Optimized Anti-pathogenic Agents Based on Core/Shell Nanostructures and 2-((4-Ethylphenoxy)ethyl)-N-(substituted-phenylcarbamothioyl)-benzamides
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Chemical Characterization
3. Experimental Section
3.1. Synthesis and Characterization of Core/Shell Nanostructure
3.2. Synthesis and Characterization of Adsorption-Shell
3.2.1. Chemistry
3.2.2. General Synthesis Procedure of the New Thioureides
3.2.3. Characterization of Coated-Shell
3.2.3.1. 2-((4-Ethylphenoxy)methyl)-N-(3,4-dichlorophenylcarbamothioyl)benzamide (1a)
3.2.3.2. 2-((4-Ethylphenoxy)methyl)-N-(2,4,5-trichlorophenylcarbamothioyl)benzamide (1b)
3.2.3.3. 2-((4-Ethylphenoxy)methyl)-N-(2-nitro-4-chlorophenylcarbamothioyl)benzamide (1c)
3.3. Fabrication of Prosthetic Device Coated with Core/Shell/Adsorption-Shell Nanostructure
3.4. Microbial Adherence to the Inert and Modified Prosthetic Devices
3.5. Direct Examination of Biofilm Architecture by SEM
3.6. Statistical Analysis
4. Conclusions
Acknowledgments
References
- Liav, A.; Angala, S.K.; Brennan, P.J.; Jackson, M. N-D-Aldopentofuranosyl-N′-[p-(isoamyloxy)phenyl]thiourea derivatives: Potential anti-TB therapeutic agents. Bioorg. Med. Chem. Lett 2008, 18, 2649–2651. [Google Scholar]
- Walchshofer, N.; Delabre-Defayolle, I.; Paris, J.; Petavy, A.F. In vivo morphological damage induced by a new benzimidazole prodrug in Echinococcus multilocularis metacestodes. J. Pharm. Sci 1990, 79, 606–608. [Google Scholar]
- Mishra, A.; Srivastava, K.; Tripathi, R.; Puri, S.K.; Batra, S. Search for new pharmacophores for antimalarial activity. Part III: Synthesis and bioevaluation of new 6-thioureido-4-anilinoquinazolines. Eur. J. Med. Chem 2009, 44, 4404–4412. [Google Scholar]
- Çikla, P.; Küçükgüzel, Ş.G.; Küçükgüzel, I.; Rollas, S.; De Clercq, E.; Pannecouque, C.; Andrei, G.; Snoeck, R.; Şahin, F.; Bayrak, Ö.F. Synthesis and evaluation of antiviral, antitubercular and anticancer activities of some novel thioureas derived from 4-aminobenzohydrazide hydrazones. Marmara Pharm. J 2010, 14, 13–20. [Google Scholar]
- Park, H.G.; Choi, J.Y.; Choi, S.H.; Park, M.K.; Lee, J.; Suh, Y.G.; Cho, H.; Oh, U.; Lee, J.; Kang, S.U.; et al. N-4-Substituted-benzyl-N′-tert-butylbenzyl thioureas as vanilloid receptor ligands: Investigation on the role of methanesulfonamido group in antagonistic activity. Bioorg. Med. Chem. Lett 2004, 14, 787–791. [Google Scholar]
- Patel, R.B.; Chikhalia, K.H.; Pannecouque, C.; de Clercq, E. Synthesis of novel PETT analogues: 3,4-Dimethoxy phenyl ethyl-1,3,5-triazinyl thiourea derivatives and their antibacterial and anti-HIV studies. J. Braz. Chem. Soc 2007, 18, 312–321. [Google Scholar]
- Kayser, H.; Eilinger, P. Metabolism of diafenthiuron by microsomal oxidation: procide activation and inactivation as mechanisms contributing to selectivity. Pest Manag. Sci 2001, 57, 975–980. [Google Scholar]
- Ramadas, K.; Suresh, G.; Janarthanan, N.; Masilamani, S. Antifungal activity of 1,3-disubstituted symmetrical and unsymmetrical thioureas. Pestic. Sci 1998, 52, 145–151. [Google Scholar]
- Ke, S.Y.; Xue, S.J. Synthesis and herbicidal activity of N-(o-fluorophenoxyacetyl)thioureas derivatives and related fused heterocyclic compounds. ARKIVOC 2006, 63–68. [Google Scholar]
- Kumar, S.; Awasthi, V.; Kanwar, J.K. Influence of growth regulators and nitrogenous compounds on in vitro bulblet formation and growth in oriental lily. Hort. Sci (Prague) 2007, 34, 77–83. [Google Scholar]
- Gülkok, Y; Biçer, T.; Kaynak Onurdag, F.; Özgen, S.; ŠAHIN, M.F.; Doğruer, D.S. Synthesis of some new urea and thiourea derivatives and evaluation of their antimicrobial activities. Turk. J. Chem. 2012, 30, 279–291. [Google Scholar]
- Sarmah, K.N.; Patel, T.V. Synthesis, characterization, antimicrobial studies of certain triayole containing s-triazine derived compound. Chem. Mat. Res 2011, 1, 1–9. [Google Scholar]
- Reddy, N.S.; Rao, A.S.; Chari, M.A.; Kumar, V.R.; Jyothi, V.; Himabindu, V. Synthesis and antibacterial activity of urea and thiourea derivatives at C-8 alkyl chain of anacardic acid mixture isolated from a natural product cashew nut shell liquid (CNSL). Int. J. Org. Chem 2011, 1, 167–175. [Google Scholar]
- Patel, N.B.; Patel, S.D.; Patel, J.N.; Patel, J.C.; Gorgamwala, Y.S. Synthesis and antibacterial activity of thioureido amide of fluoroquinolone. Int. J. Biol. Chem. 2011, 5, 37–45. [Google Scholar]
- Pathak, A.K.; Chawla, V.; Saraf, S.K. Synthesis of 2-(6′-fluorobenzothiazol-2′-ylamino)-4,6-(disubstituted thioureido)-1,3-pyrimidine derivatives as antimicrobial agents. E. J. Chem 2011, 8, 240–244. [Google Scholar]
- Modi, K.N.; Panchal, S.D.; Sen, D.J. Structure activity relationship studies of substituted Mannich bases of 2-oxo-4,6-diphenyl-2,6-dihydropyrazolo[1,5-α][1,3,5]triazine-7 carbonyl ring system with variable electronegative atoms (urea/thiourea/guanidine) for antimicrobial and antifungal activity. Int. J. Drug Dev. Res 2011, 3, 334–343. [Google Scholar]
- Sarmah, K.; Patel, T.V. Synthesis, characterization, antimicrobial studies of certain s-triazine derived compounds and analogues. Arch. Appl. Sci. Res 2011, 3, 428–436. [Google Scholar]
- Lohray, V.B.; Lohray, B.B.; Srivastava, B.K. Novel anti-infective compounds. Pure Appl. Chem 2005, 77, 195–200. [Google Scholar]
- Tokuyama, R.; Takahashi, Y.; Tomita, Y.; Tsubouchi, M.; Yoshida, T.; Iwasaki, N.; Kado, N.; Okezaki, E.; Nagata, O. Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents.2. Relationship between lipophilicity and antibacterial activity in 5-thiocarbonyl oxazolidinones. Chem. Pharm. Bull 2001, 49, 353–360. [Google Scholar]
- Hasegawa, H.; Endo, I.; Koyama, S.; Isozaki, M.; Yoshiyama, Y.; Nozawa, S.; Arakawa, N. Thiourea derivatives and antimicrobial agent and antiulcer agent containing the same. US Patent 5,190,961, 2 March 1993. [Google Scholar]
- Cotar, A.I.; Chifiriuc, M.C.; Holban, A.M.; Banu, O.; Lazar, V. Prevalence of agr specificity groups among Staphylococcus aureus strains isolated from different clinical specimens patients with cardiovascular surgery associated infections. Biointerface Res. Appl. Chem 2012, 2, 264–270. [Google Scholar]
- Marinaş, I.; Grumezescu, A.M.; Saviuc, C.; Chifiriuc, C.; Mihaiescu, D.; Lazar, V. Rosmarinus officinalis essential oil as antibiotic potentiator against Staphylococcus aureus. Biointerface Res Appl. Chem 2012, 2, 271–276. [Google Scholar]
- EARS-Net Database home page. Available online: http://www.ecdc.europa.eu/en/activities/surveillance/EARS-Net/database/Pages/database.aspx access on 6 June 2012.
- Cotar, A.I; Chifiriuc, M.C.; Dinu, S.; Bucur, M.; Iordache, C.; Banu, O.; Dracea, O.; Larion, C; Lazar, V. Screening of Molecular Virulence Markers in Staphylococcus aureus and Pseudomonas aeruginosa Strains Isolated from Clinical Infections. Int. J. Mol. Sci. 2010, 11, 5273–5291. [Google Scholar]
- Subhasree, R.S.; Selvakumar, D.; Kumar, N.S. Hydrothermal mediated synthesis of ZnO nanorods and their antibacterial properties. Lett. Appl. NanoBioSci 2012, 1, 2–7. [Google Scholar]
- Labouta, I.H.; Schneider, M. Tailor-made biofunctionalized nanoparticles using layer-by-layer technology. Int. J. Pharm. 2010, 395, 236–242. [Google Scholar]
- Grumezescu, A.M; Saviuc, C.; Holban, A.; Hristu, R.; Croitoru, C.; Stanciu, G.; Chifiriuc, C; Mihaiescu, D.; Balaure, P.; Lazar, V. Magnetic chitosan for drug targeting and in vitro drug delivery response. Biointerface Res. Appl. Chem. 2011, 1, 160–165. [Google Scholar]
- Wang, H.; Wang, S.; Liao, Z.; Zhao, P.; Su, W.; Niu, R.; Chang, J. Folate-targeting magnetic core-shell nanocarriers for selective drug release and imaging. Int. J. Pharm 2011, 430, 343. [Google Scholar]
- Chifiriuc, M.C.; Grumezescu, V.; Grumezescu, A.M.; Saviuc, M.C.; Lazar, V.; Andronescu, E. Hybrid magnetite nanoparticles/Rosmarinus officinalis essential oil nanobiosystem with antibiofilm activity. Nanoscale Res. Lett 2012, 7, 209. [Google Scholar]
- Schweiger, C.; Pietzonka, C.; Heverhagen, J.; Kissel, T. Novel magnetic iron oxide nanoparticles coated with poly(ethylene imine)-g-poly(ethylene glycol) for potential biomedical application: Synthesis, stability, cytotoxicity and MR imaging. Int. J. Pharm 2011, 408, 130–137. [Google Scholar]
- Mantle, M.D. Quantitative magnetic resonance micro-imaging methods for pharmaceutical research. Int. J. Pharm 2011, 417, 173. [Google Scholar]
- Andronescu, E.; Ficai, M.; Voicu, G.; Manzu, D.; Ficai, A. Synthesis and characterization of collagen/hydroxyapatite—Magnetite composite material for bone cancer treatment. J. Mater. Sci.-Mater. M 2010, 21, 2237–2242. [Google Scholar]
- Poole, K. Multidrug efflux pumps and antimicrobial resistance in Pseudomonas aeruginosa and related organisms. J. Mol. Microbiol. Biotechnol 2001, 3, 255–264. [Google Scholar]
- Grumezescu, A.M.; Ficai, A.; Mihaiescu, D.E.; Vasile, B.S.; Bleotu, C. Synthesis, characterization and bioevaluation of core/shell nanostructure. Lett. Appl. NanoBioSci 2012, 1, 31–35. [Google Scholar]
- Limban, C.; Missir, A.V.; Chiriţă, I.C.; Niţulescu, G.M.; Ilie, C.; Căproiu, M.T. Some new 2-(4-ethyl-phenoxymethyl)benzoic acid thioureides: synthesis and spectral characterisation. Rev. Chim. (Bucharest) 2009, 60, 657–661. [Google Scholar]
- Saviuc, C.; Grumezescu, A.M.; Chifiriuc, M.C.; Bleotu, C.; Stanciu, G.; Hristu, R.; Mihaiescu, D.; Lazar, V. In vitro methods for the study of microbial biofilms. Biointerface Res. Appl. Chem 2011, 1, 32–40. [Google Scholar]
- Grumezescu, A.M.; Saviuc, C.; Chifiriuc, M.C.; Hristu, R.; Mihaiescu, D.E.; Balaure, P.; Stanciu, G.; Lazar, V. Inhibitory Activity of Fe3O4/Oleic Acid/Usnic Acid—Core/Shell/Extra-Shell Nanofluid on S. aureus Biofilm Development. IEEE Trans. Nanobiosci 2011, 10, 269–274. [Google Scholar]
- Saviuc, C.; Grumezescu, A.M.; Bleotu, C.; Holban, A.; Chifiriuc, C.; Balaure, P.; Lazar, V. Phenotipical studies for raw and nanosystem embedded Eugenia carryophyllata buds essential oil effect on Pseudomonas aeruginosa and Staphylococcus aureus strains. Biointerface Res. Appl. Chem 2011, 1, 111–118. [Google Scholar]
Compound | C% | H% | N% | S% | Molecular weight | Melting point (°C) | Yield (%) | ||||
---|---|---|---|---|---|---|---|---|---|---|---|
c. | e. | c. | e. | c. | e. | c. | e. | ||||
1a. | 60.13 | 60.45 | 4.39 | 4.27 | 6.10 | 6.17 | 6.98 | 6.91 | 459.39 | 139–141 | 78 |
1b. | 55.94 | 56.17 | 3.88 | 3.79 | 5.67 | 5.62 | 6.49 | 6.54 | 493.83 | 160–161 | 81 |
1c. | 58.78 | 58.59 | 4.29 | 4.34 | 8.94 | 8.82 | 6.82 | 6.89 | 469.94 | 144–145 | 76 |
© 2012 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
Share and Cite
Limban, C.; Grumezescu, A.M.; Saviuc, C.; Voicu, G.; Predan, G.; Sakizlian, R.; Chifiriuc, M.C. Optimized Anti-pathogenic Agents Based on Core/Shell Nanostructures and 2-((4-Ethylphenoxy)ethyl)-N-(substituted-phenylcarbamothioyl)-benzamides. Int. J. Mol. Sci. 2012, 13, 12584-12597. https://doi.org/10.3390/ijms131012584
Limban C, Grumezescu AM, Saviuc C, Voicu G, Predan G, Sakizlian R, Chifiriuc MC. Optimized Anti-pathogenic Agents Based on Core/Shell Nanostructures and 2-((4-Ethylphenoxy)ethyl)-N-(substituted-phenylcarbamothioyl)-benzamides. International Journal of Molecular Sciences. 2012; 13(10):12584-12597. https://doi.org/10.3390/ijms131012584
Chicago/Turabian StyleLimban, Carmen, Alexandru Mihai Grumezescu, Crina Saviuc, Georgeta Voicu, Gentiana Predan, Robert Sakizlian, and Mariana Carmen Chifiriuc. 2012. "Optimized Anti-pathogenic Agents Based on Core/Shell Nanostructures and 2-((4-Ethylphenoxy)ethyl)-N-(substituted-phenylcarbamothioyl)-benzamides" International Journal of Molecular Sciences 13, no. 10: 12584-12597. https://doi.org/10.3390/ijms131012584