European Journal of Chemistry 2015, 6(3), 325-336 | doi: https://doi.org/10.5155/eurjchem.6.3.325-336.1282 | Get rights and content






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Solvatochromic absorption and fluorescence studies of adenine, thymine and uracil thio-derived acyclonucleosides


Hassan Hasan Hammud (1) , Mohammad Hasan El-Dakdouki (2) , Nada Mohamd Sonji (3) , Kamal Hani Bouhadir (4,*)

(1) Department of Chemistry, Faculty of Science, King Faisal University, Al-Ahsa, 31982, Saudi Arabia
(2) Department of Chemistry, Faculty of Science, Beirut Arab University, Debbieh, 11-5020, Lebanon
(3) Department of Chemistry, Faculty of Science, Beirut Arab University, Debbieh, 11-5020, Lebanon
(4) Department of Chemistry, Faculty of Arts and Sciences, American University of Beirut, Beirut, 11-0236, Lebanon
(*) Corresponding Author

Received: 09 Jun 2015 | Revised: 08 Jul 2015 | Accepted: 15 Jul 2015 | Published: 30 Sep 2015 | Issue Date: September 2015

Abstract


Adenine, thymine and uracil thio-derived acyclonucleosides were synthesized and characterized by UV-Vis, FT-IR, 1H and 13C NMR spectroscopic techniques. The photophysical properties of the derivatives were evaluated in solvents with diverse polarities and at various pH values. The solvent dependent absorbance and emission spectral shifts were analysed using physical parameters of the selected solvents. The regression and correlation coefficients were calculated using multiple regression techniques. The fitting coefficients gave an estimate of the contribution of each interaction to the total spectral shift in various solutions. Multiple linear regression studies, Kamlet-Taft equation and stokes shift correlation with orientation polarizability provide valuable information concerning spectroscopic characteristics of the studied molecules.


Keywords


Absorption; Nucleobases; Fluorescence; Solvatochromism; Multiple regression analysis; Thio-derived acyclonucleosides

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DOI: 10.5155/eurjchem.6.3.325-336.1282

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Funding information


Kamal Shair Central Research Science Laboratory (KAS-CRSL); Lebanese National Research Council (LNCSR) and the University Research Board (URB) at the American University of Beirut, Lebanon

Citations

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[1]. Hassan H. Hammud, Mohammad H. El-Dakdouki, Nada Sonji, Ghassan Sonji, Kamal H. Bouhadir
Interactions of Some Divalent Metal Ions with Thymine and Uracil Thiosemicarbazide Derivatives
Nucleosides, Nucleotides and Nucleic Acids  35(5), 259, 2016
DOI: 10.1080/15257770.2016.1143558
/


[2]. Mira Diab El-Harakeh, Rachel Njeim, Ali Youssef, Natalie Youssef, Assaad A. Eid, Kamal H. Bouhadir
Novel triazine-based pyrimidines suppress glomerular mesangial cells proliferation and matrix protein accumulation through a ROS-dependent mechanism in the diabetic milieu
Bioorganic & Medicinal Chemistry Letters  29(13), 1580, 2019
DOI: 10.1016/j.bmcl.2019.04.052
/


References

[1]. Dinesh, S.; Shikha, G.; Bhavana, G.; Nidhi, S.; Dileep, S. J. Pharm. Sci. Innov. 2012, 1(2), 29-34.

[2]. Jain, K. S.; Chitre, T. S.; Miniyar, P. B.; Kathiravan, M. K.; Bendre, V. S.; Veer, V. S.; Shahane, S. R.; Shishoo, C. J. Curr. Sci. India 2006, 90(6), 793-803.

[3]. De Clercq, E.; Field, H. Brit. J. Pharmacol. 2006, 147(1), 1-11.
http://dx.doi.org/10.1038/sj.bjp.0706446

[4]. Barral, K.; Courcambeck, J.; Pepe, G.; Balzarini, J.; Neyts, J.; De Clercq, E.; Camplo, M. J. Med. Chem. 2005, 48(2), 450-456.
http://dx.doi.org/10.1021/jm0493966

[5]. Freeman, S.; Gardiner, J. M. Mol. Biotechnol. 1996, 5(2), 125-137.
http://dx.doi.org/10.1007/BF02789061

[6]. Arora, S.; Agarwal, S.; Singhal, S. Int. J. Pharm. Pharm. Sci. 2014, 6(9), 34-41.

[7]. Pandeya, S. N.; Sriram, D.; Nath, G.; DeClercq, E. Eur. J. Pharm. Sci. 1999, 9, 25-31.
http://dx.doi.org/10.1016/S0928-0987(99)00038-X

[8]. Reshma, J. N.; Avinash, S. D. Der Pharma Chemica 2013, 5(2), 45-49.

[9]. Singh, S. P.; Bahadur, S. Arch. Pharm. 1983, 316(10), 817–821.
http://dx.doi.org/10.1002/ardp.19833161002

[10]. Siwek, A.; Stefanska, J.; Dzitko, K.; Ruszczak, A. J. Mol. Model. 2012, 18(9), 4159-4170.
http://dx.doi.org/10.1007/s00894-012-1420-5

[11]. Thomas, A. M.; Naik, A. D.; Nethaji, M.; Chakravarty, A. R. Inorg. Chim. Acta 2004, 357, 2315-2323.
http://dx.doi.org/10.1016/j.ica.2004.01.031

[12]. Beraldo, H.; Gambino, D. Mini-Rev. Med. Chem. 2004, 4, 31-39.
http://dx.doi.org/10.2174/1389557043487484

[13]. Khatua, P. K.; Ghosh, S. K.; Bhattacharya, S. C. J. Oleo Sci. 2003, 52(7), 387-391.
http://dx.doi.org/10.5650/jos.52.387

[14]. Mehranpour, A. M.; Hashemnia, S. J. Chin. Chem. Soc-Taip. 2006, 53, 759-765.
http://dx.doi.org/10.1002/jccs.200600101

[15]. Daniels, M.; Hauswirth, W. Science 1971, 171, 675-677.
http://dx.doi.org/10.1126/science.171.3972.675

[16]. Serrano-Andres, L.; Merchan, M. J. Photoch. Photobio. C 2009, 10, 21-32.

[17]. Masternak, A.; Wenska, G.; Milecki, J.; Skalski, B.; Franzen, S. J. Phys. Chem. A 2005, 109, 759-766.
http://dx.doi.org/10.1021/jp047098e

[18]. Abdullah, Z.; Mohd Tahir, N.; Abas, M. R.; Aiyub, Z.; Low, B. K. Molecules 2004, 9(7), 520-526.
http://dx.doi.org/10.3390/90700520

[19]. Mogren, M.; Al-Farhan, K.; Hasanein, A. A. J. Saudi Chem. Soc. 2013, 17, 87-95.
http://dx.doi.org/10.1016/j.jscs.2011.11.009

[20]. Valentic, N.; Uscumlic, G. S.; Radojkovic-Velickovic, M. Indian J. Chem. B 2003, 42, 1137-1140.

[21]. Mata, G.; Luedtke, N. W. Org. Lett. 2013, 15(10), 2462-2465.
http://dx.doi.org/10.1021/ol400930s

[22]. Seferoglu, Z. Arkivoc 2009, 7, 42-57.

[23]. Okabe, T.; Tanigucbi, E.; Maekawa, K. J. Fac. Agr. Kyushu U. 1975, 20, 7-14.

[24]. Hamidian, H.; Zahedian, N.; Ghazanfari, D.; Fozooni, S. J. Spectrosc. 2013, 2013, 1-6.

[25]. Masoud, M. S.; Haggag, S. S.; El-Nahas, H. M.; Abd El-Hi, N. Acta Chim. Hung. 1993, 130(6), 783-804.

[26]. Toba, M.; Takeoka, Y.; Rikokawa, M. Synthetic Met. 2003, 135(136), 339-340.
http://dx.doi.org/10.1016/S0379-6779(02)00621-5

[27]. Lira, E. P.; Huffman, C. W. J. Org. Chem. 1966, 31, 2188-2191.
http://dx.doi.org/10.1021/jo01345a028

[28]. Zhang, Y. M.; Ding, Y.; Tang, W.; Luo, W.; Gu, M.; Lu, W.; Tang, J.; Zuo, J. P.; Nan, F. J. Bioorgan. Med. Chem. 2008, 16, 9212-9216.
http://dx.doi.org/10.1016/j.bmc.2008.09.017

[29]. Chung, D. J.; Matsuda, T. J. Ind. Eng. Chem. 1998, 4(4), 340-344.

[30]. Liu, X.; Zhang, L.; Tan, J. G.; Xu, H. H. Bioorgan. Med. Chem. 2013, 21, 4687-4697.
http://dx.doi.org/10.1016/j.bmc.2013.05.010

[31]. Kannappan, V.; Vidhya, P.; Sathyanarayanamoorthi, V. J. Mol. Liq. 2015, 207, 7-13.
http://dx.doi.org/10.1016/j.molliq.2015.03.012

[32]. Poritere, S.; Paegle, R.; Lidaks, M. Khim. Geterotsikl. Soedin. 1985, 1, 126-130.

[33]. Amberlang, J. C.; Johnson, T. B. J. Am. Chem. Soc. 1939, 61, 632-633.
http://dx.doi.org/10.1021/ja01872a024

[34]. Uher, M.; Berkes, D.; Lesko, J.; Floch, L. Collect. Czech. Chem. C 1983, 48(6), 1651-1658.
http://dx.doi.org/10.1135/cccc19831651

[35]. El-Zayat, W.; El-Sayed, W.; Abdel-Rahman, A. Z. Naturforsch. C 2009, 64, 6-10.

[36]. Kumar, S.; Koh, J.; Kim, H.; Gupta, M. K.; Dutta, P. K. Int. J. Biol. Macromol. 2012, 50, 493-502.
http://dx.doi.org/10.1016/j.ijbiomac.2012.01.015

[37]. Johnston, P.; Izgorodina, E. I.; Saito, K. Photochem. Photobio. S. 2012, 11, 1938-1951.
http://dx.doi.org/10.1039/c2pp25228g

[38]. Masoud, M. S.; Ali, A. E.; Shaker, M. A.; Abdul Ghani, M. Spectrochim. Acta A 2005, 61, 3102-3107.
http://dx.doi.org/10.1016/j.saa.2004.10.043

[39]. Masoud, M. S.; Ali, A. E.; Shaker, M. A.; Abdul Ghani, M. Spectrochim. Acta A 2004, 60, 3155-3159.
http://dx.doi.org/10.1016/j.saa.2004.02.030

[40]. David, G.; Hallam, H. E. Spectrochim. Acta A 1967, 23, 593-603.
http://dx.doi.org/10.1016/0584-8539(67)80316-7

[41]. McRae, E. G. J. Phys. Chem-US 1957, 61, 562-572.

[42]. Kirkwood, J. G. J. Chem. Phys. 1935, 3, 300-310.
http://dx.doi.org/10.1063/1.1749657

[43]. Masoud, M. S.; El‐Moniem Khalil, E. A.; Abou El Enein, S. A.; Kamel, H. M. Eur. J. Chem. 2011, 2(3), 420‐432.
http://dx.doi.org/10.5155/eurjchem.2.3.420-432.407

[44]. Costinela-Laura, G.; Ioan, P.; Ioan, B. Dyes Pigments 2008, 76(2), 455-462.
http://dx.doi.org/10.1016/j.dyepig.2006.10.001

[45]. Hammud, H. H.; Ghannoum, A. M.; Masoud, M. S. Spectrochim. Acta A 2006, 63(2), 255-265.
http://dx.doi.org/10.1016/j.saa.2005.04.020

[46]. Hammud, H. H.; Ghannoum, A. M.; Fares, F. A.; Abramian, L. K.; Bouhadir, K. H. J. Mol. Struct. 2008, 881, 11-20.
http://dx.doi.org/10.1016/j.molstruc.2007.08.026

[47]. Taft, R.W.; Kamlet, M.J. J. Am. Chem. Soc. 1976, 98, 2886-2894.
http://dx.doi.org/10.1021/ja00426a036

[48]. Eto, M.; Tajiri, O.; Nakagawa, H.; Harano, K. Tetrahedron1998, 54, 8009-8014.
http://dx.doi.org/10.1016/S0040-4020(98)00438-4

[49]. Nagachandra, K. H.; Mannekutla, J. R.; Amarayya, S. M.; Inamdar, S. R. Eur. J. Chem. 2012, 3 (2), 163‐171.
http://dx.doi.org/10.5155/eurjchem.3.2.163-171.538

[50]. Rusu, E.; Dorohoi, D. O.; Airinei, A. J. Mol. Struct. 2008, 887, 216-219.
http://dx.doi.org/10.1016/j.molstruc.2008.01.053

[51]. Masoud, M. S.; Shaker, M. A.; Ali, A. E.; Elasal, G. S. Spectrochim. Acta A 2011, 79, 538-547.
http://dx.doi.org/10.1016/j.saa.2011.03.029

[52]. Mataga, N.; Kaifu, Y.; Koizumi, M. B. Chem. Soc. Jpn. 1956, 29, 465-470.
http://dx.doi.org/10.1246/bcsj.29.465

[53]. Swaminathan, M.; Dogra, S. K. J. Am. Chem. Soc. 1983, 105, 6223-6228.
http://dx.doi.org/10.1021/ja00358a005

[54]. Hammud, H. H.; Bouhadir, K. H.; Masoud, M. S.; Ghannoum, A. M.; Assi, S. A. J. Solution Chem. 2008, 37, 895-917.
http://dx.doi.org/10.1007/s10953-008-9289-8

How to cite


Hammud, H.; El-Dakdouki, M.; Sonji, N.; Bouhadir, K. Eur. J. Chem. 2015, 6(3), 325-336. doi:10.5155/eurjchem.6.3.325-336.1282
Hammud, H.; El-Dakdouki, M.; Sonji, N.; Bouhadir, K. Solvatochromic absorption and fluorescence studies of adenine, thymine and uracil thio-derived acyclonucleosides. Eur. J. Chem. 2015, 6(3), 325-336. doi:10.5155/eurjchem.6.3.325-336.1282
Hammud, H., El-Dakdouki, M., Sonji, N., & Bouhadir, K. (2015). Solvatochromic absorption and fluorescence studies of adenine, thymine and uracil thio-derived acyclonucleosides. European Journal of Chemistry, 6(3), 325-336. doi:10.5155/eurjchem.6.3.325-336.1282
Hammud, Hassan, Mohammad Hasan El-Dakdouki, Nada Mohamd Sonji, & Kamal Hani Bouhadir. "Solvatochromic absorption and fluorescence studies of adenine, thymine and uracil thio-derived acyclonucleosides." European Journal of Chemistry [Online], 6.3 (2015): 325-336. Web. 27 May. 2020
Hammud, Hassan, El-Dakdouki, Mohammad, Sonji, Nada, AND Bouhadir, Kamal. "Solvatochromic absorption and fluorescence studies of adenine, thymine and uracil thio-derived acyclonucleosides" European Journal of Chemistry [Online], Volume 6 Number 3 (30 September 2015)

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