Synthesis of isatin thiosemicarbazones derivatives: In vitro anti-cancer, DNA binding and cleavage activities

Ali, Amna Qasem; Teoh, Siang Guan; Salhin, Abdussalam; Eltayeb, Naser Eltaher; Ahamed, Mohamed B. Khadeer; Majid, Amin Malik Shah Abdul

doi:10.1016/j.saa.2014.01.086

Cited by 40 publications

(29 citation statements)

References 43 publications

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“…The antiproliferative activity of some substituted indole and biindole derivatives against breast, colon, and lung cancer cells has been reported (Katdare et al, 1998;Chinni and Sarkar, 2002;Frydoonfar et al, 2002Frydoonfar et al, , 2003Hong et al, 2002;Howells et al, 2002;Zheng et al, 2002;Hudson et al, 2003;Nachshon-Kedmi et al, 2003;Rahman et al, 2003;Weng et al, 2008;Ji et al, 2013;Ali et al, 2014). The antiproliferative and cytotoxic activities of 2 against HeLa, C6, and HT29 cell lines were tested and documented for the first time in this study.…”

Section: Discussionmentioning

confidence: 66%

In vitro antiproliferative/cytotoxic activity of 2,3ʹ-biindole againstvarious cancer cell lines

Ökten

Erenler²,

Köprülü³

et al. 2015

Turk J Biol

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2,3'-Biindole (2) was synthesized via bromination of indole (1) with molecular bromine and underwent simultaneous dimerization. Antiproliferative and cytotoxic activity of 2 was investigated in vitro on C6 (rat brain tumor), HeLa (human cervix carcinoma), and HT29 (human colon carcinoma) cells lines by using BrdU cell proliferation ELISA and lactate dehydrogenase (LDH) assays. In contrast to 5-fluorouracil (5-FU), 2,3'-biindole (2) significantly inhibited proliferation of HeLa and HT29 cell lines. According to LDH assay, the cytotoxicity of compound 2 was low on HT29 cell lines and high on HeLa and C6 cell lines. Moreover, 2 did not cause any DNA laddering on the DNA of tested cells; therefore, it is suggested that the mechanism of action of this compound may not involve apoptosis. In addition, 2 inhibited relaxation of supercoiled plasmid DNA by topoisomerase activity. Results of the present study indicates that biindole (2) may have promising anticancer and antitopoisomerase potential with an unknown mechanism of action.

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Section: Discussionmentioning

confidence: 66%

In vitro antiproliferative/cytotoxic activity of 2,3ʹ-biindole againstvarious cancer cell lines

Ökten

Erenler²,

Köprülü³

et al. 2015

Turk J Biol

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“…The 1 H NMR (DMSO‐ d 6 ) spectra of the Pd(II) complexes showed approximately the same peaks identical to those of the free ligands, except that the signal of thiosemicarbazide N─NH proton in the spectra of the ligands disappeared in the spectra of the complexes. This finding provides additional evidence of ligand deprotonation during metal chelation.…”

Section: Resultsmentioning

confidence: 77%

“…The characteristic IR bands recorded for the free ligands differed from those of the related complexes, and provided significant indications of the bonding sites of thiosemicarbazone ligands. Compared with the spectra of the Schiff bases, PdL1 to PdL6 exhibited the ν(C═O) band from 1635 to 1650 cm −1 , showing a shift to lower wavenumbers.…”

Section: Resultsmentioning

confidence: 96%

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Synthesis, structure and in vitro anticancer, DNA binding and cleavage activity of palladium (II) complexes based on isatin thiosemicarbazone derivatives

Ali

Teoh

Eltayeb

et al. 2017

Applied Organom Chemis

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Six novel palladium(II) complexes of a thiosemicarbazone Schiff base with isatin moiety (PdL1 to PdL6) were synthesized by the reaction of palladium(II) with the following: (Z)‐2‐(2‐oxoindolin‐3‐ylidene)‐N‐phenylhydrazinecarbothioamide (L1H), (Z)‐2‐(5‐methyl‐2‐oxoindolin‐3‐ylidene)‐N‐phenylhydrazinecarbothioamide (L2H), (Z)‐2‐(5‐fluoro‐2‐oxoindolin‐3‐ylidene)‐N‐phenylhydrazinecarbothioamide (L3H), (Z)‐N‐methyl‐2‐(5‐nitro‐2‐oxoindolin‐3‐ylidene)hydrazinecarbothioamide (L4H), (Z)‐N‐methyl‐2‐(5‐methyl‐2‐oxoindolin‐3‐ylidene)hydrazinecarbothioamide (L5H) and (Z)‐N‐ethyl‐2‐(5‐methyl‐2‐oxoindolin‐3‐ylidene)hydrazinecarbothioamide (L6H). The structures of these complexes were characterized using elemental analysis and infrared, UV–visible, 1H NMR and mass spectroscopies. The structure of PdL5 was further characterized using single‐crystal X‐ray diffraction. The interaction of these complexes with calf thymus DNA was characterized with a high intrinsic binding constant (Kb = 5.78 × 104 to 1.79 × 106 M−1), which reflected the intercalative activity of these complexes towards calf thymus DNA. This result was also confirmed from viscosity data. Electrophoresis studies revealed that complexes PdL1 to PdL6 could cleave DNA via an oxidative pathway in the presence of an external agent. Data obtained from an in vitro anti‐proliferative study clearly established the anticancer potency of these compounds against the human colorectal carcinoma cell line HCT 116.

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“…In addition, thiosemicarbazones were often chosen as primary ligands for vanadium owing to their wide range of physiological and pharmacological activities including antifungal [14], antitumor [15], antibacterial [16] and antiviral activities [17]. Oxovanadium complexes incorporated with thiosemicarbazones have demonstrated both in vitro antibacterial and antiproliferative properties [18][19] as well as intense interaction with DNA [20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, DNA-binding, Photocleavage and in vitro Cytotoxicity of Novel Imidazole[4,5-f][1,10]phenanthroline-based Oxovanadium Complexes

Ying¹

2014

Med chem

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Synthesis of isatin thiosemicarbazones derivatives: In vitro anti-cancer, DNA binding and cleavage activities

Cited by 40 publications

References 43 publications

In vitro antiproliferative/cytotoxic activity of 2,3ʹ-biindole againstvarious cancer cell lines

In vitro antiproliferative/cytotoxic activity of 2,3ʹ-biindole againstvarious cancer cell lines

Synthesis, structure and in vitro anticancer, DNA binding and cleavage activity of palladium (II) complexes based on isatin thiosemicarbazone derivatives

Synthesis, DNA-binding, Photocleavage and in vitro Cytotoxicity of Novel Imidazole[4,5-f][1,10]phenanthroline-based Oxovanadium Complexes

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