Optimized anti-pathogenic agents based on core/shell nanostructures and 2-((4-ethylphenoxy)ethyl)-N-(substitutedphenylcarbamothioyl)-benzamides

International Journal of Molecular Sciences

Volumn 13, Issue 10, 2012, Pages 12584-12597

  Limban, Carmen ^a   Grumezescu, Alexandru Mihai ^b   Saviuc, Crina ^c   Voicu, Georgeta ^b   Predan, Gentiana ^c   Sakizlian, Robert ^c   Chifiriuc, Mariana Carmen ^c  

^a CAROL DAVILA UNIVERSITY OF MEDICINE AND PHARMACY   (Romania)

^b UNIVERSITY POLITEHNICA OF BUCHAREST   (Romania)

^c UNIVERSITY OF BUCHAREST   (Romania)

Author keywords

Anti biofilm; Benzamides; Biointerface application; Core shell nanostructure; Magnetite; Thiourea derivatives

Indexed keywords

2 [(4 ETHYLPHENOXY)METHYL] N (2 NITRO 4 CHLOROPHENYLCARBAMOTHIOYL)BENZAMIDE; 2 [(4 ETHYLPHENOXY)METHYL] N (2,4,5 TRICHLOROPHENYLCARBAMOTHIOYL)BENZAMIDE; 2 [(4 ETHYLPHENOXY)METHYL] N (3,4 DICHLOROPHENYLCARBAMOTHIOYL)BENZAMIDE; ANTIINFECTIVE AGENT; LAURIC ACID; NANOPARTICLE; UNCLASSIFIED DRUG; BENZAMIDE DERIVATIVE; NANOMATERIAL; THIOUREA;

ARTICLE; BACTERIAL CELL; BACTERIAL COLONIZATION; BACTERIUM ADHERENCE; BACTERIUM CULTURE; BIOASSAY; CELL COUNT; CELL VIABILITY; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; INFRARED RADIATION; INFRARED SPECTROSCOPY; MAGNETIC FIELD; MATERIAL COATING; NANOFABRICATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PARTICLE SIZE; PROCESS OPTIMIZATION; PSEUDOMONAS AERUGINOSA; SCANNING ELECTRON MICROSCOPY; STAPHYLOCOCCUS AUREUS; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION; ANALOGS AND DERIVATIVES; BIOFILM; CHEMISTRY; DRUG EFFECTS; PHYSIOLOGY;

ANTI-INFECTIVE AGENTS; BENZAMIDES; BIOFILMS; NANOSTRUCTURES; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; THIOUREA;

EID: 84867815908     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms131012584     Document Type: Article

References (38)

1. 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. Ramadas, K.; Suresh, G.; Janarthanan, N.; Masilamani, S. Antifungal activity of 1,3-disubstituted symmetrical and unsymmetrical thioureas. Pestic. Sci. 1998, 52, 145-151.
9. 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.
10. 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.
11. Gülkok, Y; Biçer, T.; Kaynak Onurdag, F.; Özgen, S.; Şahin, M.F., Doǧruer, D.S. Synthesis of some new urea and thiourea derivatives and evaluation of their antimicrobial activities. Turk. J. Chem. 2012, 30, 279-291.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.
17. 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.
18. Lohray, V.B.; Lohray, B.B.; Srivastava, B.K. Novel anti- infective compounds. Pure Appl. Chem. 2005, 77, 195-200.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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).
24. 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.
25. 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.
26. Labouta, I.H.; Schneider M. Tailor-made biofunctionalized nanoparticles using layer-by-layer technology. Int. J. Pharm. 2010, 395, 236-242.
27. 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.
28. 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.
29. 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.
30. 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.
31. Mantle, M.D. Quantitative magnetic resonance micro-imaging methods for pharmaceutical research. Int. J. Pharm. 2011, 417, 173.
32. 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.
33. Poole, K. Multidrug efflux pumps and antimicrobial resistance in Pseudomonas aeruginosa and related organisms, J. Mol. Microbiol. Biotechnol. 2001, 3, 255-264.
34. 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.
35. Limban, C.; Missir, A.V.; Chiriţǎ, I.C.; Niţulescu, G.M.; Ilie, C.; Cǎproiu M.T. Some new 2-(4-ethyl-phenoxymethyl)benzoic acid thioureides: synthesis and spectral characterisation. Rev. Chim. (Bucharest) 2009, 60, 657-661.
36. 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.
37. 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.
38. 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.