Synthesis and Evaluation of Aromatic Surfactants as Potential Antibacterial and Cytotoxic Agents

Author(s): Kenia Barrantes, Mary Fuentes, Luz Chacón, Rosario Achí, Jorge Granados-Zuñiga, María José Alvarado, Luis Somarribas, José Vázquez-Tato, M. Pilar Vázquez-Tato, Julio A. Seijas, Víctor Soto Tellini*.

Journal Name: Letters in Organic Chemistry

Volume 16 , Issue 6 , 2019

Become EABM
Become Reviewer

Graphical Abstract:


Abstract:

Two ether and one ester derivatives of the 4-nitro-3-hydroxybenzoic acid were synthesized and characterized. The in vitro antimicrobial and cytotoxic activities of the three novel compounds were also evaluated. The aromatic derivatives showed antibacterial activity against one of the four microorganisms tested and two compounds (C8 and NOBA) had a lower IC50 in HeLa cells.

Keywords: Surfactants, cytotoxic activity, antimicrobial activity, aromatic, 4-nitro-3-hidroxybenzoic acid, organic chemistry.

[1]
World Health Organization. WHO Global Strategy for Containment of Antimicrobial Strategy for Containment of Antimicrobial Resistance 2001.
[2]
Alanis, A.J. Arch. Med. Res., 2005, 36(6), 697-705.
[3]
Peirano, G.; Agersø, Y.; Aarestrup, F.M.; dos Reis, E.M.F.; dos Prazeres, R.D. J. Antimicrob. Chemother., 2006, 58(2), 305-309.
[4]
Committee on New Directions in the Study of Antimicrobial Therapeutics: New Classes of Antimicrobials, C. on N. D. in the S. of A.T. I. Treating Infectious Diseases in a Microbial World: Report of Two Workshops on Novel Antimicrobial Therapeutics;. 2006.
[5]
Housman, G.; Byler, S.; Heerboth, S.; Lapinska, K.; Longacre, M.; Snyder, N.; Sarkar, S. Cancers (Basel), 2014, 6(3), 1769-1792.
[6]
Ahronian, L.G.; Corcoran, R.B. Genome Med., 2017, 9(1), 1-12.
[7]
Upmanyu, N.; Kumar, S.; Kharya, M-D.; Sha, K.; Mishra, P. Acta Pol. Pharm., 2011, 68(2), 213-221.
[8]
Effendy, I.; Maibach, H.I. Contact Derm., 1995, 33(4), 217-225.
[9]
Brycki, B.E.; Kowalczyk, I.H.; Szulc, A.; Kaczerewska, O.; Pakiet, M. Applications and Characterization of Surfactants; INTECH, 2017.
[10]
Schramm, L.L.; Stasiuk, E.N.; Marangoni, D.G. Annu. Rep. Prog. Chem.. Sect. C: Phys. Chem.., 2003, 99, 3-48.
[11]
Schreier, S.; Malheiros, S.V.; de Paula, E. Biochim. Biophys. Acta, 2000, 1508(210-234), 210-234.
[12]
Huang, L.; Sun, Y.; Zhu, H.; Zhang, Y.; Xu, J.; Shen, Y.M. Steroids, 2009, 74(8), 701-706.
[13]
Cho, W.; Markowitz, M.; Kezdy, F.J. J. Am. Chem. Soc., 1988, 110, 5166-5171.
[14]
Bragg, R.; Janse, A.; Coetzee, M.; van der Westhuizen, W.; Boucher, C. Infectious Diseases and Nanomedicine II: Advances in Experimental Medicine and Biology; Springer: London, 2014.
[15]
Cooper, M.A. Nat. Rev. Drug Discov., 2015, 14(9), 587-588.
[16]
Fuhrmann, E.; Talbiersky, J. Org. Process Res. Dev., 2005, 9(2), 206-211.
[17]
Kulikov, O.V.; Incarvito, C.; Hamilton, A.D. Tetrahedron Lett., 2011, 52(29), 3705-3709.
[18]
Shin, H.; Gennadios, H.A.; Whittington, D.A.; Christianson, D.W. Bioorg. Med. Chem., 2007, 15(7), 2617-2623.
[19]
Pirolla, R.A.S.; Baldasso, P.A.; Marangoni, S.; Moran, P.J.S.; Rodrigues, J.A.R. J. Braz. Chem. Soc., 2011, 22(2), 300-307.
[20]
El-Sadek, B.M. Adv. Appl. Sci. Res., 2011, 2(3), 363-372.
[21]
Bhat, R.; Preethi, M.V.; Shetty, P. Adv. Biores., 2011, 2(2), 52-62.
[22]
Zhang, S.; Ding, S.; Yu, J.; Chen, X.; Lei, Q.; Fang, W. Langmuir, 2015, 31(44), 12161-12169.
[23]
Silhavy, T.; Kahne, D.; Walker, S. Cold Spring Harb. Perspect. Biol., 2010, 2(5), 1-16.
[24]
Kanjilal, S.; Sunitha, S.; Reddy, P.S.; Kumar, K.P.; Murty, K.P.K.; Prasad, R.B.N. Eur. J. Lipid Sci. Technol., 2009, 111(9), 941-948.
[25]
Mo, F.; Ren, H.; Chen, S.; Ge, Z. Mater. Lett., 2015, 145, 174-176.
[26]
Bustelo, M.; Pinazo, A.; Manresa, M.A.; Mitjans, M.; Vinardell, M.P.; Pérez, L. Colloids Surf. A Physicochem. Eng. Asp., 2017, 532, 501-509.
[27]
Tehrani-Bagha, A.R.; Holmberg, K. Langmuir, 2010, 26(12), 9276-9282.
[28]
Lu, B.; Vayssade, M.; Miao, Y.; Chagnault, V.; Grand, E.; Wadouachi, A.; Postel, D.; Drelich, A.; Egles, C.; Pezron, I. Colloids Surf. B Biointerfaces, 2016, 145, 79-86.
[29]
Cserhati, T. Environ. Health Perspect., 1995, 103(4), 358-364.
[30]
Palermo, E.F.; Kuroda, K. Biomacromolecules, 2009, 10(6), 1416-1428.
[31]
Hoque, J.; Akkapeddi, P.; Yadav, V.; Manjunath, G.B.; Uppu, D.S.S.M.; Konai, M.M.; Yarlagadda, V.; Sanyal, K.; Haldar, J. ACS Appl. Mater. Interfaces, 2015, 7(3), 1804-1815.
[32]
Fronza, M.; Murillo, R.; Ślusarczyk, S.; Adams, M.; Hamburger, M.; Heinzmann, B.; Laufer, S.; Merfort, I. Bioorg. Med. Chem., 2011, 19(16), 4876-4881.
[33]
Pauly, D.; Worbs, S.; Kirchner, S.; Shatohina, O.; Dorner, M.B.; Dorner, B.G. PLoS One, 2012, 7(4), e35360.


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 16
ISSUE: 6
Year: 2019
Page: [478 - 484]
Pages: 7
DOI: 10.2174/1570178615666181023151308
Price: $65

Article Metrics

PDF: 21
HTML: 2

Special-new-year-discount