European Journal of Chemistry

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

Article Sidebar

PDF CIF FILE
Published: Mar 31, 2017
DOI: https://doi.org/10.5155/eurjchem.8.1.60-65.1540
Keywords:
Lipophilicity, Dithiosalicylic acid, Dithio-bis-benzoates, Antibacterial activity, Phospholipid binding, X-ray crystallography
Section
Research Article
Issue
Vol. 8 No. 1 (2017): March 2017
Dates
Received 2016-12-30
Accepted 2017-01-25
Published 2017-03-31


Main Article Content

Sabina Jhaumeer Laulloo
Department of Chemistry, Faculty of Science, University of Mauritius, Reduit 80837, Mauritius
Minu Gupta Bhowon
Department of Chemistry, Faculty of Science, University of Mauritius, Reduit 80837, Mauritius
Matthew Akerman
University of KwaZulu-Natal, Private Bag X01, Scottsville, Pietermaritzburg 3209, South Africaa
Nausheen Joondan
Department of Chemistry, Faculty of Science, University of Mauritius, Reduit 80837, Mauritius
Marie Jessika Momus
Department of Chemistry, Faculty of Science, University of Mauritius, Reduit 80837, Mauritius

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 1475 times | icon graph Article PDF downloaded 791 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
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe 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 © 2025 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).