Synthesis and<i>in vitro</i>evaluation of naphthalimide–benzimidazole conjugates as potential antitumor agents

Singh, Iqubal; Luxami, Vijay; Paul, Kamaldeep

doi:10.1039/c8ob02973c

Cited by 24 publications

(21 citation statements)

References 48 publications

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“…The value of the intrinsic binding constant K b for compounds 1 and 2 were derived to be 0.4 (± 0.06) × 10 5 M −1 and 1.5 (± 0.3) × 10 5 M −1 , respectively. These values are weaker or comparable to those of the other benzimidazole compounds …”

Section: Resultsmentioning

confidence: 61%

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Synthesis, Characterization, and Antiproliferative Activity Studies of Novel Benzimidazole‐Imidazopyridine Hybrids as DNA Groove Binders

et al. 2020

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A novel benzimidazole‐imidazo[1,2‐a]pyridine hybrid; 2‐(imidazo[1,2‐a]pyridine‐8‐yl)benzimidazole and its symmetrical bis‐ derivative 2,2′‐bis‐(imidazo[1,2‐a]pyridine‐8‐yl)‐1H,1H′‐[5,5′]‐bisbenzimidazole were synthesized and characterized. It was found that these two compounds have a strong DNA groove binding and peroxide mediated DNA‐cleavage properties. Furthermore, these molecules were screened against three different human cell lines namely HepG2, DLD‐1 and MDA‐MB‐231, and these compounds were found to have high cytotoxic activities.

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Section: Resultsmentioning

confidence: 61%

“…have created indispensable examples for development of new therapeutic agents . A great number of 2‐substituted benzimidazoles have been synthesized and their biological activities reported (Figure ) . A number of these studies has also focused on symmetrical and unsymmetrically substituted bis‐benzimidazoles .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antiproliferative Activity Studies of Novel Benzimidazole‐Imidazopyridine Hybrids as DNA Groove Binders

et al. 2020

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“…To determine the spontaneity for formation of complex between conjugate 7 and HSA, change in free energy has been calculated that was found to be −8.4 kcal/mol by employing following equation 1 [36] . The negative value of ▵G demonstrates spontaneity and existence of hydrophobic interaction among HSA : TPE‐naph.

true Δ G = - R T \ln K_{b}

…”

Section: Fluorescence Spectroscopymentioning

confidence: 99%

Synthesis of Triphenylethylene‐Naphthalimide Conjugates as topoisomerase‐IIα inhibitor and HSA binder

2021

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A series of triphenylethylene‐naphthalimide (TPE‐naph) conjugates was synthesized by a molecular hybridization technique, and their anticancer activity was evaluated in vitro on 60 human cancer cell lines through their cytotoxicity. The ratios of E and Z isomers were determined on the basis of HPLC methodology and NMR spectroscopy. The structure‐activity relationship for anticancer activity was deduced on the basis of the nature and bulkiness of the amine attached to the C‐4 position of the naphthalene ring. Experimental and molecular modeling studies of the most active TPE‐naph conjugate bearing a morpholinyl group showed that it was able to inhibit topoisomerase‐II (TOPO‐II) as a possible intracellular target. Moreover, the transportation behavior of TPE‐naph conjugate towards human serum albumin (HSA) indicated efficient binding affinity. The steady‐state and time‐dependent fluorescent results suggested that this conjugate quenched HSA significantly through static as well as dynamic quenching. Thus, this report discloses the scope of triphenylethylene‐naphthalimide (TPE‐naph) conjugates as efficient anticancer agents.

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“…The complexes may enter the cell more easily after hydrolysis and the antitumor activity of some complexes may be reduced after hydrolysis. [34][35][36] Figure 3. The calculated hydrolysis rate constants and half life period are listed in Table 3.…”

Section: Hydrolysismentioning

confidence: 99%

Lysosomal‐targeted anticancer half‐sandwich iridium(III) complexes modified with lonidamine amide derivatives

Xie

Zhang

et al. 2020

Applied Organom Chemis

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Ten half‐sandwich iridium complexes containing lonidamine amide derivatives were synthesized and characterized. Unlike lonidamine, which acts on mitochondria, its iridium complexes successfully targeted lysosomes and induced lysosomal damage. Antiproliferation studies showed that most of the complexes have higher anticancer activity against A549 and HeLa cells than cisplatin. The antitumor activity of complex 6 is 2.69 times that of cisplatin against A549 cells. We also performed antitumor tests on ligands L1 and L5, and proved that they exhibit excellent antitumor activity only after binding to the metal center. The bovine serum albumin (BSA) binding test showed that the complexes had the ability to bind to BSA, and they interact with BSA by a static mechanism. The complexes can also cause changes in mitochondrial membrane potential and can produce active oxygen species better than active control. NADH/NAD+ transformation experiments were used to determine if the production of ROS was caused by the transformation of NADH/NAD+. We also explored the way that the complexes enter cells.

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Synthesis andin vitroevaluation of naphthalimide–benzimidazole conjugates as potential antitumor agents

Abstract: A novel series of benzimidazole-naphthalimide conjugates was synthesized for the first time and screened for in vitro biological activity for 60 human cancer cell lines representing nine different cancer types.

Cited by 24 publications

References 48 publications

Synthesis, Characterization, and Antiproliferative Activity Studies of Novel Benzimidazole‐Imidazopyridine Hybrids as DNA Groove Binders

Synthesis, Characterization, and Antiproliferative Activity Studies of Novel Benzimidazole‐Imidazopyridine Hybrids as DNA Groove Binders

Synthesis of Triphenylethylene‐Naphthalimide Conjugates as topoisomerase‐IIα inhibitor and HSA binder

Lysosomal‐targeted anticancer half‐sandwich iridium(III) complexes modified with lonidamine amide derivatives

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