Structural characterization and cytotoxicity studies of different forms of a combretastatin A4 analogue

Figueiredo, Laysa Pires de; Ibiapino, Amanda Laura; Amaral, Daniel Nascimento do; Ferraz, Letícia Silva; Rodrigues, Tiago; Barreiro, Eliezer J.; Lima, Lı́dia Moreira; Ferreira, Fábio Furlan

doi:10.1016/j.molstruc.2017.06.093

Cited by 11 publications

(6 citation statements)

References 16 publications

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“…The NDI/Zn-W pattern was indexed following some detailed procedures described elsewhere. − Briefly, we selected the first 20 peaks of the diffraction pattern and used the software TOPAS- Academic v7 to index the pattern . The peak shapes were modeled using a fundamental parameters approach implemented in the TOPAS- Academic v7 software.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Two Novel Naphthalenediimide/Zinc Phosphonate Crystalline Materials Precipitated from Different Solvents

Melo,

Gregório Junior,

de Oliveira

et al. 2023

ACS Omega

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Hybrid naphthalenediimide/zinc phosphonate materials (NDI/Zn) were prepared by mixing solutions of N,N′-bis(2phosphonoethyl)-1,4,5,8-naphthalenediimide (PNDI) and zinc nitrate, resulting in the precipitation of the desired compounds. Samples precipitated from water and N,N-dimethylformamide (DMF) were produced. The obtained samples had the expected elemental composition, and the presence of naphthalenediimides (NDI) was ascertained by infrared and UV−visible spectroscopy. All the samples were crystalline, according to powder X-ray diffraction. Nitrogen adsorption isotherms showed the presence of porosity in the NDI/Zn samples. Mesopores with a diameter = 4.1 nm were present in the sample from DMF, with total pore volume reaching 0.13 cm 3 /g.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Two Novel Naphthalenediimide/Zinc Phosphonate Crystalline Materials Precipitated from Different Solvents

Melo,

Gregório Junior,

de Oliveira

et al. 2023

ACS Omega

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“…The crystal structure of the Nit–OH compound was determined using X-ray powder diffraction data and a simulated annealing approach implemented in DASH software; the detailed procedure is described elsewhere. − Nit–OH crystallized in a monoclinic crystal system and space group Pa (nr. 7).…”

Section: Resultsmentioning

confidence: 99%

Mechanisms for the Deactivation of the Electronic Excited States of α-(2-Hydroxyphenyl)-N-phenylnitrone: From Intramolecular Proton and Charge Transfer to Structure Twisting and Aggregation

et al. 2022

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The search for new prominent chemosensors is significantly related to the rationalization of possible multiple pathways of excited-state deactivation. We have prepared and studied compound α-(2-hydroxyphenyl)-N-phenylnitrone (Nit–OH), observing that Nit–OH is stable in acetonitrile solution under UV–vis light. The experimentally observed 540 nm fluorescence for Nit–OH was shown to be related to excitation at 360 nm from the highest occupied molecular orbital to the lowest unoccupied molecular orbital (HOMO–LUMO transition). Potential energy curves (PECs) for the S1 state of Nit–OH did show that there are structures associated with excited-state intramolecular proton transfer (ESIPT), and the existence of an intramolecular H-bonding was confirmed using X-ray powder diffraction (XRD). Twisted intramolecular charge transfer (TICT) took place following ESIPT, and a nonradiative deactivation at the S1/S0 conical intersection occurred; aggregation-induced emission was observed at 540 nm associated with the formation of a stacked dimer. Anti-Kasha emission from the S2 was proposed based on the dependence of the fluorescence excitation wavelength on Nit–OH concentration. From the calculation of the PEC for the S2 state, we obtained radiative transitions at 379 and 432 nm, similar to the obtained experimental values of 383 and 453 nm. We proposed a Jablonski-like diagram that depicts all experimental and theoretical electronic transitions for Nit–OH, summarizing the unique intricate photophysical behavior of this nitrone derivative.

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“…Literature survey indicated that hydrazide-hydrazones and oxamide structures are the subject of intense studies due to their anticancer effects. The reported anti-cancer activity for hydrazide-hydrazones could be due to their apoptotic induction through activating the caspases along with microtubule polymerization and angiogenesis inhibition as well [11][12][13][14] Besides it, oxamide, a unique representative of amide pharmacophore, have drawn signi cant attention owing to the anticancer and anti-proliferative property [15][16][17][18][19] Given the above data, we synthesized a wide variety of hybrid moieties comprising of hydrazide and oxamide pharmacophores and then performed preliminary screening towards different cancer cells. Our initial ndings represented a desirable anti-breast cancer effect via G1/S cell cycle arrest for one of the compounds (compound A) against MDA-MB-231 as in vitro model of TNBC [20].…”

Section: Introductionmentioning

confidence: 99%

Development of the potential synthesized compound to cause triple negative breast cancer cell death through intrinsic apoptosis mechanism

Tahmasvand

Dehghani

Kooshafar

et al. 2023

Preprint

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Triple-negative breast cancer (TNBC) is a subtype of breast cancer with poor clinical outcome, and currently no effective targeted therapies are available. Since cancer develops owing to deregulation of apoptosis, employing therapeutic strategies with ability to target the molecules involved in apoptosis induction, would provide a valid approach to hinder tumor progression. Hydrazide-hydrazones and oxamide molecules are the subject of intense studies due to their anticancer effects via apoptosis induction. In the present study, we attempted to elucidate the mechanism of action of a synthesized compound (compound A) and understand if the cell death occurs through inducing the apoptosis. These properties were investigated using the, annexin/PI and Western blotting analyses, DAPI staining, and mitochondrial membrane potential probe. Compound A also impeded the tumor growth in a 4T1 syngeneic mouse model as evidenced by hematoxylin and eosin staining of the tumors. Apart from that, it significantly diminished the expression of pro-caspase-3, Ki67 and CD31 markers in the tumor sections. Conclusively, this study for the first time reports the anti-cancer efficacy of compound A in both in vitro and in vivo models, which may serve as a potent candidate in triple negative breast cancer (TNBC) treatment.

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Structural characterization and cytotoxicity studies of different forms of a combretastatin A4 analogue

Cited by 11 publications

References 16 publications

Synthesis and Characterization of Two Novel Naphthalenediimide/Zinc Phosphonate Crystalline Materials Precipitated from Different Solvents

Synthesis and Characterization of Two Novel Naphthalenediimide/Zinc Phosphonate Crystalline Materials Precipitated from Different Solvents

Mechanisms for the Deactivation of the Electronic Excited States of α-(2-Hydroxyphenyl)-N-phenylnitrone: From Intramolecular Proton and Charge Transfer to Structure Twisting and Aggregation

Development of the potential synthesized compound to cause triple negative breast cancer cell death through intrinsic apoptosis mechanism

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