Transition metal complexes of neocryptolepine analogues. Part I: Synthesis, spectroscopic characterization, and in vitro anticancer activity of copper(II) complexes

Emam, Sanaa M.; Sayed, Ibrahim El Tantawy El; Nassar, Nagla

doi:10.1016/j.saa.2014.03.114

Cited by 54 publications

(40 citation statements)

References 68 publications

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“…In addition, the nature of metal–ligand bond is characterized by using the energies of d‐d electronic transitions. The bonding parameters α 2 , β 2 and γ 2 which are taken as measure of covalence of in‐plane σ bonds, in‐plane and out‐of‐plane π bonds; respectively will be calculated by these equations:

\propto^{2} = \frac{A_{true‖}}{0.036} + ((), g_{∣} - g_{e}) + \frac{3 ((), g_{⊥} - g_{e})}{7} + 0.04

\propto^{2} β^{2} = K_{‖}^{2} = \frac{((), g_{‖} - g_{e}) Δ_{1}}{8 λ_{0}}

α^{2} γ^{2} = K_{⊥}^{2} = \frac{((), g_{⊥} - g_{e}) Δ_{2}}{2 λ_{0}}

…”

Section: Resultsmentioning

confidence: 99%

Structural characterization, thermal investigation and biological activity of metal complexes containing Schiff Base ligand (Z)‐3‐(1‐((4,6‐dimethyl‐1H‐pyrazolo[3,4‐b] pyridin‐3‐yl)imino)ethyl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one

Emam

Abouel‐Enein

Abdel‐Satar

2019

Applied Organom Chemis

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A new series of metal complexes containing Co(II), Pd(II), Fe(III) chloride and Cu(II) salts (chloride, bromide, sulphate and perchlorate) have been prepared with Schiff base ligand (HL). The synthesized compounds were elucidated using elemental analyses, spectral techniques, molar conductance, magnetic measurements and thermogravimetric studies. The analytical data established (1 M:1 L) stoichiometry for complexes (1), (2), (4), (6) and (7) as well as (1 M:2 L) and (2 M:3 L) stoichiometry for complexes (5) and (3), respectively. As a result, the ligand HL coordinates in complexes (1), (2), (4), (6) as a monobasic tridentate ONN moiety via the oxygen atom of the deprotonated phenolic OH, the nitrogen atoms of the azomethine and the imine group in pyrazolopyridine ring. While, it behaves as a neutral bidentate in complexes (3,7), chelates via oxygen and nitrogen atoms of enolic OH and azomethine groups. Also, in complex (5) Cu2+ ion binds via NO sits of two ligand molecules in its monobasic and neutral forms. The magnetic moment and electronic spectral data proposed octahedral structure for complexes (2, 3 and 7) as well as triagonal bipyramidal and square pyramidal geometry for complexes (1 and 4), while, chelates (5) and (6) possess square planar geometry. TG/DTG studies confirmed the chemical formula for these complexes and established the thermal decomposition processes ended with the formation of metal or metal oxides contaminated with carbon residue. An axial electron spin resonance spectra were suggested for Cu(II) complexes pointing to 2B1g as a ground state with hyperfine structure for complex (4). In vitro antibacterial and antioxidant activities were performed for HL ligand and its metal complexes. The biological studies indicate that complex (3) has better antibacterial activity compared to the ligand and the other complexes.

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\propto^{2} = \frac{A_{true‖}}{0.036} + ((), g_{∣} - g_{e}) + \frac{3 ((), g_{⊥} - g_{e})}{7} + 0.04

\propto^{2} β^{2} = K_{‖}^{2} = \frac{((), g_{‖} - g_{e}) Δ_{1}}{8 λ_{0}}

α^{2} γ^{2} = K_{⊥}^{2} = \frac{((), g_{⊥} - g_{e}) Δ_{2}}{2 λ_{0}}

…”

Section: Resultsmentioning

confidence: 99%

Structural characterization, thermal investigation and biological activity of metal complexes containing Schiff Base ligand (Z)‐3‐(1‐((4,6‐dimethyl‐1H‐pyrazolo[3,4‐b] pyridin‐3‐yl)imino)ethyl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one

Emam

Abouel‐Enein

Abdel‐Satar

2019

Applied Organom Chemis

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“…Hence their mechanism with interaction with DNA has attracted more attention in the design of new compounds which can bind to DNA via covalent or non-covalent type of binding (intercalating, grooves or electrostatic). Copper has a long history of medical application and the anticancer and antiparasitic properties of copper complexes have increased the interest of scientists in their thorough studies [13,14]. The present work stems from our continued interest in defining and evaluating antioxidant, DNA binding and cleaving properties of NNS donor copper complexes since copper is widely distributed in the biological system and display a broad spectrum activities.…”

Section: Introductionmentioning

confidence: 99%

Crystal structures of o , o ′-( N , N ′-dipicolinyldene)diazadiphenyl disulfide and its copper (II) complex: Antioxidant, antibacterial and DNA-binding properties

Moosun

Jhaumeer‐Laulloo

Hosten

et al. 2015

Inorganica Chimica Acta

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“…All reactions were followed by thin layer chromatography (TLC) on kiesel gel F254 precoated plates (Merck). Starting materials sulfonyl and carbonyl hydrazides were synthesized and purified according to literature procedures (Goyal et al, 2016;Brandes, et al, 2005;Bader et al, 2008;Kumaraswamy et al, 2008;Surendiran et al, 2012;xie, et al, 2012). Moreover, the compounds 3 and 4 were commercially available and purchased from Sigma-Aldrich.…”

Section: General Methodsmentioning

confidence: 99%

“…Fig. 1) which are naturally occurred as indoloquinoline alkaloids isolated from the shrub Cryptolepis sanguinolenta, that is growing in west Africa, used for treatment of endemic disease such as malaria fever and various disorder of the body are important due to their wide spectrum of biological properties (Cimanga et al, 1996;El Sayed et al, 2009;Jonckers et al, 2002;Lavrado et al, 2010;Lu et al, 2013;Prakash et al, 2011;Mei et al, 2013;Wang et al, 2013Xu and Pieters 2013;Emam et al, 2015;Okada et al, 2016;Larghi et al, 2015;Peng et al, 2012) However, a direct comparison of the cytotoxicity of cryptolepine and neocryptolepine demonstrated that the latter was much less cytotoxic and high affinity towards DNA. (Bailly et al, 2000;Guittat et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Activity of Novel Neocryptolepine-Hydrazides Hybrids

2017

J App Pharm Sci

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By combining the structural features of neocryptolepine and hydrazides, novel hybrid compounds 8a-d and 9a-j were synthesized using a simple and convenient method. Evaluation of these compounds against human hepatocellular carcinoma (HepG2) cell line using MTT assay was performed. Compound 8c was identified as the most active anticancer agent as it showed effectiveness at low concentration with IC50 2.51 μM on the tested cell line when compared with reference drug 5-FU. It is worth to note that all tested compounds showed antiproliferative activity at very lower micro molar concentrated when compared with the reference drug except compounds 9a, 9e, and 9j which were less active than 5-FU. The anticancer screening results of the tested compounds provide an encouraging framework that could lead to the development of potent new anticancer agents based on neocryptolepine core structure.

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Transition metal complexes of neocryptolepine analogues. Part I: Synthesis, spectroscopic characterization, and in vitro anticancer activity of copper(II) complexes

Cited by 54 publications

References 68 publications

Structural characterization, thermal investigation and biological activity of metal complexes containing Schiff Base ligand (Z)‐3‐(1‐((4,6‐dimethyl‐1H‐pyrazolo[3,4‐b] pyridin‐3‐yl)imino)ethyl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one

Structural characterization, thermal investigation and biological activity of metal complexes containing Schiff Base ligand (Z)‐3‐(1‐((4,6‐dimethyl‐1H‐pyrazolo[3,4‐b] pyridin‐3‐yl)imino)ethyl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one

Crystal structures of o , o ′-( N , N ′-dipicolinyldene)diazadiphenyl disulfide and its copper (II) complex: Antioxidant, antibacterial and DNA-binding properties

Synthesis and Antiproliferative Activity of Novel Neocryptolepine-Hydrazides Hybrids

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