Dichlorido-platinum(II) complexes with kinetin derivatives as promising cytotoxic agents avoiding resistance of cancer cells: Contrasting results between cisplatin and oxaliplatin analogues

Křikavová, Radka; Hanousková, Lucie; Dvořák, Zdeněk; Trávníček, Zdeněk

doi:10.1016/j.poly.2015.01.033

Cited by 14 publications

(7 citation statements)

References 41 publications

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“…Due to the low stability of the platinum complexes in DMSO-d 6 and taking into account the previous cytotoxicity studies on platinum(II) complexes performed in DMF/water solutions by several groups, , we also analyzed the stability of our complexes in DMF-d 7 by 1 H NMR (see Figures SI17–SI20). Consequently, we determined that the stability of complexes [Pt-L1] – [Pt-L4] in DMF-d 7 after 24 h is higher than in DMSO-d 6 .…”

Section: Results and Discussionmentioning

confidence: 94%

Appended Aromatic Moieties Determine the Cytotoxicity of Neutral Cyclometalated Platinum(II) Complexes Derived from 2-(2-Pyridyl)benzimidazole

et al. 2020

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A new family of neutral chiral cyclometalated platinum(II) complexes with formula [Pt(κ2-(C^N))Cl(κ1-(L))], where (C^N) = 2-phenylpyridinate and (L) = 2-(2-pyridyl)benzimidazole (L1) or (N-(CH2)-Ar-(2-(2-pyridyl)benzimidazole) ligands; (Ar = phenyl (L2), naphthyl (L3), pyrenyl (L4)), have been synthesized and completely characterized. The unexpected κ1 coordination mode of the 2-(2-pyridyl)benzimidazole-derived ligands has been confirmed by spectroscopic techniques and X-ray diffraction. The aromatic moieties on the ligands in the new platinum(II) complexes have a remarkable influence on the cytotoxicity and in the binding mode to DNA. [Pt-L1]–[Pt-L4] complexes internalized more than cisplatin in the SW480 cancer cells even though only [Pt-L1] and [Pt-L2] display high cytotoxicity. 1H NMR and 13P{1H}NMR pointed out that [Pt-L1] and [Pt-L2] complexes bind covalently to dGMP, while the electrophoresis assays and CD experiments indicate that only [Pt-L2] is able to covalently interact with DNA, inducing the same conformational changes in the plasmid DNA as cisplatin. Although the complex [Pt-L4] intercalates into DNA, probably through the pyrenyl moiety, no biological activity is observed.

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Section: Results and Discussionmentioning

confidence: 94%

Appended Aromatic Moieties Determine the Cytotoxicity of Neutral Cyclometalated Platinum(II) Complexes Derived from 2-(2-Pyridyl)benzimidazole

et al. 2020

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“…Photophysical properties of novel compounds (3)(4)(5) in THF solutions were examined via UV-vis absorption and emission spectroscopy. Normalized absorption spectra of compounds (3-5) were shown in Figure 3a.…”

Section: Photophysical and Photochemical Propertiesmentioning

confidence: 99%

“…Stokes shifts of the compounds 4 and 5 were about 61 and 62 nm respectively (Table 2). Absorption spectra of compounds (3)(4)(5) in THF solutions were investigated at different concentrations (10 -6 -10 -5 M for 3 and 10 -5 -10 -4 M for 4 and 5) and any change at absorption wavelength was observed (Fig. S8a, S9a, S10a).…”

Section: Photophysical and Photochemical Propertiesmentioning

confidence: 99%

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Bodipy Based Iridium and Ruthenium Complexes: Synthesis, Photophysical and Photochemical Properties

Cabir,

Cetindere

2024

Preprint

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The design, synthesis, and characterization of novel BODPY based iridium and ruthenium complexes were reported. The structures of new compounds were fully characterized by FT-IR, MALDI-TOF Mass analysis, 1H, and 19F NMR spectroscopies. Precursor BODIPY was characterized by single-crystal X-ray diffraction technique for the first time. Photophysical properties including absorption and emission profiles and fluorescence lifetimes were investigated via UV–vis absorption and fluorescence emission spectroscopy. Photochemical properties were investigated via direct method and the singlet oxygen production capabilities of new complexes were determined by NIR phosphorescence methods. BODIPY-based ruthenium complex more efficient at producing 1O2 than that of the BODIPY-based iridium complex. Besides, both complexes showed more remarkable photosensitization ability than some commonly used photosensitizer based on BODIPY derivatives. This study points out that novel complexes are effective 1O2 photosensitizers that might be used for different application areas like as photodynamic therapy.

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“…Recently, oxalate platinum(II) complexes involving 7-azaindole halogeno-derivatives (nHaza), namely, [Pt(ox)(3ClHaza) 2 ] and [Pt(ox)(3BrHaza) 2 ], where 3ClHaza symbolizes 3-chloro-7-azaindole and 3BrHaza symbolizes 3-bromo-7-azaindole, have been synthesized [ 20 ]. Other oxalate platinum(II) complexes contain derivatives of the plant hormone kinetin (N6-furfuryladenine), namely, [Pt(ox)(L 1 )] and [Pt(ox)(L 2 )], where L 1 -2-chloro-N6-furfuryl-9-isopropyladenine and L 2 -2-chloro-N6-(5-methylfurfuryl)- 9-isopropyladenine [ 21 ]. Additionally, our previous initial in vitro antiproliferative activity tests proved that symmetric malonato platinum(II) complexes of the general formula [Pt(mal)(L) 2 ], where L is 7-isobutyl-5-methyl-1,2,4-triazolo[1,5- a ]pyrimidine (ibmtp) and 5,7-di tert butyl- 1,2,4-triazolo-[1,5- a ]pyrimidine (dbtp), exhibit excellent in vitro activity against the cisplatin-resistant human ductal breast epithelial tumor cell line (T47D) and against a lung adenocarcinoma epithelial cell line (A549).…”

Section: Introductionmentioning

confidence: 99%

Platinum(II) Complexes with Bulky Disubstitute Triazolopyrimidines as Promising Materials for Anticancer Agents

et al. 2020

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Herein, we present dicarboxylate platinum(II) complexes of the general formula [Pt(mal)(DMSO)(L)] and [Pt(CBDC)(DMSO)(L)], where L is dbtp 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine) or ibmtp (7-isobutyl-5-methyl-1,2,4- triazolo[1,5-a]pyrimidine), as prospective prodrugs. The platinum(II) complexes were synthesized in a one-pot reaction between cis-[PtCl2(DMSO)2], silver malonate or silver cyclobutane-1,1-dicarboxylate and triazolopyrimidines. All platinum(II) compounds were characterized by FT-IR, and 1H, 13C, 15N and 195Pt NMR; and their square planar geometries with one monodentate N(3)-bonded 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine, one S-bonded molecule of dimethyl sulfoxide and one O,O-chelating malonato (1, 2) or O,O-chelating cyclobutane-1,1-dicarboxylato (3, 4) was determined. Additionally, [Pt(CBDC)(dbtp)(DMSO)] (3) exhibited (i) substantial in vitro cytotoxicity against the lung adenocarcinoma epithelial cell line (A549) (IC50 = 5.00 µM) and the cisplatin-resistant human ductal breast epithelial tumor cell line (T47D) (IC50 = 6.60 µM); and (ii) definitely exhibited low toxicity against normal murine embryonic fibroblast cells (BALB/3T3).

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Dichlorido-platinum(II) complexes with kinetin derivatives as promising cytotoxic agents avoiding resistance of cancer cells: Contrasting results between cisplatin and oxaliplatin analogues

Cited by 14 publications

References 41 publications

Appended Aromatic Moieties Determine the Cytotoxicity of Neutral Cyclometalated Platinum(II) Complexes Derived from 2-(2-Pyridyl)benzimidazole

Appended Aromatic Moieties Determine the Cytotoxicity of Neutral Cyclometalated Platinum(II) Complexes Derived from 2-(2-Pyridyl)benzimidazole

Bodipy Based Iridium and Ruthenium Complexes: Synthesis, Photophysical and Photochemical Properties

Platinum(II) Complexes with Bulky Disubstitute Triazolopyrimidines as Promising Materials for Anticancer Agents

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