The cellular effects of novel triazine nitrogen mustards in glioblastoma LBC3, LN-18 and LN-229 cell lines

Krętowski, Rafał; Drozdowska, Danuta; Kolesińska, Beata; Kamiński, Zbigniew J.; Frączyk, Justyna; Cechowska-Pasko, Marzanna

doi:10.1007/s10637-018-0712-8

Cited by 8 publications

(7 citation statements)

References 34 publications

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“…Preparation However, due to their impermanence, they are easily dealkylated [28,29]. Use of DABCO as a tertiary amine enables derivatives containing the 2-chloroethylamine substituent characteristic of nitrogen Scheme 1 Multi-stage synthesis of nitrogen mustard derivatives 7a-f containing dipeptide substituents on the 1,3,5-triazine ring mustard to be obtained as a result of the bicyclic ring opening process [24,25]. Finally, six new analogues of nitrogen mustards 7 with different dipeptide substituents on the 1,3,5-triazine ring were prepared (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and cellular effects of novel 1,3,5-triazine derivatives in DLD and Ht-29 human colon cancer cell lines

et al. 2019

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Summary This study provides new information on the cellular effects of 1,3,5-triazine nitrogen mustards with different peptide groups in DLD and Ht-29 human colon cancer cell lines. A novel series of 2,4,6-trisubstituted 1,3,5-triazine derivatives bearing 2-chloroethyl and oligopeptide moieties was designed and synthesized. The most cytotoxic derivative was triazine with an Ala-Ala-OMe substituent on the ring (compound 7b). This compound induced time- and dose-dependent cytotoxicity in the DLD-1 and HT-29 colon cancer cell lines. The triazine derivative furthermore induced apoptosis through intracellular signaling pathway attenuation. Compound 7b may be a candidate for further evaluation as a chemotherapeutic agent against colorectal cancer.

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Section: Resultsmentioning

confidence: 99%

“…Compound C caused apoptosis, necrosis and strong cell shrinkage, reducing the number of apoptotic bodies. It can therefore be considered as a candidate for further evaluation as a chemotherapeutic agent against glioma cells [25].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and cellular effects of novel 1,3,5-triazine derivatives in DLD and Ht-29 human colon cancer cell lines

et al. 2019

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“…N'phenyl-4,6-bis(arylamino)-1,3,5-triazine-2-carbohydrazides derivatives 27-29 (Figure 8) were evaluated for their ability to inhibit Rad6B ubiquitin conjugation in the human cancer cell lines: OV90 (ovarian cancer), H1299 (human non-small cell lung carcinoma), A549, MCF-7, MDA-MB231, and HT-29 (colon cancer). For all of the examined compounds lower than for TZ9 IC50 values were obtained (3.3-22 µM) (Figure 8) [32].…”

Section: Ubiquitin Conjugating Enzyme Inhibitorsmentioning

confidence: 86%

Recent Advances in the Biological Activity of s-Triazine Core Compounds

Maliszewski

Drozdowska

2022

Pharmaceuticals

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An effective strategy for successful chemotherapy relies on creating compounds with high selectivity against cancer cells compared to normal cells and relatively low cytotoxicity. One such approach is the discovery of critical points in cancer cells, i.e., where specific enzymes that are potential therapeutic targets are generated. Triazine is a six-membered heterocyclic ring compound with three nitrogen replacing carbon-hydrogen units in the benzene ring structure. The subject of this review is the symmetrical 1,3,5-triazine, known as s-triazine. 1,3,5-triazine is one of the oldest heterocyclic compounds available. Because of its low cost and high availability, it has attracted researcher attention for novel synthesis. s-Triazine has a weak base, it has much weaker resonance energy than benzene, therefore, nucleophilic substitution is preferred to electrophilic substitution. Heterocyclic bearing a symmetrical s-triazine core represents an interesting class of compounds possessing a wide spectrum of biological properties such as anti-cancer, antiviral, fungicidal, insecticidal, bactericidal, herbicidal and antimicrobial, antimalarial agents. They also have applications as dyes, lubricants, and analytical reagents. Hence, the group of 1,3,5-triazine derivatives has developed over the years. Triazine is not only the core amongst them, but is also a factor increasing the kinetic potential of the entire derivatives. Modifying the structure and introducing new substituents makes it possible to obtain compounds with broad inhibitory activity on processes such as proliferation. In some cases, s-triazine derivatives induce cell apoptosis. In this review we will present currently investigated 1,3,5-triazine derivatives with anti-cancer activities, with particular emphasis on their inhibition of enzymes involved in the process of tumorigenesis.

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“…Preliminary work support its versatility in the synthesis of pharmaceutically active compounds. [14][15][16] While other potential applications include use as new chiral auxiliaries 17 building blocks, and pesticides 18 etc.…”

Section: Discussionmentioning

confidence: 99%

Reactions of quinine with 2-chloro-4,6-dimethoxy-1,3,5-triazine

Sukiennik¹,

Kasperowicz-Frankowska²,

Szczesio³

et al. 2020

Arkivoc

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Quinine reacts with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) via a multistage process leading to destruction of the quinuclidine fragment and attachment of two triazinyl substituents. In the first, reversible stage, CDMT reacts with the aromatic nitrogen of the quinoline, followed by the slow migration of triazine moiety on the bridgehead nitrogen atom of quinuclidine. The bicyclic system, after quaternization with CDMT, was opened by privileged attack of nucleophilic chloride on methylene carbon in the bridge substituted with vinyl group. In the final stage the second 4,6-dimethoxy-1,3,5-triazin-2-yl moiety was attached to the hydroxy group. The product structure was confirmed by X-ray crystallographic measurements, MS, 1 H and 13 C NMR, and IR spectroscopy.

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The cellular effects of novel triazine nitrogen mustards in glioblastoma LBC3, LN-18 and LN-229 cell lines

Cited by 8 publications

References 34 publications

Synthesis and cellular effects of novel 1,3,5-triazine derivatives in DLD and Ht-29 human colon cancer cell lines

Synthesis and cellular effects of novel 1,3,5-triazine derivatives in DLD and Ht-29 human colon cancer cell lines

Recent Advances in the Biological Activity of s-Triazine Core Compounds

Reactions of quinine with 2-chloro-4,6-dimethoxy-1,3,5-triazine

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