Anticancer Compounds Based on Isatin-Derivatives: Strategies to Ameliorate Selectivity and Efficiency

被引:103
作者
Ferraz de Paiva, Raphael Enoque [1 ]
Vieira, Eduardo Guimaraes [1 ]
Rodrigues da Silva, Daniel [1 ]
Wegermann, Camila Anchau [1 ,2 ]
Costa Ferreira, Ana Maria [1 ]
机构
[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Sao Paulo, Brazil
[2] Univ Fed Fluminense, Niteroi, RJ, Brazil
基金
巴西圣保罗研究基金会;
关键词
oxindoles; isatin; anticancer activity; metallodrugs; mechanisms of action; improvement strategies;
D O I
10.3389/fmolb.2020.627272
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In this review we compare and discuss results of compounds already reported as anticancer agents based on isatin-derivatives, metalated as well as non-metallated. Isatin compounds can be obtained from plants, marine animals, and is also found in human fluids as a metabolite of amino acids. Its derivatives include imines, hydrazones, thiosemicarbazones, among others, already focused on numerous anticancer studies. Some of them have entered in pre-clinical and clinical tests as antiangiogenic compounds or inhibitors of crucial proteins. As free ligands or coordinated to metal ions, such isatin derivatives showed promising antiproliferative properties against different cancer cells, targeting different biomolecules or organelles. Binding to metal ions usually improves its biological properties, indicating a modulation by the metal and by the ligand in a synergistic process. They also reveal diverse mechanisms of action, being able of binding DNA, generating reactive species that cause oxidative damage, and inhibiting selected proteins. Strategies used to improve the efficiency and selectivity of these compounds comprise structural modification of the ligands, metalation with different ions, syntheses of mononuclear and dinuclear species, and use of inserted or anchored compounds in selected drug delivery systems.
引用
收藏
页数:24
相关论文
共 132 条
[1]   Design, synthesis and pharmacophoric model building of novel substituted nicotinic acid hydrazones with potential antiproliferative activity [J].
Abdel-Aziz, Hatem A. ;
Aboul-Fadl, Tarek ;
Al-Obaid, Abdul-Rahman M. ;
Ghazzali, Mohamed ;
Al-Dhfyan, Abdullah ;
Contini, Alessandro .
ARCHIVES OF PHARMACAL RESEARCH, 2012, 35 (09) :1543-1552
[2]   Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: Design, synthesis, QSAR analysis and anticancer activity [J].
Alafeefy, Ahmed M. ;
Ashour, Abdelkader E. ;
Prasad, Onkar ;
Sinha, Leena ;
Pathak, Shilendra ;
Alasmari, Fatimah A. ;
Rishi, Arun K. ;
Abdel-Aziz, Hatem A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 :191-201
[3]   Bis[2-(2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamidato-kappa O-3, N-2, S]-nickel(II) dimethylformamide monosolvate [J].
Ali, Amna Qasem ;
Eltayeb, Naser Eltaher ;
Teoh, Siang Guan ;
Salhin, Abdussalam ;
Fun, Hoong-Kun .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 :M538-U363
[4]   Preparation and structural characterization of nickel(II), cobalt(II), zinc(II) and tin(IV) complexes of the isatin Schiff bases of S-methyl and S-benzyldithiocarbazates [J].
Ali, M. Akbar ;
Mirza, A. H. ;
Abu Bakar, Hjh Junaidah Hj ;
Bernhardt, Paul V. .
POLYHEDRON, 2011, 30 (04) :556-564
[5]   Synthesis of Oxindole-Based Bioorganometallic Kinase Inhibitors Incorporating One or More Ferrocene Groups [J].
Amin, Jahangir ;
Chuckowree, Irina S. ;
Wang, Minghua ;
Tizzard, Graham J. ;
Coles, Simon J. ;
Spencer, John .
ORGANOMETALLICS, 2013, 32 (20) :5818-5825
[6]   Design and development of Isatin-triazole hydrazones as potential inhibitors of microtubule affinity-regulating kinase 4 for the therapeutic management of cell proliferation and metastasis [J].
Aneja, Babita ;
Khan, Nashrah Sharif ;
Khan, Parvez ;
Queen, Aarfa ;
Hussain, Afzal ;
Rehman, Md. Tabish ;
Alajmi, Mohamed F. ;
El-Seedi, Hesham R. ;
Ali, Sher ;
Hassan, Md. Imtaiyaz ;
Abid, Mohammad .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 163 :840-852
[7]   Sunitinib in patients with metastatic renal cell carcinoma: Birmingham experience [J].
Ansari, Jawaher ;
Fatima, Arfeen ;
Fernando, Kieran ;
Collins, Stuart ;
James, Nicholas D. ;
Porfiri, Emilio .
ONCOLOGY REPORTS, 2010, 24 (02) :507-510
[8]   Heterobinuclear copper(II)-platinum(II) complexes with oxindolimine ligands: Interactions with DNA, and inhibition of kinase and alkaline phosphatase proteins [J].
Aranda, Esther Escribano ;
da Luz, Juliana Silva ;
Oliveira, Carla Columbano ;
Divina Petersen, Philippe A. ;
Petrilli, Helena M. ;
da Costa Ferreira, Ana M. .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2020, 203
[9]   Design, syntheses, characterization, and cytotoxicity studies of novel heterobinuclear oxindolimine copper(II)-platinum(II) complexes [J].
Aranda, Esther Escribano ;
Matias, Tiago Araujo ;
Araki, Koiti ;
Vieira, Adriana Pires ;
de Mattos, Elaine Andrade ;
Colepicolo, Pio ;
Luz, Carolina Portela ;
Navarro Marques, Fabio Luiz ;
da Costa Ferreira, Ana Maria .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2016, 165 :108-118
[10]   Synthesis, biological activity and docking study of some new isatin Schiff base derivatives [J].
Azizian, Javad ;
Mohammadi, Mohammad K. ;
Firuzi, Omidreza ;
Razzaghi-asl, Nima ;
Miri, Ramin .
MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (11) :3730-3740