European Journal of Chemistry 2017, 8(1), 60-65 | doi: https://doi.org/10.5155/eurjchem.8.1.60-65.1540 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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


Sabina Jhaumeer Laulloo (1,*) , Minu Gupta Bhowon (2) , Matthew Akerman (3) , Nausheen Joondan (4) , Marie Jessika Momus (5)

(1) Department of Chemistry, Faculty of Science, University of Mauritius, Reduit 80837, Mauritius
(2) Department of Chemistry, Faculty of Science, University of Mauritius, Reduit 80837, Mauritius
(3) University of KwaZulu-Natal, Private Bag X01, Scottsville, Pietermaritzburg 3209, South Africaa
(4) Department of Chemistry, Faculty of Science, University of Mauritius, Reduit 80837, Mauritius
(5) Department of Chemistry, Faculty of Science, University of Mauritius, Reduit 80837, Mauritius
(*) Corresponding Author

Received: 30 Dec 2016 | Accepted: 25 Jan 2017 | Published: 31 Mar 2017 | Issue Date: March 2017

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.


Keywords


Lipophilicity; Dithiosalicylic acid; Dithio-bis-benzoates; Antibacterial activity; Phospholipid binding; X-ray crystallography

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.8.1.60-65.1540

Links for Article


| | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 468 times | PDF Article downloaded 188 times

Funding information


University of Mauritius, Reduit 80837, Mauritius

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 information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Laulloo, S.; Bhowon, M.; Akerman, M.; Joondan, N.; Momus, M. Eur. J. Chem. 2017, 8(1), 60-65. doi:10.5155/eurjchem.8.1.60-65.1540
Laulloo, S.; Bhowon, M.; Akerman, M.; Joondan, N.; Momus, M. Synthesis, antibacterial activities and phospholipid membrane interactions of novel dialkyl 2,2’-disulfanediyldibenzoates. Eur. J. Chem. 2017, 8(1), 60-65. doi:10.5155/eurjchem.8.1.60-65.1540
Laulloo, S., Bhowon, M., Akerman, M., Joondan, N., & Momus, M. (2017). Synthesis, antibacterial activities and phospholipid membrane interactions of novel dialkyl 2,2’-disulfanediyldibenzoates. European Journal of Chemistry, 8(1), 60-65. doi:10.5155/eurjchem.8.1.60-65.1540
Laulloo, Sabina, Minu Gupta Bhowon, Matthew Akerman, Nausheen Joondan, & Marie Jessika Momus. "Synthesis, antibacterial activities and phospholipid membrane interactions of novel dialkyl 2,2’-disulfanediyldibenzoates." European Journal of Chemistry [Online], 8.1 (2017): 60-65. Web. 29 Feb. 2020
Laulloo, Sabina, Bhowon, Minu, Akerman, Matthew, Joondan, Nausheen, AND Momus, Marie. "Synthesis, antibacterial activities and phospholipid membrane interactions of novel dialkyl 2,2’-disulfanediyldibenzoates" European Journal of Chemistry [Online], Volume 8 Number 1 (31 March 2017)

DOI Link: https://doi.org/10.5155/eurjchem.8.1.60-65.1540

| | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2017, 8(1), 60-65 | doi: https://doi.org/10.5155/eurjchem.8.1.60-65.1540 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort