Copyright (c) 2021 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and in vitro Antimicrobial, Anticancer Activity of Random Copolyester using Orcinol
Corresponding Author(s) : T. Sivaramakrishnan
Asian Journal of Chemistry,
Vol. 33 No. 9 (2021): Vol 33 Issue 9, 2021
Abstract
In present study, a novel random copolyester i.e. poly(3-oxy-5-methylphenyl-4-oxynaphthal-1-yl)isophthalate (PONI) was synthesized through solution polycondensation methodology involving orcinol, 1,4-naphthalene diol and isophthaloyl chloride and its solubility in common solvents along with viscosity measurements were performed. The structure of the repeat units in the polyester chain were ascertained based on the spectral characterization of UV-visible, FTIR, 1H & 13C NMR techniques. Thermal analysis of the copolyester were performed by TGA and DSC studies. The activation energy for thermal decomposition of polyester was estimated by well-known kinetic methods. The surface morphology and crystalline nature of the polymer were explored by employing SEM and WAXD methods. The antimicrobial efficacy of copolyester was assessed through well-diffusion method using a Gram-positive and a Gram-negative bacteria. The in vitro cytotoxicity of the polyester prepared was verified against HeLa cell line using MTT assay.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- V. Tserki, P. Matzinos, E. Pavlidou, D. Vachliotis and C. Panayiotou, Polym. Degrad. Stab., 91, 367 (2006); https://doi.org/10.1016/j.polymdegradstab.2005.04.035
- R.J. Müller, I. Kleeberg and W.D. Deckwer, J. Biotechnol., 86, 87 (2001); https://doi.org/10.1016/S0168-1656(00)00407-7
- C.-P. Yang, Y. Oishi, M.-A. Kakimoto and Y. Imai, J. Polym. Sci. A Polym. Chem., 28, 1353 (1990); https://doi.org/10.1002/pola.1990.080280604
- Y. Wu, J. Hu, C. Feng, G. Chen and J. Yang, Mater. Des., 172, 107772 (2019); https://doi.org/10.1016/j.matdes.2019.107772
- J.C. Morales-Huerta, A.M. Ilarduya and S. Muñoz-Guerra, Polymers, 10, 483 (2018); https://doi.org/10.3390/polym10050483
- J. Ubach, A.M. de Ilarduya, R. Quintana, A. Alla, E. Rudé and S. MuñozGuerra, J. Appl. Polym. Sci., 115, 1823 (2010); https://doi.org/10.1002/app.31308
- H.E. Edling, H. Liu, H. Sun, R.J. Mondschein, D.A. Schiraldi, T.E. Long and S.R. Turner, Polymer, 135, 120 (2018); https://doi.org/10.1016/j.polymer.2017.12.004
- P.K. Bhowmik, E.D. Atkins, R.W. Lenz and H. Han, Macromolecules, 29, 3778 (1996); https://doi.org/10.1021/ma951809c
- M. Bagheri, K. Didehban, Z. Rezvani and A. Akbar Entezami, Eur. Polym. J., 40, 865 (2004); https://doi.org/10.1016/j.eurpolymj.2003.11.026
- R.D. Shingte, D. Chatterjee, B.V. Tawade, B. Shrimant and P.P. Wadgaonkar, J. Macromole. Sci. Part A, 56, 136 (2019); https://doi.org/10.1080/10601325.2018.1549950
- S. Quattrosoldi, R. Androsch, A. Janke, M. Soccio and N. Lotti, Polymers, 12, 235 (2020); https://doi.org/10.3390/polym12010235
- G. Totaro, L. Sisti, N.B. Cionci, G.A. Martinez, D. Di Gioia and A. Celli, Polym. Test., 90, 106719 (2020); https://doi.org/10.1016/j.polymertesting.2020.106719
- W. Duan, X. Li, Y. Shen, K. Yang and H. Zhang, E-Polymers, 21, 027 (2020); https://doi.org/10.1515/epoly-2021-0004
- G.P. Karayannidis, I.D. Sideridou, D.N. Zamboulis, D.N. Bikiaris and A.J. Sakalis, J. Appl. Polym. Sci., 78, 200 (2000); https://doi.org/10.1002/1097-4628(20001003)78:1<200::AIDAPP240>3.0.CO;2-R
- S.H. Hsiao and H.W. Chiang, Eur. Polym. J., 40, 1691 (2004); https://doi.org/10.1016/j.eurpolymj.2004.03.006
- H.W. Schmidt and D. Guo, Macromol. Chem. Phys., 189, 2029 (1988); https://doi.org/10.1002/macp.1988.021890906
- M.I. Rais, S.A. Ali and D.R. Jonathan, Asian J. Chem., 30, 1675 (2018); https://doi.org/10.14233/ajchem.2018.21324
- S.S. Nagane, S.S. Kuhire, U.A. Jadhav, S.A. Dhanmane and P.P. Wadgaonkar, J. Polym. Sci. A Polym. Chem., 57, 630 (2019); https://doi.org/10.1002/pola.29303
- B. Tamami, H. Yeganeh and G. Ali Kohmareh, Eur. Polym. J., 40, 1651 (2004); https://doi.org/10.1016/j.eurpolymj.2004.04.014
- L. Zhu, C.L. Wang, X.C. Mao, Z.Z. Huang and S.R. Sheng, High Perform. Polym., 29, 1090 (2017); https://doi.org/10.1177/0954008316669571
- R. Kotek, K. Pang, B. Schmidt and A. Tonelli, J. Polym. Sci., B, Polym. Phys., 42, 4247 (2004); https://doi.org/10.1002/polb.20284
- D.J. Liaw, B.Y. Liaw, J.J. Hsu and Y.C. Cheng, J. Polym. Sci. A Polym. Chem., 38, 4451 (2000); https://doi.org/10.1002/1099-0518(20001215)38:24<4451::AIDPOLA140>3.0.CO;2-Q
- S.S. Vibhute, M.D. Joshi, P.P. Wadgaonkar, A.S. Patil and N.N. Maldar, J. Polym. Sci. A Polym. Chem., 35, 3227 (1997); https://doi.org/10.1002/(SICI)1099-0518(19971115)35:15<3227:: AID-POLA15>3.0.CO;2-D
- H.J. Jeong, M.A. Kakimoto and Y. Imai, J. Polym. Sci. A Polym. Chem., 29, 1293 (1991); https://doi.org/10.1002/pola.1991.080290908
- G. Deepa, R. Balamurugan and P. Kannan, J. Mol. Struct., 963, 219 (2010); https://doi.org/10.1016/j.molstruc.2009.10.038
- S.J. Chung, K.K. Kim and J.I. Jin, Polymer, 40, 1943 (1999); https://doi.org/10.1016/S0032-3861(98)00420-0
- E. Bucio, J.C.I. Lara-Estevez, F.A. Ruiz-Trevino and A. Acosta-Huerta, Polym. Bull., 56, 163 (2006); https://doi.org/10.1007/s00289-005-0487-x
- S.H. Hsiao and H.Y. Chang, J. Polym. Res., 2, 99 (1995); https://doi.org/10.1007/BF01493209
- L. Sun, L. Huang, X. Wang, H. Hu, J. Guo, R. Zhu and S. He, Polymers, 12, 1733 (2020); https://doi.org/10.3390/polym12081733
- S. Zaidi, M.J. Soares, A. Bougarech, S. Thiyagarajan, N. Guigo, S. Abid, M. Abid, A.J.D. Silvestre and A.F. Sousa, Eur. Polym. J., 150, 110413 (2021); https://doi.org/10.1016/j.eurpolymj.2021.110413
- M.I. Loría-Bastarrachea, H. Vázquez-Torres and M.D.J. Aguilar-Vega, J. Appl. Polym. Sci., 86, 2515 (2002); https://doi.org/10.1002/app.11033
- A. Subramani, K.M. Mustaque and T.K. Shabeer, Asian J. Chem., 29, 1168 (2017); https://doi.org/10.14233/ajchem.2017.20547
- X. Ma, H. Niu, W. Cai, T. Xiao, C. Wang, X. Bai, Y. Zhang and W. Wang, React. Funct. Polym., 108, 63 (2016); https://doi.org/10.1016/j.reactfunctpolym.2016.05.005
- Y. Nakayama, W. Yagumo, R. Tanaka, T. Shiono, K. Inumaru, C. Tsutsumi, N. Kawasaki, N. Yamano and A. Nakayama, Polym. Degrad. Stabil., 174, 109095 (2020); https://doi.org/10.1016/j.polymdegradstab.2020.109095
- M.C. Cardeña-Vazquez, M. Aguilar-Vega and C. Carrera-Figueiras, High Perform. Polym., 22, 184 (2010); https://doi.org/10.1177/0954008308101197
- Z. Ping, W. Linbo and L. Bo-Geng, Polym. Degrad. Stab., 94, 1261 (2009); https://doi.org/10.1016/j.polymdegradstab.2009.04.015
- T. Kijchavengkul, R. Auras and M. Rubino, Polym. Test., 27, 55 (2008); https://doi.org/10.1016/j.polymertesting.2007.08.007
- K.H. Paek and S.G. Im, Green Chem., 22, 4570 (2020); https://doi.org/10.1039/D0GC01549K
- D. Wei, J. Hua and Z. Wang, J. Appl. Polym. Sci., 131, (2014); https://doi.org/10.1002/app.40986
- S.H. Hsiao and J.H. Chiou, Polym. J., 33, 95 (2001); https://doi.org/10.1295/polymj.33.95
- S.G. Charati, A.Y. Houde, S.S. Kulkarni and M.G. Kulkarni, J. Polym. Sci., B Polym. Phys., 29, 921 (1991); https://doi.org/10.1002/polb.1991.090290803
- K.I. Aly, Polym. Int., 47, 483 (1998); https://doi.org/10.1002/(SICI)1097-0126(199812)47:4<483::AIDPI91>3.0.CO;2-F
- B. Kalpana and R. Nanthini, Asian J. Chem., 31, 2341 (2019); https://doi.org/10.14233/ajchem.2019.21997
- M.N. Kim, B.Y. Lee, I.M. Lee, H.S. Lee and J.S. Yoon, J. Environ. Sci. Health Part A Tox. Hazard. Subst. Environ. Eng., 36, 447 (2001); https://doi.org/10.1081/ESE-100103475
- K.I. Aly, M.A. Abdel-Rahman and M.M. Qutai, J. Polym. Res., 25, 185 (2018); https://doi.org/10.1007/s10965-018-1579-2
- C. Hamciuc, T. Vlad-Bubulac, O. Petreus and G. Lisa, Eur. Polym. J., 43, 980 (2007); https://doi.org/10.1016/j.eurpolymj.2006.12.018
- L. Lakshmi, Asian J. Chem., 22, 5344 (2010).
- K. Chrissafis, K.M. Paraskevopoulos and D.N. Bikiaris, Polym. Degrad. Stab., 91, 60 (2006); https://doi.org/10.1016/j.polymdegradstab.2005.04.028
References
V. Tserki, P. Matzinos, E. Pavlidou, D. Vachliotis and C. Panayiotou, Polym. Degrad. Stab., 91, 367 (2006); https://doi.org/10.1016/j.polymdegradstab.2005.04.035
R.J. Müller, I. Kleeberg and W.D. Deckwer, J. Biotechnol., 86, 87 (2001); https://doi.org/10.1016/S0168-1656(00)00407-7
C.-P. Yang, Y. Oishi, M.-A. Kakimoto and Y. Imai, J. Polym. Sci. A Polym. Chem., 28, 1353 (1990); https://doi.org/10.1002/pola.1990.080280604
Y. Wu, J. Hu, C. Feng, G. Chen and J. Yang, Mater. Des., 172, 107772 (2019); https://doi.org/10.1016/j.matdes.2019.107772
J.C. Morales-Huerta, A.M. Ilarduya and S. Muñoz-Guerra, Polymers, 10, 483 (2018); https://doi.org/10.3390/polym10050483
J. Ubach, A.M. de Ilarduya, R. Quintana, A. Alla, E. Rudé and S. MuñozGuerra, J. Appl. Polym. Sci., 115, 1823 (2010); https://doi.org/10.1002/app.31308
H.E. Edling, H. Liu, H. Sun, R.J. Mondschein, D.A. Schiraldi, T.E. Long and S.R. Turner, Polymer, 135, 120 (2018); https://doi.org/10.1016/j.polymer.2017.12.004
P.K. Bhowmik, E.D. Atkins, R.W. Lenz and H. Han, Macromolecules, 29, 3778 (1996); https://doi.org/10.1021/ma951809c
M. Bagheri, K. Didehban, Z. Rezvani and A. Akbar Entezami, Eur. Polym. J., 40, 865 (2004); https://doi.org/10.1016/j.eurpolymj.2003.11.026
R.D. Shingte, D. Chatterjee, B.V. Tawade, B. Shrimant and P.P. Wadgaonkar, J. Macromole. Sci. Part A, 56, 136 (2019); https://doi.org/10.1080/10601325.2018.1549950
S. Quattrosoldi, R. Androsch, A. Janke, M. Soccio and N. Lotti, Polymers, 12, 235 (2020); https://doi.org/10.3390/polym12010235
G. Totaro, L. Sisti, N.B. Cionci, G.A. Martinez, D. Di Gioia and A. Celli, Polym. Test., 90, 106719 (2020); https://doi.org/10.1016/j.polymertesting.2020.106719
W. Duan, X. Li, Y. Shen, K. Yang and H. Zhang, E-Polymers, 21, 027 (2020); https://doi.org/10.1515/epoly-2021-0004
G.P. Karayannidis, I.D. Sideridou, D.N. Zamboulis, D.N. Bikiaris and A.J. Sakalis, J. Appl. Polym. Sci., 78, 200 (2000); https://doi.org/10.1002/1097-4628(20001003)78:1<200::AIDAPP240>3.0.CO;2-R
S.H. Hsiao and H.W. Chiang, Eur. Polym. J., 40, 1691 (2004); https://doi.org/10.1016/j.eurpolymj.2004.03.006
H.W. Schmidt and D. Guo, Macromol. Chem. Phys., 189, 2029 (1988); https://doi.org/10.1002/macp.1988.021890906
M.I. Rais, S.A. Ali and D.R. Jonathan, Asian J. Chem., 30, 1675 (2018); https://doi.org/10.14233/ajchem.2018.21324
S.S. Nagane, S.S. Kuhire, U.A. Jadhav, S.A. Dhanmane and P.P. Wadgaonkar, J. Polym. Sci. A Polym. Chem., 57, 630 (2019); https://doi.org/10.1002/pola.29303
B. Tamami, H. Yeganeh and G. Ali Kohmareh, Eur. Polym. J., 40, 1651 (2004); https://doi.org/10.1016/j.eurpolymj.2004.04.014
L. Zhu, C.L. Wang, X.C. Mao, Z.Z. Huang and S.R. Sheng, High Perform. Polym., 29, 1090 (2017); https://doi.org/10.1177/0954008316669571
R. Kotek, K. Pang, B. Schmidt and A. Tonelli, J. Polym. Sci., B, Polym. Phys., 42, 4247 (2004); https://doi.org/10.1002/polb.20284
D.J. Liaw, B.Y. Liaw, J.J. Hsu and Y.C. Cheng, J. Polym. Sci. A Polym. Chem., 38, 4451 (2000); https://doi.org/10.1002/1099-0518(20001215)38:24<4451::AIDPOLA140>3.0.CO;2-Q
S.S. Vibhute, M.D. Joshi, P.P. Wadgaonkar, A.S. Patil and N.N. Maldar, J. Polym. Sci. A Polym. Chem., 35, 3227 (1997); https://doi.org/10.1002/(SICI)1099-0518(19971115)35:15<3227:: AID-POLA15>3.0.CO;2-D
H.J. Jeong, M.A. Kakimoto and Y. Imai, J. Polym. Sci. A Polym. Chem., 29, 1293 (1991); https://doi.org/10.1002/pola.1991.080290908
G. Deepa, R. Balamurugan and P. Kannan, J. Mol. Struct., 963, 219 (2010); https://doi.org/10.1016/j.molstruc.2009.10.038
S.J. Chung, K.K. Kim and J.I. Jin, Polymer, 40, 1943 (1999); https://doi.org/10.1016/S0032-3861(98)00420-0
E. Bucio, J.C.I. Lara-Estevez, F.A. Ruiz-Trevino and A. Acosta-Huerta, Polym. Bull., 56, 163 (2006); https://doi.org/10.1007/s00289-005-0487-x
S.H. Hsiao and H.Y. Chang, J. Polym. Res., 2, 99 (1995); https://doi.org/10.1007/BF01493209
L. Sun, L. Huang, X. Wang, H. Hu, J. Guo, R. Zhu and S. He, Polymers, 12, 1733 (2020); https://doi.org/10.3390/polym12081733
S. Zaidi, M.J. Soares, A. Bougarech, S. Thiyagarajan, N. Guigo, S. Abid, M. Abid, A.J.D. Silvestre and A.F. Sousa, Eur. Polym. J., 150, 110413 (2021); https://doi.org/10.1016/j.eurpolymj.2021.110413
M.I. Loría-Bastarrachea, H. Vázquez-Torres and M.D.J. Aguilar-Vega, J. Appl. Polym. Sci., 86, 2515 (2002); https://doi.org/10.1002/app.11033
A. Subramani, K.M. Mustaque and T.K. Shabeer, Asian J. Chem., 29, 1168 (2017); https://doi.org/10.14233/ajchem.2017.20547
X. Ma, H. Niu, W. Cai, T. Xiao, C. Wang, X. Bai, Y. Zhang and W. Wang, React. Funct. Polym., 108, 63 (2016); https://doi.org/10.1016/j.reactfunctpolym.2016.05.005
Y. Nakayama, W. Yagumo, R. Tanaka, T. Shiono, K. Inumaru, C. Tsutsumi, N. Kawasaki, N. Yamano and A. Nakayama, Polym. Degrad. Stabil., 174, 109095 (2020); https://doi.org/10.1016/j.polymdegradstab.2020.109095
M.C. Cardeña-Vazquez, M. Aguilar-Vega and C. Carrera-Figueiras, High Perform. Polym., 22, 184 (2010); https://doi.org/10.1177/0954008308101197
Z. Ping, W. Linbo and L. Bo-Geng, Polym. Degrad. Stab., 94, 1261 (2009); https://doi.org/10.1016/j.polymdegradstab.2009.04.015
T. Kijchavengkul, R. Auras and M. Rubino, Polym. Test., 27, 55 (2008); https://doi.org/10.1016/j.polymertesting.2007.08.007
K.H. Paek and S.G. Im, Green Chem., 22, 4570 (2020); https://doi.org/10.1039/D0GC01549K
D. Wei, J. Hua and Z. Wang, J. Appl. Polym. Sci., 131, (2014); https://doi.org/10.1002/app.40986
S.H. Hsiao and J.H. Chiou, Polym. J., 33, 95 (2001); https://doi.org/10.1295/polymj.33.95
S.G. Charati, A.Y. Houde, S.S. Kulkarni and M.G. Kulkarni, J. Polym. Sci., B Polym. Phys., 29, 921 (1991); https://doi.org/10.1002/polb.1991.090290803
K.I. Aly, Polym. Int., 47, 483 (1998); https://doi.org/10.1002/(SICI)1097-0126(199812)47:4<483::AIDPI91>3.0.CO;2-F
B. Kalpana and R. Nanthini, Asian J. Chem., 31, 2341 (2019); https://doi.org/10.14233/ajchem.2019.21997
M.N. Kim, B.Y. Lee, I.M. Lee, H.S. Lee and J.S. Yoon, J. Environ. Sci. Health Part A Tox. Hazard. Subst. Environ. Eng., 36, 447 (2001); https://doi.org/10.1081/ESE-100103475
K.I. Aly, M.A. Abdel-Rahman and M.M. Qutai, J. Polym. Res., 25, 185 (2018); https://doi.org/10.1007/s10965-018-1579-2
C. Hamciuc, T. Vlad-Bubulac, O. Petreus and G. Lisa, Eur. Polym. J., 43, 980 (2007); https://doi.org/10.1016/j.eurpolymj.2006.12.018
L. Lakshmi, Asian J. Chem., 22, 5344 (2010).
K. Chrissafis, K.M. Paraskevopoulos and D.N. Bikiaris, Polym. Degrad. Stab., 91, 60 (2006); https://doi.org/10.1016/j.polymdegradstab.2005.04.028