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Synthesis, characterization, DNA-binding study and anticancer properties of ternary metal(II) complexes of edda and an intercalating ligand

Ng CH, Kong KC, Von ST, Balraj P, Jensen P, Thirthagiri E, et al.

Dalton Trans, 2008 Jan 28.
PMID: 18185860 DOI: 10.1039/b709269e

A series of ternary metal(ii) complexes {M(phen)(edda); 1a (Cu), 1b (Co), 1c (Zn), 1d (Ni); H(2)edda = N,N(')-ethylenediaminediacetic acid} of N,N'-ethylene-bridged diglycine and 1,10-phenanthroline were synthesized and characterized by elemental analysis, FTIR, UV-visible spectroscopy and magnetic susceptibility measurement. The interaction of these complexes with DNA was investigated using CD and EPR spectroscopy. MTT assay results of 1a-1c , screened on MCF-7 cancer cell lines, show that synergy between the metal and ligands results in significant enhancement of their antiproliferative properties. Preliminary results from apoptosis and cell cycle analyses with flow cytometry are reported. seems to be able to induce cell cycle arrest at G(0)/G(1). The crystal structure of 1a is also included.

Matched MeSH terms: Intercalating Agents/chemical synthesis*; Intercalating Agents/pharmacology*; Intercalating Agents/chemistry
Fulltext Interaction of DNA with Simple and Mixed Ligand Copper(II) Complexes of 1,10-Phenanthrolines as Studied by DNA-Fiber EPR Spectroscopy

Chikira M, Ng CH, Palaniandavar M

Int J Mol Sci, 2015;16(9):22754-80.
PMID: 26402668 DOI: 10.3390/ijms160922754

The interaction of simple and ternary Cu(II) complexes of 1,10-phenanthrolines with DNA has been studied extensively because of their various interesting and important functions such as DNA cleavage activity, cytotoxicity towards cancer cells, and DNA based asymmetric catalysis. Such functions are closely related to the DNA binding modes of the complexes such as intercalation, groove binding, and electrostatic surface binding. A variety of spectroscopic methods have been used to study the DNA binding mode of the Cu(II) complexes. Of all these methods, DNA-fiber electron paramagnetic resonance (EPR) spectroscopy affords unique information on the DNA binding structures of the complexes. In this review we summarize the results of our DNA-fiber EPR studies on the DNA binding structure of the complexes and discuss them together with the data accumulated by using other measurements.

Matched MeSH terms: Intercalating Agents
Understanding pore formation and structural deformation in carbon spheres during KOH activation

Mohammed Salisu Musa, Mohd Marsin Sanagi, Wan Aini Wan Ibrahim, Hadi Nur

Sains Malaysiana, 2015;44:613-618.

Carbon spheres (CSs) were synthesized from sucrose by hydrothermal reaction. The synthesized materials were further
activated with potassium hydroxide (KOH) at different concentrations. The effects of KOH concentration on the surface area
and morphology were investigated. The route for pore formation and structural deformation in carbon spheres during
activation has been proposed and discussed based on micrographs and porosity trends. It was suggested that the pore
formation and structural deformation phenomena were due to the intercalating power of energized K+ into the carbon.
This work provides an insight of the pore formation in carbon spheres for the development of adsorbents as well as for
the understanding of the structural deformation of such materials at higher KOH concentrations.

Matched MeSH terms: Intercalating Agents
Fulltext Nanolayered composite with enhanced ultraviolet ray absorption properties from simultaneous intercalation of sunscreen molecules

Megat Nabil Mohsin S, Hussein MZ, Sarijo SH, Fakurazi S, Arulselvan P, Taufiq-Yap YH

Int J Nanomedicine, 2018;13:6359-6374.
PMID: 30349255 DOI: 10.2147/IJN.S171390

Introduction: The potential of layered double hydroxide (LDH) as a host of multiple ultraviolet-ray absorbers was investigated by simultaneous intercalation of benzophenone 4 (B4) and Eusolex® 232 (EUS) in Zn/Al LDH.
Methods: The nanocomposites were prepared via coprecipitation method at various molar ratios of B4 and EUS.
Results: At equal molar ratios, the obtained nanocomposite showed an intercalation selectivity that is preferential to EUS. However, the selectivity ratio of intercalated anions was shown to be capable of being altered by adjusting the molar ratio of intended guests during synthesis. Dual-guest nanocomposite synthesized with B4:EUS molar ratio 3:1 (ZEB [3:1]) showed an intercalation selectivity ratio of B4:EUS =53:47. Properties of ZEB (3:1) were monitored using powder X-ray diffractometer to show a basal spacing of 21.8 Å. Direct-injection mass spectra, Fourier transform infrared spectra, and ultraviolet-visible spectra confirmed the dual intercalation of both anions into the interlayer regions of dual-guest nanocomposite. The cytotoxicity study of dual-guest nanocomposite ZEB (3:1) on human dermal fibroblast cells showed no significant toxicity until 25 μg/mL.
Conclusion: Overall, the findings demonstrate successful customization of ultraviolet-ray absorbers composition in LDH host.

Matched MeSH terms: Intercalating Agents/administration & dosage*; Intercalating Agents/chemistry
Synthesis and characterization of lawsone-lntercalated Zn-Al-layered double hydroxides

Yasin Y, Ismail NM, Hussein MZ, Aminudin N

J Biomed Nanotechnol, 2011 Jun;7(3):486-8.
PMID: 21830495

A drug-inorganic nanostructured material involving pharmaceutically active compound lawsone intercalated Zn-Al layered double hydroxides (Law-LDHs) with Zn/AI = 4 has been assembled by co-precipitation and ion exchange methods. Powder X-ray diffraction (XRD) and Fourier transform infrared spectra (FTIR) analysis indicate a successful intercalation of lawsone between the layers of layered double hydroxides. It suggests that layered double hydroxides may have application as the basis of a drug delivery system.

Matched MeSH terms: Intercalating Agents/chemistry*
Fulltext On the Use of OPEFB-Derived Microcrystalline Cellulose and Nano-Bentonite for Development of Thermoplastic Starch Hybrid Bio-Composites with Improved Performance

Lai DS, Osman AF, Adnan SA, Ibrahim I, Alrashdi AA, Ahmad Salimi MN, et al.

Polymers (Basel), 2021 Mar 15;13(6).
PMID: 33803984 DOI: 10.3390/polym13060897

Thermoplastic starch (TPS) hybrid bio-composite films containing microcrystalline cellulose (C) and nano-bentonite (B) as hybrid fillers were studied to replace the conventional non-degradable plastic in packaging applications. Raw oil palm empty fruit bunch (OPEFB) was subjected to chemical treatment and acid hydrolysis to obtain C filler. B filler was ultra-sonicated for better dispersion in the TPS films to improve the filler-matrix interactions. The morphology and structure of fillers were characterized by scanning electron microscope (SEM), Fourier transform infrared spectroscopy (FTIR) and X-ray diffraction (XRD). TPS hybrid bio-composite films were produced by the casting method with different ratios of B and C fillers. The best ratio of B/C was determined through the data of the tensile test. FTIR analysis proved the molecular interactions between the TPS and the hybrid fillers due to the presence of polar groups in their structure. XRD analysis confirmed the intercalation of the TPS chains between the B inter-platelets as a result of well-developed interactions between the TPS and hybrid fillers. SEM images suggested that more plastic deformation occurred in the fractured surface of the TPS hybrid bio-composite film due to the higher degree of stretching after being subjected to tensile loading. Overall, the results indicate that incorporating the hybrid B/C fillers could tremendously improve the mechanical properties of the films. The best ratio of B/C in the TPS was found to be 4:1, in which the tensile strength (8.52MPa), Young's modulus (42.0 MPa), elongation at break (116.4%) and tensile toughness of the film were increased by 92%, 146%, 156% and 338%, respectively. The significantly improved strength, modulus, flexibility and toughness of the film indicate the benefits of using the hybrid fillers, since these features are useful for the development of sustainable flexible packaging film.

Matched MeSH terms: Intercalating Agents
Fulltext PREPARATION AND CHARACTERIZATION OF MAGNESIUM/ALUMINIUM LAYERED DOUBLE HYDROXIDE AS FILLER IN LOW-DENSITY POLYETHYLENE COMPOSITE

NUR ATHIRAH ZULKIFLI, MOHD AIDIL ADHHA ABDULLAH, MAZIDAH MAMAT

UMT Journal of Undergraduate Research, 2021;3(1):1-6.
MyJurnal

Polymer had been widely used in industries nowadays. However, the properties of the polymer itself are limited to a particular application. This study describes synthetic clay, layered double hydroxide (LDH), as a filler in low-density polyethylene (LDPE) composite. LDHs of magnesium/aluminium-dodecyl sulfate (Mg/Al-DS) and its grafted with triethoxymethylsilane (TEMS), (TEMS-g-Mg/Al-DS) were synthesized through co-precipitation and salinization reaction methods. The presence of alkyl group, v(C-H) in both LDH had confirmed through Fourier transform infrared (FTIR). The appearance of peaks in FTIR spectra within the absorbance range of 2800 – 2930 cm-1indicates a successful surface modification of LDH, supported by the changes of interlayer spacing and the presence of carbon from X-ray diffractogram and CHNS elemental analysis, respectively. The synthesized LDH was mixed with LDPE via melt intercalation method. The LDH modification resulted in higher interaction and compatibility between the LDPE matrix and LDH by the formation exfoliated type of nanocomposites, as suggested by XRD analysis.

Matched MeSH terms: Intercalating Agents
Fulltext Morphology observation and physical properties of phenolic resin-silicate layered nanocomposites

Norul Azlin, M.Z., Senin, H.B., Kok Sheng, C.

Journal of Nuclear and Related Technologies, 2009;2009(1):121-134.
MyJurnal

Phenolic resin-silica nanocomposites samples in pellet shape have been successfully prepared by intercalation of polymer solution through the hot pressing method. The phenolic resin is modified with organic elastomers of silica nanoparticles, which is about 20 nanometer in diameter. The change of density and porosity was studied based on the addition of silica content in the phenolic resin composites. The densities of composites increased with the addition of the silica content from 10 wt.% to 40 wt.%. On the other hand, the porosity percentage was decreased with increasing of silica contents. The mechanical properties (Young’s modulus, energy to break and time to failure) of the nanocomposites samples were identified using the Universal Testing Material Machine (UTM). The results of Young’s modulus, energy to break and time to failure of the phenolic resin composites were found to be slightly increased with silica content from 10 wt.% to 30 wt.%. The X-Ray Microtomogaphy (XRM) topographies have shown that the porosity exists on fracture structure for each nanocomposite. The nanocomposites surface structure has been analyzed using Scanning Electron Microscope (SEM). The observation shows that the fracture surface of the pure phenolic resin is relatively smooth and glassy, which is typical for a brittle material, but the phenolic resin- silica composites fracture surface is not smooth at all. The observations indicate the pure phenolic resin is brittle than phenolic resin-silica nanocomposites. Consequently, the physical properties of the phenolic resin-silica nanocomposites were improved with the addition of 10 wt.% to 30 wt.% silica contents, as compared to that of the pure phenolic resin.

Matched MeSH terms: Intercalating Agents
Fulltext Development and validation of high resolution melting assays for high-throughput screening of BDNF rs6265 and DAT1 rs40184

Asraa Faris, Hadri Hadi Md Yusof, Shahidee Zainal Abidin, Omar Habib, Cheah, Pike-See, Stanslas, Johnson, et al.

Malaysian Journal of Medicine and Health Sciences, 2018;14(101):64-71.
MyJurnal

Introduction: One of the commonly used techniques for mutation screening is High Resolution Melting (HRM) analysis. HRM is a post PCR method that relies on the detection of the fluorescent signals acquired due to the release of DNA intercalated dyes upon the melting of dsDNA to ssDNA. The method is simple, inexpensive and does not require post PCR-handling, making it suitable for high throughput screening. Methods: This study aimed to develop and validate HRM technique for the screening of two disease-associated single nucleotide polymorphisms (SNPs) namely BDNF rs6265 and DAT1 rs40184 using a total of 30 gDNA samples. The obtained results were confirmed and validated by sequencing. Results: HRM analysis showed that the predicted genotypes of BDNF rs6265 and DAT1 rs40184 among all the gDNA samples were in 100% concordance with the sequencing results, making it an accurate and sensitive method for the detection of SNPs. Conclusions: The application of HRM can accurately determine the genotype of BDNF rs6265 and DAT1 rs40184 SNPs, making it a promising tool for rapid and high-throughput screening of targeted SNPs in a large population study.

Matched MeSH terms: Intercalating Agents
Factors affecting nucleolytic efficiency of some ternary metal complexes with DNA binding and recognition domains. Crystal and molecular structure of Zn(phen)(edda)

Seng HL, Ong HK, Rahman RN, Yamin BM, Tiekink ER, Tan KW, et al.

J Inorg Biochem, 2008 Nov;102(11):1997-2011.
PMID: 18778856 DOI: 10.1016/j.jinorgbio.2008.07.015

The binding selectivity of the M(phen)(edda) (M=Cu, Co, Ni, Zn; phen=1,10-phenanthroline, edda=ethylenediaminediacetic acid) complexes towards ds(CG)(6), ds(AT)(6) and ds(CGCGAATTCGCG) B-form oligonucleotide duplexes were studied by CD spectroscopy and molecular modeling. The binding mode is intercalation and there is selectivity towards AT-sequence and stacking preference for A/A parallel or diagonal adjacent base steps in their intercalation. The nucleolytic properties of these complexes were investigated and the factors affecting the extent of cleavage were determined to be: concentration of complex, the nature of metal(II) ion, type of buffer, pH of buffer, incubation time, incubation temperature, and the presence of hydrogen peroxide or ascorbic acid as exogenous reagents. The fluorescence property of these complexes and its origin were also investigated. The crystal structure of the Zn(phen)(edda) complex is reported in which the zinc atom displays a distorted trans-N(4)O(2) octahedral geometry; the crystal packing features double layers of complex molecules held together by extensive hydrogen bonding that inter-digitate with adjacent double layers via pi...pi interactions between 1,10-phenanthroline residues. The structure is compared with that of the recently described copper(II) analogue and, with the latter, included in molecular modeling.

Matched MeSH terms: Intercalating Agents/chemistry
Fulltext A ruthenium polypyridyl intercalator stalls DNA replication forks, radiosensitizes human cancer cells and is enhanced by Chk1 inhibition

Gill MR, Harun SN, Halder S, Boghozian RA, Ramadan K, Ahmad H, et al.

Sci Rep, 2016 08 25;6:31973.
PMID: 27558808 DOI: 10.1038/srep31973

Ruthenium(II) polypyridyl complexes can intercalate DNA with high affinity and prevent cell proliferation; however, the direct impact of ruthenium-based intercalation on cellular DNA replication remains unknown. Here we show the multi-intercalator [Ru(dppz)2(PIP)](2+) (dppz = dipyridophenazine, PIP = 2-(phenyl)imidazo[4,5-f][1,10]phenanthroline) immediately stalls replication fork progression in HeLa human cervical cancer cells. In response to this replication blockade, the DNA damage response (DDR) cell signalling network is activated, with checkpoint kinase 1 (Chk1) activation indicating prolonged replication-associated DNA damage, and cell proliferation is inhibited by G1-S cell-cycle arrest. Co-incubation with a Chk1 inhibitor achieves synergistic apoptosis in cancer cells, with a significant increase in phospho(Ser139) histone H2AX (γ-H2AX) levels and foci indicating increased conversion of stalled replication forks to double-strand breaks (DSBs). Normal human epithelial cells remain unaffected by this concurrent treatment. Furthermore, pre-treatment of HeLa cells with [Ru(dppz)2(PIP)](2+) before external beam ionising radiation results in a supra-additive decrease in cell survival accompanied by increased γ-H2AX expression, indicating the compound functions as a radiosensitizer. Together, these results indicate ruthenium-based intercalation can block replication fork progression and demonstrate how these DNA-binding agents may be combined with DDR inhibitors or ionising radiation to achieve more efficient cancer cell killing.

Matched MeSH terms: Intercalating Agents/metabolism; Intercalating Agents/toxicity; Intercalating Agents/chemistry*
Synthesis, characterization and dna binding studies of [ruthenium(ii)(bpy)2 l]2+ where l are derivatives of imidazo[4,5-f]-1,10-phenanthrolines

Ting T, Crouse K, Ahmad H

Sains Malaysiana, 2015;44:619-628.

Three novel ruthenium(II) complexes of the general formula [Ru(II)(bpy)2
L]2+ were synthesized, where L =
1,10-phenanthroline derivatives of position 2 imidazole having 3,4-didecyloxy-phenyl (ddip), 3,4-ditetradecyloxy-phenyl
(dtip) and 3,4-dihexadecyloxy-phenyl (dhip). All complexes were characterized by elemental analysis, 1
H-NMR and ESI-MS.
Their photophysical properties have also been studied by UV-visible spectroscopy and fluorescence spectroscopy. The
complexes exhibit Ru(II) metal centered emission at approximately 610 nm in acetonitrile solution at room temperature. DNA
binding studies were carried out by UV-visible titration, luminescence titration and viscosity studies. The results indicated
that [Ru(bpy)2
(ddip)]2+ binds to CT-DNA by partial intercalation mode, while [Ru(bpy)2
(dtip)]2+ and [Ru(bpy)2
(dhip)]2+
bind intercalatively via extended ligands.

Matched MeSH terms: Intercalating Agents
Fulltext Synergy of ruthenium metallo-intercalator, [Ru(dppz)2(PIP)]2+, with PARP inhibitor Olaparib in non-small cell lung cancer cells

Yusoh NA, Chia SL, Saad N, Ahmad H, Gill MR

Sci Rep, 2023 Jan 26;13(1):1456.
PMID: 36702871 DOI: 10.1038/s41598-023-28454-x

Poly(ADP-ribose) polymerase (PARP) are critical DNA repair enzymes that are activated as part of the DNA damage response (DDR). Although inhibitors of PARP (PARPi) have emerged as small molecule drugs and have shown promising therapeutic effects, PARPi used as single agents are clinically limited to patients with mutations in germline breast cancer susceptibility gene (BRCA). Thus, novel PARPi combination strategies may expand their usage and combat drug resistance. In recent years, ruthenium polypyridyl complexes (RPCs) have emerged as promising anti-cancer candidates due to their attractive DNA binding properties and distinct mechanisms of action. Previously, we reported the rational combination of the RPC DNA replication inhibitor [Ru(dppz)2(PIP)]2+ (dppz = dipyrido[3,2-a:2',3'-c]phenazine, PIP = 2-(phenyl)-imidazo[4,5-f][1,10]phenanthroline), "Ru-PIP", with the PARPi Olaparib in breast cancer cells. Here, we expand upon this work and examine the combination of Ru-PIP with Olaparib for synergy in lung cancer cells, including in 3D lung cancer spheroids, to further elucidate mechanisms of synergy and additionally assess toxicity in a zebrafish embryo model. Compared to single agents alone, Ru-PIP and Olaparib synergy was observed in both A549 and H1975 lung cancer cell lines with mild impact on normal lung fibroblast MRC5 cells. Employing the A549 cell line, synergy was confirmed by loss in clonogenic potential and reduced migration properties. Mechanistic studies indicated that synergy is accompanied by increased double-strand break (DSB) DNA damage and reactive oxygen species (ROS) levels which subsequently lead to cell death via apoptosis. Moreover, the identified combination was successfully able to inhibit the growth of A549 lung cancer spheroids and acute zebrafish embryos toxicity studies revealed that this combination showed reduced toxicity compared to single-agent Ru-PIP.

Matched MeSH terms: Intercalating Agents
Synthesis of a DNA-targeting nickel (II) complex with testosterone thiosemicarbazone which exhibits selective cytotoxicity towards human prostate cancer cells (LNCaP)

Heng MP, Sinniah SK, Teoh WY, Sim KS, Ng SW, Cheah YK, et al.

Spectrochim Acta A Mol Biomol Spectrosc, 2015 Nov 5;150:360-72.
PMID: 26057090 DOI: 10.1016/j.saa.2015.05.095

Testosterone thiosemicarbazone, L and its nickel (II) complex 1 were synthesized and characterized by using FTIR, CHN, (1)H NMR, and X-ray crystallography. X-ray diffraction study confirmed the formation of L from condensation of testosterone and thiosemicarbazide. Mononuclear complex 1 is coordinated to two Schiff base ligands via two imine nitrogens and two tautomeric thiol sulfurs. The cytotoxicity of both compounds was investigated via MTT assay with cisplatin as positive reference standard. L is more potent towards androgen-dependent LNCaP (prostate) and HCT 116 (colon). On the other hand, complex 1, which is in a distorted square planar environment with L acting as a bidentate NS-donor ligand, is capable of inhibiting the growth of all the cancer cell lines tested, including PC-3 (prostate). It is noteworthy that both compounds are less toxic towards human colon cell CCD-18Co. The intrinsic DNA binding constant (Kb) of both compounds were evaluated via UV-Vis spectrophotometry. Both compounds showed Kb values which are comparable to the reported Kb value of typical classical intercalator such as ethidium bromide. The binding constant of the complex is almost double compared with ligand L. Both compounds were unable to inhibit the action topoisomerase I, which is the common target in cancer treatment (especially colon cancer). This suggest a topoisomerase I independent-cell death mechanism.

Matched MeSH terms: Intercalating Agents
Fulltext Enhanced anti-inflammatory potential of cinnamate-zinc layered hydroxide in lipopolysaccharide-stimulated RAW 264.7 macrophages

Adewoyin M, Mohsin SM, Arulselvan P, Hussein MZ, Fakurazi S

Drug Des Devel Ther, 2015;9:2475-84.
PMID: 25995619 DOI: 10.2147/DDDT.S72716

BACKGROUND: Cinnamic acid (CA) is a phytochemical originally derived from Cinnamomum cassia, a plant with numerous pharmacological properties. The intercalation of CA with a nanocarrier, zinc layered hydroxide, produces cinnamate-zinc layered hydroxide (ZCA), which has been previously characterized. Intercalation is expected to improve the solubility and cell specificity of CA. The nanocarrier will also protect CA from degradation and sustain its release. The aim of this study was to assess the effect of intercalation on the anti-inflammatory capacity of CA.
METHODS: In this study, the anti-inflammatory activity of ZCA was investigated and compared with that of nonintercalated CA. Evaluations were based on the capacity of ZCA and CA to modulate the release of nitric oxide, prostaglandin E2, interleukin (IL)-6, tumor necrosis factor alpha (TNF-α), IL-1β, and IL-10 in lipopolysaccharide-induced RAW 264.7 cells. Additionally, the expression of proinflammatory enzymes, ie, cyclooxygenase-2, inducible nitric oxide synthase, and nuclear factor kappa B (NF-κB), were examined.
RESULTS: Although both ZCA and CA downregulated nitric oxide, prostaglandin E2, tumor necrosis factor alpha, IL-1β, and IL-6, ZCA clearly displayed better activity. Similarly, expression of cyclooxygenase-2 and inducible nitric oxide synthase were inhibited in samples treated with ZCA and CA. The two compounds effectively inactivated the transcription factor NF-κB, but the anti-inflammatory cytokine, IL-10, was significantly upregulated by ZCA only.
CONCLUSION: The present findings suggest that ZCA possesses better anti-inflammatory potential than CA, while zinc layered hydroxide had little or no effect, and these results were comparable with the positive control.

Matched MeSH terms: Intercalating Agents
Fulltext Controlled release and angiotensin-converting enzyme inhibition properties of an antihypertensive drug based on a perindopril erbumine-layered double hydroxide nanocomposite

Hussein Al Ali SH, Al-Qubaisi M, Hussein MZ, Ismail M, Zainal Z, Hakim MN

Int J Nanomedicine, 2012;7:2129-41.
PMID: 22619549 DOI: 10.2147/IJN.S30461

The intercalation of perindopril erbumine into Zn/Al-NO(3)-layered double hydroxide resulted in the formation of a host-guest type of material. By virtue of the ion-exchange properties of layered double hydroxide, perindopril erbumine was released in a sustained manner. Therefore, this intercalated material can be used as a controlled-release formulation.

Matched MeSH terms: Intercalating Agents

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