 48(16), 5140–5153. https://doi.org/10.1021/jm048997u
  • Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., & Puschmann, H. (2009). OLEX2: A complete structure solution, refinement and analysis program. Journal of Applied Crystallography, 42(2), 339–341. https://doi.org/10.1107/S0021889808042726
  • Dong, X.-M. M., Lou, Y.-Y. Y., Zhou, K.-L. L., & Shi, J.-H. H. (2018). Exploration of association of telmisartan with calf thymus DNA using a series of spectroscopic methodologies and theoretical calculation. Journal of Molecular Liquids, 266, 1–9. https://doi.org/10.1016/j.molliq.2018.06.057
  • Gan, C., Huang, X., Zhan, J., Liu, X., Huang, Y., & Cui, J. (2020). Study on the interactions between B-norcholesteryl benzimidazole compounds with ct-DNA. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 227, 117525. https://doi.org/10.1016/j.saa.2019.117525
  • Gemma, S., Campiani, G., Butini, S., Kukreja, G., Joshi, B. P., Persico, M., Catalanotti, B., Novellino, E., Fattorusso, E., Nacci, V., Savini, L., Taramelli, D., Basilico, N., Morace, G., Yardley, V., & Fattorusso, C. (2007). Design and synthesis of potent antimalarial agents based on clotrimazole scaffold: Exploring an innovative pharmacophore. Journal of Medicinal Chemistry, 50(4), 595–598. https://doi.org/10.1021/jm061429p
  • Göppert‐Mayer, M. (1931). Über Elementarakte mit zwei Quantensprüngen. Annalen Der Physik, 401(3), 273–294. https://doi.org/10.1002/andp.19314010303
  • Güngör, Ö., Çeşme, M., Çınar, M. E., & Gölcü, A. (2019). The new metal-based compound from anticancer drug cytarabine: Spectral, electrochemical, DNA-binding, antiproliferative effect and in silico studies. Journal of Molecular Structure, 1193, 532–543. https://doi.org/10.1016/j.molstruc.2019.05.014
  • Isika, D., Çeşme, M., Osonga, F. J., & Sadik, O. A. (2020). Novel quercetin and apigenin-acetamide derivatives: Design, synthesis, characterization, biological evaluation and molecular docking studies. RSC Advances, 10(42), 25046–25058. https://doi.org/10.1039/D0RA04559D
  • Jamshidvand, A., Sahihi, M., Mirkhani, V., Moghadam, M., Mohammadpoor-Baltork, I., Tangestaninejad, S., Amiri Rudbari, H., Kargar, H., Keshavarzi, R., & Gharaghani, S. (2018). Studies on DNA binding properties of new Schiff base ligands using spectroscopic, electrochemical and computational methods: Influence of substitutions on DNA-binding. Journal of Molecular Liquids, 253, 61–71. https://doi.org/10.1016/j.molliq.2018.01.029
  • Lakshmi, B., Shivananda, K. N., Prakash, G. A., Isloor, A. M., & Mahendra, K. N. (2012). Synthesis and characterization of schiff base metal complexes and reactivity studies with malemide epoxy resin. Bulletin of the Korean Chemical Society, 33(2), 473–482. https://doi.org/10.5012/bkcs.2012.33.2.473
  • Lakshmipraba, J., Arunachalam, S., Solomon, R. V., Venuvanalingam, P., Riyasdeen, A., Dhivya, R., & Akbarsha, M. A. (2015). Surfactant-copper(II) Schiff base complexes: Synthesis, structural investigation, DNA interaction, docking studies, and cytotoxic activity. Journal of Biomolecular Structure & Dynamics, 33(4), 877–891. https://doi.org/10.1080/07391102.2014.918523
  • Lennette, E. H., Spaulding, E. H., & Truant, J. P. (1974). Manual of clinical microbiology (7th ed., 970p). ASM Press. https://doi.org/10.4269/ajtmh.1971.20.3.tm0200030508a
  • McCord, J. M., & Fridovich, I. (1969). Superoxide dismutase. An enzymic function for erythrocuprein (hemocuprein). Journal of Biological Chemistry, 244(22), 6049–6055. https://europepmc.org/article/med/5389100 https://doi.org/10.1016/S0021-9258(18)63504-5
  • Nafisi, S., Saboury, A. A., Keramat, N., Neault, J. F., & Tajmir-Riahi, H. A. (2007). Stability and structural features of DNA intercalation with ethidium bromide, acridine orange and methylene blue. Journal of Molecular Structure, 827(1–3), 35–43. https://doi.org/10.1016/j.molstruc.2006.05.004
  • Onur, S., Köse, M., Koçer, F., & Tümer, F. (2020). Synthesis, characterization and antibacterial effect of diarylmethylamine-based imines. Journal of Molecular Structure, 1214, 128150. https://doi.org/10.1016/j.molstruc.2020.128150
  • Plobeck, N., Delorme, D., Wei, Z. Y., Yang, H., Zhou, F., Schwarz, P., Gawell, L., Gagnon, H., Pelcman, B., Schmidt, R., Yue, S. Y., Walpole, C., Brown, W., Zhou, E., Labarre, M., Payza, K., St-Onge, S., Kamassah, A., Morin, P. E., … Roberts, E. (2000). New diarylmethylpiperazines as potent and selective nonpeptidic delta opioid receptor agonists with increased In vitro metabolic stability. Journal of Medicinal Chemistry, 43(21), 3878–3894. https://doi.org/10.1021/jm000228x
  • Power, D. A., & McCuen, P. J. (1988). Manual of BBL products and laboratory procedures. In Becton Dickinson Microbiology Systems (6th ed., pp. 67–72). Becton, Dickinson and Company.
  • Riley, D. P., Lennon, P. J., Neumann, W. L., & Weiss, R. H. (1997). Toward the rational design of superoxide dismutase mimics: Mechanistic studies for the elucidation of substituent effects on the catalytic activity of macrocyclic manganese(II) complexes. Journal of the American Chemical Society, 119(28), 6522–6528. https://doi.org/10.1021/ja964271e
  • Roy, D., & Panda, G. (2020). Benzhydryl amines: Synthesis and their biological perspective. ACS Omega, 5(1), 19–30. https://doi.org/10.1021/acsomega.9b03090
  • Sha, Y., Chen, X., Niu, B., & Chen, Q. (2017). The interaction mode of groove binding between quercetin and calf thymus DNA based on spectrometry and simulation. Chemistry & Biodiversity, 14(10), e1700133. https://doi.org/10.1002/cbdv.201700133
  • Shah, A., Nosheen, E., Munir, S., Badshah, A., Qureshi, R., Rehman, Z. U., Muhammad, N., & Hussain, H. (2013). Characterization and DNA binding studies of unexplored imidazolidines by electronic absorption spectroscopy and cyclic voltammetry. Journal of Photochemistry and Photobiology B: Biology, 120, 90–97. https://doi.org/10.1016/j.jphotobiol.2012.12.015
  • Sheldrick, G. M. (2015). SHELXT - integrated space-group and crystal-structure determination. Acta Crystallographica. Section A, Foundations and Advances, 71(Pt 1), 3–8. https://doi.org/10.1107/S2053273314026370
  • Shi, J. H., Chen, J., Wang, J., & Zhu, Y. Y. (2015a). Binding interaction between sorafenib and calf thymus DNA: Spectroscopic methodology, viscosity measurement and molecular docking. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 136(PB), 443–450. https://doi.org/10.1016/j.saa.2014.09.056
  • Shi, J. H., Liu, T. T., Jiang, M., Chen, J., & Wang, Q. (2015b). Characterization of interaction of calf thymus DNA with gefitinib: Spectroscopic methods and molecular docking. Journal of Photochemistry and Photobiology B: Biology, 147, 47–55. https://doi.org/10.1016/j.jphotobiol.2015.03.005
  • Shi, J. H., Zhou, K. L., Lou, Y. Y., & Pan, D. Q. (2018). Multi-spectroscopic and molecular docking studies on the interaction of darunavir, a HIV protease inhibitor with calf thymus DNA. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 193, 14–22. https://doi.org/10.1016/j.saa.2017.11.061
  • Shi, J.-H. H., Lou, Y.-Y. Y., Zhou, K.-L. L., & Pan, D.-Q. Q. (2018). Exploration of intermolecular interaction of calf thymus DNA with sulfosulfuron using multi-spectroscopic and molecular docking techniques. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 204, 209–216. https://doi.org/10.1016/j.saa.2018.06.054
  • Sirajuddin, M., Ali, S., & Badshah, A. (2013). Drug-DNA interactions and their study by UV-Visible, fluorescence spectroscopies and cyclic voltametry. Journal of Photochemistry and Photobiology B: Biology, 124(October 2015), 1–19. https://doi.org/10.1016/j.jphotobiol.2013.03.013
  • Soliman, A. A., & Linert, W. (2007). Structural features of ONS-donor salicylidene Schiff base complexes. In Monatshefte fur Chemie (Vol. 138, No. 3, pp. 175–189). Springer Wien. https://doi.org/10.1007/s00706-007-0585-6
  • Thomas, J. B., Herault, X. M., Rothman, R. B., Atkinson, R. N., Burgess, J. P., Mascarella, S. W., Dersch, C. M., Xu, H., Flippen-Anderson, J. L., George, C. F., & Carroll, F. I. (2001). Factors influencing agonist potency and selectivity for the opioid delta receptor are revealed in structure-activity relationship studies of the 4-[(N-substituted-4-piperidinyl)arylamino]-N,N-diethylbenzamides. Journal of Medicinal Chemistry, 44(6), 972–987. https://doi.org/10.1021/jm000427g
  • Wang, B. L., Kou, S. B., Lin, Z. Y., & Shi, J. H. (2020). Investigation on the binding behavior between BSA and lenvatinib with the help of various spectroscopic and in silico methods. Journal of Molecular Structure, 1204, 127521. https://doi.org/10.1016/j.molstruc.2019.127521
  • Xu, X., Wang, D., Sun, X., Zeng, S., Li, L., & Sun, D. (2009). Thermodynamic and spectrographic studies on the interactions of ct-DNA with 5-fluorouracil and tegafur. Thermochimica Acta, 493(1–2), 30–36. https://doi.org/10.1016/j.tca.2009.03.017
  • Yang, L., Zhu, W., Fang, M., Zhang, Q., & Li, C. (2013). A new carbazole-based Schiff-base as fluorescent chemosensor for selective detection of Fe3+ and Cu2+. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 109, 186–192. https://doi.org/10.1016/j.saa.2013.02.043

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.