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Antimicrobial and Drug Releasing Studies of Novel Acrylate Polymer based on Triazine
Corresponding Author(s) : A. Arun
Asian Journal of Chemistry,
Vol. 33 No. 11 (2021): Vol 33 Issue 11, 2021
Abstract
This work is focused on the synthesis and characterization of versatile acrylate polymer of chalcone based triazine for their antibacterial activity and cumulative drug release behaviour studies. The novel acrylate monomer 4-(3-(4-((4-(4-(3-(4-((7-chloroquinolin-4-yl)amino)-phenyl)-3-oxoprop-1-en-1-yl)phenoxy)-6-((4-nitrophenyl)amino)-1,3,5-triazin-2-yl)oxy)phenyl)-3-oxoprop-1-en-1-yl)phenylacrylate (SCP) is from novel chalcone and acryloyl chloride. Homo and copolymers of SCP were prepared using acrylic acid and hydroxyethyl acrylate. Physical characterization confirms the formation of the above compounds. Prepared drug molecules possess chalcone moiety as well as quinoline so it has the greater effect to inhibit the growth of the Gram-negative bacteria (15.63 ± 0.4 μg/mL) was confirmed by MIC method. The weight average molecular weight of the polymer is 10,000 g/mol. The polymer decomposes at 325 ºC. Drug releasing in vitro behaviour of the synthesized drug is controlled by the nature of comonomer, pH and the temperature.
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- M.S. Alajely, Front. Drug Chem. Clin. Res., 2, 1 (2019); https://doi.org/10.15761/FDCCR.1000119
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References
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T. Wang, N. Zhang, W. Bai and Y. Bao, Polym. Chem., 11, 3095 (2020); https://doi.org/10.1039/D0PY00336K
T. Endo, M. Yonekawa and A. Sudo, Polym. Int., 70, 1176 (2021); https://doi.org/10.1002/pi.6222
Y. Chang, Y.N. Kim, I. Noh and C. Kim, Macromol. Chem. Phys., 201, 1808 (2000); https://doi.org/10.1002/1521-3935(20000901)201:14<1808::AIDMACP1808>3.0.CO;2-K
J. Zhou, J. Wang, K. Jin, J. Sun and Q. Fang, Polymer, 102, 301 (2016); https://doi.org/10.1016/j.polymer.2016.09.027
P. Wen, X. Wang, B. Wang, B. Yuan, K. Zhou, L. Song, Y. Hu and R.K.K. Yuen, Polym. Degrad. Stab., 110, 165 (2014); https://doi.org/10.1016/j.polymdegradstab.2014.08.019
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R. Gomes and A. Bhaumik, RSC Adv., 6, 28047 (2016); https://doi.org/10.1039/C6RA01717G
M.X. Wu and Y.W. Yang, Chin. Chem. Lett., 28, 1135 (2017); https://doi.org/10.1016/j.cclet.2017.03.026
A. Liu, J. Zhang and X. Lv, Chin. J. Catal., 39, 1320 (2018); https://doi.org/10.1016/S1872-2067(18)63040-2
C.-H. Yu, C.-H. Huang and C.-S. Tan, Aerosol Air Qual. Res., 12, 745 (2012); https://doi.org/10.4209/aaqr.2012.05.0132
B. Lv, B. Guo, Z. Zhou and G. Jing, Environ. Sci. Technol., 49, 10728 (2015); https://doi.org/10.1021/acs.est.5b02356
J.-R. Li, J. Sculley and H.-C. Zhou, Chem. Rev., 112, 869 (2012); https://doi.org/10.1021/cr200190s
H.H. Al-Rasheed, S.Z. Mohammady, K. Dahlous, M.R.H. Siddiqui and A. El-Faham, J. Polym. Res., 27, 10 (2020); https://doi.org/10.1007/s10965-019-1961-8
J. Zhou, J. Wang, Y. Tao and L. Fang, ACS Sustainable Chem. Eng., 6, 5620 (2018); https://doi.org/10.1021/acssuschemeng.8b00655
J.W. Grate, K.F. Mo and M.D. Daily, Angew. Chem. Int. Ed., 55, 3925 (2016); https://doi.org/10.1002/anie.201509864
V.K. Daukshas, Y.Y. Ramanauskas, B. Udrenaite, A.B. Brukshtus, V.V. Lapinskas, R.S. Maskalyunas and M.K. Misyunaite, Pharm. Chem. J., 18, 471 (1984); https://doi.org/10.1007/BF00769801
P.D. Bremner and J.J. Meyer, Planta Med., 64, 777 (1998); https://doi.org/10.1055/s-2006-957585
S.F. Nielsen, T. Boesen, M. Larsen, K. Schønning and H. Kromann, Bioorg. Med. Chem., 12, 3047 (2004); https://doi.org/10.1016/j.bmc.2004.03.071
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M. Liu, P. Wilairat and M.-L. Go, J. Med. Chem., 44, 4443 (2001); https://doi.org/10.1021/jm0101747
L. Svetaz, A. Tapia, S.N. Lopez, R.L. Furlan, E. Petenatti, R. Pioli, G. Schmeda-Hirschmann and S.A. Zacchino, J. Agric. Food Chem., 52, 3297 (2004); https://doi.org/10.1021/jf035213x
Z. Nowakowska, Eur. J. Med. Chem., 42, 125 (2007); https://doi.org/10.1016/j.ejmech.2006.09.019
M.R. Ahmed, V.G. Sasttry and N. Bano, Rasayan J. Chem., 4, 289 (2004).
A. Arun, B.S.R. Reddy and M. Rajkumar, J. Bioact. Compat. Polym., 18, 219 (2003); https://doi.org/10.1177/0883911503035385
C.D. Ercegovich, R.L. Chrzanowski, H. Cole, N. Herendeen and S. Witkonton, Can. J. Microbiol., 19, 329 (1973); https://doi.org/10.1139/m73-055
J. Suresh, E. Vakees, S. Karthik, M. Kayalvizhi and A. Arun, Des. Monomers Polym., 17, 753 (2014); https://doi.org/10.1080/15685551.2014.918014
P. Uma, J. Suresh and S. Revathy, S. Karthik and A. Arun, J. Biomater. Sci. Polym. Ed., 26, 128 (2015); https://doi.org/10.1080/09205063.2014.985022
J. Suresh, E. Vakees, P. Uma, R. Selvaraj, A. Karthikeyan and A. Arun, Macromol. Symp., 362, 11 (2016); https://doi.org/10.1002/masy.201400231
J. Bolard, P. Legrand, F. Heitz and B. Cybulska, Biochemistry, 30, 5707 (1991); https://doi.org/10.1021/bi00237a011
A. Arun and B.S.R. Reddy, Biomaterials, 26, 1185 (2005); https://doi.org/10.1016/j.biomaterials.2004.04.023
T. Sharkawi, D. Leyni-Barbaz, N. Chikh and J.N. Mcmullen, J. Bioact. Compat. Polym., 20, 153 (2005); https://doi.org/10.1177/0883911505051661
A. Gallardo, C. Parejo and J. San Román, J. Control. Rel., 71, 127 (2001); https://doi.org/10.1016/S0168-3659(01)00212-7
C. Elvira, A. Gallardo, N. Lacroix, E. Schacht and J. San román, J. Mater. Sci. Mater. Med., 12, 535 (2001); https://doi.org/10.1023/A:1011223814666
S. Davaran, J. Hanaee and A. Khosravi, J. Control. Rel., 58, 279 (1999); https://doi.org/10.1016/S0168-3659(98)00167-9