Synthesis and Characterization of Chiral Tetraaza Macrocyclic Nickel(II) and Palladium(II) Complexes

Du, Guodong; Ellern, and Arkady; Woo, L. Keith

doi:10.1021/ic025818v

Cited by 19 publications

(10 citation statements)

References 30 publications

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“…energy and chirality (Randazzo et al, 2008). However, the study of chiral macrocyclic metal complexes has been limited due to the difficult of preparation, although these complexes are ve ry useful for chiral building blocks (Du et al, 2003;Gao et al, 2005). Here, we report the synthesis and crystal structure of copper(II) azamacrocyclic chiral complex, trans-Dithiocyanato (1,8-di(S-α-methylbenzyl)-1,3,6,8,10,13-hexaazacyclotetradecane)copper(II), with two thiocyanate ions axially.…”

mentioning

confidence: 99%

trans-{1,8-Bis[(S)-1-phenylethyl]-1,3,6,8,10,13-hexaazacyclotetradecane}bis(thiocyanato-κN)copper(II)

et al. 2010

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In the title thiocyanate-coordinated aza-macrocyclic copper(II) complex, [Cu(NCS)2(C24H38N6)], the CuII atom is coordinated by the four secondary N atoms of the aza-macrocyclic ligand and by the two N atoms of the thiocyanate ions in a tetragonally distorted octahedral geometry. The average equatorial Cu—N bond length is shorter than the average axial Cu—N bond length [2.010 (2) and 2.528 (4) Å, respectively]. An N—H⋯N hydrogen-bonding interaction between the secondary amine N atom and the adjacent thiocyanate ion leads to a polymeric chain along the a axis.

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confidence: 99%

trans-{1,8-Bis[(S)-1-phenylethyl]-1,3,6,8,10,13-hexaazacyclotetradecane}bis(thiocyanato-κN)copper(II)

et al. 2010

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“…Complexes 1 and 2 exhibited broad absorption bands at 3222 cm –1 and 3253 cm –1 , respectively which were assigned to O–H stretching vibration of water molecule . Absorption bands due to ν(CH 2 ) vibrations of the cyclohexyl ring of DACH were observed at 2857–2948 cm −1 . Complexes 1 and 2 exhibited sharp absorption bands at 3128 cm –1 and 3134 cm –1 , respectively assigned to N–H stretching frequency of flufenamate or DACH ligand coordinated to M(II) centres .…”

Section: Resultsmentioning

confidence: 99%

New Ionic Cu(II) and Co(II) DACH–Flufenamate Conjugate Complexes: Spectroscopic Characterization, Single X–Ray Studies and Cytotoxic Activity on Human Cancer Cell Lines

et al. 2018

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New ionic antitumor drug entities [{Cu(DACH) 2 (H 2 O)Cl}.(fluf)], 1 and [{Co(DACH) 2 (H 2 O)Cl}.(fluf)], 2 where DACH = 1,2-diamminocyclohexane and fluf = flufenamate anion were prepared and characterized by spectroscopic studies and single X-ray crystallography. In order to evaluate the potential of these complexes to act as antitumor drug candidates, in vitro binding studies of 1 and 2 with ct-DNA have been carried out by biophysical methods which revealed electrostatic binding mode of these drug entities with ct-DNA preferably by external surface or groove binding mode contrary to other nonsteroidal anti-inflammatory (NSAIDs) drugs which show intercalative binding. Comparative electron paramagnetic reso-nance (EPR) titrations were performed which revealed that there was no significant change in EPR spectra of complexes upon incubation with ct-DNA implicating that coordination geometry of metal ions does not alter. Validation of antitumor potential of 1 and 2 was done by cytotoxicity experiments against human cancer cell lines by Sulforhodamine B (SRB) assay. Complex 1 was active against all tested cell lines with an exceptionally low GI 50 value = 2.9 μg/ml against MCF-7 (breast cancer) cell line showing its preferential selectivity. On the contrary, complex 2 showed poor activity against all tested cancer cell lines.

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“…23 Absorption bands due to m(CH 2 ) vibrations of the cyclohexyl ring was observed at 2857-2948 cm 21 . 24 Further supportive evidence for this coordination mode is provided by presence of m(MÀ ÀO) and m(MÀ ÀN) bands at ca. 589-432 and 585-433 cm 21 , respectively.…”

Section: Ir Spectroscopymentioning

confidence: 84%

A mechanistic approach for the DNA binding of chiral enantiomeric L‐ and D‐tryptophan‐derived metal complexes of 1,2‐DACH: Cleavage and antitumor activity

Arjmand

Muddassir

2010

Chirality

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A new chiral series of potential antitumor metal-based complexes 1-3(a and b) of L- and D-tryptophan have been synthesized and thoroughly characterized. Both enantiomers of 1-3 bind DNA noncovalently via phosphate interaction with slight preference of metal center for covalent coordination to nucleobases. The K(b) values of L-enantiomer, however, possess higher propensity for DNA binding in comparison with the D-enantiomeric analogs. The relative trend in K(b) values is as follows: 2(a) > 2(b) > 3(a) > 1(a) > 3(b) > 1(b). These observations together with the findings of circular dichoric and fluorescence studies reveal maximal potential of L-enantiomeric form of copper complex to bind DNA, thereby exerting its therapeutic effect. The complex 2a exhibits a remarkable DNA cleavage activity with pBR322DNA in the presence of different activators such as H(2) O(2) , ascorbic acid, 3-mercaptopropionic acid, and glutathione, suggesting the involvement of active oxygen species for the DNA scission. In vitro anticancer activity of complexes 1-3(a) were screened against 14 different human carcinoma cell lines of different histological origin, and the results reveal that 2a shows significant antitumor activity in comparison with both 1a and 3a and is particularly selective for MIAPACA2 (pancreatic cancer cell line).

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Synthesis and Characterization of Chiral Tetraaza Macrocyclic Nickel(II) and Palladium(II) Complexes

Cited by 19 publications

References 30 publications

trans-{1,8-Bis[(S)-1-phenylethyl]-1,3,6,8,10,13-hexaazacyclotetradecane}bis(thiocyanato-κN)copper(II)

trans-{1,8-Bis[(S)-1-phenylethyl]-1,3,6,8,10,13-hexaazacyclotetradecane}bis(thiocyanato-κN)copper(II)

New Ionic Cu(II) and Co(II) DACH–Flufenamate Conjugate Complexes: Spectroscopic Characterization, Single X–Ray Studies and Cytotoxic Activity on Human Cancer Cell Lines

A mechanistic approach for the DNA binding of chiral enantiomeric L‐ and D‐tryptophan‐derived metal complexes of 1,2‐DACH: Cleavage and antitumor activity

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