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Article

Novel N-Substituted Amino Acid Hydrazone-Isatin Derivatives: Synthesis, Antioxidant Activity, and Anticancer Activity in 2D and 3D Models In Vitro

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Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, LT-50254 Kaunas, Lithuania
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Department of Physical and Inorganic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, LT-50254 Kaunas, Lithuania
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Laboratory of Drug Targets Histopathology, Institute of Cardiology, Lithuanian University of Health Sciences, Sukilėlių pr. 13, LT-50162 Kaunas, Lithuania
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Institute of Physiology and Pharmacology, Faculty of Medicine, Lithuanian University of Health Sciences, A. Mickevičiaus g. 9, LT-44307 Kaunas, Lithuania
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Life Sciences Center, Institute of Biotechnology, Vilnius University, Saulėtekio al. 7, LT-10257 Vilnius, Lithuania
*
Author to whom correspondence should be addressed.
Academic Editor: Silvie Rimpelova
Int. J. Mol. Sci. 2021, 22(15), 7799; https://doi.org/10.3390/ijms22157799
Received: 18 June 2021 / Revised: 16 July 2021 / Accepted: 19 July 2021 / Published: 21 July 2021
(This article belongs to the Special Issue Quo Vadis Cancer Research? On Molecular Mechanisms and Drug Discovery)
A series of novel mono and bishydrazones each bearing a 2-oxindole moiety along with substituted phenylaminopropanamide, pyrrolidin-2-one, benzimidazole, diphenylmethane, or diphenylamine fragments were synthesized, and their anticancer activities were tested by MTT assay against human melanoma A375 and colon adenocarcinoma HT-29 cell lines. In general, the synthesized compounds were more cytotoxic against HT-29 than A375. 3-((4-Methoxyphenyl)(3-oxo-3-(2-(2-oxoindolin-3-ylidene)hydrazinyl)propyl)amino)-N′-(2-oxoindolin-3-ylidene)propanehydrazide and (N′,N‴)-1,1′-(methylenebis(4,1-phenylene))bis(5-oxo-N′-(2-oxoindolin-3-ylidene)pyrrolidine-3-carbohydrazide) were identified as the most active compounds against HT-29 in 2D and 3D cell cultures. The same compounds showed the highest antioxidant activity among the synthesized compounds screened by ferric reducing antioxidant power assay (FRAP). Their antioxidant activity is on par with that of a well-known antioxidant ascorbic acid. View Full-Text
Keywords: hydrazone; isatin; 2-oxindole; pyrrolidin-2-one; colon cancer; melanoma; 3D tumor model; clonogenic hydrazone; isatin; 2-oxindole; pyrrolidin-2-one; colon cancer; melanoma; 3D tumor model; clonogenic
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MDPI and ACS Style

Tumosienė, I.; Jonuškienė, I.; Kantminienė, K.; Mickevičius, V.; Petrikaitė, V. Novel N-Substituted Amino Acid Hydrazone-Isatin Derivatives: Synthesis, Antioxidant Activity, and Anticancer Activity in 2D and 3D Models In Vitro. Int. J. Mol. Sci. 2021, 22, 7799. https://doi.org/10.3390/ijms22157799

AMA Style

Tumosienė I, Jonuškienė I, Kantminienė K, Mickevičius V, Petrikaitė V. Novel N-Substituted Amino Acid Hydrazone-Isatin Derivatives: Synthesis, Antioxidant Activity, and Anticancer Activity in 2D and 3D Models In Vitro. International Journal of Molecular Sciences. 2021; 22(15):7799. https://doi.org/10.3390/ijms22157799

Chicago/Turabian Style

Tumosienė, Ingrida, Ilona Jonuškienė, Kristina Kantminienė, Vytautas Mickevičius, and Vilma Petrikaitė. 2021. "Novel N-Substituted Amino Acid Hydrazone-Isatin Derivatives: Synthesis, Antioxidant Activity, and Anticancer Activity in 2D and 3D Models In Vitro" International Journal of Molecular Sciences 22, no. 15: 7799. https://doi.org/10.3390/ijms22157799

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