Topoisomerase inhibition and albumin interaction studies of acridine-thiosemicarbazone derivatives

Filho, Francivaldo Araújo da Silva; Souza, Thaís de; Ribeiro, Amélia Galdino; Alves, Josival Emanuel Ferreira; Oliveira, Jamerson Ferreira de; Souza, Túlio Ricardo Couto de Lima; Moura, Ricardo Olímpio de; Lima, Maria do Carmo Alves de; Carvalho, Luiz Bezerra de; Almeida, Sinara Mônica Vitalino de

doi:10.1016/j.ijbiomac.2019.07.097

Cited by 18 publications

(6 citation statements)

References 40 publications

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“…Both present the presence of the ligand chlorine (-Cl), in the position R1, and only for the 4 the presence of chlorine in R1, but absence of substitution in R2. Results similar to those found by Silva Filho et al (2019), evaluating the interaction of acridinethiosemicarbazone derivatives (3a-3h) with bovine serum albumin, obtained Ksv values ranging from 1.62 x10 4 to 8.71x10 5 L/mol. They observed that compound 3e (with the highest Ksv value) had a chloro substituent in its structure.…”

Section: Interaction Assays Of Compounds With Human Albumin (Hsa)supporting

confidence: 85%

Preliminary evaluation of the interaction with Albumin/DNA and in vitro evaluation of the antioxidant properties promoted by thiosemicarbazones and thiazole compounds

Nascimento,

Santos,

Pereira

et al. 2024

Sci. Electronic Arch

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Thiosemicarbazones and thiazoles are known for their diverse biological activities. This study introduced two series of molecules, 4-(3-(4-nitrophenyl)-4-phenylthiazol-2(3H)-ylidene)-hydrazine)-methyl)-phenol and 4-(3-(4-chlorophenyl)-4-phenylthiazol-2(3H)-ylidene)-hydrazine)-methyl)-phenol, which exhibit biological potential as antioxidant agents. The study also assessed the interaction of these compounds with various HSA/DNA macromolecules. The results of the antioxidant activity showed that thiazoles in the DPPH assay exhibited IC50 values ranging from 439.4 to 691.67 µM. In the ABTS assay, thiosemicarbazones exhibited significant activity, ranging from 39.19 to 50.03 µM. Interaction assays were carried out with human serum albumin (HSA) and DNA. All compounds were able to interact with both DNA (low to moderate interaction) and HSA (moderate to high interaction).

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Section: Interaction Assays Of Compounds With Human Albumin (Hsa)supporting

confidence: 85%

Preliminary evaluation of the interaction with Albumin/DNA and in vitro evaluation of the antioxidant properties promoted by thiosemicarbazones and thiazole compounds

Nascimento,

Santos,

Pereira

et al. 2024

Sci. Electronic Arch

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“…The human topoisomerase IIα inhibition activity was determined for compounds 14 and 15 using pUC19 DNA plasmid and recombinant human topoisomerase IIα in buffer (50 mM Tris-HCl, pH 8.0, 120 mM KCl, 10 mM MgCl 2 , 0.5 mM ATP and 0.5 mM dithiothreitol). Both compounds were found to have inhibited Topo IIα activity at the same concentration of the control, mAMSA.It is worth noting here that the naphthyl-substituted indolethiosemicarbazones had also demonstrated anti-topoisomerase IIα effects, suggesting the importance of thiosemicarbazone moieties in the inhibition of the enzyme(da Silva Filho et al, 2019).A study byZhang et al (2016) described the synthesis of a series of 9-benzylamino acridine derivatives (16-27) and the investigation of their biological activity. Most of these acridine compounds displayed antiproliferative activity at IC 50 values.…”

mentioning

confidence: 82%

“…Filho et al (2019), acridinethiosemicarbazone derivatives were tested for their interaction properties with BSA. In order to evaluate the anti-topoisomerase potential of these compounds, a docking study between each of the compounds and a Topo IIα/DNA complex was performed as a preliminary analysis.…”

mentioning

confidence: 99%

Acridine derivatives as inhibitors/poisons of topoisomerase II

Kožurková

2021

J of Applied Toxicology

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The potential of acridines (amsacrine) as a topoisomerase II inhibitor or poison was first discovered in 1984, and since then, a considerable number of acridine derivatives have been tested as topoisomerase inhibitors/poisons, containing different substituents on the acridine chromophore. This review will discuss a series of studies published over the course of the last decade, which have investigated various novel acridine derivatives against topoisomerase II activity.

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“…The results obtained from the SwissADME analysis are presented in tables 8 and 9. There are five Lipinski rules which suggest that, in general, an orally active drug should not violate more than one of the following criteria: MW ≤ 500, number of H bond donors ≤ 5, number of H bond acceptors ≤ 10, mLogP ≤ 4.15 [18,27,28], rotatable bonds ≤ 10 and TPSA ≤ 140 [27,29]. Based on the data obtained, the two derivative compounds can be considered orally active drugs and compliant with Lipinski's rule.…”

Section: Lipinski's Rule and Admet Prediction Of Bisoprolol Derivativesmentioning

confidence: 99%

Potential application of bisoprolol derivative compounds as antihypertensive drugs: synthesis and in silico study

Oktaviani,

Ivansyah,

Saputra

et al. 2023

R. Soc. Open Sci.

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Two bisoprolol derivatives, N -acetyl bisoprolol and N -formyl bisoprolol, belonging to the beta-blocker class of antihypertensive drugs, were synthesized using acetylation and formylation reactions. The yields of the reactions were determined to be 32.40% for N -acetyl bisoprolol and 20.20% for N -formyl bisoprolol. In silico methods such as molecular docking, molecular dynamics simulation and SwissADME prediction were employed to evaluate the potential of these bisoprolol derivatives as antihypertensive drugs. These methods were used to assess the interaction between the bisoprolol derivatives and various receptors associated with hypertension, including human angiotensin I-converting enzyme (PDB ID: 1O8A), renin (PDB ID: 2V0Z), beta-1 adrenergic receptors (PDB ID: 4BVN, 7BVQ), voltage-dependent L-type calcium channel subunit alpha-1S (PDB ID: 6JP5) and mineralocorticoid receptor (PDB ID: 6L88). Our results demonstrated the highest binding energy when bisoprolol and its derivatives bound to 4BVN, with binding energy values of 6.74 kcal mol −1 , 7.03 kcal mol −1 and 7.63 kcal mol −1 for bisoprolol, N -acetyl bisoprolol and N -formyl bisoprolol, respectively. The stability of these complexes was confirmed by molecular dynamics simulations, with a root-mean-square deviation value of approximately 2. Furthermore, the SwissADME results indicated that both derivatives exhibited similar properties to the reference drug bisoprolol.

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Topoisomerase inhibition and albumin interaction studies of acridine-thiosemicarbazone derivatives

Cited by 18 publications

References 40 publications

Preliminary evaluation of the interaction with Albumin/DNA and in vitro evaluation of the antioxidant properties promoted by thiosemicarbazones and thiazole compounds

Preliminary evaluation of the interaction with Albumin/DNA and in vitro evaluation of the antioxidant properties promoted by thiosemicarbazones and thiazole compounds

Acridine derivatives as inhibitors/poisons of topoisomerase II

Potential application of bisoprolol derivative compounds as antihypertensive drugs: synthesis and in silico study

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