Main Article Content
Abstract
This article discusses the definition, history, characteristics, and properties of thiosemicarbazone ligands. These compounds exhibit significant biological activities, including antiviral, antifungal, antibacterial, antitumor, anticancer, antioxidant, and insulin-mimicking properties. Coordination of thiosemicarbazone ligands occurs through donor atoms such as sulfur, nitrogen, and sometimes a third donor atom. The study's findings indicate that the presence of amide, amine, and thione groups makes thiosemicarbazones potential polydentate ligands. The aim of this review, which employs a descriptive-analytical approach, is to provide a comprehensive definition of these ligands, discuss their characteristics, structural features, and coordination behaviors.
Keywords
Article Details
Copyright (c) 2024 Reserved for Kabul University
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
References
- Simmons G, Hobson LB, Resnick A, et al. Trans. Annu. Meet. Natl. Tuberc. Assoc. 1950, 46, 124–127.
- Casas JS, Garcia-Tasende MS, Sordo J, Main group metal complexes of semicarbazones and thiosemicarbazones, A structural review. Coord. Chem. Rev. 2000, 209, 197-261.
- Lobana, T.S., Sharma, R., Bawa, G., Khanna, S., 2009, Bonding and structure trends of thiosemicarbazone derivatives of metals—An overview. Coord. Chem. Rev. 253, 977–1055.
- Arion VB, Coordination chemistry of S-substituted isothiosemicarbazides and isothiosemicarbazones. Coord. Chem. Rev. 2019, 387, 348–397.
- Pelosi G, Thiosemicarbazone Metal Complexes: From Structure to Activity. The Open Crystallography Journal. 2010, 3, 16–28.
- Steinhagen H, The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. By Enrique Raviña. ChemMedChem. 2011, 6, 1746–1747.
- Brockman R., Thomson JR, Bell MJ, Skipper H.E, Observations on the antileukemic activity of pyridine-2-carboxaldehyde thiosemicarbazone and thiocarbohydrazone. Cancer Res. 1956, 16, 167–170.
- Finch RA, Liu MC, Cory AH, Cory JG, Sartorelli AC, Triapine (3-aminopyridine-2- carboxaldehyde thiosemicarbazone; 3-ap): an inhibitor of ribonucleotide reductase with antineoplastic activity. Adv. Enzyme Regul. 1999, 39, 3–12.
- Jansson PJ, Kalinowski DS, Lane DJR, Kovacevic Z, Seebacher NA, Fouani L, Sahni S, Merlot AM, Richardson DR, The renaissance of polypharmacology in the development of anti-cancer therapeutics: Inhibition of the “Triad of Death” in cancer by Di-2-pyridylketone thiosemicarbazones. Pharmacol Res. 2015, 100, 255–260.
- Salim KY, Danter WR, Maleki VS, Koropatnick J, COTI-2, a novel small molecule that is active against multiple human cancer cell lines in vitro and in vivo. Oncotarget. 2016, 7, 41363–41379.
- Tion YP, Duan CY, Lu ZL, You XZ, Fun HK, Kandasamy S, Crystal structure and spectroscopic studies on metal complexes containing ns donor ligands derived from S-benzyldithiocarbazate andp-dimethylaminobenzaldehyde. Polyhedron. 1996, 15, 2263–2271.
- Souza P, Matesanz IA, Fernandez V, Copper(II) and cobalt(II) complexes of methyl 2-pyridyl ketone thiosemicarbazone (HL); single-crystal structure of [Cu(HL)L]NCS. Dalton Trans. 1996, 14, 3011–3013.
- Basuli F, Peng SM, Bhattacharya S, Steric Control of the Coordination Mode of the Salicylaldehyde Thiosemicarbazone Ligand. Syntheses, Structures, and Redox Properties of Ruthenium and Osmium Complexes. Inorg. Chem. 1997, 36, 5645–5647.
- Ainscough EW, Brodie AM, Denny WA, Finlay GJ, Ranford JD, Nitrogen, sulfur and oxygen donor adducts with copper(II) complexes of antitumor 2-formylpyridinethiosemicarbazone analogs: Physicochemical and cytotoxic studies. J. Inorg. Biochem. 1998, 70, 175–185.
- Singh NK, Kumbhar AA, Pokharel YR, Yadav PN, Anticancer potency of copper(II) complexes of thiosemicarbazones. J. Inorg. Biochem. 2020, 210, 111342.
- Karatepe M, Karatas F, Antioxidant, pro-oxidant effect of the thiosemicarbazone derivative Schiff base (4-(1-phenylmethylcyclobutane-3-yl)-2-(2-hydroxybenzylidene hydra zino)thiazole) and its metal complexes on rats. Cell Biochemistry & Function. 2006, 24, 547–554.
- Gerbeleu NV, Arion VB, Burgess J. Template Synthesis of Macrocyclic Compounds, Wiley-VCH, Weinheim ; 1999.
- Malinovskii TI, Simonov YuA, Gerbeleu NV, Yampol’skaya MD, Shova SG, The structure of 3d metal complexes with ligands derived from S-alkylisothiosemicarbazides, The structure of 3d metal complexes with ligands derived from S-alkylisothiosemicarbazides. in: Problems of Crystal Chemistry, Nauka . 1985, 39–69.
- Yamazaki C, The Structure of Isothiosemicarbazones. Can. J. Chem. 1975, 53, 610–615.
- Gasparri GF, Mangio A, Nardelli M, The crystal and molecular structure of monothiosemicarbazidesilver(I) chloride. Acta Crystallographica Section B. 1968, 24, 367–374.
- Campbell MJM, Transition metal complexes of thiosemicarbazide and thiosemicarbazones. Coord. Chem. Rev. 1975, 15, 279–319.
- Livingstone SE, Metal complexes of ligands containing sulphur, selenium, or tellurium as donor atoms, Quarterly Reviews. Chemical Society. 1965, 19, 386–425.
- Akbar Ali M, Livingstone SE, Metal complexes of sulphur-nitrogen chelating agents. Coord. Chem. Rev. 1974, 13, 101–132.
- Gerasimov VN, Biushkin VN, Gerbeleu NV, Dang Do VY, Revenko MV, Belov NV. Kristallografiya. 1978, 23, 195–201.
- Khan A, Sharma P, Rajnikant Gupta VK, Padya N, Sharma R, Synthesis and crystal structure of [chlorobis(triphenylphospino) (p-chlorobenzaldehyde thiosemicarbazone)] copper(I) complex. Chem. Sci. J. 2016, 128, 185–191.
- Wang Z, Wu Yu, Fu , Li M, Tai Y, Li Y, Synthesis, structure investigation and biological evaluation of 2-thiophene N(4)-phenylthiosemicarbazone and its three metal derivatives. J. Mol. Struct. 2015, 1100, 376–383.
- Revenco MD, Simonov YuA, Duca GG, Bourosh PN, Bulmaga PI, Kukushkin VYu, Jora EI, Gdaniec M, Versatility and Reactivity of Salicylaldehyde S –Methylisothiosemicarbazone in Palladium(II) Complexes. Russ. J. Inorg. Chem. 2009, 54, 698–707.
- Şahin M, Şahin N, Bal Demirci T, Ülküseven B, Dinçer M, Soylu MS, Structural and spectroscopic characterization of a thiosemicarbazidatodioxouranium(VI) complex: A combined experimental and DFT study. Spectrochimica Acta Part A. 2015, 135, 994–1001.
References
Simmons G, Hobson LB, Resnick A, et al. Trans. Annu. Meet. Natl. Tuberc. Assoc. 1950, 46, 124–127.
Casas JS, Garcia-Tasende MS, Sordo J, Main group metal complexes of semicarbazones and thiosemicarbazones, A structural review. Coord. Chem. Rev. 2000, 209, 197-261.
Lobana, T.S., Sharma, R., Bawa, G., Khanna, S., 2009, Bonding and structure trends of thiosemicarbazone derivatives of metals—An overview. Coord. Chem. Rev. 253, 977–1055.
Arion VB, Coordination chemistry of S-substituted isothiosemicarbazides and isothiosemicarbazones. Coord. Chem. Rev. 2019, 387, 348–397.
Pelosi G, Thiosemicarbazone Metal Complexes: From Structure to Activity. The Open Crystallography Journal. 2010, 3, 16–28.
Steinhagen H, The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. By Enrique Raviña. ChemMedChem. 2011, 6, 1746–1747.
Brockman R., Thomson JR, Bell MJ, Skipper H.E, Observations on the antileukemic activity of pyridine-2-carboxaldehyde thiosemicarbazone and thiocarbohydrazone. Cancer Res. 1956, 16, 167–170.
Finch RA, Liu MC, Cory AH, Cory JG, Sartorelli AC, Triapine (3-aminopyridine-2- carboxaldehyde thiosemicarbazone; 3-ap): an inhibitor of ribonucleotide reductase with antineoplastic activity. Adv. Enzyme Regul. 1999, 39, 3–12.
Jansson PJ, Kalinowski DS, Lane DJR, Kovacevic Z, Seebacher NA, Fouani L, Sahni S, Merlot AM, Richardson DR, The renaissance of polypharmacology in the development of anti-cancer therapeutics: Inhibition of the “Triad of Death” in cancer by Di-2-pyridylketone thiosemicarbazones. Pharmacol Res. 2015, 100, 255–260.
Salim KY, Danter WR, Maleki VS, Koropatnick J, COTI-2, a novel small molecule that is active against multiple human cancer cell lines in vitro and in vivo. Oncotarget. 2016, 7, 41363–41379.
Tion YP, Duan CY, Lu ZL, You XZ, Fun HK, Kandasamy S, Crystal structure and spectroscopic studies on metal complexes containing ns donor ligands derived from S-benzyldithiocarbazate andp-dimethylaminobenzaldehyde. Polyhedron. 1996, 15, 2263–2271.
Souza P, Matesanz IA, Fernandez V, Copper(II) and cobalt(II) complexes of methyl 2-pyridyl ketone thiosemicarbazone (HL); single-crystal structure of [Cu(HL)L]NCS. Dalton Trans. 1996, 14, 3011–3013.
Basuli F, Peng SM, Bhattacharya S, Steric Control of the Coordination Mode of the Salicylaldehyde Thiosemicarbazone Ligand. Syntheses, Structures, and Redox Properties of Ruthenium and Osmium Complexes. Inorg. Chem. 1997, 36, 5645–5647.
Ainscough EW, Brodie AM, Denny WA, Finlay GJ, Ranford JD, Nitrogen, sulfur and oxygen donor adducts with copper(II) complexes of antitumor 2-formylpyridinethiosemicarbazone analogs: Physicochemical and cytotoxic studies. J. Inorg. Biochem. 1998, 70, 175–185.
Singh NK, Kumbhar AA, Pokharel YR, Yadav PN, Anticancer potency of copper(II) complexes of thiosemicarbazones. J. Inorg. Biochem. 2020, 210, 111342.
Karatepe M, Karatas F, Antioxidant, pro-oxidant effect of the thiosemicarbazone derivative Schiff base (4-(1-phenylmethylcyclobutane-3-yl)-2-(2-hydroxybenzylidene hydra zino)thiazole) and its metal complexes on rats. Cell Biochemistry & Function. 2006, 24, 547–554.
Gerbeleu NV, Arion VB, Burgess J. Template Synthesis of Macrocyclic Compounds, Wiley-VCH, Weinheim ; 1999.
Malinovskii TI, Simonov YuA, Gerbeleu NV, Yampol’skaya MD, Shova SG, The structure of 3d metal complexes with ligands derived from S-alkylisothiosemicarbazides, The structure of 3d metal complexes with ligands derived from S-alkylisothiosemicarbazides. in: Problems of Crystal Chemistry, Nauka . 1985, 39–69.
Yamazaki C, The Structure of Isothiosemicarbazones. Can. J. Chem. 1975, 53, 610–615.
Gasparri GF, Mangio A, Nardelli M, The crystal and molecular structure of monothiosemicarbazidesilver(I) chloride. Acta Crystallographica Section B. 1968, 24, 367–374.
Campbell MJM, Transition metal complexes of thiosemicarbazide and thiosemicarbazones. Coord. Chem. Rev. 1975, 15, 279–319.
Livingstone SE, Metal complexes of ligands containing sulphur, selenium, or tellurium as donor atoms, Quarterly Reviews. Chemical Society. 1965, 19, 386–425.
Akbar Ali M, Livingstone SE, Metal complexes of sulphur-nitrogen chelating agents. Coord. Chem. Rev. 1974, 13, 101–132.
Gerasimov VN, Biushkin VN, Gerbeleu NV, Dang Do VY, Revenko MV, Belov NV. Kristallografiya. 1978, 23, 195–201.
Khan A, Sharma P, Rajnikant Gupta VK, Padya N, Sharma R, Synthesis and crystal structure of [chlorobis(triphenylphospino) (p-chlorobenzaldehyde thiosemicarbazone)] copper(I) complex. Chem. Sci. J. 2016, 128, 185–191.
Wang Z, Wu Yu, Fu , Li M, Tai Y, Li Y, Synthesis, structure investigation and biological evaluation of 2-thiophene N(4)-phenylthiosemicarbazone and its three metal derivatives. J. Mol. Struct. 2015, 1100, 376–383.
Revenco MD, Simonov YuA, Duca GG, Bourosh PN, Bulmaga PI, Kukushkin VYu, Jora EI, Gdaniec M, Versatility and Reactivity of Salicylaldehyde S –Methylisothiosemicarbazone in Palladium(II) Complexes. Russ. J. Inorg. Chem. 2009, 54, 698–707.
Şahin M, Şahin N, Bal Demirci T, Ülküseven B, Dinçer M, Soylu MS, Structural and spectroscopic characterization of a thiosemicarbazidatodioxouranium(VI) complex: A combined experimental and DFT study. Spectrochimica Acta Part A. 2015, 135, 994–1001.