Exploring the anticancer potential of pyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-one derivatives: The effect on apoptosis induction, cell cycle and proliferation

Mingoia, Francesco; Sano, Caterina Di; Blasi, Francesco Di; Fazzari, Marco; Martorana, Annamaria; Almerico, Anna Maria; Lauria, Antonino

doi:10.1016/j.ejmech.2013.03.046

Cited by 19 publications

(21 citation statements)

References 35 publications

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“…benzo [1,2,3,4]tetrazin-3-one derivatives (PBTs). [3] Optimization performed by in house developed in silico lock and key based approach.…”

Section: Nucleic Acidsmentioning

confidence: 99%

“…[1,2,3,4]tetrazine-3one derivatives: 8-Cl; 8-Me; 9-Cl; 8,9-di-Me; 8,9-di-Cl ( Figure 2) were synthesized and characterized as previously described by us. Docking grids were generated by Glide using the co-crystallized ligand at the center of the grid box.…”

Section: Ligands Dockingmentioning

confidence: 99%

“…[1] Recently, a new series of pyrazolo [1,2-a]benzo [1,2,3,4]tetrazine-3-one derivatives (PBTs) has been evaluated by the National Cancer Institute (NCI, Bethesda, MD, USA) against several cancer panels including 60 human cell lines. [1] Recently, a new series of pyrazolo [1,2-a]benzo [1,2,3,4]tetrazine-3-one derivatives (PBTs) has been evaluated by the National Cancer Institute (NCI, Bethesda, MD, USA) against several cancer panels including 60 human cell lines.…”

Section: Introductionmentioning

confidence: 99%

“…[1] Recently, a new series of pyrazolo [1,2-a]benzo [1,2,3,4]tetrazine-3-one derivatives (PBTs) has been evaluated by the National Cancer Institute (NCI, Bethesda, MD, USA) against several cancer panels including 60 human cell lines. Along with the improved antiproliferative activity, apoptosis induction in the low-micromolar range and cell cycle arrest promoters on S phase (Figure 1a) [3] has been assessed. Again, these further investigations permitted us to move forward in the optimization process.…”

Section: Introductionmentioning

confidence: 99%

“…

CorrespondenceFrancesco Mingoia, Istituto per lo Studio dei Materiali Nanostrutturati (ISMN), Consiglio Nazionale delle Ricerche Due to the scarce biological profile, the pyrazolo[1,2-a]benzo [1,2,3,4]tetrazine-3one scaffold (PBT) has been recently explored as promising core for potential anticancer candidates. Several suitably decorated derivatives (PBTs) exhibited antiproliferative activity in the low-micromolar range associated with apoptosis induction and cell cycle arrest on S phase.

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confidence: 99%

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New insights into the mechanism of action of pyrazolo[1,2‐a]benzo[1,2,3,4]tetrazin‐3‐one derivatives endowed with anticancer potential

et al. 2017

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Due to the scarce biological profile, the pyrazolo[1,2-a]benzo[1,2,3,4]tetrazine-3-one scaffold (PBT) has been recently explored as promising core for potential anticancer candidates. Several suitably decorated derivatives (PBTs) exhibited antiproliferative activity in the low-micromolar range associated with apoptosis induction and cell cycle arrest on S phase. Herein, we selected the most active derivatives and submitted them to further biological explorations to deepen the mechanism of action. At first, a DNA targeting is approached by means of flow Linear Dichroism experiments so as to evaluate how small planar molecules might interact with DNA, including the interference with the catalytic cycle of topoisomerase II and the influence on the cleavable complex stabilization (poisoning effect). In support of the experimental data, in silico studies have been achieved to better understand the chemical space of the interactions. Interestingly some meaningful structural features, useful for further developments, were found. The 8,9-di-Cl substituted derivative revealed as the most effective in the intercalative process, as well as on the inhibition of catalytic activity of topoisomerase II. Predicted ADME studies confirm that PBTs are promising as potential drug candidates.

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“…benzo [1,2,3,4]tetrazin-3-one derivatives (PBTs). [3] Optimization performed by in house developed in silico lock and key based approach.…”

Section: Nucleic Acidsmentioning

confidence: 99%

Section: Ligands Dockingmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…[1] Recently, a new series of pyrazolo [1,2-a]benzo [1,2,3,4]tetrazine-3-one derivatives (PBTs) has been evaluated by the National Cancer Institute (NCI, Bethesda, MD, USA) against several cancer panels including 60 human cell lines. Along with the improved antiproliferative activity, apoptosis induction in the low-micromolar range and cell cycle arrest promoters on S phase (Figure 1a) [3] has been assessed. Again, these further investigations permitted us to move forward in the optimization process.…”

Section: Introductionmentioning

confidence: 99%

“…

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mentioning

confidence: 99%

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New insights into the mechanism of action of pyrazolo[1,2‐a]benzo[1,2,3,4]tetrazin‐3‐one derivatives endowed with anticancer potential

et al. 2017

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Energetic 1,2,3,4‐Tetrazines

Churakov

Klenov

Voronin

et al. 2022

Nitrogen‐Rich Energetic Materials

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ChemInform Abstract: Exploring the Anticancer Potential of Pyrazolo[1,2‐a]benzo[1,2,3,4]tetrazin‐3‐one Derivatives: The Effect on Apoptosis Induction, Cell Cycle and Proliferation.

Mingoia¹,

Sano²,

Blasi³

et al. 2013

ChemInform

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Exploring the Anticancer Potential of Pyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-one Derivatives: The Effect on Apoptosis Induction, Cell Cycle and Proliferation. -The highest activity in terms of apoptosis induction is found for derivative (IVb). -(MINGOIA*, F.; DI SANO, C.; DI BLASI, F.; FAZZARI, M.; MARTORANA, A.; ALMERICO, A. M.; LAURIA, A.; Eur. J. Med. Chem. 64 (2013) 345-356, http://dx.doi.org/10.1016/j.ejmech.2013.03.046 ; CNR, Ist. Stud. Mater. Nanostrutt., I-90146 Palermo, Italy; Eng.) -G. Mueller 43-115

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Exploring the anticancer potential of pyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-one derivatives: The effect on apoptosis induction, cell cycle and proliferation

Cited by 19 publications

References 35 publications

New insights into the mechanism of action of pyrazolo[1,2‐a]benzo[1,2,3,4]tetrazin‐3‐one derivatives endowed with anticancer potential

New insights into the mechanism of action of pyrazolo[1,2‐a]benzo[1,2,3,4]tetrazin‐3‐one derivatives endowed with anticancer potential

Energetic 1,2,3,4‐Tetrazines

ChemInform Abstract: Exploring the Anticancer Potential of Pyrazolo[1,2‐a]benzo[1,2,3,4]tetrazin‐3‐one Derivatives: The Effect on Apoptosis Induction, Cell Cycle and Proliferation.

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