European Journal of Chemistry

Synthesis, antibacterial activities and phospholipid membrane interactions of novel dialkyl 2,2’-disulfanediyldibenzoates



Main Article Content

Sabina Jhaumeer Laulloo
Minu Gupta Bhowon
Matthew Akerman
Nausheen Joondan
Marie Jessika Momus

Abstract

A series of dialkyl 2,2’-disulfanediyldibenzoates with alkyl chain length C8 to C12 were synthesized and characterized by spectral studies. The structure of compound 3 was also confirmed by X-ray crystallography. The compounds were found to possess good antibacterial activity, especially with respect to Gram positive bacteria, and the activity was found to increase with concomitant increase in chain length. Binding studies of compound 3 with the synthetic phospholipid 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) showed that the compound interacts with biological membrane mainly via hydrophobic interactions.


icon graph This Abstract was viewed 1268 times | icon graph Article PDF downloaded 618 times icon graph Article CIF FILE downloaded 0 times

How to Cite
(1)
Laulloo, S. J.; Bhowon, M. G.; Akerman, M.; Joondan, N.; Momus, M. J. Synthesis, Antibacterial Activities and Phospholipid Membrane Interactions of Novel Dialkyl 2,2’-Disulfanediyldibenzoates. Eur. J. Chem. 2017, 8, 60-65.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Ceylan, M.; Gürdere, M. B.; Karaman, I.; Gezegen, H. Med. Chem. Res. 2011, 20, 109-115.
https://doi.org/10.1007/s00044-009-9279-4

[2]. Fletcher, J. M.; Huhues, R. A. Tetrahedron Lett. 2004, 45, 6999-7001.
https://doi.org/10.1016/j.tetlet.2004.08.002

[3]. Khan, K. M.; Taha, M.; Naz, F.; Khan, M.; Rahim, R.; Perveen, S. S.; Choudhary, I. M. Med. Chem. 2002, 2, 129-146.

[4]. Jhy-Jia, J.; Tsu-Chung, C.; Wen-Li, H.; Jinh-Min, H.; Ling-Yih, H. Chem. Pharm. Bull. 2003, 511, 1307-1310.

[5]. Vara Prasad, J. V. N.; Loo, J. A.; Boyer, F. E.; Stier, M. A.; Gogliotti, R. D.; Turner, W. J.; Harvey, P. J.; Kramer, M. R.; Mack, D. P.; Scholten, J. D.; Gracheck, S. J.; Domagala, J. M. Bioorg. Med. Chem. 1998, 6, 1707-1730.
https://doi.org/10.1016/S0968-0896(98)00118-7

[6]. Witrouw, M.; Balzarini, M. J.; Pannecouque, C.; Jhaumeer Laulloo, S.; ESTE, J. A.; Schols, D.; Cherepanov, P.; Scmit, J. C.; Debyser, Z.; Vandamme, A. M.; Desmyter, J.; Ramadas, S. R.; De Clercq, E. Antimicrob. Agents. Chemother. 1997, 41, 262-268.

[7]. Eshghi, H.; Rahimizadeh, M.; Zokaei, M.; Eshghi, S.; Faghihi, Z.; Tabasi, E.; Kihanyan, M. Eur. J. Chem. 2011, 2, 47-50.
https://doi.org/10.5155/eurjchem.2.1.47-50.260

[8]. Bonaccorsi, P.; Barattucci, A.; Papalia, T.; Criseo, G.; Faggio, C.; Romeo, O. J. Sulfur Chem. 2015, 36, 317-325.
https://doi.org/10.1080/17415993.2015.1024679

[9]. Bhowon, M. G.; Jhaumeer laulloo, S.; Soukhee, N.; Allibacus, A.; Shiboo, V. J. Coord. Chem. 2007, 60(12), 1335–1343.
https://doi.org/10.1080/00958970601110451

[10]. Jhaumeer Laulloo, S.; Bhowon, M. G.; Ravikumar, S.; Kalaiyarasi, A.; Raja, M.; Vijayakumar, V. Int. J. Med. Med. Sci. 2013, 5(4), 260-263.

[11]. Balgavy, P.; Devinsky, F. Adv. Colloid. Interface. Sci. 1996, 66, 23-63.
https://doi.org/10.1016/0001-8686(96)00295-3

[12]. Joondan, N.; Jhaumeer Laulloo, S.; Caumul, P. J. Surfactants. Deterg. 2015, 18, 1095-1104.
https://doi.org/10.1007/s11743-015-1720-8

[13]. Turos, E.; Revell, K. D.; Ramaraju, P.; Gergeres, D. A.; Greenhalgh, K.; Young, A.; Sathyanarayan, N.; Dickey, S.; Lim, D.; Alhamadsheh, M. M.; Reynolds, K. Bioorg. Med. Chem. 2008, 16, 6501-6508.
https://doi.org/10.1016/j.bmc.2008.05.032

[14]. Nyamato, G. S.; Ojwach, S. O.; Akerman, M. P. Dalton Trans. 2016, 45, 3407-3416.
https://doi.org/10.1039/C5DT04667J

[15]. Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA, 2012.

[16]. Sheldrick, G. M. Acta Cryst. 2015, C71, 3–8.

[17]. Farrugia, L. J. J. Appl. Cryst. 2012, 45, 849-854.
https://doi.org/10.1107/S0021889812029111

[18]. Joondan, N.; Caumul, P.; Jhaumeer Laulloo, S. J. Surfactants. Deterg. 2016. DOI: 10. 1007/s11743-016-1895-7.

[19]. Joondan, N.; Jhaumeer Laulloo, S.; Caumul, P. Microbiol. Res. 2014, 169, 675-685.
https://doi.org/10.1016/j.micres.2014.02.010

[20]. Bruno, I. J.; Cole, J. C.; Kessler, M.; Jie, L.; Motherwell, W. D. S.; Purkis, L. H.; Smith, B. R.; Taylor, R.; Cooper, R. I.; Harris, S. E.; Orpen, A. G. J. Chem. Inf. Comput. Sci. 2004, 44, 2133-2144.
https://doi.org/10.1021/ci049780b

[21]. Groom, C. R.; Bruno, I. J.; Lightfoot, M. P.; Ward, S. C. Acta Cryst. 2016, B72, 171-179.

[22]. Kucsman, A.; Kapovits, L. J. Mol. Struct. 1984, 125, 331 – 347.
https://doi.org/10.1016/0022-2860(84)85031-0

[23]. Ringer, A. L.; Seneko, A.; Sherrill, D. Protein Science, 2007, 16, 2216 – 2223.
https://doi.org/10.1110/ps.073002307

[24]. Daeffler, K. N. M.; Lester, H. A.; Dougherty, D. A. J. Am. Chem. Soc. 2012, 134, 14890 – 14896.
https://doi.org/10.1021/ja304560x

[25]. Pineiro, C.; Novo, M.; Al-Soufi, W. Adv. Colloid. Int. Sci. 2015, 215, 1-12.
https://doi.org/10.1016/j.cis.2014.10.010

[26]. Klevens, H. B. J. Am. Oil. Chem. Soc. 1953, 30, 74-80.
https://doi.org/10.1007/BF02635002

[27]. Lindstedt, M.; Allenmark, S.; Thompson, R. A.; Edebo, L. Antimicrob. Agents. Chemother. 1990, 34, 1949-1954.
https://doi.org/10.1128/AAC.34.10.1949

[28]. Campbell, N. 3rd ed, Benjamin Cummings Publishing, Redwood City, Calif, 1993.

[29]. Joondan, N.; Caumul, P.; Akerman, M.; Jhaumeer Laulloo, S. Bioorg. Chem. 2015, 58, 117-129.
https://doi.org/10.1016/j.bioorg.2015.01.001

Supporting Agencies

University of Mauritius, Reduit 80837, Mauritius
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).