European Journal of Chemistry

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



Main Article Content

Naglaa Salah El-Deen Mohamed
Ragab Mohamed AbuEl-Hamd

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.


icon graph This Abstract was viewed 1535 times | icon graph Article PDF downloaded 681 times

How to Cite
(1)
Mohamed, N. S. E.-D.; AbuEl-Hamd, R. M. Synthesis, Spectroscopic and Antimicrobial Studies of Some Novel Cyanine Dyes Based on Bis-Coumarin Heterocycles Derivatives. Eur. J. Chem. 2016, 7, 66-72.

Article Details

Share
Crossref - Scopus - Google - European PMC
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

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).