Synthesis and biological evaluation of 2,4,6-trinitroaniline derivatives as potent antitumor agents

Basit Öğe Kaydı
dc.authoridGungor, Tugba/0000-0001-5261-1856
dc.authoridComert Onder, Ferah/0000-0002-4037-1979
dc.authoridAY, Mehmet/0000-0002-1095-1614
dc.contributor.authorHacioglu, Nelin
dc.contributor.authorGungor, Tugba
dc.contributor.authorTokay, Esra
dc.contributor.authorOnder, Ferah Comert
dc.contributor.authorAy, Mehmet
dc.contributor.authorKockar, Feray
dc.date.accessioned2025-01-27T20:31:49Z
dc.date.available2025-01-27T20:31:49Z
dc.date.issued2020
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractNitro group-containing compounds are well known as effective anticancer drugs. The aim of the study is to synthesize a series of trinitroaniline derivatives to determine their potential antitumor activities on diverse cancer cell models, anti-apoptotic and anti-metastatic features on hepatoma cells. The anti-proliferative studies show that IC(50)values ofN-phenyl-2,4,6-trinitroaniline,N-(2,4,6-trinitrophenyl)naphthalen-1-amine,N-(2,4,6-trinitrophenyl)naphthalen-2-amine,N-(3-nitrophenyl)-2,4,6-trinitroaniline were similar to IC(50)value of cisplatin in Hep3B cells. In fact, IC(50)value ofN-(3,5-difluorophenyl)-2,4,6-trinitroaniline is better than cisplatin. In addition, all compounds could decrease the expression of the cell cycle checkpoint protein cyclin D1. To investigate the effect of compounds on the apoptotic pathway, mRNA and protein expressions of Bcl-2 and Bax were analyzed with qRT-PCR and Western blot. Annexin V staining assay, apoptotic mRNA and protein analysis indicate thatN-isopropyl-2,4,6-trinitroaniline,N-(2,4,6-trinitrophenyl)-5-methylisoxazole-3-amine,N-(3-nitrophenyl)-2,4,6-trinitroaniline,N-(4-nitrophenyl)-2,4,6-trinitroaniline induce intrinsic apoptosis by increasing the ratio of Bax/Bcl-2 expression. In addition, colony formation and wound healing assays confirmed that these compounds also inhibit the metastatic activity of Hep3B cells. 2,4,6-Trinitroaniline derivatives, especiallyN-(3-nitrophenyl)-2,4,6-trinitroaniline might be used as candidate for the development of new antitumor drugs.
dc.description.sponsorshipScientific and Technological Research Council of Turkey-TUBITAK [110T754-113Z706]; Balkesir University Scientific Research Project [2017-024]
dc.description.sponsorshipThis work was supported by Scientific and Technological Research Council of Turkey-TUBITAK grant numbers 110T754-113Z706, and Balkesir University Scientific Research Project Grant Number 2017-024.
dc.identifier.doi10.1007/s00706-020-02690-7
dc.identifier.endpage1641
dc.identifier.issn0026-9247
dc.identifier.issn1434-4475
dc.identifier.issue10
dc.identifier.scopus2-s2.0-85092558927
dc.identifier.scopusqualityQ2
dc.identifier.startpage1629
dc.identifier.urihttps://doi.org/10.1007/s00706-020-02690-7
dc.identifier.urihttps://hdl.handle.net/20.500.12428/23280
dc.identifier.volume151
dc.identifier.wosWOS:000577249800004
dc.identifier.wosqualityQ4
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer Wien
dc.relation.ispartofMonatshefte Fur Chemie
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectCytotoxicity
dc.subjectTrinitroaniline
dc.subjectSynthesis
dc.subjectNitro compound
dc.subjectApoptosis
dc.subjectHepatocellular carcinoma
dc.titleSynthesis and biological evaluation of 2,4,6-trinitroaniline derivatives as potent antitumor agents
dc.typeArticle

Dosyalar

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu