European Journal of Chemistry 2016, 7(1), 66-72. doi:10.5155/eurjchem.7.1.66-72.1319

Synthesis, spectroscopic and antimicrobial studies of some novel cyanine dyes based on bis-coumarin heterocycles derivatives


Naglaa Salah El-Deen Mohamed (1,*) , Ragab Mohamed AbuEl-Hamd (2)

(1) Department of Chemistry, Faculty of Science and Arts, Najran University, Najran, 11114, Kingdom Saudi Arabia
(2) Department of Chemistry, Faculty of Science, Aswan University, Aswan, 81528, Egypt
(*) Corresponding Author

Received: 12 Sep 2015, Accepted: 29 Nov 2015, Published: 31 Mar 2016

Abstract


Novel symmetrical and unsymmetrical cyanine dyes, incorporating merocyanine monomethine like, pentamethine cyanine, monomethine-meso-substituted-pentamethine and mono-5[2(4)]-methine cyanine dye have been prepared through the synthesis of new starting compound derivatives named as 1,3-bis-(2-oxo-2H-chromen-3-yl) propane-1,3-dione and (3-oxo1,3-bis(2-oxo-2H-chromen-3-yl)prop-1-enyloxy) copper, cobalt and nickel chloride salt complexes. Structure determination of the new compounds has been characterized on the basis of elemental analysis, IR, 1H NMR and MS spectra. Structure photosensitization relationship of new dyes have been discussed on the basis of their spectral behavior as criteria of photosensitizing effect through the UV visible-absorption spectra of all synthesized dyes which investigated in 95% ethanol. Antimicrobial properties of some selected cyanine dyes have been investigated against Streptococcus sp, Staphylococcus sp, Salmonella sp. and Shigella sp.


Keywords


Absorption; Merocyanine; Metal complex; Photosensitization; Antimicrobial activity; Bis-coumarin-β-dicarbonyl

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.7.1.66-72.1319

Article Metrics


This Abstract was viewed 610 times | PDF Article downloaded 220 times

References

[1]. Denisov, K.; Uzhinov, B. Chem. Heterocycl. Compd. (Engl. Transl.) 1980, 16, 553-564.

[2]. Zhanna, A.; Vladimir, A.; Lyubov, V.; Evgeniya, O.; Sergei, G. Mendeleev. Commun. 2013, 23, 212-214.
http://dx.doi.org/10.1016/j.mencom.2013.07.011

[3]. Padhye, R.; Varadarajan, S.; Deshpande, V. Spectrosc. Let. 1984, 17, 369-376.
http://dx.doi.org/10.1080/00387018408062695

[4]. Jianhong, C.; Weimin, L.; Bingjiang, Z.; Guangle, N.; Hongyan, Z.; Jiasheng, W.; Ying, W.; Weigang, J.; Pengfei, W. J. Org. Chem. 2013, 78, 6121-6130.
http://dx.doi.org/10.1021/jo400783x

[5]. Kovalska, B.; Volkova, D.; Manaev, V.; Losytsky, Y.; Okhrimenko, N.; Traven, F.; Yarmoluk, S. Dyes Pigments 2010, 84, 159-164.
http://dx.doi.org/10.1016/j.dyepig.2009.07.009

[6]. Yuan, L.; Lin, W. J. Chem. Commun. 2010, 46, 7930-7932.
http://dx.doi.org/10.1039/c0cc02390f

[7]. Fujii, K.; Iyi, N.; Hashizume, H.; Shimomura, S.; Ando, T. Chem. Mater. 2009, 21, 1179-1181.
http://dx.doi.org/10.1021/cm803315h

[8]. Bethea, D.; Fullmer, B.; Syed, S.; Seltzer, G.; Tiano, J.; Rischko, C.; Gillespie, L.; Brown, D.; Gasparro, P. J. Dermatol. Sci. 1999, 19, 78-88.
http://dx.doi.org/10.1016/S0923-1811(98)00064-4

[9]. Hora, M. E.; Miranda, A.; Olivenia, C. M.; Severino, D.; Nicodem, E. J. Photochem. Photobiol. A. Chem. 2001, 146, 75- 81.
http://dx.doi.org/10.1016/S1010-6030(01)00552-4

[10]. Traven, F.; Podkhalyuzina, Y.; Kanevskii, S. Chem. Heterocycl. Compd. (Engl. Transl.) 2003, 39, 866-871.
http://dx.doi.org/10.1023/A:1026186002637

[11]. Zipper, H.; Brunner, H.; Bernhagen, J.; Vitzthum, F. Nucl. Acids Res. 2004, 32, 103-110.
http://dx.doi.org/10.1093/nar/gnh101

[12]. Bethge, L.; Jarikote, V.; Seitz, O. Bioorg. Med. Chem. 2008, 16, 114-125.
http://dx.doi.org/10.1016/j.bmc.2006.12.044

[13]. Masamoto Y. Yakugaku Zasshi 2001, 121(1), 97-103.
http://dx.doi.org/10.1248/yakushi.121.97

[14]. Bryantseva, N.; Sokolova, I.; Tsyrenzhapova, A.; Selivanov, N.; Khilya, V.; Garazd, Y. J. Appl. Spect. 2008, 75, 700-705.
http://dx.doi.org/10.1007/s10812-008-9100-z

[15]. Zhan, W.; Hua, J.; Jin, Y.; Teng, X.; Tian, H. Res. n Chem. Inter. 2008, 34, 229-239.

[16]. Watanabe, K.; Nishimura, Y.; Oka.; T.; Nomoto, T.; Kon, T.; Shintou, T.; Hirano, M.; Shimada, Y.; Umemoto, N.; Kuroyanagi, J.; Wang, Z.; Zhang, Z.; Nishimura, N.; Miyazaki, T.; Imamura, T.; Tanaka, T. BMC. Neuroscience 2010, 11, 116-127.
http://dx.doi.org/10.1186/1471-2202-11-116

[17]. Hoult, R.; Paya, M. Gen. Pharmacol. 1996, 27, 713-722.
http://dx.doi.org/10.1016/0306-3623(95)02112-4

[18]. Wu, L.; Wang, X.; Xu, W.; Farzaneh, F.; Xu, R. Curr. Med. Chem. 2009, 16, 4236- 4260.
http://dx.doi.org/10.2174/092986709789578187

[19]. Cottiglia, F.; Loy, G.; Garau, D.; Floris, C.; Casu, M.; Pompei, R.; Bonsignore, L. Phytomedicine 2001, 8, 302-305.
http://dx.doi.org/10.1078/0944-7113-00036

[20]. Manolov, I.; Kostova, I.; Konstantinov, S.; Karaivanova, M. Eur. J. Med. Chem. 1999, 34, 853-858.
http://dx.doi.org/10.1016/S0223-5234(99)00207-X

[21]. Garcia-Argaez, A. N.; RamírezApan, TO.; Parra Delgado, H.; Velazquez, A. N.; Martinez-Vazquez, M. Planta. Medica. 2000, 66, 279-281.

[22]. Silvan, A.; Abad, M.; Bermejo, P.; Sollhuber, M.; Villar, A. J . Nat. Prod. 1996, 59, 1183-1185.
http://dx.doi.org/10.1021/np960422f

[23]. Kawaii, S.; Tomono, Y.; Ogawa, K.; Sugiura, M.; Yano, M.; Yoshizawa, Y.; Ito, C.; Furukawa, H. Anticancer Res. 2001, 21, 1905- 1911.

[24]. Sanghyun, L.; Dong-Sun, S.; Ju Sun, K.; Ki-Bong, O.; Sam Sik, K. Arch. Pharmacal. Res. 2003, 26, 449-452.

[25]. Spino, C.; Dodier, M.; Sotheeswaran, S. Bioorg. Med. Chem. Lett. 1998, 8, 3475-3478.
http://dx.doi.org/10.1016/S0960-894X(98)00628-3

[26]. Sardari, S.; Mori, Y.; Horita, K.; Micetich, R. G.; Nishibe, S.; Daneshtalab, M. Bioorg. Med. Chem. 1999, 7, 1933-1940.
http://dx.doi.org/10.1016/S0968-0896(99)00138-8

[27]. Kostova, I. Mini. Rev. Med. Chem. 2006, 6, 365-374.
http://dx.doi.org/10.2174/138955706776361457

[28]. Yu, J.; Wang, L.; Walzem, R.; L.; Miller, E.; G.; Pike, L.; M.; Patil, B. S. J. Agricul. Food Chem. 2005, 53, 2009-2014.
http://dx.doi.org/10.1021/jf0484632

[29]. Kostova, I.; Bhatia, S.; Grigorov, P. Curr. Med. Chem. 2011, 18, 3929-3951.
http://dx.doi.org/10.2174/092986711803414395

[30]. Gursoy, A.; Karali, N. Turk. J. Chem. 2003, 27, 545 - 551.

[31]. Abd-El-Aal, R. M.; Koraiem, A. I. M. Dyes Pigments 2002, 54, 121-129.
http://dx.doi.org/10.1016/S0143-7208(02)00034-7

[32]. Nakamoto, K.; Martell, A. J. Chem. Phys. 1960, 32, 588- 597.
http://dx.doi.org/10.1063/1.1730741

[33]. Nakamoto, K.; Mcarthy, J.; Ruby, A.; Martell, A. J. Am. Chem. Soc. 1961, 83, 4528-4532.
http://dx.doi.org/10.1021/ja01483a009

[34]. Nakamoto, K.; Moriomoto, Y.; Martell, A. J. Phys. Chem. 1962, 66, 346-348.
http://dx.doi.org/10.1021/j100808a036

[35]. Abd El-Aal, R. M.; Koraiem, A. I. M.; Salah El-Deen, N. Coloration Tech. 2005, 121, 228-236.
http://dx.doi.org/10.1111/j.1478-4408.2005.tb00278.x

[36]. Abd El-Aal, R. M.; Koraiem, A. I. M.; El-Deen, N. S. Dyes Pigments 2004, 63, 301-314.
http://dx.doi.org/10.1016/j.dyepig.2004.03.008

[37]. Gomaa, M. M.; El-Deen, N. S.; El-Kanzi, N. A. Eur. J. Chem. 2012, 3, 461-467.
http://dx.doi.org/10.5155/eurjchem.3.4.461-467.699

[38]. Koraiem, A. I. M.; Abd El-Aal, R. M.; Salah El-Deen, N. M. Dyes Pigments 2006, 68, 235- 242.
http://dx.doi.org/10.1016/j.dyepig.2005.01.007

[39]. Abd El-Aal, R. M.; Koraiem, A. I. M. J. Chin. Chem. Soc. 2000, 47, 389-395.
http://dx.doi.org/10.1002/jccs.200000052


How to cite


Mohamed, N.; AbuEl-Hamd, R. Eur. J. Chem. 2016, 7(1), 66-72. doi:10.5155/eurjchem.7.1.66-72.1319
Mohamed, N.; AbuEl-Hamd, R. Synthesis, spectroscopic and antimicrobial studies of some novel cyanine dyes based on bis-coumarin heterocycles derivatives. Eur. J. Chem. 2016, 7(1), 66-72. doi:10.5155/eurjchem.7.1.66-72.1319
Mohamed, N., & AbuEl-Hamd, R. (2016). Synthesis, spectroscopic and antimicrobial studies of some novel cyanine dyes based on bis-coumarin heterocycles derivatives. European Journal of Chemistry, 7(1), 66-72. doi:10.5155/eurjchem.7.1.66-72.1319
Mohamed, Naglaa, & Ragab Mohamed AbuEl-Hamd. "Synthesis, spectroscopic and antimicrobial studies of some novel cyanine dyes based on bis-coumarin heterocycles derivatives." European Journal of Chemistry [Online], 7.1 (2016): 66-72. Web. 21 Oct. 2019
Mohamed, Naglaa, AND AbuEl-Hamd, Ragab. "Synthesis, spectroscopic and antimicrobial studies of some novel cyanine dyes based on bis-coumarin heterocycles derivatives" European Journal of Chemistry [Online], Volume 7 Number 1 (31 March 2016)

DOI Link: https://doi.org/10.5155/eurjchem.7.1.66-72.1319

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.