An Insight into the Effect of Schiff Base and their d and f Block Metal Complexes on Various Cancer Cell Lines as Anticancer Agents: A Review


Cite item

Full Text

Abstract

Over the last few decades, an alarming rise in the percentage of individuals with cancer and those with multi-resistant illnesses has forced researchers to explore possibilities for novel therapeutic approaches. Numerous medications currently exist to treat various disorders, and the development of small molecules as anticancer agents has considerable potential. However, the widespread prevalence of resistance to multiple drugs in cancer indicates that it is necessary to discover novel and promising compounds with ideal characteristics that could overcome the multidrug resistance issue. The utilisation of metallo-drugs has served as a productive anticancer chemotherapeutic method, and this approach may be implemented for combating multi-resistant tumours more successfully. Schiff bases have been receiving a lot of attention as a group of compounds due to their adaptable metal chelating abilities, innate biologic properties, and versatility to tweak the structure to optimise it for a specific biological purpose. The biological relevance of Schiff base and related complexes, notably their anticancer effects, has increased in their popularity as bio-inorganic chemistry has progressed. As a result of learning about Schiff bases antitumor efficacy against multiple cancer cell lines and their complexes, researchers are motivated to develop novel, side-effect-free anticancer treatments. According to study reports from the past ten years, we are still seeking a powerful anticancer contender. This study highlights the potential of Schiff bases, a broad class of chemical molecules, as potent anticancer agents. In combination with other anticancer strategies, they enhance the efficacy of treatment by elevating the cytotoxicity of chemotherapy, surmounting drug resistance, and promoting targeted therapy. Schiff bases also cause cancer cell DNA repair, improve immunotherapy, prevent angiogenesis, cause apoptosis, and lessen the side effects of chemotherapy. The present review explores the development of potential Schiff base and their d and f block metal complexes as anticancer agents against various cancer cell lines.

About the authors

Presenjit

Radiological Nuclear and Imaging Science, Institute of Nuclear Medicine & Allied Sciences, DRDO

Email: info@benthamscience.net

Shubhra Chaturvedi

Radiological Nuclear and Imaging Science, Institute of Nuclear Medicine & Allied Sciences, DRDO

Email: info@benthamscience.net

Akanksha Singh

Department of Zoology, Swami Shraddhanand College, University of Delhi

Email: info@benthamscience.net

Divya Gautam

Radiological Nuclear and Imaging Science, Institute of Nuclear Medicine & Allied Sciences, DRDO

Email: info@benthamscience.net

Kaman Singh

Department of Chemistry, Babasaheb Bhimrao Ambedkar University,

Author for correspondence.
Email: info@benthamscience.net

Anil Mishra

Radiological Nuclear and Imaging Science, Institute of Nuclear Medicine & Allied Sciences, DRDO

Author for correspondence.
Email: info@benthamscience.net

References

  1. Sumrra, S.H.; Arshad, Z.; Zafar, W.; Mahmood, K.; Ashfaq, M.; Hassan, A.U.; Mughal, E.U.; Irfan, A.; Imran, M. Metal incorporated aminothiazole-derived compounds: Synthesis, density function theory analysis, in vitro antibacterial and antioxidant evaluation. R. Soc. Open Sci., 2021, 8(9), 210910. doi: 10.1098/rsos.210910 PMID: 34631124
  2. Khalid, S.; Sumrra, S.H.; Chohan, Z.H. Isatin endowed metal chelates as antibacterial and antifungal agents. Sains Malays., 2020, 49(8), 1891-1904. doi: 10.17576/jsm-2020-4908-11
  3. Maurya, R.C.; Malik, B.A.; Mir, J.M.; Sharma, A.K. Synthesis, characterization, thermal behavior, and DFT aspects of some oxovanadium(IV) complexes involving ONO-donor sugar Schiff bases. J. Coord. Chem., 2014, 67(18), 3084-3106. doi: 10.1080/00958972.2014.959508
  4. Kelland, L. The resurgence of platinum-based cancer chemotherapy. Nat. Rev. Cancer, 2007, 7(8), 573-584. doi: 10.1038/nrc2167 PMID: 17625587
  5. Yang, Z.Y.; Yang, R.D.; Li, F.S.; Yu, K.B. Crystal structure and antitumor activity of some rare earth metal complexes with Schiff base. Polyhedron, 2000, 19(26-27), 2599-2604. doi: 10.1016/S0277-5387(00)00562-3
  6. Gupta, A.D.; Patil, A.M.; Ambekar, J.G.; Das, S.N.; Dhundasi, S.A.; Das, K.K. L-ascorbic acid protects the antioxidant defense system in nickel-exposed albino rat lung tissue. J. Basic Clin. Physiol. Pharmacol., 2006, 17(2), 87-100. doi: 10.1515/JBCPP.2006.17.2.87 PMID: 16910314
  7. Zhao, P.; Zhai, S.; Dong, J.; Gao, L.; Liu, X.; Wang, L.; Kong, J.; Li, L. Synthesis, structure, DNA interaction, and SOD activity of three nickel (II) complexes containing L-phenylalanine Schiff base and 1, 10-phenanthroline. Bioinorg. Chem. Appl., 2018, 2018, 1-16. doi: 10.1155/2018/8478152 PMID: 30073020
  8. Mei, H.; Jean, M.; Albalat, M.; Vanthuyne, N.; Roussel, C.; Moriwaki, H.; Yin, Z.; Han, J.; Soloshonok, V.A. Effect of substituents on the configurational stability of the stereogenic nitrogen in metal(II) complexes of α‐amino acid Schiff bases. Chirality, 2019, 31(5), 401-409. doi: 10.1002/chir.23066 PMID: 30916841
  9. Elerman, Y.; Kabak, M.; Elmali, A. Crystal structure and conformation of N-(5-Chlorosalicylidene)- 2-hydroxy-5-chloroaniline. Z. Naturforsch. B. J. Chem. Sci., 2002, 57(6), 651-656. doi: 10.1515/znb-2002-0610
  10. Harney, A.S.; Lee, J.; Manus, L.M.; Wang, P.; Ballweg, D.M.; LaBonne, C.; Meade, T.J. Targeted inhibition of Snail family zinc finger transcription factors by oligonucleotide-Co(III) Schiff base conjugate. Proc. Natl. Acad. Sci., 2009, 106(33), 13667-13672. doi: 10.1073/pnas.0906423106 PMID: 19666616
  11. Hassan, A.U.; Sumrra, S.H. Exploring the bioactive sites of new sulfonamide metal chelates for multi-drug resistance: An experimental versus theoretical design. J. Inorg. Organomet. Polym. Mater., 2022, 32(2), 513-535. doi: 10.1007/s10904-021-02135-6
  12. Matela, G. Schiff bases and complexes: A review on anticancer activity. Anticancer Agents Med Chem, 2020, 20(16), 1908-1917.
  13. Chohan, Z.H.; Shad, H.A. Metal-based new sulfonamides: Design, synthesis, antibacterial, antifungal, and cytotoxic properties. J. Enzyme Inhib. Med. Chem., 2012, 27(3), 403-412. doi: 10.3109/14756366.2011.593515 PMID: 21815774
  14. Hameed, A.; al-Rashida, M.; Uroos, M.; Abid Ali, S.; Khan, K.M. Schiff bases in medicinal chemistry: A patent review (2010-2015). Expert Opin. Ther. Pat., 2017, 27(1), 63-79. doi: 10.1080/13543776.2017.1252752 PMID: 27774821
  15. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods, 1983, 65(1-2), 55-63. doi: 10.1016/0022-1759(83)90303-4 PMID: 6606682
  16. Russo, A.; Piovano, M.; Lombardo, L.; Vanella, L.; Cardile, V.; Garbarino, J. Pannarin inhibits cell growth and induces cell death in human prostate carcinoma DU-145 cells. Anticancer Drugs, 2006, 17(10), 1163-1169. doi: 10.1097/01.cad.0000236310.66080.ed PMID: 17075315
  17. Economou, M.A.; Andersson, S.; Vasilcanu, D.; All-Ericsson, C.; Menu, E.; Girnita, A.; Girnita, L.; Axelson, M.; Seregard, S.; Larsson, O. Oral picropodophyllin (PPP) is well tolerated in vivo and inhibits IGF-1R expression and growth of uveal melanoma. Invest. Ophthalmol. Vis. Sci., 2008, 49(6), 2337-2342. doi: 10.1167/iovs.07-0819 PMID: 18515579
  18. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J.T.; Bokesch, H.; Kenney, S.; Boyd, M.R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 1990, 82(13), 1107-1112. doi: 10.1093/jnci/82.13.1107 PMID: 2359136
  19. Aroua, L.M.; Al-Hakimi, A.N.; Abdulghani, M.A.M.; Alhag, S.K. Cytotoxic urea Schiff base complexes for multidrug discovery as anticancer activity and low in vivo oral assessing toxicity. Arab. J. Chem., 2022, 15(8), 103986. doi: 10.1016/j.arabjc.2022.103986
  20. Hassan, A.M.; Said, A.O.; Heakal, B.H.; Younis, A.; Aboulthana, W.M.; Mady, M.F. Green synthesis, characterization, antimicrobial and anticancer screening of new metal complexes incorporating schiff base. ACS Omega, 2022, 7(36), 32418-32431. doi: 10.1021/acsomega.2c03911 PMID: 36120022
  21. Sayed, F.N.; Mohamed, G.G. Newly synthesized lanthanides complexes of ferrocene-based Schiff base with high biological activities and improved molecular docking data. J. Organomet. Chem., 2022, 977, 122450. doi: 10.1016/j.jorganchem.2022.122450
  22. Basaran, E.; Gamze Sogukomerogullari, H.; Cakmak, R.; Akkoc, S.; Taskin-Tok, T.; Köse, A. Novel chiral Schiff base Palladium(II), Nickel(II), Copper(II) and Iron(II) complexes: Synthesis, characterization, anticancer activity and molecular docking studies. Bioorg. Chem., 2022, 129, 106176. doi: 10.1016/j.bioorg.2022.106176 PMID: 36209564
  23. Mokhtari, P.; Mohammadnezhad, G. Anti-cancer properties and catalytic oxidation of sulfides based on vanadium(V) complexes of unprotected sugar-based Schiff-base ligands. Polyhedron, 2022, 215, 115655. doi: 10.1016/j.poly.2022.115655
  24. Mohamed, G.G.; Omar, M.M.A.; Moustafa, B.S. AbdEl-Halim, H.F.; Farag, N.A. Spectroscopic investigation, thermal, molecular structure, antimicrobial and anticancer activity with modelling studies of some metal complexes derived from isatin Schiff base ligand. Inorg. Chem. Commun., 2022, 141, 109606. doi: 10.1016/j.inoche.2022.109606
  25. Mishra, V.R.; Ghanavatkar, C.W.; Mali, S.N.; Chaudhari, H.K.; Sekar, N. Schiff base clubbed benzothiazole: Synthesis, potent antimicrobial and MCF-7 anticancer activity, DNA cleavage and computational study. J. Biomol. Struct. Dyn., 2019, 1-14. doi: 10.1080/07391102.2019.1621213 PMID: 31107179
  26. Terenzi, A.; Bonsignore, R.; Spinello, A.; Gentile, C.; Martorana, A.; Ducani, C.; Högberg, B.; Almerico, A.M.; Lauria, A.; Barone, G. Selective G-quadruplex stabilizers: Schiff-base metal complexes with anticancer activity. RSC Advances, 2014, 4(63), 33245-33256. doi: 10.1039/C4RA05355A
  27. Gou, Y.; Li, J.; Fan, B.; Xu, B.; Zhou, M.; Yang, F. Structure and biological properties of mixed-ligand Cu(II) Schiff base complexes as potential anticancer agents. Eur. J. Med. Chem., 2017, 134, 207-217. doi: 10.1016/j.ejmech.2017.04.026 PMID: 28415010
  28. Jiang, Q.; Xiao, N.; Shi, P.; Zhu, Y.; Guo, Z. Design of artificial metallonucleases with oxidative mechanism. Coord. Chem. Rev., 2007, 251(15-16), 1951-1972. doi: 10.1016/j.ccr.2007.02.013
  29. Abd El-Halim, H.F.; Omar, M.M.; Anwar, M.N. Preparation, characterization, antimicrobial and anticancer activities of Schiff base mixed ligand complexes. J. Therm. Anal. Calorim., 2017, 130(2), 1069-1083. doi: 10.1007/s10973-017-6491-1
  30. Ebrahimipour, S.Y.; Sheikhshoaie, I.; Kautz, A.C.; Ameri, M.; Pasban-Aliabadi, H.; Amiri, R.H.; Bruno, G.; Janiak, C. Mono- and dioxido-vanadium(V) complexes of a tridentate ONO Schiff base ligand: Synthesis, spectral characterization, X-ray crystal structure, and anticancer activity. Polyhedron, 2015, 93, 99-105. doi: 10.1016/j.poly.2015.03.037
  31. Ariyaeifar, M.; Amiri Rudbari, H.; Sahihi, M.; Kazemi, Z.; Kajani, A.A.; Zali-Boeini, H.; Kordestani, N.; Bruno, G.; Gharaghani, S. Chiral halogenated Schiff base compounds: Green synthesis, anticancer activity and DNA-binding study. J. Mol. Struct., 2018, 1161, 497-511. doi: 10.1016/j.molstruc.2018.02.042
  32. Dhahagani, K.; Kesavan, M.P.; Gujuluva, G.V.K.; Ravi, L.; Rajagopal, G.; Rajesh, J. Crystal structure, optical properties, DFT analysis of new morpholine based Schiff base ligands and their copper(II) complexes: DNA, protein docking analyses, antibacterial study and anticancer evaluation. Mater. Sci. Eng. C, 2018, 90, 119-130. doi: 10.1016/j.msec.2018.04.032 PMID: 29853075
  33. Shiju, C.; Arish, D.; Kumaresan, S. Novel water soluble Schiff base metal complexes: Synthesis, characterization, antimicrobial-, DNA cleavage, and anticancer activity. J. Mol. Struct., 2020, 1221, 128770. doi: 10.1016/j.molstruc.2020.128770
  34. Abd El-Halim, H.F.; Mohamed, G.G.; Anwar, M.N. Antimicrobial and anticancer activities of Schiff base ligand and its transition metal mixed ligand complexes with heterocyclic base. Appl. Organomet. Chem., 2018, 32(1), e3899. doi: 10.1002/aoc.3899
  35. Abdel-Rahman, L.H.; Abu-Dief, A.M.; El-Khatib, R.M.; Abdel-Fatah, S.M. Some new nano-sized Fe(II), Cd(II) and Zn(II) Schiff base complexes as precursor for metal oxides: Sonochemical synthesis, characterization, DNA interaction, in vitro antimicrobial and anticancer activities. Bioorg. Chem., 2016, 69, 140-152. doi: 10.1016/j.bioorg.2016.10.009 PMID: 27816797
  36. Abd-Elzaher, M.M.; Labib, A.A.; Mousa, H.A.; Moustafa, S.A.; Ali, M.M.; El-Rashedy, A.A. Synthesis, anticancer activity and molecular docking study of Schiff base complexes containing thiazole moiety. Beni-suef Univ. J. Basic Appl. Sci., 2016, 5(1), 85-96.
  37. Aslan, H.G.; Akkoç, S.; Kökbudak, Z. Anticancer activities of various new metal complexes prepared from a Schiff base on A549 cell line. Inorg. Chem. Commun., 2020, 111, 107645. doi: 10.1016/j.inoche.2019.107645
  38. Pradeepa, S.M.; Bhojya, N.H.S.; Vinay Kumar, B.; Indira, P.K.; Barik, A.; Ravikumar, N.T.R.; Prabhakara, M.C. Metal based photosensitizers of tetradentate Schiff base: Promising role in antitumor activity through singlet oxygen generation mechanism. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2013, 115, 12-21. doi: 10.1016/j.saa.2013.06.009 PMID: 23831972
  39. Xie, J.; Shen, S.; Chen, R.; Xu, J.; Dong, K.; Huang, J.; Lu, Q.; Zhu, W.; Ma, T.; Jia, L.; Cai, H.; Zhu, T. Synthesis, characterization and antitumor activity of Ln(III) complexes with hydrazone Schiff base derived from 2-acetylpyridine and isonicotinohydrazone. Oncol. Lett., 2017, 13(6), 4413-4419. doi: 10.3892/ol.2017.6018 PMID: 28599443
  40. Mir, J.M.; Jain, N.; Jaget, P.S.; Maurya, R.C. Density functionalized Ru II (NO)(Salen)(Cl) complex: Computational photodynamics and in vitro anticancer facets. Photodiagn. Photodyn. Ther., 2017, 19, 363-374. doi: 10.1016/j.pdpdt.2017.07.006 PMID: 28743589
  41. Damercheli, M.; Dayyani, D.; Behzad, M.; Mehravi, B.; Shafiee Ardestani, M. New salen-type manganese(III) Schiff base complexes derived from meso -1,2-diphenyl-1,2-ethylenediamine: in vitro anticancer activity, mechanism of action, and molecular docking studies. J. Coord. Chem., 2015, 68(9), 1500-1513. doi: 10.1080/00958972.2015.1027697
  42. Aidi, M.; Keypour, H.; Shooshtari, A.; Bayat, M.; Hosseinzadeh, L.; Rudbari, H.A.; Gable, R.W. Coordination chemistry of some new Mn(II), Cd(II) and Zn(II) macrocyclic Schiff base complexes containing a homopiperazine head unit. Spectral, X-ray crystal structural, theoretical studies and anticancer activity. Inorg. Chim. Acta, 2019, 490, 294-302. doi: 10.1016/j.ica.2018.12.046
  43. Abdel-Rahman, L.H.; Ismail, N.M.; Ismael, M.; Abu-Dief, A.M.; Ahmed, E.A.H. Synthesis, characterization, DFT calculations and biological studies of Mn(II), Fe(II), Co(II) and Cd(II) complexes based on a tetradentate ONNO donor Schiff base ligand. J. Mol. Struct., 2017, 1134, 851-862. doi: 10.1016/j.molstruc.2017.01.036
  44. Xia, Y.; Liu, X.; Zhang, L.; Zhang, J.; Li, C.; Zhang, N.; Xu, H.; Li, Y. A new Schiff base coordinated copper(II) compound induces apoptosis and inhibits tumor growth in gastric cancer. Cancer Cell Int., 2019, 19(1), 81. doi: 10.1186/s12935-019-0801-6 PMID: 30988662
  45. Howsaui, H.B.; Basaleh, A.S.; Abdellattif, M.H.; Hassan, W.M.I.; Hussien, M.A. Synthesis, structural investigations, molecular docking, and anticancer activity of some novel Schiff bases and their uranyl complexes. Biomolecules, 2021, 11(8), 1138. doi: 10.3390/biom11081138 PMID: 34439805
  46. Kordestani, N.; Amiri Rudbari, H.; Correia, I.; Valente, A.; Côrte-Real, L.; Islam, M.K.; Micale, N.; Braun, J.D.; Herbert, D.E.; Tumanov, N.; Wouters, J.; Enamullah, M. Heteroleptic enantiopure Pd(II)-complexes derived from halogen-substituted Schiff bases and 2-picolylamine: Synthesis, experimental and computational characterization and investigation of the influence of chirality and halogen atoms on the anticancer activity. New J. Chem., 2021, 45(20), 9163-9180. doi: 10.1039/D1NJ01491A
  47. Rudbari, H.A.; Kordestani, N.; Cuevas-Vicario, J.V.; Zhou, M.; Efferth, T.; Correia, I.; Schirmeister, T.; Barthels, F.; Enamullah, M.; Fernandes, A.R.; Micale, N. Investigation of the influence of chirality and halogen atoms on the anticancer activity of enantiopure palladium( II ) complexes derived from chiral amino-alcohol Schiff bases and 2-picolylamine. New J. Chem., 2022, 46(14), 6470-6483. doi: 10.1039/D2NJ00321J
  48. Parsekar, S.U.; Paliwal, K.; Haldar, P.; Antharjanam, P.K.S.; Kumar, M. Synthesis, characterization, crystal structure, DNA and HSA Interactions, and anticancer activity of a mononuclear Cu (II) complex with a Schiff base ligand containing a thiadiazoline moiety. ACS Omega, 2022, 7(3), 2881-2896. doi: 10.1021/acsomega.1c05750 PMID: 35097283
  49. Deghadi, R.G.; Abbas, A.A.; Mohamed, G.G. Theoretical and experimental investigations of new bis (amino triazole) schiff base ligand: Preparation of its UO 2 (II), Er (III), and La (III) complexes, studying of their antibacterial, anticancer, and molecular docking. Appl. Organomet. Chem., 2021, 35(8), e6292. doi: 10.1002/aoc.6292
  50. Alyar, S.; Özmen, Ü.Ö. Adem, Ş.; Alyar, H.; Bilen, E.; Kaya, K. Synthesis, spectroscopic characterizations, carbonic anhydrase II inhibitory activity, anticancer activity and docking studies of new Schiff bases of sulfa drugs. J. Mol. Struct., 2021, 1223, 128911. doi: 10.1016/j.molstruc.2020.128911
  51. Ismail, B.A.; Nassar, D.A.; Abd El-Wahab, Z.H.; Ali, O.A.M. Synthesis, characterization, thermal, DFT computational studies and anticancer activity of furfural-type schiff base complexes. J. Mol. Struct., 2021, 1227, 129393. doi: 10.1016/j.molstruc.2020.129393
  52. Alkış, M.E.; Keleştemür, Ü.; Alan, Y.; Turan, N.; Buldurun, K. Cobalt and ruthenium complexes with pyrimidine based schiff base: Synthesis, characterization, anticancer activities and electrochemotherapy efficiency. J. Mol. Struct., 2021, 1226, 129402. doi: 10.1016/j.molstruc.2020.129402
  53. Wongsuwan, S.; Chatwichien, J.; Pinchaipat, B.; Kumphune, S.; Harding, D.J.; Harding, P.; Boonmak, J.; Youngme, S.; Chotima, R. Synthesis, characterization and anticancer activity of Fe(II) and Fe(III) complexes containing N-(8-quinolyl)salicylaldimine Schiff base ligands. J. Biol. Inorg. Chem., 2021, 26(2-3), 327-339. doi: 10.1007/s00775-021-01857-9 PMID: 33606116
  54. Omar, M.M.; Abd El-Halim, H.F.; Khalil, E.A.M. Synthesis, characterization, and biological and anticancer studies of mixed ligand complexes with Schiff base and 2,2′‐bipyridine. Appl. Organomet. Chem., 2017, 31(10), e3724. doi: 10.1002/aoc.3724
  55. Zhang, N.; Fan, Y.; Zhang, Z.; Zuo, J.; Zhang, P.; Wang, Q.; Liu, S.; Bi, C. Syntheses, crystal structures and anticancer activities of three novel transition metal complexes with Schiff base derived from 2-acetylpyridine and l-tryptophan. Inorg. Chem. Commun., 2012, 22, 68-72. doi: 10.1016/j.inoche.2012.05.022
  56. Andiappan, K.; Sanmugam, A.; Deivanayagam, E.; Karuppasamy, K.; Kim, H.S.; Vikraman, D. In vitro cytotoxicity activity of novel Schiff base ligand–lanthanide complexes. Sci. Rep., 2018, 8(1), 3054. doi: 10.1038/s41598-018-21366-1 PMID: 29445233
  57. Li, X.; Bi, C.; Fan, Y.; Zhang, X.; Meng, X.; Cui, L. Synthesis, crystal structure and anticancer activity of a novel ternary copper(II) complex with Schiff base derived from 2-amino-4-fluorobenzoic acid and salicylaldehyde. Inorg. Chem. Commun., 2014, 50, 35-41. doi: 10.1016/j.inoche.2014.10.014
  58. Chow, M.J.; Licona, C.; Yuan Qiang Wong, D.; Pastorin, G.; Gaiddon, C.; Ang, W.H. Discovery and investigation of anticancer ruthenium-arene Schiff-base complexes via water-promoted combinatorial three-component assembly. J. Med. Chem., 2014, 57(14), 6043-6059. doi: 10.1021/jm500455p PMID: 25023617
  59. Sathiyaraj, S.; Sampath, K.; Butcher, R.J.; Pallepogu, R.; Jayabalakrishnan, C. Designing, structural elucidation, comparison of DNA binding, cleavage, radical scavenging activity and anticancer activity of copper(I) complex with 5-dimethyl-2-phenyl-4-(pyridin-2-ylmethylene)-amino-1,2-dihydro-pyrazol-3-one Schiff base ligand. Eur. J. Med. Chem., 2013, 64, 81-89. doi: 10.1016/j.ejmech.2013.03.047 PMID: 23644191
  60. Şahin, Ö.; Özdemir, Ü.Ö.; Seferoğlu, N.; Genc, Z.K.; Kaya, K.; Aydıner, B.; Tekin, S.; Seferoğlu, Z. New platinum (II) and palladium (II) complexes of coumarin-thiazole Schiff base with a fluorescent chemosensor properties: Synthesis, spectroscopic characterization, X-ray structure determination, in vitro anticancer activity on various human carcinoma cell lines and computational studies. J. Photochem. Photobiol. B, 2018, 178, 428-439. doi: 10.1016/j.jphotobiol.2017.11.030 PMID: 29216566
  61. Asadi, Z.; Asadi, M.; Dehghani Firuzabadi, F.; Yousefi, R.; Jamshidi, M. Synthesis, characterization, anticancer activity, thermal and electrochemical studies of some novel uranyl Schiff base complexes. J. Indian Chem. Soc., 2014, 11, 423-429.
  62. Elsayed, S.A.; Butler, I.S.; Claude, B.J.; Mostafa, S.I. Synthesis, characterization and anticancer activity of 3-formylchromone benzoylhydrazone metal complexes. Trans. Met. Chem., 2015, 40(2), 179-187. doi: 10.1007/s11243-014-9904-z
  63. Muhammad, N.; Guo, Z. Metal-based anticancer chemotherapeutic agents. Curr. Opin. Chem. Biol., 2014, 19, 144-153. doi: 10.1016/j.cbpa.2014.02.003 PMID: 24608084
  64. Hannon, M.J. Metal-based anticancer drugs: From a past anchored in platinum chemistry to a post-genomic future of diverse chemistry and biology. Pure Appl. Chem., 2007, 79(12), 2243-2261. doi: 10.1351/pac200779122243
  65. Kaim, W.; Schwederski, B.; Klein, A. Bioinorganic Chemistry-Inorganic Elements in the Chemistry of Life: An Introduction and Guide; John Wiley & Sons, 2013.
  66. Wheate, N.J.; Walker, S.; Craig, G.E.; Oun, R. The status of platinum anticancer drugs in the clinic and in clinical trials. Dalton Trans., 2010, 39(35), 8113-8127. doi: 10.1039/c0dt00292e PMID: 20593091
  67. Oun, R.; Moussa, Y.E.; Wheate, N.J. The side effects of platinumbased chemotherapy drugs: A review for chemists. Dalton Trans., 2018, 47(19), 6645-6653. doi: 10.1039/C8DT00838H PMID: 29632935
  68. Dasari, S.; Bernard, T.P. Cisplatin in cancer therapy: Molecular mechanisms of action. Eur. J. Pharmacol., 2014, 740, 364-378. doi: 10.1016/j.ejphar.2014.07.025 PMID: 25058905
  69. Rigamonti, L.; Reginato, F.; Ferrari, E.; Pigani, L.; Gigli, L.; Demitri, N.; Kopel, P.; Tesarova, B.; Heger, Z. From solid state to in vitro anticancer activity of copper(II) compounds with electronically-modulated NNO Schiff base ligands. Dalton Trans., 2020, 49(41), 14626-14639. doi: 10.1039/D0DT03038D PMID: 33057512
  70. Davis, K.J.; Assadawi, N.M.O.; Pham, S.Q.T.; Birrento, M.L.; Richardson, C.; Beck, J.L.; Willis, A.C.; Ralph, S.F. Effect of structure variations on the quadruplex DNA binding ability of nickel Schiff base complexes. Dalton Trans., 2018, 47(38), 13573-13591. doi: 10.1039/C8DT02727G PMID: 30206589
  71. King, A.P.; Gellineau, H.A.; MacMillan, S.N.; Wilson, J.J. Physical properties, ligand substitution reactions, and biological activity of Co( III )-Schiff base complexes. Dalton Trans., 2019, 48(18), 5987-6002. doi: 10.1039/C8DT04606A PMID: 30672949
  72. Elamathi, C.; Butcher, R.; Prabhakaran, R. Anomalous coordination behaviour of 6‐methyl‐2‐oxo‐1,2‐dihydroquinoline‐3‐carboxaldehyde‐4(N)‐substituted Schiff bases in Cu(II) complexes: Studies of structure, biomolecular interactions and cytotoxicity. Appl. Organomet. Chem., 2019, 33(4), e4659. doi: 10.1002/aoc.4659
  73. Ayaz, F. Gonul, İ.; Demirbag, B.; Ocakoglu, K. Differential immunomodulatory activities of Schiff base complexes depending on their metal conjugation. Inflammation, 2019, 42(5), 1878-1885. doi: 10.1007/s10753-019-01050-w PMID: 31267275
  74. da Silva, C.M.; da Silva, D.L.; Modolo, L.V.; Alves, R.B.; de Resende, M.A.; Martins, C.V.B.; de Fátima, . Schiff bases: A short review of their antimicrobial activities. J. Adv. Res., 2011, 2(1), 1-8. doi: 10.1016/j.jare.2010.05.004
  75. Denoyer, D.; Masaldan, S.; La Fontaine, S.; Cater, M.A. Targeting copper in cancer therapy: ‘Copper That Cancer’. Metallomics, 2015, 7(11), 1459-1476. doi: 10.1039/C5MT00149H PMID: 26313539
  76. Turski, M.L.; Thiele, D.J. New roles for copper metabolism in cell proliferation, signaling, and disease. J. Biol. Chem., 2009, 284(2), 717-721. doi: 10.1074/jbc.R800055200 PMID: 18757361
  77. Brissos, R.F.; Torrents, E. Mariana dos, S.M.F.; Carvalho, P.W.; de Paula Silveira-Lacerda, E.; Caballero, A.B.; Caubet, A.; Massera, C.; Roubeau, O.; Teat, S.J.; Gamez, P. Highly cytotoxic DNA-interacting copper(II) coordination compounds. Metallomics, 2014, 6(10), 1853-1868. doi: 10.1039/C4MT00152D PMID: 25096758
  78. Ali, I.; Lone, M.; Al-Othman, Z.; Al-Warthan, A.; Sanagi, M. Heterocyclic scaffolds: Centrality in anticancer drug development. Curr. Drug Targets, 2015, 16(7), 711-734. doi: 10.2174/1389450116666150309115922 PMID: 25751009
  79. Sreenivasulu, R.; Tej, M.B.; Jadav, S.S.; Sujitha, P.; Kumar, C.G.; Raju, R.R. Synthesis, anticancer evaluation and molecular docking studies of 2,5-bis(indolyl)-1,3,4-oxadiazoles, Nortopsentin analogues. J. Mol. Struct., 2020, 1208, 127875. doi: 10.1016/j.molstruc.2020.127875
  80. Saeed, H.K.; Sreedharan, S.; Thomas, J.A. Photoactive metal complexes that bind DNA and other biomolecules as cell probes, therapeutics, and theranostics. Chem. Commun., 2020, 56(10), 1464-1480. doi: 10.1039/C9CC09312E PMID: 31967621
  81. Dhanaraj, C.J.; Johnson, J.; Joseph, J.; Joseyphus, R.S. Quinoxaline-based Schiff base transition metal complexes: Review. J. Coord. Chem., 2013, 66(8), 1416-1450. doi: 10.1080/00958972.2013.782008
  82. Martins, P.; Jesus, J.; Santos, S.; Raposo, L.; Roma-Rodrigues, C.; Baptista, P.; Fernandes, A. Heterocyclic anticancer compounds: Recent advances and the paradigm shift towards the use of nanomedicine’s tool box. Molecules, 2015, 20(9), 16852-16891. doi: 10.3390/molecules200916852 PMID: 26389876
  83. Sumrra, S.H.; Sahrish, I.; Raza, M.A.; Ahmad, Z.; Zafar, M.N.; Chohan, Z.H.; Khalid, M.; Ahmed, S. Efficient synthesis, characterization, and in vitro bactericidal studies of unsymmetrically substituted triazole-derived Schiff base ligand and its transition metal complexes. Monatsh. Chem., 2020, 151(4), 549-557. doi: 10.1007/s00706-020-02571-z
  84. Ekennia, A.C.; Onwudiwe, D.C.; Osowole, A.A.; Okpareke, O.C.; Olubiyi, O.O.; Lane, J.R. Coordination compounds of heterocyclic bases: Synthesis, characterization, computational and biological studies. Res. Chem. Intermed., 2019, 45(3), 1169-1205. doi: 10.1007/s11164-018-3664-x
  85. Moro, S.; Chipman, J.K.; Wegener, J.W.; Hamberger, C.; Dekant, W.; Mally, A. Furan in heat‐treated foods: Formation, exposure, toxicity, and aspects of risk assessment. Mol. Nutr. Food Res., 2012, 56(8), 1197-1211. doi: 10.1002/mnfr.201200093 PMID: 22641279
  86. Guo, J.; Zhao, R.; Li, J.; Wu, D.; Yang, Q.; Zhang, Y.; Wang, S. Furan formation from ingredient interactions and furan mitigation by sugar alcohols and antioxidants of bamboo leaves in milk beverage model systems. J. Sci. Food Agric., 2019, 99(11), 4993-4999. doi: 10.1002/jsfa.9739 PMID: 30977142
  87. Ali, O.A.M. Abd El -Wahab, Z.H.; Ismail, B.A. Synthesis, structural characterization and evaluation of catalytic and antimicrobial properties of new mononuclear Ag(I), Mn(II), Cu(II) and Pt(IV) complexes. J. Mol. Struct., 2017, 1139, 175-195. doi: 10.1016/j.molstruc.2017.03.025
  88. Mohamed, G.G.; Zayed, E.M.; Hindy, A.M.M. Coordination behavior of new bis Schiff base ligand derived from 2-furan carboxaldehyde and propane-1,3-diamine. Spectroscopic, thermal, anticancer and antibacterial activity studies. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2015, 145, 76-84. doi: 10.1016/j.saa.2015.01.129 PMID: 25767990
  89. Benabid, W.; Ouari, K.; Bendia, S.; Bourzami, R.; Ait Ali, M. Crystal structure, spectroscopic studies, DFT calculations, cyclic voltammetry and biological activity of a copper (II) Schiff base complex. J. Mol. Struct., 2020, 1203, 127313. doi: 10.1016/j.molstruc.2019.127313
  90. Bandyopadhyay, D.; Layek, M.; Fleck, M.; Saha, R.; Rizzoli, C. Synthesis, crystal structure and antibacterial activity of azido complexes of cobalt(III) containing heteroaromatic Schiff bases. Inorg. Chim. Acta, 2017, 461, 174-182. doi: 10.1016/j.ica.2017.02.018
  91. Gündüzalp, A.B. Özsen, İ.; Alyar, H.; Alyar, S.; Özbek, N. Biologically active Schiff bases containing thiophene/furan ring and their copper(II) complexes: Synthesis, spectral, nonlinear optical and density functional studies. J. Mol. Struct., 2016, 1120, 259-266. doi: 10.1016/j.molstruc.2016.05.002
  92. Shelke, V.A.; Jadhav, S.M.; Patharkar, V.R.; Shankarwar, S.G.; Munde, A.S.; Chondhekar, T.K. Synthesis, spectroscopic characterization and thermal studies of some rare earth metal complexes of unsymmetrical tetradentate Schiff base ligand. Arab. J. Chem., 2012, 5(4), 501-507. doi: 10.1016/j.arabjc.2010.09.018
  93. Raman, N.; Sobha, S.; Selvaganapathy, M.; Mahalakshmi, R. DNA binding mode of novel tetradentate amino acid based 2-hydroxybenzylidene-4-aminoantipyrine complexes. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2012, 96, 698-708. doi: 10.1016/j.saa.2012.07.051 PMID: 22885083
  94. Morgan, S.M.; El-Sonbati, A.Z.; Eissa, H.R. Geometrical structures, thermal properties and spectroscopic studies of Schiff base complexes: Correlation between ionic radius of metal complexes and DNA binding. J. Mol. Liq., 2017, 240, 752-776. doi: 10.1016/j.molliq.2017.05.114
  95. Palanimurugan, A.; Dhanalakshmi, A.; Selvapandian, P.; Kulandaisamy, A. Electrochemical behavior, structural, morphological, Calf Thymus-DNA interaction and in vitro antimicrobial studies of synthesized Schiff base transition metal complexes. Heliyon, 2019, 5(7), e02039. doi: 10.1016/j.heliyon.2019.e02039 PMID: 31334376
  96. Marchetti, F.; Pettinari, C.; Di Nicola, C.; Tombesi, A.; Pettinari, R. Coordination chemistry of pyrazolone-based ligands and applications of their metal complexes. Coord. Chem. Rev., 2019, 401, 213069. doi: 10.1016/j.ccr.2019.213069
  97. Finkelstein, A.E.; Walz, D.T.; Batista, V.; Mizraji, M.; Roisman, F.; Misher, A. Auranofin. New oral gold compound for treatment of rheumatoid arthritis. Ann. Rheum. Dis., 1976, 35(3), 251-257. doi: 10.1136/ard.35.3.251 PMID: 791161
  98. Milacic, V.; Fregona, D.; Dou, Q.P. Gold complexes as prospective metal-based anticancer drugs. Histol. Histopathol., 2008, 23(1), 101-108. PMID: 17952862
  99. Nardon, C.; Boscutti, G.; Fregona, D. Beyond platinums: Gold complexes as anticancer agents. Anticancer Res., 2014, 34(1), 487-492. PMID: 24403506
  100. Nasser, A.T.; Al-Asadi, R. Schiff bases ligands derived from o-phthalaldehyde and their metal complexes with Cu2+ and Ni2+: Synthesis, anti-breast cancer and molecular docking study. Trends in Sciences, 2023, 20(9), 5675-5675. doi: 10.48048/tis.2023.5675
  101. Hosny, S.; Ragab, M.S.; Abd El-Baki, R.F. Synthesis of a new sulfadimidine Schiff base and their nano complexes as potential anti-COVID-19 and anti-cancer activity. Sci. Rep., 2023, 13(1), 1502. doi: 10.1038/s41598-023-28402-9 PMID: 36707628
  102. Al-Fakeh, M.S.; Alsikhan, M.A.; Alnawmasi, J.S. Physico-chemical study of Mn(II), Co(II), Cu(II), Cr(III), and Pd(II) complexes with schiff-base and aminopyrimidyl derivatives and anti-cancer, antioxidant, antimicrobial applications. Molecules, 2023, 28(6), 2555. doi: 10.3390/molecules28062555 PMID: 36985526
  103. Moscicki, A.B.; Darragh, T.M.; Berry-Lawhorn, J.M.; Roberts, J.M.; Khan, M.J.; Boardman, L.A.; Palefsky, J.M. Screening for anal cancer in women. J Low Genit Tract Dis, 2015, 19(3 0 1), S26-S41. doi: 10.1097/LGT.0000000000000117
  104. Amolegbe, S.A.; Akinremi, C.A.; Adewuyi, S.; Lawal, A.; Bamigboye, M.O.; Obaleye, J.A. Some nontoxic metal-based drugs for selected prevalent tropical pathogenic diseases. J. Biol. Inorg. Chem., 2017, 22(1), 1-18. doi: 10.1007/s00775-016-1421-4 PMID: 27904956
  105. Levina, A.; Crans, D.C.; Lay, P.A. Speciation of metal drugs, supplements and toxins in media and bodily fluids controls in vitro activities. Coord. Chem. Rev., 2017, 352, 473-498. doi: 10.1016/j.ccr.2017.01.002
  106. Egorova, K.S.; Ananikov, V.P. Toxicity of metal compounds: Knowledge and myths. Organometallics, 2017, 36(21), 4071-4090. doi: 10.1021/acs.organomet.7b00605
  107. Majid, S.A.; Mir, J.M.; Jan, G.; Shalla, A.H. Schiff base complexes, cancer cell lines, and anticancer evaluation: A review. J. Coord. Chem., 2022, 75(15-16), 2018-2038. doi: 10.1080/00958972.2022.2131402
  108. Zoroddu, M.A.; Aaseth, J.; Crisponi, G.; Medici, S.; Peana, M.; Nurchi, V.M. The essential metals for humans: A brief overview. J. Inorg. Biochem., 2019, 195, 120-129. doi: 10.1016/j.jinorgbio.2019.03.013 PMID: 30939379
  109. Diehn, M.; Cho, R.W.; Lobo, N.A.; Kalisky, T.; Dorie, M.J.; Kulp, A.N.; Clarke, M.F. Association of reactive oxygen species levels and radioresistance in cancer stem cells. Nature, 2009, 458(7239), 780-783.
  110. Aldib, I.; Soubhye, J.; Zouaoui Boudjeltia, K.; Vanhaeverbeek, M.; Rousseau, A.; Furtmüller, P.G.; Obinger, C.; Dufrasne, F.; Nève, J.; Van Antwerpen, P.; Prévost, M. Evaluation of new scaffolds of myeloperoxidase inhibitors by rational design combined with high-throughput virtual screening. J. Med. Chem., 2012, 55(16), 7208-7218. doi: 10.1021/jm3007245 PMID: 22793255
  111. Sánchez-Valle, V.; Chávez-Tapia, N.C.; Uribe, M.; Méndez-Sánchez, N. Role of oxidative stress and molecular changes in liver fibrosis: A review. Curr. Med. Chem., 2012, 19(28), 4850-4860. doi: 10.2174/092986712803341520 PMID: 22709007
  112. Halliwell, B.; Gutteridge, J.M. Free radicals in biology and medicine; Oxford university press: USA, 2015. doi: 10.1093/acprof:oso/9780198717478.001.0001
  113. de Souza, I.C.A.; Faro, L.V.; Pinheiro, C.B.; Gonzaga, D.T.G.; da Silva, F.C.; Ferreira, V.F.; Miranda, F.S.; Scarpellini, M.; Lanznaster, M. Investigation of cobalt(III)-triazole systems as prototypes for hypoxia-activated drug delivery. Dalton Trans., 2016, 45(35), 13671-13674. doi: 10.1039/C6DT02456D PMID: 27488398
  114. Yamamoto, N.; Renfrew, A.K.; Kim, B.J.; Bryce, N.S.; Hambley, T.W. Dual targeting of hypoxic and acidic tumor environments with a cobalt(III) chaperone complex. J. Med. Chem., 2012, 55(24), 11013-11021. doi: 10.1021/jm3014713 PMID: 23199008
  115. Renfrew, A.K.; Bryce, N.S.; Hambley, T.W. Delivery and release of curcumin by a hypoxia-activated cobalt chaperone: A XANES and FLIM study. Chem. Sci. (Camb.), 2013, 4(9), 3731-3739. doi: 10.1039/c3sc51530c
  116. Bustamante, F.L.S.; Metello, J.M.; de Castro, F.A.V.; Pinheiro, C.B.; Pereira, M.D.; Lanznaster, M. Lawsone dimerization in cobalt(III) complexes toward the design of new prototypes of bioreductive prodrugs. Inorg. Chem., 2013, 52(3), 1167-1169. doi: 10.1021/ic302175t PMID: 23343393
  117. Ware, D.C.; Brothers, P.J.; Clark, G.R.; Denny, W.A.; Palmer, B.D.; Wilson, W.R. Synthesis, structures and hypoxia-selective cytotoxicity of cobalt(III) complexes containing tridentate amine and nitrogen mustard ligands. J. Chem. Soc., Dalton Trans., 2000, (6), 925-932. doi: 10.1039/a909447d
  118. Parker, L.L.; Lacy, S.M.; Farrugia, L.J.; Evans, C.; Robins, D.J.; O’Hare, C.C.; Hartley, J.A.; Jaffar, M.; Stratford, I.J. A novel design strategy for stable metal complexes of nitrogen mustards as bioreductive prodrugs. J. Med. Chem., 2004, 47(23), 5683-5689. doi: 10.1021/jm049866w PMID: 15509167
  119. Craig, P.R.; Brothers, P.J.; Clark, G.R.; Wilson, W.R.; Denny, W.A.; Ware, D.C. Anionic carbonato and oxalato cobalt(iii) nitrogen mustard complexes. Dalton Trans., 2004, 611-618.
  120. Failes, T.W.; Hambley, T.W. Models of hypoxia activated prodrugs: Co(iii) complexes of hydroxamic acids. Dalton Trans., 2006, (15), 1895-1901. doi: 10.1039/b512322d PMID: 16585977
  121. Renfrew, A.K.; Bryce, N.S.; Hambley, T. Cobalt (III) chaperone complexes of curcumin: Photoreduction, cellular accumulation and light selective toxicity towards tumour cells. Chemistry, 2015, 21(43), 15224-15234. doi: 10.1002/chem.201502702 PMID: 26471438
  122. Bansal, A.; Saleh-E-In, M.M.; Kar, P.; Roy, A.; Sharma, N.R. Synthesis of carvacrol derivatives as potential new anticancer agent against lung cancer. Molecules, 2022, 27(14), 4597. doi: 10.3390/molecules27144597 PMID: 35889476
  123. Yan, F.; Cao, X.X.; Jiang, H.X.; Zhao, X.L.; Wang, J.Y.; Lin, Y.H.; Liu, Q.L.; Zhang, C.; Jiang, B.; Guo, F. A novel watersoluble gossypol derivative increases chemotherapeutic sensitivity and promotes growth inhibition in colon cancer. J. Med. Chem., 2010, 53(15), 5502-5510. doi: 10.1021/jm1001698 PMID: 20684596
  124. O’Neal, S.L.; Zheng, W. Manganese toxicity upon overexposure: A decade in review. Curr. Environ. Health Rep., 2015, 2(3), 315-328. doi: 10.1007/s40572-015-0056-x PMID: 26231508
  125. Zhang, C.J.; Valic, M.S.; Chen, J.; Zheng, G. In vivo potential of manganese chelated porphysomes as MRI contrast agents. SFJ, 2017, 3(1), 47-53. doi: 10.17975/sfj-2017-007
  126. Chang, G.L.; Li, Z.; Niu, M.J. andSu-NaWang,"Studiesonthe manganese and copper complexes derived from chiral Schiff base: Synthesis, structure, cytotoxicity and DNA/BSA inter- action,". J. Coord. Chem., 2019, 72(14), 2422-2436. doi: 10.1080/00958972.2019.1652275
  127. Haque, M.; Rahman, M.Z.; Pervin, M.; Kabir, M.H.; Imran, M.S. Biological screening of some ferrocene deriv- ative metal complexes. Pak. J. Biol. Sci., 2005, 8(12), 1746-1750. doi: 10.3923/pjbs.2005.1746.1750
  128. Prihantono, I.R.; Irfandi, R.; Raya, I. Warsinggih, Potential anticancer activity of Mn (II) complexes containing arginine dithiocarbamate ligand on MCF-7 breast cancer cell lines. Ann. Med. Surg., 2020, 60, 396-402. doi: 10.1016/j.amsu.2020.11.018 PMID: 33235715

Supplementary files

Supplementary Files
Action
1. JATS XML

Copyright (c) 2024 Bentham Science Publishers