Login Register Cart 0
Generic placeholder image

Anti-Cancer Agents in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1871-5206
ISSN (Online): 1875-5992

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

Imidazolidine Derivatives in Cancer Research: What is known?

Author(s): Auvani Antunes da Silva Júnior, Marina Galdino da Rocha Pitta, Mardonny Bruno de Oliveira Chagas, Moacyr Jesus Barreto de Melo Rêgo, Michelle Melgarejo da Rosa and Maira Galdino da Rocha Pitta*

Volume 22, Issue 7, 2022

Published on: 27 July, 2021

Page: [1272 - 1277] Pages: 6

DOI: 10.2174/1871520621666210727113639

Price: $65

conference banner
Abstract

It is well known that cancer is the second leading cause of death worldwide. Due to this fact, new results for the treatment of cancer are constantly being introduced and verified. Imidazolidine derivatives regulate cell cycle progression and DNA stability. Structurally, a heterocyclic nucleus favors a direct DNA interaction and therefore, control of the DNA replication process. This review aims not only to discuss the role of imidazolidines in cancer therapy but also explore the functionality of such agents in the future aspects of cancer prognosis and treatment. Convincing data from 1996 to 2021 has presented imidazolidine derivatives as a relevant therapeutic tool to modulate cancer progression and malignancy. Here we highlight these aspects in a variety of cell lines, cancer types, involving in vitro and in vivo techniques.

Keywords: Apoptosis, cancer, cell cycle, DNA, imidazolidine, anticancer.

« Previous Next »
Graphical Abstract

[1]
INCA, Instituto Nacional de Câncer. Estimativa 2018: Incidência de câncer no Brasil / Instituto Nacional de Câncer José Alencar Gomes da Silva. Coordenação de Prevenção e Vigilância. – Rio de Janeiro: INCA 2017. http://www.inca.gov.br/estimativa/2018/estimativa-2018.pdf
[2]
Bray, F.; Ferlay, J.; Soerjomataram, I.; Siegel, R.L.; Torre, L.A.; Jemal, A. Global cancer statistics 2018: GLOBOCAN estimates of inci-dence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J. Clin., 2018, 68(6), 394-424.https://onlinelibrary.wiley.com/doi/full/10.3322/caac.21492
[3]
Sierra, M.S.; Soerjomataram, I.; Antoni, S.; Laversanne, M.; Piñeros, M.; de Vries, E.; Forman, D. Cancer patterns and trends in Central and South America. Cancer Epidemiol., 2016, 44(Suppl. 1), S23-S42.
[http://dx.doi.org/10.1016/j.canep.2016.07.013] [PMID: 27678320]
[4]
Freitas, R.M.; Rodrigues, A.M.X.; Matos, A.F. Jr; Oliveira, G.A.L. Risk factors and main cytopathological changes in oral cancer: A litera-ture review. RBAC, 2016, 48(1), 13-18.
[5]
Czorny, R.C.N.; Pinto, M.E.; Pompeo, D.A.; Bereta, D.; Cardoso, L.V.; Silva, D.M. Prostate cancer risk factors: Population from a basic health unit. Cogitare enferm, 2017, 22(4), 1-10.
[6]
Matos-Rocha, T.J.; Lima, M.C.A.; Veras, D.L.; Santos, A.F.; Silva, A.L.; Almeida Júnior, A.S.A.; Pitta-Galdino, M.R.; Pitta, I.R.; Pitta, M.G.R.; Alves, L.C.F.; Brayner, F.A. In vivo study of schistosomicidal action of (Z)-1-(2-chloro-6-fluoro-benzyl)-5-thioxo-4-(2,4,6-trimethoxy-benzylidene)-imidazolidin-2-one. Braz. J. Biol., 2020, 80(1), 187-189.
[http://dx.doi.org/10.1590/1519-6984.190062] [PMID: 31166369]
[7]
Santos, S.L.F.D.; Alves, H.H.D.S.; Pessoa, C.V.; Saraiva, H.S.T.T.; Barros, K.B.N.T. Evidências do cuidado farmacêutico na prática clínica da oncologia. Revista da Faculdade de Ciências Médicas de Sorocaba, 2018, 20(2), 77-81.
[http://dx.doi.org/10.23925/1984-4840.2018v20i2a4]
[8]
Cho, S.; Kim, S.H.; Shin, D. Recent applications of hydantoin and thiohydantoin in medicinal chemistry. Eur. J. Med. Chem., 2019, 164, 517-545.
[http://dx.doi.org/10.1016/j.ejmech.2018.12.066] [PMID: 30622025]
[9]
Munder, A.; Moskovitz, Y.; Redko, B.; Levy, A.R.; Ruthstein, S.; Gellerman, G.; Gruzman, A. Antiproliferative effect of novel aminoacri-dine-based compounds. Med. Chem., 2015, 11(4), 373-382.
[http://dx.doi.org/10.2174/1573406411666141217110946] [PMID: 25524547]
[10]
Kwan, J.Y.; Nyhof-Young, J.; Catton, P.; Giuliani, M.E. Mapping the future: Towards oncology curriculum reform in undergraduate medi-cal education at a Canadian medical school. Int. J. Radiat. Oncol. Biol. Phys., 2015, 91(3), 669-677.
[http://dx.doi.org/10.1016/j.ijrobp.2014.11.017] [PMID: 25583687]
[11]
da Silva, L.C.A.; Signor, A.C.; Pilati, A.C.L.; Dalfollo, B.R.; Oliveira, D.R. Educational approach to cancer patients: Strategies for guidance on chemotherapy treatment. Rev. Bras. Cancerol., 2019, 65(1), e.-06305
[http://dx.doi.org/10.32635/2176-9745.RBC.2019v65n1.305]
[12]
Leite, M.A.C.; Nogueira, D.A.; Terra, F.S. Aspectos sociais e clínicos de pacientes oncológicos de um serviço quimioterápico. Rev Rene., 2015, 16(1), 38-45.
[http://dx.doi.org/10.15253/2175-6783.2015000100006]
[13]
National Comprehensive Cancer Network (NCCN). NCCN guidelines. [Internet]. Philadelphia; c 2017. Available from: https://www.nccn.org/professionals/physician_gls/f_guidelines.asp [cited 2017 May 6]
[14]
European Society for Medical Oncology (ESMO) Clinical practice guidelines [Internet]. Lugano: ESMO; c 2017. Available from: http://www.esmo.org/Guidelines [cited 2017 May 5].
[15]
Kaliks, R.A.; Matos, T.F.; Silva, V.A.; Barros, L.H.C. Diferenças no tratamento sistêmico do câncer no Brasil: meu SUS é diferente do teu SUS. Braz J Oncol, 2017, 13(44), 1-12.
[16]
Hand, C.M.; Kim, S.; Waldow, S.M. Overview of radiobiology.Washington CM, Leaver D, editores. Principles and practice of radiation therapy, 2nd ed; Mosby: Missouri, 2004, pp. 55-85.
[17]
Paredes, W.E.; Andrade, D. Geraldo, Radioterapia Oncológica: efectos y repercusión en la cavidad bucal: Evaluación in vitro de la composición y microdureza de los tejidos duros de la ... sometidos a la radioterapia (Spanish Edition) , 2017.
[18]
Spezzia, S. O uso do bolus na radioterapia. Revista da Faculdade de Ciências Médicas de Sorocaba, 2016, 18(4), 183-186.
[19]
Guedes, J.B.R.; Guerra, M.R.; Alvim, M.M.; Leite, I.C.G. Factors associated with adherence and persistence to hormonal therapy in wom-en with breast cancer. Rev. Bras. Epidemiol., 2017, 20(4), 636-649.
[http://dx.doi.org/10.1590/1980-5497201700040007] [PMID: 29267749]
[20]
Pellegrini, I.; Sarradon-Eck, A.; Soussan, P.B.; Lacour, A.C.; Largillier, R.; Tallet, A.; Tarpin, C.; Julian-Reynier, C. Women’s perceptions and experience of adjuvant tamoxifen therapy account for their adherence: Breast cancer patients’ point of view. Psychooncology, 2010, 19(5), 472-479.
[http://dx.doi.org/10.1002/pon.1593] [PMID: 19507263]
[21]
Liu, H.; Yang, Z.; Pan, Z. Synthesis of highly substituted imidazolidine-2,4-dione (hydantoin) through Tf2O-mediated dual activation of Boc-protected dipeptidyl compounds. Org. Lett., 2014, 16(22), 5902-5905.
[http://dx.doi.org/10.1021/ol502900j] [PMID: 25357005]
[22]
Šmit, B.M.; Pavlović, R.Z. Three-step synthetic pathway to fused bicyclic hydantoins involving a selenocyclization step. Tetrahedron, 2015, 71(7), 1101-1108.
[http://dx.doi.org/10.1016/j.tet.2014.12.088]
[23]
Castro, N.R.; Marçal, L.L. Estudo da síntese de derivados de imidazolidinas-2, 4-dionas e obtenção de novos derivados. Revista Eletrônica Perspectivas da Ciência e Tecnologia,, 2018, 10, 150. ISSN: 1984-5693
[24]
Caterina, M.C.; Perillo, I.A.; Boiani, L.; Pezaroglo, H.; Cerecetto, H.; González, M.; Salerno, A. Imidazolidines as new anti-Trypanosoma cruzi agents: Biological evaluation and structure-activity relationships. Bioorg. Med. Chem., 2008, 16(5), 2226-2234.
[http://dx.doi.org/10.1016/j.bmc.2007.11.077] [PMID: 18083035]
[25]
Rogawski, M.A.; Löscher, W. The neurobiology of antiepileptic drugs for the treatment of nonepileptic conditions. Nat. Med., 2004, 10(7), 685-692.
[http://dx.doi.org/10.1038/nm1074] [PMID: 15229516]
[26]
Moguilewsky, M.; Bertagna, C.; Hucher, M. Pharmacological and clinical studies of the antiandrogen anandron. J. Steroid Biochem., 1910, 1954(27), 871-875.
[27]
Bakalova, A.G.; Buyukliev, R.T.; Nikolova, A.T.; Momekov, G.T. Synthesis, characterization and cytotoxic activity of new palladium complexes with 3-Thiolanespiro- 5“-Hydantoin and 4-Thio-1hTretrahydropyranespiro-5”-Hydantoin. Ame. J. Pharm. Res., 2014.
[28]
Matos-Rocha, T.J.; Alves de Lima, M.C.; Lauro da Silva, A.; Ferreira de Oliveira, J.; Gouveia, A.L.A.; Ribeiro da Silva, V.B.; Alves de Almeida Júnior, A.S.; Brayner, F.A.; Cardoso, P.R.G.; Pitta-Galdino, M.R.; Pitta, I.R.; Rêgo, M.J.B.M.; Alves, L.C.; Pitta, M.G.R. Synthesis and biological evaluation of novel imidazolidine derivatives as candidates to schistosomicidal agent. Rev. Inst. Med. Trop. São Paulo, 2017, 59, e8.
[29]
López-López, L.I.; de Loera-Carrera, D.A.; de Jesús Rivera-Ávalos, E.; Saénz-Galindo, A. Hydantoin and derivatives as structures of importance in medicinal chemistry: Recent advances. Affinity: J. Theoret. Appl. Chem., 2018, 75(584), 279-289.
[30]
Sharma, V.; Crankshaw, C.L.; Piwnica-Worms, D. Effects of multidrug resistance (MDR1) P-glycoprotein expression levels and coordina-tion metal on the cytotoxic potency of multidentate (N4O2) (ethylenediamine)bis[propyl(R-benzylimino)]metal(III) cations. J. Med. Chem., 1996, 39(18), 3483-3490.
[http://dx.doi.org/10.1021/jm950823c] [PMID: 8784446]
[31]
Kavitha, C.V.; Nambiar, M.; Ananda Kumar, C.S.; Choudhary, B.; Muniyappa, K.; Rangappa, K.S.; Raghavan, S.C. Novel derivatives of spirohydantoin induce growth inhibition followed by apoptosis in leukemia cells. Biochem. Pharmacol., 2009, 77(3), 348-363.
[http://dx.doi.org/10.1016/j.bcp.2008.10.018] [PMID: 19014909]
[32]
Ghosh, M.; Bhattacharya, S.; Sadhu, U.; Dutta, S.; Sanyal, U. Evaluation of β-tethymustine, a new anticancer compound, in murine tumour models. Cancer Lett., 1997, 119(1), 7-12.
[http://dx.doi.org/10.1016/S0304-3835(97)00244-9] [PMID: 18372515]
[33]
Mukherjee, A.; Dutta, S.; Chashoo, G.; Bhagat, M.; Saxena, A.K.; Sanyal, U. Evaluation of fluoren-NU as a novel antitumor agent. Oncol. Res., 2009, 17(9), 387-396.
[http://dx.doi.org/10.3727/096504009788912516] [PMID: 19718945]
[34]
El-Sawy, E.; Bassyouni, F.; Abu-Bakr, S.; Rady, H.; Abdlla, M. Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivatives. Acta Pharm., 2010, 60(1), 55-71.
[35]
Shah, A.; Nosheen, E.; Munir, S.; Badshah, A.; Qureshi, R.; Rehman, Z.U.; Muhammad, N.; Hussain, H. Characterization and DNA bind-ing studies of unexplored imidazolidines by electronic absorption spectroscopy and cyclic voltammetry. J. Photochem. Photobiol. B, 2013, 120, 90-97.
[http://dx.doi.org/10.1016/j.jphotobiol.2012.12.015] [PMID: 23474470]
[36]
Sakthivel, K.M.; Guruvayoorappan, C. Acacia ferruginea inhibits tumor progression by regulating inflammatory mediators-(TNF-a, iNOS, COX-2, IL-1β, IL-6, IFN-γ, IL-2, GM-CSF) and pro-angiogenic growth factor- VEGF. Asian Pac. J. Cancer Prev., 2013, 14(6), 3909-3919.
[http://dx.doi.org/10.7314/APJCP.2013.14.6.3909] [PMID: 23886206]
[37]
Kavitha, C.V.; Nambiar, M.; Narayanaswamy, P.B.; Thomas, E.; Rathore, U.; Ananda Kumar, C.S.; Choudhary, B.; Rangappa, K.S.; Raghavan, S.C. Propyl-2-(8-(3,4-difluorobenzyl)-2¢,5¢-dioxo-8-azaspiro[bicyclo[3.2.1] octane-3,4¢-imidazolidine]-1¢-yl) acetate induces apoptosis in human leukemia cells through mitochondrial pathway following cell cycle arrest. PLoS One, 2013, 8(7), e69103.
[http://dx.doi.org/10.1371/journal.pone.0069103] [PMID: 23922684]
[38]
Cižeková, L.; Grolmusová, A.; Ipóthová, Z.; Barbieriková, Z.; Brezová, V.; Hunáková, L.; Imrich, J.; Janovec, L.; Dovinová, I.; Paulíková, H. Novel 3,6-bis(imidazolidine)acridines as effective photosensitizers for photodynamic therapy. Bioorg. Med. Chem., 2014, 22(17), 4684-4693.
[http://dx.doi.org/10.1016/j.bmc.2014.07.013] [PMID: 25096820]
[39]
Koczor, C.A.; Shokolenko, I.N.; Boyd, A.K.; Balk, S.P.; Wilson, G.L.; LeDoux, S.P. Mitochondrial DNA damage initiates a cell cycle ar-rest by a Chk2-associated mechanism in mammalian cells. J. Biol. Chem., 2009, 284(52), 36191-36201.
[http://dx.doi.org/10.1074/jbc.M109.036020] [PMID: 19840931]
[40]
Ivanenkov, Y.A.; Vasilevski, S.V.; Beloglazkina, E.K.; Kukushkin, M.E.; Machulkin, A.E.; Veselov, M.S.; Chufarova, N.V.; Chernyagi-nab, E.S.; Vanzcool, A.S.; Zyk, N.V.; Skvortsov, D.A.; Khutornenko, A.A.; Rusanov, A.L.; Tonevitsky, A.G.; Dontsova, O.A.; Majouga, A.G. Design, synthesis and biological evaluation of novel potent MDM2/p53 small-molecule inhibitors. Bioorg. Med. Chem. Lett., 2015, 25(2), 404-409.
[http://dx.doi.org/10.1016/j.bmcl.2014.09.070] [PMID: 25479770]
[41]
Dar, A.M. Shamsuzzaman; Khan, S. Spectroscopic, viscositic, DNA binding and cytotoxic studies of newly synthesized steroidal imid-azolidines. J. Fluoresc., 2016, 26(2), 639-649.
[http://dx.doi.org/10.1007/s10895-015-1750-7] [PMID: 26698876]
[42]
Lafayette, E.A.; de Almeida, S.M.V.; Cavalcanti Santos, R.V.; de Oliveira, J.F.; Amorim, C.A.D.C.; da Silva, R.M.F.; Pitta, M.G.D.R.; Pitta, I.D.R.; de Moura, R.O.; de Carvalho Júnior, L.B.; de Melo Rêgo, M.J.B.; de Lima, M.D.C.A. Synthesis of novel indole derivatives as promising DNA-binding agents and evaluation of antitumor and antitopoisomerase I activities. Eur. J. Med. Chem., 2017, 136, 511-522.
[http://dx.doi.org/10.1016/j.ejmech.2017.05.012] [PMID: 28531811]
[43]
Aboeldahab, A.M.A.; Beshr, E.A.M.; Shoman, M.E.; Rabea, S.M.; Aly, O.M. Spirohydantoins and 1,2,4-triazole-3-carboxamide deriva-tives as inhibitors of histone deacetylase: Design, synthesis, and biological evaluation. Eur. J. Med. Chem., 2018, 146, 79-92.
[http://dx.doi.org/10.1016/j.ejmech.2018.01.021] [PMID: 29396364]
[44]
Cherneva, E.; Atanasova, M.; Buyukliev, R.; Tomovic, K.; Smelcerovic, Z.; Bakalova, A.; Smelcerovic, A. 3¢-Methyl-4-thio-1H-tetrahydropyranspiro-5¢-hydantoin platinum complex as a novel potent anticancer agent and xanthine oxidase inhibitor. Arch. Pharm. (Weinheim), 2020, 353(7), e2000039.
[http://dx.doi.org/10.1002/ardp.202000039] [PMID: 32329137]
[45]
Yao, C.H.; Hsieh, T.C.; Song, J.S.; Lee, J.C. Design, synthesis and anticancer evaluation of β-carboline-1-one hydantoins. Future Med. Chem., 2020, 12(3), 183-192.
[http://dx.doi.org/10.4155/fmc-2019-0276] [PMID: 31813284]
[46]
Ali, W.; Spengler, G.; Kincses, A.; Nové, M.; Battistelli, C.; Latacz, G.; Starek, M.; Dąbrowska, M.; Honkisz-Orzechowska, E.; Romanelli, A.; Rasile, M.M.; Szymańska, E.; Jacob, C.; Zwergel, C.; Handzlik, J. Discovery of phenylselenoether-hydantoin hybrids as ABCB1 efflux pump modulating agents with cytotoxic and antiproliferative actions in resistant T-lymphoma. Eur. J. Med. Chem., 2020, 200, 112435.
[http://dx.doi.org/10.1016/j.ejmech.2020.112435] [PMID: 32505850]
[47]
Upadhyay, N.; Tilekar, K.; Loiodice, F.; Anisimova, N.Y.; Spirina, T.S.; Sokolova, D.V.; Smirnova, G.B.; Choe, J.Y.; Meyer-Almes, F.J.; Pokrovsky, V.S.; Lavecchia, A.; Ramaa, C.S. Pharmacophore hybridization approach to discover novel pyrazoline-based hydantoin analogs with anti-tumor efficacy. Bioorg. Chem., 2021, 107, 104527.
[http://dx.doi.org/10.1016/j.bioorg.2020.104527] [PMID: 33317839]

Rights & Permissions Print Cite
Article Metrics
20
1
© 2024 Bentham Science Publishers | Privacy Policy