Biological activity of non-radical <i>vs.</i> stable radical of a pyridazine-sulfonamide aminophenol-type compound

Chatterjee, Himadri Sekhar; Maity, Suvendu; Halder, Satyajit; Ghosh, Prasanta; Jana, Kuladip; Mahapatra, Pradip Kumar; Sinha, Chittaranjan

doi:10.1039/d2nj03308a

Cited by 2 publications

(2 citation statements)

References 21 publications

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“…The elevation in the γ-H2AX expression level observed in Western blot analysis also supports the findings of DNA damage (Figure e–g). Together, these results suggest that NMOF 1 treatment leads to DNA damage and inhibition of cell cycle progression in MDA-MB 231 cells, which could contribute to the antiproliferative effects of the compound …”

Section: Resultsmentioning

confidence: 75%

Glutathione Depleting a Chemoselective Novel Pro-oxidant Nano Metal–Organic Framework Induced G2/M Arrest and ROS-Mediated Apoptotic Cell Death in a Human Triple-Negative Breast Cancer Cell Line

Karim

Halder

Mukherjee³

et al. 2023

ACS Appl. Mater. Interfaces

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The progression of a new class of compounds to inhibit the uncontrolled proliferation of carcinoma cells has become one of the most powerful weapons to combat “cancer”. To this end, a new Mn(II)-based metal–organic framework, namely, [{Mn(5N3-IPA)(3-pmh)}(H2O)]α (5N3H2-IPA = 5-azidoisophthalic acid and 3-pmh = (3-pyridylmethylene)hydrazone), has been synthesized adopting a mixed ligand approach and exploited as a successful anticancer agent via systematic in vitro and in vivo studies. Single-crystal X-ray diffraction analyses depict that MOF 1 exhibits a 2D pillar-layer structure consisting of water molecules in each 2D void space. Due to the insolubility of the as-synthesized MOF 1, a green hand grinding methodology has been adopted to scale down the particle size to the nanoregime keeping its structural integrity intact. The nanoscale metal–organic framework (NMOF 1) adopts a discrete spherical morphology as affirmed by scanning electron microscopic analysis. The photoluminescence studies revealed that NMOF 1 is highly luminescent, enhancing its biomedical proficiency. Initially, the affinity of the synthesized NMOF 1 for GSH-reduced has been evaluated by various physicochemical techniques. NMOF 1 constrains the proliferation of cancer cells in vitro by inducing G2/M seizure and accordingly leads to apoptotic cell death. More significantly, compared to cancer cells, NMOF 1 exhibits less cytotoxicity against normal cells. It has been demonstrated that NMOF 1 interacts with GSH, causing a drop in cellular GSH levels and the production of intercellular ROS. It is quite intriguing that we discovered that NMOF 1-mediated ROS generation aids in significantly modifying the mitochondrial redox status, which is a crucial factor in apoptosis. According to mechanistic research, NMOF 1 increases the production of proapoptotic proteins and lowers the expression of antiapoptotic proteins, which significantly aids in activating caspase 3 and the subsequent cleavage of PARP1 and cell death via intrinsic apoptotic pathways. Finally, an in vivo investigation using immuno-competent syngeneic mice demonstrates that NMOF 1 can stop tumor growth without causing adverse side effects.

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Section: Resultsmentioning

confidence: 75%

Glutathione Depleting a Chemoselective Novel Pro-oxidant Nano Metal–Organic Framework Induced G2/M Arrest and ROS-Mediated Apoptotic Cell Death in a Human Triple-Negative Breast Cancer Cell Line

Karim

Halder

Mukherjee³

et al. 2023

ACS Appl. Mater. Interfaces

Self Cite

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“…However, there are “noninnocent” ligands named by Jørgensen, which could also participate in redox process. − It has been well determined that the interaction of metals with noninnocent ligands is important to promote electron transfer processes in biological or chemical reactions. − In addition, the noninnocent ligands deeply offer more features in establishing “correct” electronic distribution . Hence, a profusion of noninnocent ligands with the N, O, and S atoms is utilized more frequently in the coordination, organometallic chemistry, and biochemistry, such as dithiolenes, , semiquinone (SQ) − or the hybrid o -aminophenol, − glyoxal-bis(2-mercaptoanil) (H 2 gma), − etc.…”

Section: Introductionmentioning

confidence: 99%

Electronic Transition and Magnetic Coupling Regulation in Trimetallic Complexes Featuring a New Bridging Ligand Obtained by Oxidative Addition

Huang

Zhu

et al. 2023

Inorg. Chem.

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A series of trimetallic complexes [Fe III (μ-L)(py)] 2 M II (py) n (n = 2, M II = Mn II , 1; Fe II , 2; Co II , 3; Zn II , 4; n = 3, M II = Cd II , 5) with a new bridging ligand L 4− (deprotonated 1,2-N 1 ,N 2 -bis(2-mercaptoanil) oxalimidic acid) were synthesized and fully characterized by elemental analysis, single-crystal X-ray crystallography, IR, and Mossbauer spectra. Interestingly, the bridging ligand was obtained by oxidative addition of the (gma • ) 3− ligand from the mononuclear precursor Fe(gma)py (gma = glyoxalbis(2-mercaptoanil)). In the obtained complexes, the bridging ligand L 4− coordinates to the terminal Fe III ions (intermediate-spin with S Fe = 3/2) by the N, S atoms, and coordinate to the central metal M II ion by the four O atoms. The resonance structure of the bridging ligand can be described as the two 4π-electron delocalized systems connected by one single-bond (C 1 −C 2 ), which is different from the electronic structure of the precursor Fe(gma)py. Remarkably, the magnetic coupling interaction can be regulated through the central metal. The ferromagnetic coupling constant J gradually decreases as M II changes from Fe II to Co II and Mn II , while the paramagnetic behaviors are presented when M II = Zn II and Cd II , confirmed by the magnetic susceptibility measurements and further supported by using the PHI program. Furthermore, the bridging ligand to the terminal Fe III charge transfer (LMCT) transitions emerged in all complexes but the central Fe II to terminal Fe III charge transfer (MMCT) only presented in complex 2, strongly supported by the UV/vis−NIR electronic spectra and TDDFT calculations.

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Biological activity of non-radical vs. stable radical of a pyridazine-sulfonamide aminophenol-type compound

Cited by 2 publications

References 21 publications

Glutathione Depleting a Chemoselective Novel Pro-oxidant Nano Metal–Organic Framework Induced G2/M Arrest and ROS-Mediated Apoptotic Cell Death in a Human Triple-Negative Breast Cancer Cell Line

Glutathione Depleting a Chemoselective Novel Pro-oxidant Nano Metal–Organic Framework Induced G2/M Arrest and ROS-Mediated Apoptotic Cell Death in a Human Triple-Negative Breast Cancer Cell Line

Electronic Transition and Magnetic Coupling Regulation in Trimetallic Complexes Featuring a New Bridging Ligand Obtained by Oxidative Addition

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