Copyright (c) 2023 ABHAY BAGUL, DIGAMBER GAIKWAD, YOGESH PATIL, NILESH BHUSARI
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization, Antimicrobial and Cytotoxic Investigations of Some Transition Metal(II) Complexes with Tridentate Schiff Base Derived from Pyrrolopyrimidine
Corresponding Author(s) : DIGAMBER GAIKWAD
Asian Journal of Chemistry,
Vol. 35 No. 11 (2023): Vol 35 Issue 11, 2023
Abstract
A Schiff base pyrrolopyrimidine-hydrazide-m-chlorobenzaldehyde (HPPHmCB) was synthesized via condensation reaction between a pyrrolopyrimidinehydrazide and 3-chlorobenzaldehyde and its transition metal(II) complexes complexes followed by the characterization and electrochemical analysis. The magnetic susceptibility, electrolytic conductivity, elemental analysis, FT-IR, electronic absorption, ESR and PMR spectra were employed to elucidate the structural properties. The Schiff base HPPHmCB ligand acts as a tridentate N,N,N donor and produces complexes of type [M(PPHmCB)2], which exhibit a square planar geometry for Pd(II) complex, tetrahedral for Hg(II), Cd(II) and Zn(II) complexes and octahedral geometry for Mn(II), Cu(II), Fe(II), Co(II) and Ni(II) complexes. The minimum inhibitory concentration (MIC) approach was used to screen the in vitro antibacterial and antifungal activities of synthesized Schiff base HPPHmCB ligand and its metal(II) complexes. The results showed that the significant microbial activities by both ligand and its transition metal(II) complexes. Moreover, in vitro cytotoxicity properties of Schiff base HPPHmCB ligand and its metal(II) complexes were also investigated against Artemia salina using the brine shrimp bioassay.
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- R. Herna’ndez-Molina and A. Mederos, in Comprehensive Coordination Chemistry II, vol. 1, ed. by J.A. McCleverty, T.J. Meyer (Elsevier, Amsterdam, 2004), p. 411.
- M. Andruh and F. Tuna, in Focus on Organometallic Chemistry Research, ed. by M.A. Cato (Nova Publishers, Hauppauge, 2005), p. 144.
- A.J. Atkins, D. Black, A.J. Blake, A. Marin-Becerra, S. Parsons, L. Ruiz-Ramirez and M. Schröder, Chem. Commun. (Camb.), 4, 457 (1996); https://doi.org/10.1039/CC9960000457
- P.A. Vigato and S. Tamburini, Coord. Chem. Rev., 248, 1717 (2004); https://doi.org/10.1016/j.cct.2003.09.003
- P.A. Vigato, S. Tamburini and L. Bertolo, Coord. Chem. Rev., 251, 1311 (2007); https://doi.org/10.1016/j.ccr.2006.11.016
- M. Sakamoto, K. Maneski and H. Okawa, Coord. Chem. Rev., 219–221, 379 (2001); https://doi.org/10.1016/S0010-8545(01)00341-1
- G. Ceyhan, C. Celik, S. Urus, I. Demirtas, M. Elmastas and M. Tu¨mer, Spectrochim. Acta A Mol. Biomol. Spectrosc., 81, 184 (2011); https://doi.org/10.1016/j.saa.2011.05.106
- R. Herchel, I. Nemec, M. Machata and Z. Trávníèek, Inorg. Chem., 54, 8625 (2015); https://doi.org/10.1021/acs.inorgchem.5b01271
- N.S. Youssef, E.A. El-Zahany and M.A. El-Seidy, Phosphorus Sulfur Silicon Relat. Elem., 185, 785 (2010); https://doi.org/10.1080/10426500902967904
- N.K. Chaudhary and P. Mishra, Bioinorg. Chem. Appl., 2017, 1 (2017); https://doi.org/10.1155/2017/6927675
- W.A. Zoubi, A.A.S. Al-Hamdani and Y.G. Ko, J. Sep. Sci. Technol., 52, 1052 (2017); https://doi.org/10.1080/01496395.2016.1267756
- X. Liu and J.-R. Hamon, Coord. Chem. Rev., 389, 94 (2019); https://doi.org/10.1016/j.ccr.2019.03.010
- H.L. Singh, S. Khaturia, V.S. Solanki and N. Sharma, J. Indian Chem. Soc., 100, 100945 (2023); https://doi.org/10.1016/j.jics.2023.100945
- U. Spichiger-Kelle, Chemical Sensors and Biosensors for Medical and Biological Applications (Wiley, Weinheim, 1998).
- R. Stock and B.F.R. Cedric, Chromatographic methods. Springer, 2013.
- Y.M. Ahmed, W.H. Mahmoud, M.M. Omar and G.G. Mohamed, J. Inorg. Organomet. Polym. Mater., 31, 2339 (2021); https://doi.org/10.1007/s10904-020-01867-1
- S. Kula, P. Ledwon, A.M. Maroñ, M. Siwy, J. Grzelak, M. Szalkowski, S. Mackowski and E. Schab-Balcerzak, Dyes Pigments, 192, 109437 (2021); https://doi.org/10.1016/j.dyepig.2021.109437
- A.S. Abu-Khadra, R.S. Farag and A.E.D.M. Abdel-Hady, Am. J. Anal. Chem., 7, 233 (2016); https://doi.org/10.4236/ajac.2016.73020
- B.N. Meyer, N.R. Ferrigni, J.E. Putnam, L.B. Jacobsen, D.E.J. Nichols and J.L. McLaughlin, Planta Med., 45, 31 (1982); https://doi.org/10.1055/s-2007-971236
- R.M. Russell and J.L. Robertson, Bulletin of the ESA, 25, 191 (1979).
- A. Gencer Imer, R.H. Syan, M. Gülcan, Y.S. Ocak and A. Tombak, J. Mater. Sci. Mater. Electron., 29, 898 (2018); https://doi.org/10.1007/s10854-017-7986-z
- V.P. Singh, S. Singh, D.P. Singh, K. Tiwari and M. Mishra, J. Mol. Struct., 1058, 71 (2014); https://doi.org/10.1016/j.molstruc.2013.10.046
- W. Hernández, J. Paz, F. Carrasco, A. Vaisberg, E. Spodine, J. Manzur, L. Hennig, J. Sieler, S. Blaurock and L. Beyer, Bioinorg. Chem. Appl., 2013, 524701 (2013); https://doi.org/10.1155/2013/524701
- M. So¨nmez, M. Celebi, A. Levent, I. Berber, Z. Senturk, J. Coord. Chem., 63, 848 (2010).
- S. Ilhan, H.M. Baykara, S. Seyitoglu, A. Levent, S. Özdemir, A. Dündar, A. Öztomsuk and M.H. Cornejo, J. Mol. Struct., 1075, 32 (2014); https://doi.org/10.1016/j.molstruc.2014.06.062
- B.E. Van Kuiken, A.W. Hahn, B. Nayyar, C.E. Schiewer, S.C. Lee, F. Meyer, T. Weyhermüller, A. Nicolaou, Y.-T. Cui, J. Miyawaki, Y. Harada and S. DeBeer, Inorg. Chem., 57, 7355 (2018); https://doi.org/10.1021/acs.inorgchem.8b01010
- M. Tarrago, C. Römelt, J. Nehrkorn, A. Schnegg, F. Neese, E. Bill and S. Ye, Inorg. Chem., 60, 4966 (2021); https://doi.org/10.1021/acs.inorgchem.1c00031
- R.R. Badekar, S.W. Kulkarni, R.S. Lokhande and B.S. Thawkar, Int. J. Appl. Res., 2, 175 (2016).
- M.A. Al-Omair, Arab. J. Chem., (2018); https://doi.org/10.1016/j.arabjc.2018.11.006
- M. Orojloo, P. Zolgharnein, M. Solimannejad and S. Amani, Inorg. Chim. Acta, 467, 227 (2017); https://doi.org/10.1016/j.ica.2017.08.016
- S.M. Emam, S.A. AbouelEnein and E.M. AbdelSatar, Appl. Organomet. Chem., 33, e4847 (2019); https://doi.org/10.1002/aoc.4847
- I. Ali, W.A. Wani, A. Khan, A. Haque, A. Ahmad, K. Saleem and N. Manzoor, Microb. Pathog., 53, 66 (2012); https://doi.org/10.1016/j.micpath.2012.04.005
- C.A. Téllez S, A.C. Costa Jr., M.A. Mondragón, G.B. Ferreira, O. Versiane, J.L. Rangel, G.M. Lima and A.A. Martin, Spectrochim. Acta A Mol. Biomol. Spectrosc., 169, 95 (2016); https://doi.org/10.1016/j.saa.2016.06.018
- S.P. Sellers, B.J. Korte, J.P. Fitzgerald, W.M. Reiff and G.T. Yee, J. Am. Chem. Soc., 120, 4662 (1998); https://doi.org/10.1021/ja973787a
- L.H. Abdel-Rahman, A.M. Abu-Dief, R.M. El-Khatib, S.M. Abdel-Fatah and A.A. Seleem, Int. J. Nano. Chem., 2, 83 (2016); https://doi.org/10.18576/ijnc/020303
- H. Sakiyama, M. Kato, S. Sasaki, M. Tasaki, E. Asato and M. Koikawa, Polyhedron, 111, 32 (2016); https://doi.org/10.1016/j.poly.2016.03.005
- H. Masai, K. Sonogashira and N. Hagihara, Bull. Chem. Soc. Jpn., 44, 2226 (1971); https://doi.org/10.1246/bcsj.44.2226
- K. Peng, V. Mawamba, E. Schulz, M. Löhr, C. Hagemann and U. Schatzschneider, Inorg. Chem., 58, 11508 (2019); https://doi.org/10.1021/acs.inorgchem.9b01304
- V. Vindya, V. Sadasivan, S.S. Meena and P. Bhatt, Orient. J. Chem., 34, 45 (2018); https://doi.org/10.13005/ojc/340105
- R. Èerný, N. Penin, H. Hagemann and Y. Filinchuk, J. Phys. Chem. C, 113, 9003 (2009); https://doi.org/10.1021/jp9015883
- Y. Sindhu, C.J. Athira, M.S. Sujamol, R.S. Joseyphus and K. Mohanan, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 43, 226 (2013); https://doi.org/10.1080/15533174.2012.740711
- M.S. Suresh and V. Prakash, E-J. Chem., 8, 1408 (2011); https://doi.org/10.1155/2011/254018
- M. Stylianou, C. Drouza, Z. Viskadourakis, J. Giapintzakis and A.D. Keramidas, Dalton Trans., 6188 (2008); https://doi.org/10.1039/b803854f
- K.D. Karlin, J.C. Hayes, S. Juen, J.P. Hutchinson and J. Zubieta, Inorg. Chem., 21, 4106 (1982); https://doi.org/10.1021/ic00141a049
- M.S.S. Adam, H. Elsawy, A. Sedky and M.M. Makhlouf, J. Taiwan Inst. Chem. Eng., 136, 104425 (2022); https://doi.org/10.1016/j.jtice.2022.104425
- L. Buzón-Durán, R. Capita and C. Alonso-Calleja, Food Microbiol., 72, 220 (2018); https://doi.org/10.1016/j.fm.2017.11.018
- S. Le Page, D. Raoult and J.M. Rolain, Int. J. Antimicrob. Agents, 45, 61 (2015); https://doi.org/10.1016/j.ijantimicag.2014.08.014
References
R. Herna’ndez-Molina and A. Mederos, in Comprehensive Coordination Chemistry II, vol. 1, ed. by J.A. McCleverty, T.J. Meyer (Elsevier, Amsterdam, 2004), p. 411.
M. Andruh and F. Tuna, in Focus on Organometallic Chemistry Research, ed. by M.A. Cato (Nova Publishers, Hauppauge, 2005), p. 144.
A.J. Atkins, D. Black, A.J. Blake, A. Marin-Becerra, S. Parsons, L. Ruiz-Ramirez and M. Schröder, Chem. Commun. (Camb.), 4, 457 (1996); https://doi.org/10.1039/CC9960000457
P.A. Vigato and S. Tamburini, Coord. Chem. Rev., 248, 1717 (2004); https://doi.org/10.1016/j.cct.2003.09.003
P.A. Vigato, S. Tamburini and L. Bertolo, Coord. Chem. Rev., 251, 1311 (2007); https://doi.org/10.1016/j.ccr.2006.11.016
M. Sakamoto, K. Maneski and H. Okawa, Coord. Chem. Rev., 219–221, 379 (2001); https://doi.org/10.1016/S0010-8545(01)00341-1
G. Ceyhan, C. Celik, S. Urus, I. Demirtas, M. Elmastas and M. Tu¨mer, Spectrochim. Acta A Mol. Biomol. Spectrosc., 81, 184 (2011); https://doi.org/10.1016/j.saa.2011.05.106
R. Herchel, I. Nemec, M. Machata and Z. Trávníèek, Inorg. Chem., 54, 8625 (2015); https://doi.org/10.1021/acs.inorgchem.5b01271
N.S. Youssef, E.A. El-Zahany and M.A. El-Seidy, Phosphorus Sulfur Silicon Relat. Elem., 185, 785 (2010); https://doi.org/10.1080/10426500902967904
N.K. Chaudhary and P. Mishra, Bioinorg. Chem. Appl., 2017, 1 (2017); https://doi.org/10.1155/2017/6927675
W.A. Zoubi, A.A.S. Al-Hamdani and Y.G. Ko, J. Sep. Sci. Technol., 52, 1052 (2017); https://doi.org/10.1080/01496395.2016.1267756
X. Liu and J.-R. Hamon, Coord. Chem. Rev., 389, 94 (2019); https://doi.org/10.1016/j.ccr.2019.03.010
H.L. Singh, S. Khaturia, V.S. Solanki and N. Sharma, J. Indian Chem. Soc., 100, 100945 (2023); https://doi.org/10.1016/j.jics.2023.100945
U. Spichiger-Kelle, Chemical Sensors and Biosensors for Medical and Biological Applications (Wiley, Weinheim, 1998).
R. Stock and B.F.R. Cedric, Chromatographic methods. Springer, 2013.
Y.M. Ahmed, W.H. Mahmoud, M.M. Omar and G.G. Mohamed, J. Inorg. Organomet. Polym. Mater., 31, 2339 (2021); https://doi.org/10.1007/s10904-020-01867-1
S. Kula, P. Ledwon, A.M. Maroñ, M. Siwy, J. Grzelak, M. Szalkowski, S. Mackowski and E. Schab-Balcerzak, Dyes Pigments, 192, 109437 (2021); https://doi.org/10.1016/j.dyepig.2021.109437
A.S. Abu-Khadra, R.S. Farag and A.E.D.M. Abdel-Hady, Am. J. Anal. Chem., 7, 233 (2016); https://doi.org/10.4236/ajac.2016.73020
B.N. Meyer, N.R. Ferrigni, J.E. Putnam, L.B. Jacobsen, D.E.J. Nichols and J.L. McLaughlin, Planta Med., 45, 31 (1982); https://doi.org/10.1055/s-2007-971236
R.M. Russell and J.L. Robertson, Bulletin of the ESA, 25, 191 (1979).
A. Gencer Imer, R.H. Syan, M. Gülcan, Y.S. Ocak and A. Tombak, J. Mater. Sci. Mater. Electron., 29, 898 (2018); https://doi.org/10.1007/s10854-017-7986-z
V.P. Singh, S. Singh, D.P. Singh, K. Tiwari and M. Mishra, J. Mol. Struct., 1058, 71 (2014); https://doi.org/10.1016/j.molstruc.2013.10.046
W. Hernández, J. Paz, F. Carrasco, A. Vaisberg, E. Spodine, J. Manzur, L. Hennig, J. Sieler, S. Blaurock and L. Beyer, Bioinorg. Chem. Appl., 2013, 524701 (2013); https://doi.org/10.1155/2013/524701
M. So¨nmez, M. Celebi, A. Levent, I. Berber, Z. Senturk, J. Coord. Chem., 63, 848 (2010).
S. Ilhan, H.M. Baykara, S. Seyitoglu, A. Levent, S. Özdemir, A. Dündar, A. Öztomsuk and M.H. Cornejo, J. Mol. Struct., 1075, 32 (2014); https://doi.org/10.1016/j.molstruc.2014.06.062
B.E. Van Kuiken, A.W. Hahn, B. Nayyar, C.E. Schiewer, S.C. Lee, F. Meyer, T. Weyhermüller, A. Nicolaou, Y.-T. Cui, J. Miyawaki, Y. Harada and S. DeBeer, Inorg. Chem., 57, 7355 (2018); https://doi.org/10.1021/acs.inorgchem.8b01010
M. Tarrago, C. Römelt, J. Nehrkorn, A. Schnegg, F. Neese, E. Bill and S. Ye, Inorg. Chem., 60, 4966 (2021); https://doi.org/10.1021/acs.inorgchem.1c00031
R.R. Badekar, S.W. Kulkarni, R.S. Lokhande and B.S. Thawkar, Int. J. Appl. Res., 2, 175 (2016).
M.A. Al-Omair, Arab. J. Chem., (2018); https://doi.org/10.1016/j.arabjc.2018.11.006
M. Orojloo, P. Zolgharnein, M. Solimannejad and S. Amani, Inorg. Chim. Acta, 467, 227 (2017); https://doi.org/10.1016/j.ica.2017.08.016
S.M. Emam, S.A. AbouelEnein and E.M. AbdelSatar, Appl. Organomet. Chem., 33, e4847 (2019); https://doi.org/10.1002/aoc.4847
I. Ali, W.A. Wani, A. Khan, A. Haque, A. Ahmad, K. Saleem and N. Manzoor, Microb. Pathog., 53, 66 (2012); https://doi.org/10.1016/j.micpath.2012.04.005
C.A. Téllez S, A.C. Costa Jr., M.A. Mondragón, G.B. Ferreira, O. Versiane, J.L. Rangel, G.M. Lima and A.A. Martin, Spectrochim. Acta A Mol. Biomol. Spectrosc., 169, 95 (2016); https://doi.org/10.1016/j.saa.2016.06.018
S.P. Sellers, B.J. Korte, J.P. Fitzgerald, W.M. Reiff and G.T. Yee, J. Am. Chem. Soc., 120, 4662 (1998); https://doi.org/10.1021/ja973787a
L.H. Abdel-Rahman, A.M. Abu-Dief, R.M. El-Khatib, S.M. Abdel-Fatah and A.A. Seleem, Int. J. Nano. Chem., 2, 83 (2016); https://doi.org/10.18576/ijnc/020303
H. Sakiyama, M. Kato, S. Sasaki, M. Tasaki, E. Asato and M. Koikawa, Polyhedron, 111, 32 (2016); https://doi.org/10.1016/j.poly.2016.03.005
H. Masai, K. Sonogashira and N. Hagihara, Bull. Chem. Soc. Jpn., 44, 2226 (1971); https://doi.org/10.1246/bcsj.44.2226
K. Peng, V. Mawamba, E. Schulz, M. Löhr, C. Hagemann and U. Schatzschneider, Inorg. Chem., 58, 11508 (2019); https://doi.org/10.1021/acs.inorgchem.9b01304
V. Vindya, V. Sadasivan, S.S. Meena and P. Bhatt, Orient. J. Chem., 34, 45 (2018); https://doi.org/10.13005/ojc/340105
R. Èerný, N. Penin, H. Hagemann and Y. Filinchuk, J. Phys. Chem. C, 113, 9003 (2009); https://doi.org/10.1021/jp9015883
Y. Sindhu, C.J. Athira, M.S. Sujamol, R.S. Joseyphus and K. Mohanan, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 43, 226 (2013); https://doi.org/10.1080/15533174.2012.740711
M.S. Suresh and V. Prakash, E-J. Chem., 8, 1408 (2011); https://doi.org/10.1155/2011/254018
M. Stylianou, C. Drouza, Z. Viskadourakis, J. Giapintzakis and A.D. Keramidas, Dalton Trans., 6188 (2008); https://doi.org/10.1039/b803854f
K.D. Karlin, J.C. Hayes, S. Juen, J.P. Hutchinson and J. Zubieta, Inorg. Chem., 21, 4106 (1982); https://doi.org/10.1021/ic00141a049
M.S.S. Adam, H. Elsawy, A. Sedky and M.M. Makhlouf, J. Taiwan Inst. Chem. Eng., 136, 104425 (2022); https://doi.org/10.1016/j.jtice.2022.104425
L. Buzón-Durán, R. Capita and C. Alonso-Calleja, Food Microbiol., 72, 220 (2018); https://doi.org/10.1016/j.fm.2017.11.018
S. Le Page, D. Raoult and J.M. Rolain, Int. J. Antimicrob. Agents, 45, 61 (2015); https://doi.org/10.1016/j.ijantimicag.2014.08.014