Review
Early View Article
DOI DOI: 10.62063/rev-43

Lanthanide(III) complexes of 4-aminoantipyrine Schiff base derivatives and their antimicrobial applications: A review

Ngozi Patricia Ebosie1, Emmanuel Ikenna Nnanabu1, Christogonus Oudney Akalezi2, Gerald Okwuchi Onyedika 2, Nnaemeka Nnaji3, Martin Onwu Chidozie Ogwuegbu2
  1. 1 Department of Chemistry, Imo State University, Owerri, Imo State
  2. 2 Department of Chemistry, Federal University of Technology, Owerri, Imo State, Nigeria
  3. 3 Centre of Excellence in Carbon-based Fuels, School of Chemical and Minerals Engineering, North-West University, Potchefstroom Campus, Private Bag X6001, Potchefstroom 2520,

Abstract

Lanthanides also known as lanthanoids (inner transition elements) constitute an interesting group of fifteen elements which are predominantly trivalent and exhibit similar physicochemical properties. These elements occupy the 4f inner transition series (lanthanides) in the periodic table. Over the years, the investigation of lanthanide(III) complexes has generated increased interest due to their interesting biological, photo-physical and magnetic properties. Lanthanide(III) complexes of Schiff bases of 4-aminontipyrine derivatives constitute another class of compounds that show remarkably interesting coordination and bio-inorganic chemistry. 4-Aminoantipyrine and its derivatives have formed stable complexes with many lanthanide metal ions. This literature review examines the lanthanide(III) complexes of 4-aminoantipyrine derivatives which were synthesized and characterized using various spectro-analytical techniques from which various structures were proposed. Antimicrobial applications of some of these lanthanide(III) complexes synthesized over the years were reported. This review serves as a guide for the development of new lanthanide(III) complexes of 4-aminoantipyrine derivatives as potential antibacterial and antifungal agents as well as other applications.

How to Cite

Ebosie, N. P., Nnanabu, E. I., Akalezi, C. O., Onyedika , G. O., Nnaji, N., & Ogwuegbu, M. O. C. (2026). Lanthanide(III) complexes of 4-aminoantipyrine Schiff base derivatives and their antimicrobial applications: A review. EUCHEMBIOJ Reviews, 2(1), e26006. https://doi.org/10.62063/rev-43
Endnote/Zotero/Mendeley (RIS) BibTeX

References

  1. Abbas, A. K. (2015). Lanthanide ions complexes of 2-(4-aminoantipyrine)-L-tryptophane (AAT): Preparation, identification and antimicrobial assay. Iraqi Journal of Science, 56(4C), 3297–3309.
  2. Abd El-Wahab, Z. H., Mashaly, M. M., & Faheim, A. A. (2005). Synthesis and characterization of cobalt(II), cerium(III) and dioxouranium(IV) complexes of 2,3-dimethyl-1-phenyl-4-salicylidene-3-pyrazolin-5-one mixed ligand complexes, pyrolytic products and biological activities. Chemical Papers, 59(1), 25–36.
  3. Abid, K. K. (2013). Pentadentate N₂O₃ Schiff base complexes of rare earth metals. American Journal of Applied Chemistry, 1(5), 87–91. https://doi.org/10.11648/j.ajac.20130105.12
  4. Abraham, M., & Radhakrishnan, P. K. (1990). Rare earth perchlorate complexes of 4-(2′,4′-dihydroxyphenylazo)antipyrine. Journal of the Indian Chemical Society, 67(11), 900–901.
  5. Agarwal, R. K. (1978a). Magneto, spectral and thermal studies of lanthanide(III) chloride complexes of 4[N-benzoyl)amino]antipyrine. Journal of the Institute of Chemists (India), 60, 55.
  6. Agarwal, R. K. (1978b). Synthesis and spectroscopic investigations of complexes of lanthanide(III) perrhenates with 4[(N-acetyl)amino]antipyrine. Journal of the Institute of Chemists (India), 63, 121.
  7. Agarwal, R. K. (1991). Synthesis and spectroscopic investigations of complexes of lanthanides(III) nitrates and thiocyanates with 4[(N-acetyl)amino]antipyrine. Polish Journal of Chemistry, 65, 1211.
  8. Agarwal, R. K. (1992). Synthesis and structural investigations of lanthanide(III) perchlorates complexes of 4[(N-acetyl)amino]antipyrine. Afinidad, 437, 30.
  9. Agarwal, R. K., & Agarwal, H. (1995). Magneto, spectral and thermal investigations of some lanthanide(III) complexes of 4[(N-cinnamalideneamino)antipyrine]. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 25(5), 715–737. https://doi.org/10.1080/15533179508218258
  10. Agarwal, R. K., & Agarwal, H. (2001). The synthesis, structure and bonding in some lanthanide(III) coordination compounds of 4-[(N-furfural)amino]antipyrine. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 31(2), 263–276. https://doi.org/10.1081/SIM-100002046
  11. Agarwal, R. K., & Kumar, A. (2011). Synthesis, physicochemical and biological properties of some mixed ligand complexes of trivalent lanthanides. Journal of Applied Chemical Research, 17, 41–58.
  12. Agarwal, R. K., & Kumar, V. (2010). Effect of anions and pyridine on stereochemistry of lanthanide coordination compounds. Phosphorus, Sulfur, Silicon and Related Elements, 185(7), 1469–1483. https://doi.org/10.1080/10426500903085201
  13. Agarwal, R. K., & Prakash, B. (2005). Effect of anions and diphenyl sulfoxide on lanthanide coordination compounds. Transition Metal Chemistry, 30, 696–705. https://doi.org/10.1007/s11243-005-5717-4
  14. Agarwal, R. K., & Sarin, R. K. (1994). Synthesis and characterization of lanthanide(III) perchlorate complexes. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 24(2), 185–199. https://doi.org/10.1080/00945719408000104
  15. Agarwal, R. K., & Sarin, R. K. (1993a). Magneto and spectral investigation of lanthanide complexes. Polish Journal of Chemistry, 67(7), 1209–1217.
  16. Agarwal, R. K., & Sarin, R. K. (1993b). Synthesis and spectroscopic studies of lanthanide complexes with Schiff bases. Polish Journal of Chemistry, 67(11), 1925–1931.
  17. Agarwal, R. K., & Singh, G. (2003). Preparation and spectral studies of oxovanadium(IV) complexes. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 16(8), 1183–1196. https://doi.org/10.1080/00945718608071390
  18. Agarwal, R. K., Agarwal, H., & Manglik, A. K. (1996). Chelating behavior of antipyrine semicarbazone toward lanthanide ions. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 26(7), 1163–1177. https://doi.org/10.1080/00945719608004359
  19. Agarwal, R. K., Agarwal, H., Goel, N., & Sindhu, S. K. (2001). Synthesis and spectral studies of lanthanide complexes. Bulletin of the Chemical Society of Ethiopia, 15(1), 79–84. https://doi.org/10.4314/bcse.v15i1.71965
  20. Agarwal, R. K., Garg, R. K., & Sindhu, S. K. (2005). Magneto-spectral investigations of lanthanide complexes. Journal of the Iranian Chemical Society, 2(3), 203–211. https://doi.org/10.1007/BF03245923
  21. Aghav, B. D., & Lokhande, R. S. (2016). Study of ternary complexes of lanthanum. Journal of Chemical and Pharmaceutical Research, 8(6), 380–386.
  22. Aguilar-Llanos, E., Carrera-Pacheco, S. E., González-Pastor, R., Zúñiga-Miranda, J., Rodríguez-Pólit, C., Romero-Benavides, J. C., & Heredia-Moya, J. (2022). Synthesis and biological activity of Schiff base derivatives. Chemistry Proceedings, 12(1), 43. https://doi.org/10.3390/ecsoc-26-13684
  23. Alam, M. S., & Lee, D. (2021). Molecular structure and quantum chemical analyses of azomethine derivative. Journal of Molecular Structure, 1227, 129512. https://doi.org/10.1016/j.molstruc.2020.129512
  24. Alaudeen, M., & Radhakrishnan, P. K. (1990). Rare earth nitrate complexes of antipyrine derivatives. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 20(6), 673–679. https://doi.org/10.1080/00945719008048164
  25. Al-Zoubi, W. (2013). Biological activities of Schiff bases and their complexes: A review. International Journal of Organic Chemistry, 3, 73–95. https://doi.org/10.4236/ijoc.2013.33A008
  26. Arora, K., & Burman, K. (2009). Lanthanide(III) metal complexes with nitrogen donor ligands: A review. Reviews in Inorganic Chemistry, 29(2), 83–101. https://doi.org/10.1515/revic.2009.29.2.83
  27. Aydoğan, F., Öcal, N., Turgut, Z., & Yolaçan, Ç. (2001). Transformation of aldiamines derived from pyrrole-2-carbaldehyde. Bulletin of the Korean Chemical Society, 22(5), 476–480. https://doi.org/10.1002/chin.200215134
  28. Bao, G. (2020). Lanthanide complexes for drug delivery and therapeutics. Journal of Luminescence, 228, 117622. https://doi.org/10.1016/j.jlumin.2020.117622
  29. Bünzli, J. G. (2010). Lanthanide luminescence for biomedical analyses and imaging. Chemical Reviews, 110(5), 2729–2755. https://doi.org/10.1021/cr900362e
  30. Bünzli, J. G., & Eliseeva, S. V. (2013). Intriguing aspects of lanthanide luminescence. Chemical Science, 4, 1939–1949. https://doi.org/10.1039/c3sc22126a
  31. Cârâc, A. (2017). Biological and biomedical applications of lanthanide compounds: A mini review. Proceedings of the Romanian Academy Series B, 19(2), 69–74.
  32. Chacko, J., Prabhakaran, C. D., & Nair, C. G. R. (1975). Complexes of lanthanides with 4-aminoantipyrine. Indian Journal of Chemistry, 13(4), 411–413. https://doi.org/10.1002/chin.197529341
  33. Chacko, J., Prabhakaran, C. P., & Nair, C. G. R. (1976). Lanthanide nitrate complexes of 4-aminoantipyrine. Journal of Inorganic and Nuclear Chemistry, 38(8), 1555–1556. https://doi.org/10.1016/0022-1902(76)90027-0
  34. Chakraborthy, I., Rai, H. C., Goel, N., & Hashmi, N. M. (2002). Anionic effect on lanthanide(III) coordination compounds. Asian Journal of Chemistry, 14(2), 1035–1040.
  35. Chakraborti, I. (2003a). Synthesis and characterization of nine-coordinated lanthanide(III) complexes. Oriental Journal of Chemistry, 19(3).
  36. Chakraborti, I. (2003b). Synthesis and characterization of lanthanide(III) complexes of antipyrine derivatives. Asian Journal of Chemistry, 15(2), 813–820.
  37. Chakraborti, I. (2003c). Synthesis and characterization of lanthanide coordination compounds. Oriental Journal of Chemistry, 19(3).
  38. Chakraborti, I. (2003d). Physicochemical studies on nine-coordinated lanthanide complexes. Oriental Journal of Chemistry, 19(1).
  39. Chakraborti, I., & Goel, N. (2003). Synthesis and characterization of lanthanide complexes. Asian Journal of Chemistry, 15(2), 679–686.
  40. Chan, W. T. K., & Wong, W. (2014). Recent development in lanthanide coordination compounds for biomedical imaging. Polyhedron, 83, 150–158. https://doi.org/10.1016/j.poly.2014.05.054
  41. Chaturvedi, K., Malvi, D., Dhangar, M., Bajpai, H., Mohapatra, R. K., Srivastava, A. K., & Verma, S. (2022). Recent advances in green synthesis of lanthanide-based organic compounds. IntechOpen. https://doi.org/10.5772/intechopen.104716
  42. Chaudhary, S. (2012). Synthetic and spectral studies of nitrito complexes. Recent Research in Science and Technology, 4(5), 49–52.
  43. Chaudhary, S. (2016). Synthetic and spectral studies of isothiocyanato complexes. Green Chemistry and Technology Letters, 2(3), 144–150. https://doi.org/10.18510/gctl.2016.234
  44. Chopra, J. R., Uppal, D., Arora, U. S., & Gupta, S. K. (2000). Synthesis and spectral studies of Cu(II) complexes. Asian Journal of Chemistry, 12, 1277–1281.
  45. Cota, I., Marturano, V. S., & Tylkowski, B. (2019). Lanthanide complexes as antibacterial and antifungal agents. Coordination Chemistry Reviews, 396, 49–71. https://doi.org/10.1016/j.ccr.2019.05.019
  46. Cotruvo, J. A. (2019). The chemistry of lanthanides in biology. ACS Central Science, 5(9), 1496–1506. https://doi.org/10.1021/acscentsci.9b00642
  47. Cotton, S., & Harrowfield, J. (2012). Lanthanides: Biological activity and medical applications. https://doi.org/10.1002/9781119951438.eibc2091
  48. Chundawat, N. S., Jadoun, S., Zarrintaj, P., & Chauhan, N. P. S. (2021). Lanthanide complexes as anticancer agents: A review. Polyhedron, 207, 115387. https://doi.org/10.1016/j.poly.2021.115387
  49. Cunha, S., Oliveira, S. M., Rodrigues, M. T., Bastos, R. M., Ferrari, J., De Oliveira, C. M. A., Kato, L., Napolitano, H. B., Vencato, I., & Lariucci, C. (2005). Structural studies of 4-aminoantipyrine derivatives. Journal of Molecular Structure, 752(1–3), 32–39. https://doi.org/10.1016/j.molstruc.2005.05.016
  50. Deshmukh, P., Soni, K. P., Kankonya, A., Halve, A. K., & Dixit, R. (2015). 4-Aminoantipyrine: A significant tool for the synthesis of biologically active Schiff bases and metal complexes. International Journal of Pharmaceutical Sciences Review and Research, 34(1), 162–170.
  51. Dhabale, R. H., Shah, S., Tiwari, N., & Patani, P. (2022). Review of semicarbazone, thiosemicarbazone, and their transition metal complexes and their biological activities. Journal of Pharmaceutical Negative Results, 13(5), 2416–2424. https://doi.org/10.47750/pnr.2022.13.S05.377
  52. Dong-Dong, Y., Yan Lan, I., & Lu, S. (2007). Synthesis and characterization of diorganotin(IV) Schiff base complexes and their in vitro antitumor activity. Chinese Journal of Chemistry, 19, 1136–1140. https://doi.org/10.1002/cjoc.20010191122
  53. Donia, A. M., & El-Saied, F. A. (1988). Complexes of manganese(II), cobalt(II) and nickel(II) with antipyrine Schiff base derivatives. Polyhedron, 7(21), 2149–2153. https://doi.org/10.1016/S0277-5387(00)81794-5
  54. Døssing, A. (2005). Luminescence from lanthanide(III) ions in solution. European Journal of Inorganic Chemistry, 1425–1434. https://doi.org/10.1002/ejic.200401043
  55. Ebosie, N. P., Ogwuegbu, M. O. C., Onyedika, G. O., & Onwumere, F. C. (2021). Biological and analytical applications of Schiff base metal complexes derived from salicylidene-4-aminoantipyrine. Journal of the Iranian Chemical Society, 18(12), 3145–3175. https://doi.org/10.1007/s13738-021-02265-1
  56. Eliseeva, S. V., & Bünzli, J. G. (2010). Lanthanide luminescence for functional materials and biosciences. Chemical Society Reviews, 39(1), 189–227. https://doi.org/10.1039/b905604c
  57. Erbaş, A., Dikim, S., Arslan, F., Bodur, O. C., Arslan, S., Özdemir, F., & Sarı, N. (2025). Schiff bases from 4-aminoantipyrine: In silico, antimicrobial, and anticancer effects and glucose biosensor applications. Bioinorganic Chemistry and Applications. https://doi.org/10.1155/bca/2786064
  58. Evans, C. H. (1990). Past, present, and possible future clinical applications of the lanthanides. In Biochemistry of the lanthanides (Vol. 8). Springer. https://doi.org/10.1007/978-1-4684-8748-0_9
  59. Faulkner, S., Pope, S. J. A., & Burton-Pye, B. (2005). Lanthanide complexes for luminescence imaging applications. Applied Spectroscopy Reviews, 40(1), 1–31. https://doi.org/10.1081/asr-200038308
  60. Ghosh, P., Dey, S. K., Ara, M. H., Karim, K. M. R., & Islam, A. B. M. N. (2021). A review on synthesis and applications of Schiff bases and their metal complexes. Egyptian Journal of Chemistry, 62, 532–547. https://doi.org/10.21608/ejchem.2019.13741.1852
  61. Guo, F., Bi, C. F., Fan, Y. H., Xiao, Y., He, X. T., & Xu, J. K. (2007). Synthesis, crystal structure and antibacterial properties of antipyrine derivatives. Asian Journal of Chemistry, 19(3), 1846–1852.
  62. Harraf, E., Bikas, R., Soltani, B., & Lis, T. (2024). Synthesis, spectroscopic properties and crystal structure of lanthanide coordination compounds. Journal of Molecular Structure, 1316, 139013. https://doi.org/10.1016/j.molstruc.2024.139013
  63. Herlan, C., & Bräse, S. (2020). Lanthanide conjugates as versatile instruments for therapy and diagnostics. Dalton Transactions, 49, 2397–2402. https://doi.org/10.1039/c9dt04851k
  64. Hua, L., Li, W., Chen, Y., Liang, K., Cai, H., Wang, J., Wang, S., Yin, T., & Liang, L. (2020). Hexanuclear Nd(III) complex with antitumor and antifungal activity. Applied Organometallic Chemistry, 35(2), e6081. https://doi.org/10.1002/aoc.6081
  65. Hussein, K. A., & Shaalan, N. (2022). Synthesis, spectroscopy and biological activity of lanthanide complexes. Chemical Methodologies, 6(2), 103–113. https://doi.org/10.22034/chemm.2022.2.3
  66. Hussein, K. A., Mahdi, S., & Shaalan, N. (2023). Synthesis and bioactivity of new lanthanide complexes. Baghdad Science Journal, 20(2), 469–482. https://doi.org/10.21123/bsj.2022.7088
  67. Hussein, K. A., Shaalan, N., & Faeq, M. (2024a). Microwave-assisted preparation and biological activities of Schiff bases. Indonesian Journal of Chemistry, 24(5), 1470–1480. https://doi.org/10.22146/ijc.95419
  68. Hussein, K. A., Shaalan, N., Lafta, A. K., & Al-Akeedi, J. M. (2024b). Preparation and biological activity of lanthanide complexes. Indonesian Journal of Chemistry, 24(2), 358–369. https://doi.org/10.22146/ijc.87262
  69. Jadhav, S., Malavekar, D., Mohite, R., Shaikh, S., Kadam, K., Pawaskar, P., Kim, J., & Lee, N. (2025). A critical review of lanthanum and lanthanum-based materials: Synthesis, applications, and challenges. Rare Metals, 44, 5201–5232. https://doi.org/10.1007/s12598-024-03204-8
  70. Jastrzab, R., Nowak, M., Skrobańska, M., Tolińska, A., Zabiszak, M., Gabryel, M., Marciniak, L., & Kaczmarek, M. T. (2019). DNA as a target for lanthanide(III) complexes. Coordination Chemistry Reviews, 382, 145–159. https://doi.org/10.1016/j.ccr.2018.12.018
  71. Jing, F., & Zhang, H. (2013). Hybrid materials based on lanthanide organic complexes: A review. Chemical Society Reviews, 42, 387–410. https://doi.org/10.1039/c2cs35069f
  72. John, M., & Radhakrishnan, P. K. (1978). Synthesis and physicochemical studies of iodide complexes of lanthanides and yttrium with 4-aminoantipyrine. Asian Journal of Chemistry, 4(3), 666–669.
  73. Joseph, M., Nair, M. K. M., & Radhakrishnan, P. K. (1995). Complexes of yttrium and lanthanide bromides with antipyrine derivatives. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 25(8), 1331–1343. https://doi.org/10.1080/15533179508014678
  74. Monteiro, J. H. S. K. (2020). Recent advances in luminescence imaging of biological systems using lanthanide complexes. Molecules, 25(9), 2089. https://doi.org/10.3390/molecules25092089
  75. Kaczmarek, M. T., Zabiszak, M., Nowak, M., & Jastrzab, R. (2018). Lanthanide Schiff base complexes in cancer diagnosis and therapy. Coordination Chemistry Reviews, 370, 42–54. https://doi.org/10.1016/j.ccr.2018.05.012
  76. Kaushik, S. D. (2017). Synthesis and characterization of lanthanide(III) perchlorate complexes. Oriental Journal of Chemistry, 33(5), 2318–2323. https://doi.org/10.13005/ojc/330521
  77. Kostova, I. (2005). Lanthanides as anticancer agents. Current Medicinal Chemistry, 5(6), 591–602. https://doi.org/10.2174/156801105774574694
  78. Krishnan, M. A., Saranyaparvathi, S., Raksha, C., Vrinda, B., & Geethu, G. C. (2022). Transition metal complexes of antipyrine derivatives and antimicrobial applications. Russian Journal of Coordination Chemistry, 48(11), 696–724. https://doi.org/10.1134/S1070328422110082
  79. Lacopetta, D., Ceramella, J., Catalano, A., Manconda, A., Di Giulio, F., Saturnino, C., Longoria, P., & Sinicropi, M. S. (2023). Metal complexes with Schiff bases as antimicrobials and catalysts. Inorganics, 11(8), 320. https://doi.org/10.3390/inorganics11080320
  80. Lama, P., Aijaz, A., Neogi, S., Barbour, L. J., & Bharadwaj, P. K. (2010). Microporous La(III) metal-organic framework: Synthesis and gas adsorption studies. Crystal Growth & Design, 10(8), 3410–3417. https://doi.org/10.1021/cg100078b
  81. Leelavathy, C., & Anthony, S. A. (2013). Synthesis and biological activity of metal complexes with antipyrine derivatives. Spectrochimica Acta Part A, 113, 346–355. https://doi.org/10.1016/j.saa.2013.04.055
  82. Li, J., Tian, X., Bao, W., Zhao, J., & Jiang, Z. (2025). Advances in lanthanide-based luminescent materials. Discover Applied Sciences, 7, 1310. https://doi.org/10.1007/s42452-025-07862-w
  83. Madanhire, T., Coetzee, L. C., Adeyinka, A. S., Horne, T. K., Rashamuse, T. J., & Magwa, N. P. (2024). Lanthanides and their complexes in cancer diagnosis and therapy. Journal of Drug Delivery Science and Technology, 105, 106561. https://doi.org/10.1016/j.jddst.2024.106561
  84. Madhu, N. T., Radhakrishnan, P. K., Grüne, M., Weinberger, P., & Linert, W. (2003). Antipyrine derivatives with transition metals. Reviews in Inorganic Chemistry, 23(1), 1–24. https://doi.org/10.1515/revic.2003.23.1.1
  85. Marchetti, F., Pettinari, C., Nicola, C., Tombesi, A., & Pettinari, R. (2019). Coordination chemistry of pyrazolone-based ligands. Coordination Chemistry Reviews, 401, 213069. https://doi.org/10.1016/j.ccr.2019.213069
  86. Matczak, P., & Domagała, M. (2017). Heteroatom and solvent effects on molecular properties. Journal of Molecular Modeling, 23, 268. https://doi.org/10.1007/s00894-017-3435-4
  87. Maurya, R. C., Mishra, D. D., Trivedi, P. K., Mukherjee, S., & Shrivastava, P. K. (1992). Mixed-ligand derivatives of zinc complexes. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 22(4), 403–414. https://doi.org/10.1080/15533179208020474
  88. Miao, R., Shuoliang, L., Rudong, Y., Lan, Y., & Wenbing, Y. (2003). Synthesis and crystal structure of Schiff base pyrazolone. Indian Journal of Chemistry, 2A, 318–321.
  89. Mir, A., Ain, Q., Qadir, T., Malik, A. Q., Jan, S., Shahverdi, S., & Nabi, S. A. (2023). Semicarbazone-derived metal complexes in biomedicine. Journal of Molecular Structure, 1295, 136216. https://doi.org/10.1016/j.molstruc.2023.136216
  90. Mishra, D. P., Sahu, P. K., Acharya, B., Mishra, S. P., & Bhati, S. (2024). Azo dyes and metal complexes for antimicrobial therapies. Results in Chemistry, 10, 101712. https://doi.org/10.1016/j.rechem.2024.101712
  91. Misra, S., Gagnani, M., Shukla, R., & Iqbal, M. (2004). Biological and clinical aspects of lanthanide complexes. Bioinorganic Chemistry and Applications, 2, 155–192. https://doi.org/10.1155/s1565363304000111
  92. Mohanan, K., Athira, C. J., Sindhu, Y., & Sujamol, M. S. (2009). Lanthanide nitrate complexes with antipyrine derivatives. Journal of Rare Earths, 27(5), 705–710. https://doi.org/10.1016/S1002-0721(08)60320-8
  93. Mukhtar, S. S., Hassan, A. S., Moray, N. M., Hafez, T. S., Hassaneen, H. M., & Saleh, F. M. (2021). Schiff bases: Synthesis, reactions, and biological activities. Egyptian Journal of Chemistry, 64(11), 6541–6554. https://doi.org/10.21608/ejchem.2021.79736.3920
  94. Muraleedharan, J. E., & Viswanathan, K. P. (2025). Microwave-assisted synthesis of lanthanide complexes. Oriental Journal of Chemistry, 41(1), 254–263. https://doi.org/10.13005/ojc/410130
  95. Muraleedharan Nair, M. K., & Radhakrishnan, P. K. (1997). Thermal decomposition of lanthanide perchlorate complexes. Thermochimica Acta, 292(1–2), 115–122. https://doi.org/10.1016/S0040-6031(97)00016-6
  96. Muraleedharan Nair, M. K., & Radhakrishnan, P. K. (1995a). Thermal decomposition of lanthanum complexes. Thermochimica Acta, 261, 141–149. https://doi.org/10.1016/0040-6031(95)02313-q
  97. Muraleedharan Nair, M. K., & Radhakrishnan, P. K. (1995b). Chloride and bromide complexes of lanthanides. Proceedings of the Indian Academy of Sciences, 107, 19–24. https://doi.org/10.1007/BF02841433
  98. Muraleedharan Nair, M. K., & Radhakrishnan, P. K. (1993). Lanthanide nitrate complexes. Polyhedron, 12(10), 1227–1230. https://doi.org/10.1016/S0277-5387(00)88215-7
  99. Muraleedharan Nair, M. K., & Radhakrishnan, P. K. (1996a). Rare earth perchlorate complexes. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 26(2), 263–275. https://doi.org/10.1080/00945719608004262
  100. Muraleedharan Nair, M. K., & Radhakrishnan, P. K. (1996b). Iodide complexes of lanthanides. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 26(3), 529–541. https://doi.org/10.1080/00945719608005122
  101. Muraleedharan Nair, M. K., & Radhakrishnan, P. K. (1996c). Yttrium and lanthanide nitrate complexes. Proceedings of the Indian Academy of Sciences, 108(4), 345–350. https://doi.org/10.1007/BF02871244
  102. Muraleedharan Nair, M. K., & Radhakrishnan, P. K. (1995c). Iodide complexes of lanthanides with antipyrine derivatives. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 25(7), 1077–1089. https://doi.org/10.1080/15533179508218295
  103. Nair, C. G. R., & Chacko, J. (1978). Complexes of 4-aminoantipyrine with lanthanide thiocyanates. Current Science, 47(16), 568–570.
  104. Nair, M. K. M., & Radhakrishnan, P. K. (1995). Rare earth perchlorate complexes of antipyrine derivatives. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 25(1), 57–70. https://doi.org/10.1080/15533179508218202
  105. Patyal, M., Kaur, K., Bala, N., Gupta, N., & Malik, A. K. (2023). Innovative lanthanide complexes: Shaping the future of cancer chemotherapy. Journal of Trace Elements in Medicine and Biology, 80, 127277. https://doi.org/10.1016/j.jtemb.2023.127277
  106. Philip, S., Thomas, P. S., & Mohanan, K. (2018). Synthesis, fluorescence studies, antioxidative and α-amylase inhibitory activity of lanthanide complexes. Journal of the Serbian Chemical Society, 83(5), 561–574. https://doi.org/10.2298/jsc180918010p
  107. Piotr, P., & Bogumit, B. (2002). Spectroscopic studies and PM3 semiempirical calculations of Schiff bases. Biopolymers, 67, 61–69. https://doi.org/10.1002/bip.10043
  108. Prajapati, K., Prajapati, P., Brahmbhatt, M., & Vora, J. (2018). Lanthanide complexes and their biological importance: A review. Research Journal of Life Sciences, Bioinformatics, Pharmaceutical and Chemical Sciences. https://doi.org/10.26479/2018.04.05.56
  109. Prasad, S., Agarwal, R. K., & Kumar, A. (2011). Mixed ligand complexes of lanthanide(III): Synthesis and biological evaluation. Journal of the Iranian Chemical Society, 8(3), 825–839. https://doi.org/10.1007/BF03245913
  110. Purohit, S., & Bhojak, N. (2013). Absorption spectra of lanthanide(III) ions. Research and Reviews: Journal of Chemistry, 2(2), 1–3.
  111. Radhakrishnan, M., & Radhakrishnan, P. K. (1998). Bromide complexes of lanthanides with antipyrine derivatives. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 28(3), 339–353. https://doi.org/10.1080/00945719809349359
  112. Radhakrishnan, P. K. (1985). Lanthanide nitrate complexes of antipyrine derivatives. Inorganica Chimica Acta, 110(3), 211–213. https://doi.org/10.1016/S0020-1693(00)82309-9
  113. Radhakrishnan, P. K. (1986a). Lanthanide perchlorate complexes of antipyrine derivatives. Polyhedron, 5(4), 995–998. https://doi.org/10.1016/S0277-5387(00)80141-2
  114. Radhakrishnan, P. K. (1986b). Rare earth iodide complexes of antipyrine derivatives. Indian Journal of Chemistry, 25A, 90–91.
  115. Radhakrishnan, P. K. (1992). Lanthanide nitrate complexes of antipyrine derivatives. Proceedings of the Kerala Science Congress.
  116. Radhakrishnan, P. K. (1995). Lanthanide nitrate complexes of azo-antipyrine derivatives. Journal of the Less Common Metals, 107(1), 45–50. https://doi.org/10.1016/0022-5088(85)90239-5
  117. Radhakrishnan, P. S., & Indrasenan, P. (1989). Lanthanide perchlorate and nitrate complexes. Indian Journal of Chemistry, 28A, 234–236.
  118. Radhakrishnan, P. S., & Indrasenan, P. (1990). Lanthanide nitrate and perchlorate complexes. Journal of the Indian Chemical Society, 67(3), 243–245.
  119. Rahim, S., Antony, A., Lukose, G., Mohanan, K., Joe, I. H., & Joseyphus, R. S. (2015). Metal chelates of antipyrine derivatives: Spectral and computational study. Oriental Journal of Chemistry, 31(4). https://doi.org/10.13005/ojc/310412
  120. Rajendran, G. N., & Sreeletha, G. S. (2001). Coordination behavior of Schiff base ligands. Asian Journal of Chemistry, 13(3), 1142–1146.
  121. Rajendran, G. N., & Sreeletha, G. S. (2002). Mixed ligand complexes of lanthanide(III). Asian Journal of Chemistry, 14(3), 1639–1645.
  122. Raman, N., Johnson Raja, S., & Sakthivel, A. (2009). Transition metal complexes with Schiff base ligands: A review. Journal of Coordination Chemistry, 62(5), 691–709. https://doi.org/10.1080/00958970802326179
  123. Raman, N., Johnson Raja, S., Joseph, J., & Dhaveethu Raja, J. (2007a). DNA cleavage study of Schiff base complexes. Journal of the Chilean Chemical Society, 52(2), 1138–1141. https://doi.org/10.4067/S0717-97072007000200004
  124. Raman, N., Raja, S. J., Joseph, J., & Raja, J. D. (2007b). Oxovanadium(IV) Schiff base complexes. Russian Journal of Coordination Chemistry, 33(1), 7–11. https://doi.org/10.1134/S1070328407010022
  125. Ribeiro da Silva, M. A. V., Ribeiro, M. D. M. C., Monte, M. J. S., Monte Gonçalves, J. M., & Fernandes, E. M. R. (1997). Energetics of metal–ligand bonding. Journal of the Chemical Society, Dalton Transactions, 1257–1262. https://doi.org/10.1039/a607745e
  126. Rijulal, G., & Indrasenan, P. (1995). Lanthanide complexes with antipyrine derivatives. Journal of Rare Earths, 25(6), 670–673. https://doi.org/10.1016/S1002-0721(08)60004-6
  127. Rijulal, G., Krishnakumar, A., Anoop Krishnan, K., & Geetha Nambian, M. K. (2024). Physicochemical and biological properties of lanthanide complexes. Asian Journal of Chemistry, 36(6), 1245–1250. https://doi.org/10.14233/ajchem.2024.31337
  128. Sakthivel, A., Jeyasubramanian, K., Thangagiri, B., & Dhaveethu Raja, J. (2020). Schiff base metal complexes derived from antipyrine. Journal of Molecular Structure, 1222, 128885. https://doi.org/10.1016/j.molstruc.2020.128885
  129. Salah, H. S., Dagne, A. K., Endalkachew, A. M., & Bekele, A. (2021). Antibacterial activity of antipyrine derivatives. American Journal of Bioscience and Bioengineering, 9(1), 8–12. https://doi.org/10.11648/j.bio.20210901.12
  130. Shankar, G., Premkumar, R. R., & Ramalingam, S. K. (1986). Schiff base complexes of lanthanides. Polyhedron, 5(4), 991–994. https://doi.org/10.1016/S0277-5387(00)80140-0
  131. Singh, L., Sharma, A., & Sindhu, S. K. (1999a). Structure and bonding of lanthanide complexes. Asian Journal of Chemistry, 11(4), 1445–1450.
  132. Singh, L., Tyagi, N., Dhaka, N., & Sindhu, S. K. (1999b). Spectral and thermal studies of lanthanide complexes. Asian Journal of Chemistry, 11(2), 503–508.
  133. Singh, R., Sharma, K., & Singh, R. V. (2010). Rare earth metal complexes with Schiff bases. Journal of Sulfur Chemistry, 31(1), 61–70. https://doi.org/10.1080/17415990903173529
  134. Srivastava, A. K., Srivastava, A., & Jain, P. C. (1989). Lanthanide complexes of antipyrine derivatives. Indian Journal of Chemistry, 28A, 79–80.
  135. Suresh, M. S., & Prakash, V. (2011). Chelates of Schiff base derived from antipyrine. E-Journal of Chemistry, 8(3), 1408–1416. https://doi.org/10.1155/2011/254018
  136. Tamanna, & Mutreja, V. (2022). Biomedical applications of lanthanide complexes. Materials Today: Proceedings. https://doi.org/10.1016/j.matpr.2022.12.065
  137. Tang, K., Zhang, J. J., Zhang, D. H., Ren, N., Yan, L. Z., & Li, Y. (2013). Crystal structures and thermodynamic properties of lanthanide complexes. Journal of Chemical Thermodynamics, 56, 38–48. https://doi.org/10.1016/j.jct.2012.06.032
  138. Teran, R., Guevara, R., Mora, J., Dobronski, L., Barreiro-Costa, O., Beske, T., Pérez-Barrera, J., Araya-Maturana, R., Rojas-Silva, P., Poveda, A., & Heredia-Moya, J. (2019). Antimicrobial and antioxidant activities of antipyrine derivatives. Molecules, 24(15), 2696. https://doi.org/10.3390/molecules24152696
  139. Thomas, M. K., Muraleedharan Nair, M. K., & Radhakrishnan, P. K. (1995). Rare earth iodide complexes of antipyrine derivatives. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 25(3), 471–479. https://doi.org/10.1080/15533179508218235
  140. Thompson, K. H., & Orvig, C. (2006). Lanthanide compounds for therapeutic and diagnostic applications. Chemical Society Reviews, 35, 499. https://doi.org/10.1039/b606622b
  141. Toe, R. D., Termini, J., & Gray, H. B. (2016). Lanthanides in cancer diagnosis and therapy. Journal of Medicinal Chemistry, 59(13), 6012–6024. https://doi.org/10.1021/acs.jmedchem.5b01975
  142. Veg, E., Hashmi, K., Ahmad, M. I., Joshi, S., Khan, A. R., & Khan, T. (2025). Biological applications and mechanistic insights of thiosemicarbazone metal complexes: A review. Nature Sciences, 5(1–2), e70005. https://doi.org/10.1002/ntls.70005
  143. Vinodkumar, C. R., & Radhakrishnan, P. (1997a). Complexes of yttrium and lanthanide perchlorates with antipyrine derivatives. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 27(9), 1347–1355. https://doi.org/10.1080/00945719708000162
  144. Vinodkumar, C. R., & Radhakrishnan, P. K. (1996). Complexes of yttrium and lanthanide perchlorate with antipyrine derivatives. Proceedings of the Indian Academy of Sciences (Chemical Sciences), 108(3), 303. https://doi.org/10.1007/BF02870070
  145. Vinodkumar, C. R., & Radhakrishnan, P. K. (1997b). Lanthanide perchlorate complexes with antipyrine derivatives. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 27(9), 1365–1372. https://doi.org/10.1080/00945719708000164
  146. Vinodkumar, C. R., & Radhakrishnan, P. K. (1997c). Lanthanide perchlorate complexes with substituted antipyrine derivatives. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 27(9), 1357–1364. https://doi.org/10.1080/00945719708000163
  147. Vinodkumar, C. R., Muraleedharan Nair, M., & Radhakrishnan, P. (2000). Thermal studies on lanthanide nitrate complexes. Journal of Thermal Analysis and Calorimetry, 61(1), 143–149. https://doi.org/10.1023/A:1010120909987
  148. Wang, L., Zhao, Z., Wei, C., Wei, H., Liu, Z., Bian, Z., & Huang, C. (2019). Electroluminescence of lanthanide complexes: A review. Advanced Optical Materials, 7(11), 1801256. https://doi.org/10.1002/adom.201801256
  149. Wang, M., Kitagawa, Y., & Hasegawa, Y. (2024). Development of lanthanide complexes for biomedical applications. Chemistry – An Asian Journal, e202400038. https://doi.org/10.1002/asia.202400038
  150. Wang, Q., Zheng, G., & Yang, C. (2001). Synthesis and characterization of lanthanide nitrate complexes. Shandong Jiancai Xueyuan Xuebao, 15(1), 34–36.
  151. Wei, C., Ma, L., Wei, H. B., Liu, Z. W., Bian, Z. Q., & Huang, C. H. (2018). Advances in luminescent lanthanide complexes. Science China Technological Sciences, 61. https://doi.org/10.1007/s11431-017-9212-7
  152. Werts, M. H. V. (2005). Making sense of lanthanide luminescence. Science Progress, 88(2), 101–131. https://doi.org/10.3184/003685005783238435
  153. Woods, M., Kovacs, Z., & Sherry, A. D. (2002). Lanthanide complexes as therapeutic and diagnostic agents. Journal of Supramolecular Chemistry, 2(1–3), 1–15. https://doi.org/10.1016/S1472-7862(02)00072-2
  154. Wu, H. C., Thanasekaran, P., & Tsai, C. H. (2006). Self-assembly and photophysical properties of Schiff base complexes. Inorganic Chemistry, 45(1), 295–303. https://doi.org/10.1021/ic051235k
  155. Xi, P. X., Xu, Z. H., Liu, X. H., Chen, F. J., Zeng, Z. Z., Zhang, X. W., & Liu, Y. (2009). Antioxidant and DNA binding studies of lanthanide complexes. Journal of Fluorescence, 19(1), 63–72. https://doi.org/10.1007/s10895-008-0381-7
  156. Xian, T., Meng, Q., Gao, F., Hu, M., & Wang, X. (2023). Functionalization of lanthanide complexes for biomedical applications. Coordination Chemistry Reviews. https://doi.org/10.1016/j.ccr.2022.214866
  157. Yu, Q., Tang, Y., & Tan, M. (2002). Rare earth complexes with Schiff base ligands. Journal of Rare Earths, 20(5), 385–387.
  158. Zahra, S. B., Khan, A., Ahmed, N., Raique, M., Fatima, L., Khan, I., Hussain, J., Khalid, S., Ogaly, H. A., Ahmed, M. M., Al-Harrasi, A., & Shafiq, Z. (2025). Biological activities of thiosemicarbazone complexes. Journal of Molecular Structure, 1322, 140511. https://doi.org/10.1016/j.molstruc.2024.140511
  159. Zhang, J., Li, Y., Hao, X., Zhang, Q., Yang, K., Li, L., Wang, S., & Li, X. (2011). Therapeutic and diagnostic applications of lanthanides. Mini Reviews in Medicinal Chemistry, 11(8), 678–694. https://doi.org/10.2174/138955711796268804
  160. Zhao, M., Zhong, C., Barrett, A. G. M., & Hoffman, B. M. (2005). Magnetic properties of Schiff base complexes. Journal of the American Chemical Society, 127(27), 9769–9775. https://doi.org/10.1021/ja043811