Hyperbranched Polymers Modified with Dansyl Units and Their Cu(II) Complexes. Bioactivity Studies
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Synthesis of the Cu(II) Complex with S1
2.3. Synthesis of the Cu(II) Complex with S2
2.4. Treatment of Cotton Fabric with S1 and S2
3. Results
3.1. Chemical Structure of S1 and S2 and Their Cu(II) Complexes
3.2. Deposition of Hyperbranched Polymers onto the Cotton Fabric
3.3. Biological Properties
3.3.1. Antimicrobial Activity and MIC
3.3.2. Antimicrobial Activity of the Treated Cotton Fabrics
3.3.3. Cytotoxicity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
- Martinez, J.L. Antibiotics and Antibiotic Resistance Genes in Natural Environments. Science 2008, 321, 365–367. [Google Scholar] [CrossRef] [PubMed]
- Zhang, Q.; Lambert, G.; Liao, D.; Kim, H.; Robin, K.; Tung, C.-K.; Pourmand, N.; Austin, R.H. Acceleration of Emergence of Bacterial Antibiotic Resistance in Connected Microenvironments. Science 2011, 333, 1764–1767. [Google Scholar] [CrossRef] [PubMed]
- Laxminarayan, R.; Duse, A.; Wattal, C.; Zaidi, A.K.M.; Wertheim, H.F.L.; Sumpradit, N.; Vlieghe, E.; Hara, G.L.; Gould, I.M.; Goossens, H.; et al. Antibiotic resistance—the need for global solutions. Lancet Infect. Dis. 2013, 13, 1057–1098. [Google Scholar] [CrossRef] [Green Version]
- Stone, M.R.L.; Butler, M.S.; Phetsang, W.; Cooper, M.A.; Blaskovich, M.A.T. Fluorescent Antibiotics: New Research Tools to Fight Antibiotic Resistance. Trends Biotechnol. 2018, 36, 523–536. [Google Scholar] [CrossRef]
- Mintzer, M.A.; Grinstaff, M.W. Biomedical applications of dendrimers: A tutorial. Chem. Soc. Rev. 2011, 40, 173–190. [Google Scholar] [CrossRef]
- Pedziwiatr-Werbicka, E.; Milowska, K.; Dzmitruk, V.; Ionov, M.; Shcharbin, D.; Bryszewska, M. Dendrimers and hyperbranched structures for biomedical applications. Eur. Polym. J. 2019, 119, 61–73. [Google Scholar] [CrossRef]
- Oliveira, J.M.; Salgado, A.J.; Esousa, N.; Mano, J.F.; Reis, R.L. Dendrimers and derivatives as a potential therapeutic tool in regenerative medicine strategies—A review. Prog. Polym. Sci. 2010, 35, 1163–1194. [Google Scholar] [CrossRef] [Green Version]
- Grabchev, I.; Vasileva-Tonkova, E.; Staneva, D.; Bosch, P.; Kukeva, R.; Stoyanova, R.K. Impact of Cu(ii) and Zn(ii) ions on the functional properties of new PAMAM metallodendrimers. New J. Chem. 2018, 42, 7853–7862. [Google Scholar] [CrossRef]
- Schattschneider, C.; Kettenmann, S.D.; Hinojosa, S.; Heinrich, J.; Kulak, N. Biological activity of amphiphilic metal complexes. Co-ord. Chem. Rev. 2019, 385, 191–207. [Google Scholar] [CrossRef]
- de Almeida, A.; Bonsignore, R. Fluorescent metal-based complexes as cancer probes. Bioorganic Med. Chem. Lett. 2020, 30, 127219. [Google Scholar] [CrossRef]
- Grabchev, I.; Staneva, D.; Vasileva-Tonkova, E.; Alexandrova, R. Antimicrobial and anticancer activity of fluorescent Zn(II) complexes of poly(propyleneamine) dendrimer modified with 1,8-naphthalimides. Chemosensors 2019, 7, 17. [Google Scholar] [CrossRef] [Green Version]
- Grabchev, I.; Staneva, D.; Vasileva-Tonkova, E.; Alexandrova, R.; Cangiotti, M.; Fattori, A.; Ottaviani, M.F. Antimicrobial and anticancer activity of new poly(propyleneamine) metallodendrimers. J. Polym. Res. 2017, 24, 210. [Google Scholar] [CrossRef]
- Staneva, D.; Grabchev, I.; Bosch, P.; Vasileva-Tonkova, E.; Kukeva, R.; Stoyanova, R. Synthesis, characterisaion and antimicrobial activity of polypropylenamine metallodendrimers modified with 1,8-naphthalimides. J. Mol. Struct. 2018, 1164, 363–369. [Google Scholar] [CrossRef]
- Grabchev, I.; Vasileva-Tonkova, E.; Staneva, D.; Bosch, P.; Kukeva, R.; Stoyanova, R. Synthesis, spectral characterization, and in vitro antimicrobial activity in liquid medium and applied on cotton fabric of a new PAMAM metallodendrimer. Int. J. Polym. Anal. Charact. 2017, 23, 45–57. [Google Scholar] [CrossRef]
- Staneva, D.; Grabchev, I. Encyclopedia of Polymer Applications; Taylor & Francis: Boca Raton, FL, USA, 2018. [Google Scholar]
- Medel, S.; Bosch, P.; Grabchev, I.; De La Torre, M.C.; Ramírez, P. Click chemistry to fluorescent hyperbranched polymeric sensors. 2. Synthesis, spectroscopic and cation-sensing properties of new green fluorescent 1,8-naphthalimides. Eur. Polym. J. 2016, 74, 241–255. [Google Scholar] [CrossRef]
- Medel, S.; Martínez-Campos, E.; Acitores, D.; Vassileva-Tonkova, E.; Grabchev, I.; Bosch, P. Synthesis and spectroscopic properties of a new fluorescent acridine hyperbranched polymer: Applications to acid sensing and as antimicrobial agent. Eur. Polym. J. 2018, 102, 19–29. [Google Scholar] [CrossRef]
- Vasileva-Tonkova, E.; Grozdanov, P.; Nikolova, I.; Staneva, D.; Bosch, P.; Medel, S.; Grabchev, I. Evaluation of antimicrobial, biofilm inhibitory and cytotoxic activities of a new hiperbranched polymer modified with 1,8-naphthalimide units. Bioint. Res. Appl. Chem. 2018, 8, 3053–3059. [Google Scholar]
- Vasileva-Tonkova, E.; Staneva, D.; Medel, S.; Bosch, P.; Grozdanov, P.; Nikolova, I.; Grabchev, I. Antimicrobial, Antibiofilm and Cytotoxicity Activity of a New Acridine Hyperbranched Polymer in Solution and on Cotton Fabric. Fibers Polym. 2019, 20, 19–24. [Google Scholar] [CrossRef]
- Medel, S.; Bosch, P.; De La Torre, C.; Ramirez, P. Click chemistry to fluorescent hyperbranched polymers. 1—Synthesis, characterization and spectroscopic properties. Eur. Polym. J. 2014, 59, 290–301. [Google Scholar] [CrossRef]
- Furer, V.L.; Vandyukova, I.I.; Vandyukov, A.E.; Fuchs, S.; Majoral, J.P.; Caminade, A.M.; Kovalenko, V.I. Vibrational spectra study of fluorescent dendrimers built from the cyclotriphosphazene core with terminal dansyl and carbamate groups. Spectrochim. Acta A 2011, 79, 462–470. [Google Scholar] [CrossRef]
- Wang, X.; Xia, P.; Huang, X. A dansyl—appended N-heterocycle for Cu2+ and S2−recognitionviaadisplacement mode. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2019, 210, 98–104. [Google Scholar] [CrossRef] [PubMed]
- Peisach, J.; Blumberg, W.E. Structural implications derived from the analysis of electron paramagnetic resonance spectra of natural and artificial copper proteins. Arch. Biochem. Biophys. 1974, 165, 691–708. [Google Scholar] [CrossRef]
- Ottaviani, M.F.; Cangiotti, M.; Fattori, A.; Coppola, C.; Posocco, P.; Laurini, E.; Liu, X.; Liu, C.; Fermeglia, M.; Peng, L.; et al. Copper(ii) binding to flexible triethanolamine-core PAMAM dendrimers: A combined experimental/in silico approach. Phys. Chem. Chem. Phys. 2014, 16, 685–694. [Google Scholar] [CrossRef] [PubMed]
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L* | a* | b* | X | Y | Z | x | y | Whiteness | |
---|---|---|---|---|---|---|---|---|---|
Cotton (control) | 93.51 | −0.17 | 2.98 | 79.68 | 84.13 | 86.09 | 0.3188 | 0.3367 | 70.4 |
Cotton S1 | 92.79 | −0.57 | 3.71 | 77.91 | 82.48 | 83.68 | 0.3193 | 0.3380 | 66.2 |
Cotton + [Cu3(S1)] | 92.41 | −0.73 | 4,53 | 77.03 | 81.62 | 81.38 | 0.3209 | 0.3401 | 60.5 |
Cotton S2 | 92.2 | −1.08 | 6.26 | 76.56 | 81.31 | 78.78 | 0.3235 | 0.3436 | 57.9 |
Cotton + [Cu8(S2)] | 92.23 | −0.75 | 4.99 | 56.63 | 81.22 | 80.36 | 0.3217 | 0.3410 | 52.1 |
Strains | S1 | [Cu3(S1)] | S2 | [Cu8(S2)] | G/Ns |
---|---|---|---|---|---|
Bacillus cereus | 11 | 13 | 12 | 14 | 12 |
Pseudomonas aeruginosa | 11 | 14 | 11 | 13 | 17 |
Candida lipolytica | 13 | 14 | 13 | 14 | 9 |
Strains | MIC, µmol/L | ||||
---|---|---|---|---|---|
S1 | [Cu3(S1)] | S2 | [Cu8(S2)] | G/Ns | |
Bacillus cereus | 34.91 | 29.09 | 19.20 | 16.46 | 8.37 |
Pseudomonas aeruginosa | 93.11 | 81.47 | 41.15 | 35.66 | 16.75 |
* Candida lipolytica | 64.01 | 58.19 | 27.46 | 24.61 | 11.34 |
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Bosch, P.; Staneva, D.; Vasileva-Tonkova, E.; Grozdanov, P.; Nikolova, I.; Kukeva, R.; Stoyanova, R.; Grabchev, I. Hyperbranched Polymers Modified with Dansyl Units and Their Cu(II) Complexes. Bioactivity Studies. Materials 2020, 13, 4574. https://doi.org/10.3390/ma13204574
Bosch P, Staneva D, Vasileva-Tonkova E, Grozdanov P, Nikolova I, Kukeva R, Stoyanova R, Grabchev I. Hyperbranched Polymers Modified with Dansyl Units and Their Cu(II) Complexes. Bioactivity Studies. Materials. 2020; 13(20):4574. https://doi.org/10.3390/ma13204574
Chicago/Turabian StyleBosch, Paula, Desislava Staneva, Evgenia Vasileva-Tonkova, Petar Grozdanov, Ivanka Nikolova, Rositsa Kukeva, Radostina Stoyanova, and Ivo Grabchev. 2020. "Hyperbranched Polymers Modified with Dansyl Units and Their Cu(II) Complexes. Bioactivity Studies" Materials 13, no. 20: 4574. https://doi.org/10.3390/ma13204574