Synthesis, crystal structure and cytotoxicity studies of cis-dichloro(4,5-diazafluoren-9-one)platinum(II)

Biju, A.; Rajasekharan, M. V.; Bhat, Satish S.; Khan, Ayesha; Kumbhar, Avinash S.

doi:10.1016/j.ica.2014.09.007

Cited by 11 publications

(7 citation statements)

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“…5. A maximum DNA binding ratio of 0.0023 is obtained at around 2.5 h. This result is consistent with reported complexes that bind covalently to DNA (Nová ková et al, 1995;Biju et al, 2014;Barton & Lolis, 1985).…”

Section: Covalent Binding Assaysupporting

confidence: 92%

Synthesis, crystal structure and biological properties of a cis-dichloridobis(diimine)copper(II) complex

Bhat

Revankar

Kumbar³

et al. 2018

Acta Crystallogr C Struct Chem

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The mechanisms of interaction of inorganic complexes with DNA are important in the design and development of new metal-based drug molecules. The limitations of cis-platin have encouraged the design and development of new metal-based target-specific anticancer drugs having reduced side effects. The complex cis-dichloridobis(1,2,5-thiadiazolo[3,4-f][1,10]phenanthroline-κN,N)copper(II), [CuCl(CHNS)], has been synthesized and characterized. The complex crystallizes in the monoclinic space group C2/c. The covalent binding of the complex with DNA was studied by absorption spectroscopy. The anticancer activity of the complex on the Human Lung Carcinoma (A549) cell line was investigated by MTT assay. The complex exhibits higher toxicity than cis-platin and induces an apoptotic mode of cell death.

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Section: Covalent Binding Assaysupporting

confidence: 92%

Synthesis, crystal structure and biological properties of a cis-dichloridobis(diimine)copper(II) complex

Bhat

Revankar

Kumbar³

et al. 2018

Acta Crystallogr C Struct Chem

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“…Dafone is a ligand structurally similar to 2,2′‐bipyridine (bipy) and 1,10‐phenanthroline (phen), but possessing a much larger chelate bite (N ··· N in dafone is 2.95 Å, in phen it is 2.64 Å, in bipy it is 2.62 Å). Therefore, in almost all its known complexes, dafone chelates in a highly unsymmetrical fashion, forming one normal and one long bond,7 though a few rare examples of (nearly) symmetric chelation have also been reported 8. Several years ago we reported a tris‐chelate of dafone stabilized by a planer I 12 2– anion 1b.…”

Section: Introductionmentioning

confidence: 99%

Polyhalide Ions (Br₈^2– and I₂Br₆^2–) and Chains (···Br₃^–···Br₂··· and ···IBr₄^–···) Stabilised by Using Cu(dafone)₃²⁺ as Counter Ion (dafone = 4,5‐Diazafluoren‐9‐one)

2015

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Two new iodobromides [I 2 Br 6 2-(analogue of I 8 2and Br 8 2-) and IBr 4 -(analogue of Br 5 and I 2 Br 3 -)] and new chains formed from Br 3 -, Br 2 and IBr 4 have been obtained in three compounds all containing the same Cu II tris-chelate cation Cu(dafone) 3 2+ {[Cu(dafone) 3 ](Br 3 )(Br 5 ) (1), [Cu(dafone) 3 ]-(Br 5 )(Br 8 ) 0.5 ·CH 3 CN (2) and [Cu(dafone) 3 ](IBr 4 )(I 2 Br 6 ) 0.5 ·-[a]4689 CH 3 CN (3)} by a procedure employing bromine, iodine, Cu II bromide and dafone in acetonitrile. The formation of chains and isolated polyhalide ions is facilitated by templating with the tris-chelate cation. The Raman spectra of the polyhalides and EPR and other spectral characteristics of the fluxional Cu II complex cation are presented.

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“…The metal-to-nitrogen bond lengths and diazafluorenyl bite angles in the DFT optimized complexes of stable L1 closely resemble those found in the crystal structures of related metal–ligand complexes. 24,25 The M–N bond lengths in the calculated zinc, palladium, and platinum complexes of the stable ligand are about 2.19, 2.09, and 2.07 Å, respectively (cf. 2.13, 2.08, and 2.06 Å in the reported solid state structures of 4,5-diazafluorene complexes).…”

Section: Resultsmentioning

confidence: 99%

“…2.13, 2.08, and 2.06 Å in the reported solid state structures of 4,5-diazafluorene complexes). 24,25 In addition, the observed diazafluorenyl N–M–N bite angles range from 83.2° for zinc and 84.0° for palladium to 83.6° for platinum (cf. 84.8°, 83.7°, and 83.6° in the solid state structures).…”

Section: Resultsmentioning

confidence: 99%

“…In the earlier reported X-ray crystal structures of palladium and platinum 4,5-diazafluoren-9-one dichloride complexes, a square planar coordination geometry was observed, whereas the zinc dichloride complex of a structurally related 4,5-diazafluorene derivative revealed a tetrahedral coordination environment . The input geometries for DFT energy minimization were adapted as such, and the obtained molecular structures and relative Δ G values are presented in Figure .…”

Section: Resultsmentioning

confidence: 99%

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Allosteric Regulation of the Rotational Speed in a Light-Driven Molecular Motor

et al. 2016

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The rotational speed of an overcrowded alkene-based molecular rotary motor, having an integrated 4,5-diazafluorenyl coordination motif, can be regulated allosterically via the binding of metal ions. DFT calculations have been used to predict the relative speed of rotation of three different (i.e., zinc, palladium, and platinum) metal dichloride complexes. The photochemical and thermal isomerization behavior of these complexes has been studied in detail using UV–vis and 1H NMR spectroscopy. Our results confirm that metal coordination induces a contraction of the diazafluorenyl lower half, resulting in a reduction of the steric hindrance in the “fjord” region of the molecule, which causes an increase of the rotational speed. Importantly, metal complexation can be accomplished in situ and is found to be reversible upon the addition of a competing ligand. Consequently, the rotational behavior of these molecular motors can be dynamically controlled with chemical additives.

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Synthesis, crystal structure and cytotoxicity studies of cis-dichloro(4,5-diazafluoren-9-one)platinum(II)

Cited by 11 publications

References 51 publications

Synthesis, crystal structure and biological properties of a cis-dichloridobis(diimine)copper(II) complex

Synthesis, crystal structure and biological properties of a cis-dichloridobis(diimine)copper(II) complex

Polyhalide Ions (Br₈^2– and I₂Br₆^2–) and Chains (···Br₃^–···Br₂··· and ···IBr₄^–···) Stabilised by Using Cu(dafone)₃²⁺ as Counter Ion (dafone = 4,5‐Diazafluoren‐9‐one)

Allosteric Regulation of the Rotational Speed in a Light-Driven Molecular Motor

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Synthesis, crystal structure and cytotoxicity studies of cis-dichloro(4,5-diazafluoren-9-one)platinum(II)

Cited by 11 publications

References 51 publications

Synthesis, crystal structure and biological properties of a cis-dichloridobis(diimine)copper(II) complex

Synthesis, crystal structure and biological properties of a cis-dichloridobis(diimine)copper(II) complex

Polyhalide Ions (Br82– and I2Br62–) and Chains (···Br3–···Br2··· and ···IBr4–···) Stabilised by Using Cu(dafone)32+ as Counter Ion (dafone = 4,5‐Diazafluoren‐9‐one)

Allosteric Regulation of the Rotational Speed in a Light-Driven Molecular Motor

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Polyhalide Ions (Br₈^2– and I₂Br₆^2–) and Chains (···Br₃^–···Br₂··· and ···IBr₄^–···) Stabilised by Using Cu(dafone)₃²⁺ as Counter Ion (dafone = 4,5‐Diazafluoren‐9‐one)