Synthesis and Characterization of Camphorimine Au(I) Complexes with a Remarkably High Antibacterial Activity towards B. contaminans and P. aeruginosa
Abstract
:1. Introduction
2. Results
2.1. Synthesis and Characterization
2.2. Computational Calculations
2.3. Antibacterial Activity
2.4. Toxicity
2.5. Redox Properties
3. Materials and Methods
3.1. Synthesis
3.2. Computational Calculations
3.3. Biological Assays
3.3.1. Bacterial Strains
3.3.2. Minimal Inhibitory Concentration Assessment
3.3.3. Toxicity Assessment in Normal Cells
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
- Görnemann, T.; Nayal, R.; Pertz, H.H.; Melzig, M.F. Antispasmodic activity of essential oil from Lippia dulcis Trev. J. Ethnopharmacol. 2008, 117, 166–169. [Google Scholar] [CrossRef]
- Inoue, Y.; Takeuchi, S. Expectorant-like action of camphor derivatives. Nippon Ika Daigaku Zasshi 1969, 36, 351–354. [Google Scholar] [PubMed]
- Zuccarini, P. Camphor: Risks and benefits of a widely used natural product. J. Appl. Sci. Environ. Manag. 2009, 13, 69–74. [Google Scholar] [CrossRef] [Green Version]
- Cardoso, J.M.S.; Guerreiro, S.I.; Lourenço, A.; Alves, M.M.; Montemor, M.F.; Mira, N.P.; Leitão, J.H.; Carvalho, M.F.N.N. Ag(I) camphorimine complexes with antimicrobial activity towards clinically important bacteria and species of the Candida genus. PLoS ONE 2017, 12, e0177355. [Google Scholar] [CrossRef]
- Carvalho, M.F.N.N.; Leite, S.; Costa, J.P.; Galvão, A.M.; Leitão, J.H. Ag(I) camphor complexes: Antimicrobial activity by design. J. Inorg. Biochem. 2019, 199, 110791. [Google Scholar] [CrossRef] [PubMed]
- Costa, J.P.; Pinheiro, M.J.F.; Sousa, S.A.; Botelho do Rego, A.M.; Marques, F.; Oliveira, M.C.; Leitão, J.H.; Mira, N.; Carvalho, M.F.N.N. Antimicrobial Activity of Silver Camphorimine Complexes against Candida Strains. Antibiotics 2019, 8, 144. [Google Scholar] [CrossRef] [Green Version]
- Leitão, J.H.; Sousa, S.A.; Leite, S.; Carvalho, M.F.N.N. Silver Camphor Imine Complexes: Novel Antibacterial Compounds from Old Medicines. Antibiotics 2018, 7, 65. [Google Scholar]
- Carvalho, M.F.N.N.; Botelho do Rego, A.M.; Galvão, A.M.; Herrmann, R.; Marques, F. Search for cytotoxic compounds against ovarian cancer cells: Synthesis, characterization and assessment of the activity of new camphor carboxylate and camphor carboxamide silver complexes. J. Inorg. Biochem. 2018, 188, 88–95. [Google Scholar] [CrossRef]
- Costa, J.P.; Sousa, S.A.; Galvão, A.M.; Mata, J.M.; Leitão, J.H.; Carvalho, M.F.N.N. Key Parameters on the Antibacterial Activity of Silver Camphor Complexes. Antibiotics 2021, 10, 135. [Google Scholar] [CrossRef]
- Fernandes, T.A.; Mendes, F.; Roseiro, A.P.S.; Santos, I.; Carvalho, M.F.N.N. Insight into the cytotoxicity of polynuclear Cu(I) camphor complexes. Polyhedron 2015, 87, 215–219. [Google Scholar] [CrossRef]
- Higby, G.J. Gold in medicine. Gold Bull. 1982, 15, 130–140. [Google Scholar] [CrossRef] [Green Version]
- Evans, A.; Kavanagh, K.A. Evaluation of metal-based antimicrobial compounds for the treatment of bacterial pathogens. J. Med. Microbiol. 2021, 70, 001363. [Google Scholar] [CrossRef]
- Roder, C.; Thomson, M.J. Auranofin: Repurposing an Old Drug for a Golden New Age. Drugs R&D 2015, 15, 13–20. [Google Scholar]
- Bindolini, A.; Rigobello, M.P.; Scutari, G.; Gabbiani, C.; Casini, A.; Messori, L. Thioredoxin reductase: A target for gold compounds acting as potential anticancer drugs. Coord. Chem. Rev. 2009, 253, 1692–1707. [Google Scholar] [CrossRef]
- Glišić Biljana, Đ.; Djuran, M.I. Gold complexes as antimicrobial agents: An overview of different biological activities in relation to the oxidation state of the gold ion and the ligand structure. Dalton Trans. 2014, 43, 5950–5969. [Google Scholar] [CrossRef] [PubMed]
- Bertrand, B.; Casini, A. A golden future in medicinal inorganic chemistry: The promise of anticancer gold organometallic compounds. Dalton Trans. 2014, 43, 4209–4219. [Google Scholar] [CrossRef]
- Liu, W.; Gust, R. Update on metal N-heterocyclic carbene complexes as potential anti-tumor metallodrugs. Coord. Chem. Rev. 2016, 329, 191–213. [Google Scholar] [CrossRef]
- Geisheimer, A.R.; Katz, M.J.; Batchelor, R.J.; Leznoff, D.B. Preparation and characterization of two chiral Au(CN)2-based coordination polymers containing (1R,2R)-N,N9-dimethylcyclohexanediamine. Cryst. Eng. Comm. 2007, 9, 1078–1083. [Google Scholar] [CrossRef]
- Lefebvre, J.; Korčok, J.L.; Katz, M.J.; Leznoff, D.B. Vapochromic Behaviour of M[Au(CN)2]2-Based Coordination Polymers (M = Co, Ni). Sensors 2012, 12, 3669–3692. [Google Scholar] [CrossRef] [Green Version]
- Deák, A.; Tunyogi, T.; Pálinkás, G. Synthesis and Structure of a Cyanoaurate-Based Organotin Polymer Exhibiting Unusual Ion-Exchange Properties. J. Am. Chem. Soc. 2009, 131, 2815–2817. [Google Scholar] [CrossRef]
- Resenzweig, A.; Cromer, D.T. The crystal structure of KAu(CN)2. Acta. Cryst. 1959, 12, 709–712. [Google Scholar] [CrossRef]
- Schmidt, M.W.; Baldridge, K.K.; Boatz, J.A.; Elbert, S.T.; Gordon, M.S.; Jensen, J.H.; Koseki, S.; Matsunaga, N.; Nguyen, K.A.; Su, S.; et al. General atomic and molecular electronic structure system. J. Comput. Chem. 1993, 14, 1347–1363. [Google Scholar] [CrossRef]
- Fernandes, T.A.; Ferraria, A.M.; Galvão, A.M.; Botelho do Rego, A.M.; Suárez, A.C.M.; Carvalho, M.F.N.N. Synthesis, characterization and study of the catalytic properties of Zn(II) camphor derived complexes. J. Organometal. Chem. 2014, 760, 186–196. [Google Scholar] [CrossRef]
- Ekwall, B.; Silano, V.; Paganuzzi-Stammati, A.; Zucco, F. Toxicity Tests with Mammalian Cell Cultures. In Short-Term Toxicity Tests for Non-genotoxic Effects; John Wiley & Sons Ltd.: Hoboken, NJ, USA, 1990; Chapter 7. [Google Scholar]
- Parasuraman, S. Toxicological screening. J. Pharmacol. Pharmacother. 2011, 2, 74–79. [Google Scholar] [CrossRef] [Green Version]
- Carvalho, M.F.N.N.; Costa, L.M.G.; Pombeiro, A.J.L.; Herrmann, R.; Wagner, G. Study of the electrochemical behaviour of camphor(+) derivatives and some of their palladium complexes. Port. Electrochem. Acta 1993, 11, 99–103. [Google Scholar]
- Carvalho, M.F.N.N.; Costa, L.M.G.; Pombeiro, A.J.L.; Schier, A.; Scherer, W.; Harbi, S.K.; Verfürth, U.; Herrmann, R. Synthesis, Structure, and Electrochemistry of Palladium Complexes with Camphor-Derived Chiral Ligands. Inorg. Chem. 1994, 33, 6270–6277. [Google Scholar] [CrossRef]
- Armarego, W.L.F.; Chai, C.L.L. Purification of Laboratory Chemicals, 6th ed.; Elsevier Inc: Oxford, UK, 2008. [Google Scholar]
- Yanai, T.; Tew, D.; Handy, N. A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem. Phys. Lett. 2004, 393, 51–57. [Google Scholar]
- Fontinha, D.; Sousa, S.A.; Morais, T.S.; Prudêncio, M.; Leitão, J.H.; Le Gal, Y.; Lorcy, D.; Silva, R.A.L.; Velho, M.F.G.; Belo, D.; et al. Gold(III) bis(dithiolene) complexes: From molecular conductors to prospective anticancer, antimicrobial and antiplasmodial agents. Metallomics 2020, 12, 974–987. [Google Scholar] [CrossRef] [PubMed]
E (Volt) | MIC (µg/mL) | ||||||||
---|---|---|---|---|---|---|---|---|---|
Compound | Y or Z | % Au | E. coli ATCC25922 | P. aeruginosa 477 | B. contaminans IST408 | S. aureus Newman | |||
K[Au(CN)2(A1L)]·H2O | 1 | C6H4NH2 A1L | 35.0 | 0.78 | −1.68 | 29.7 ± 1.9 | 17.3 ± 2.1 | 4.6 ± 0.5 | 32.7 ± 4.7 |
[Au(CN)(A1L)]·CH3CN | 2 | 39.2 | 0.84 | −1.74 | 49.8 ± 3.7 | 7.9 ± 1.8 | 4.5 ± 0.4 | 29.7 ± 1.1 | |
[Au(CN)(A1L)3]·H2O | 3 | 19.9 | 0.80 | −1.74 | 250 | 9.1 ± 1.9 | 8.4 ± 1.2 | 151.5 ± 10.8 | |
K[Au(CN)2(A2L)] | 4 | C6H4CH3 A2L | 36.2 | 44.3 ± 6.1 | 5.6 ± 0.1 | 4.2 ± 0.1 | >250 | ||
[Au(CN)(A2L)2]·½CH3CN | 5 | 26.8 | 1.6 | −1.67 | 87.4 ± 6.4 | 28.1 ± 8.3 | 9.4 ± 1.4 | 250 | |
[{Au(CN)}2(A2L)]·2H2O | 6 | 53.4 | 46 ± 3.7 | 17.3 ± 1.3 | 5.3 ± 0.3 | 44.5 ± 4.3 | |||
K[Au(CN)2(A2L)2] | 7 | 24.3 | 1.69 | −1.55 | 34.03 ± 1.6 | 7.0 ± 0.8 | 7.9 ± 0.5 | >250 | |
K3[{Au(CN)2}3(A4L)] | 8 | m-OHC6H4A4L | 52.7 | −1.59 | 49.7 ± 1.2 | 3.9 ± 0.5 | 3.8 ± 0.2 | 30.8 ± 6.4 | |
K[Au(CN)2(A5L)] | 9 | NH2 A5L | 42.1 | 1.57 | −1.74 | 56.1 ± 6.8 | 6.9 ± 0.3 | 3.8 ± 0.2 | 53.9 ± 2.8 |
K[Au(CN)2(A6L)2] ·½H2O | 10 | OH A6L | 30.3 | 1.66 | −1.58 | 17.3 ± 0.3 | 8.1 ± 0.6 | 4.8 ± 0.3 | 32.9 ± 1.6 |
K3[{Au(CN)2}3(CL)]·H2O | 11 | NC6H4N CL | 53.6 | 47.5 ± 6.8 | 8.7 ± 1.4 | 5.4 ± 0.4 | 47.1 ± 1.2 | ||
K[Au(CN)2(CL)3]·H2O | 12 | 19.6 | 0.50 | ̶ | 114.3 ± 11.9 | 9.8 ± 0.3 | 8.6 ± 0.6 | >250 | |
[Au(CN)(B1L)]·CH3CN | 13 | m-C6H4 B1L | 29.5 | 0.69 | ̶ | 56.5 ± 1.2 | 28.9 ± 2.1 | 7.0 ± 0.2 | 81.2 ± 5.2 |
K3[{Au(CN)2}3(B2L)]· 3H2O | 14 | p-C6H4 B2L | 47.5 | 1.58 | −1.38 | 23.5 ± 0.7 | 4.7 ± 0.4 | 2.4 ± 0.1 | 43.2 ± 1.7 |
KAu(CN)2 | 68.7 | 1.72 | ̶ | 14.7 ± 0.1 | 13.6 ± 0.7 | 2.2 ± 0.02 | 15.6 ± 0.9 |
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Costa, J.P.; Sousa, S.A.; Soeiro, C.; Leitão, J.H.; Galvão, A.M.; Marques, F.; Carvalho, M.F.N.N. Synthesis and Characterization of Camphorimine Au(I) Complexes with a Remarkably High Antibacterial Activity towards B. contaminans and P. aeruginosa. Antibiotics 2021, 10, 1272. https://doi.org/10.3390/antibiotics10101272
Costa JP, Sousa SA, Soeiro C, Leitão JH, Galvão AM, Marques F, Carvalho MFNN. Synthesis and Characterization of Camphorimine Au(I) Complexes with a Remarkably High Antibacterial Activity towards B. contaminans and P. aeruginosa. Antibiotics. 2021; 10(10):1272. https://doi.org/10.3390/antibiotics10101272
Chicago/Turabian StyleCosta, Joana P., Sílvia A. Sousa, Catarina Soeiro, Jorge H. Leitão, Adelino M. Galvão, Fernanda Marques, and M. Fernanda N. N. Carvalho. 2021. "Synthesis and Characterization of Camphorimine Au(I) Complexes with a Remarkably High Antibacterial Activity towards B. contaminans and P. aeruginosa" Antibiotics 10, no. 10: 1272. https://doi.org/10.3390/antibiotics10101272