Prodigiosin Analogue Designed for Metal Coordination: Stable Zinc and Copper Pyrrolyldipyrrins

Chang, Tsuhen M.; Sinharay, Sanhita; Astashkin, Andrei V.; Tomat, Elisa

doi:10.1021/ic5008439

Cited by 28 publications

(19 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Cu–N bond distances are similar to those found in other tripyrrolic complexes 50–53 and in the parent compound [Cu(TD1 • )(H 2 O)]. 35 As expected for a ligand-based oxidation and also observed in the case of [Pd(TD1 • )(H 2 O)], 33 the redox state of the ligand system affects (up to ±0.05 Å) the C–N and C–C bond lengths in the conjugated system.…”

Section: Resultssupporting

confidence: 83%

Interactions of Metal-Based and Ligand-Based Electronic Spins in Neutral Tripyrrindione π Dimers

et al. 2017

Self Cite

View full text Add to dashboard Cite

The ability of tetrapyrrolic macrocycles to stabilize unpaired electrons and engage in π–π interactions is essential for many electron-transfer processes in biology and materials engineering. Herein, we demonstrate that the formation of π dimers is recapitulated in complexes of a linear tripyrrolic analog of naturally occurring pigments derived from heme decomposition. Hexaethyltripyrrindione (H3TD1) coordinates divalent transition metals (i.e., Pd, Cu, Ni) as a stable dianionic radical and was recently described as a robust redox-active ligand. The resulting planar complexes, which feature a delocalized ligand-based electronic spin, are stable at room temperature in air and support ligand-based one-electron processes. We detail the dimerization of neutral tripyrrindione complexes in solution through electron paramagnetic resonance (EPR) and visible absorption spectroscopic methods. Variable-temperature measurements using both EPR and absorption techniques allowed determination of the thermodynamic parameters of π dimerization, which resemble those previously reported for porphyrin radical cations. The inferred electronic structure, featuring coupling of ligand-based electronic spins in the π dimers, is supported by density functional theory (DFT) calculations.

show abstract

Section: Resultssupporting

confidence: 83%

Interactions of Metal-Based and Ligand-Based Electronic Spins in Neutral Tripyrrindione π Dimers

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…The characteristic SPR band of the solution was observed between 420-425 nm at a concentration of prodigiosin higher than 2 μg/ml, which could be due to the formation of spherical-shaped AgNPs (Annadhasan et al, 2014). It is well known that a surface plasmon band of spherical AgNPs appears around 420 nm (Park et al, 2003;Suber et al, 2005;Chang et al, 2014). The particle size obtained from DLS measurement was larger than TEM result (9.98 nm), because DLS measures the hydrodynamic radius that considers the prodigiosin pigment on the surface of AgNPs (El-Batal et al, 2014).…”

Section: Discussionmentioning

confidence: 95%

In silico and In vitro cytotoxic effect of prodigiosin-conjugated silver nanoparticles on liver cancer cells (HepG2)

El-Batal¹,

El-Hendawy²,

Faraag³

2017

bta

View full text Add to dashboard Cite

This study demonstrates a novel approach for the synthesis of silver nanoparticles (AgNPs) against human liver cancer cell line (HepG2) using prodigiosin pigment isolated from Serratia marcescens. It further investigates the influence of various parameters such as initial pH, temperature, silver nitrate (AgNO 3) concentration, and prodigiosin concentration on stability and optical properties of synthesized prodigiosin AgNPs. Highly stable, spherical prodigiosin-conjugated AgNPs were synthesized with a mean diameter of 9.98 nm using a rapid one-step method. The cytotoxic activity investigated in the present study indicated that prodigiosin and prodigiosin-conjugated AgNPs possessed a strong cytotoxic potency against human liver cancer. The in silico molecular docking results of prodigiosin and prodigiosin-conjugated AgNPs are congruent with the in vitro studies and these AgNPs can be considered as good inhibitors of mitogen-activated protein kinase 1 (MEK kinases). The study opened the possibility of using prodigiosin-conjugated AgNPs to increase the efficiency of liver cancer treatment.

show abstract

“…The planar nitrogens in prodigiosin and its analogs can chelate copper and zinc, and also alter cellular pH (23)(24)(25). In cultured cell lines, prodigiosin can exert effects similar to those of the polyether ionophores salinomycin and nigericin, which inhibit the activity of vacuolar H + -adenosine triphosphatase (V-ATPase) (26).…”

Section: Discussionmentioning

confidence: 99%

Prodigiosin inhibits Wnt/β-catenin signaling and exerts anticancer activity in breast cancer cells

Wang

Zhou

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

166

119

View full text Add to dashboard Cite

Prodigiosin, a natural red pigment produced by numerous bacterial species, has exhibited promising anticancer activity; however, the molecular mechanisms of action of prodigiosin on malignant cells remain unclear. Aberrant activation of the Wnt/β-catenin signaling cascade is associated with numerous human cancers. In this study, we identified prodigiosin as a potent inhibitor of the Wnt/ β-catenin pathway. Prodigiosin blocked Wnt/β-catenin signaling by targeting multiple sites of this pathway, including the lowdensity lipoprotein-receptor-related protein (LRP) 6, Dishevelled (DVL), and glycogen synthase kinase-3β (GSK3β). In breast cancer MDA-MB-231 and MDA-MB-468 cells, nanomolar concentrations of prodigiosin decreased phosphorylation of LRP6, DVL2, and GSK3β and suppressed β-catenin-stimulated Wnt target gene expression, including expression of cyclin D1. In MDA-MB-231 breast cancer xenografts and MMTV-Wnt1 transgenic mice, administration of prodigiosin slowed tumor progression and reduced the expression of phosphorylated LRP6, phosphorylated and unphosphorylated DVL2, Ser9 phosphorylated GSK3β, active β-catenin, and cyclin D1. Through its ability to inhibit Wnt/β-catenin signaling and reduce cyclin D1 levels, prodigiosin could have therapeutic activity in advanced breast cancers.prodigiosin | Wnt/beta-catenin signaling | breast cancer | LRP6 | Dishevelled (DVL)

show abstract

Prodigiosin Analogue Designed for Metal Coordination: Stable Zinc and Copper Pyrrolyldipyrrins

Cited by 28 publications

References 64 publications

Interactions of Metal-Based and Ligand-Based Electronic Spins in Neutral Tripyrrindione π Dimers

Interactions of Metal-Based and Ligand-Based Electronic Spins in Neutral Tripyrrindione π Dimers

In silico and In vitro cytotoxic effect of prodigiosin-conjugated silver nanoparticles on liver cancer cells (HepG2)

Prodigiosin inhibits Wnt/β-catenin signaling and exerts anticancer activity in breast cancer cells

Contact Info

Product

Resources

About