Specific methionine oxidation of cytochrome c in complexes with zwitterionic lipids by hydrogen peroxide: potential implications for apoptosis

Capdevila, Daiana A.; Marmisollé, Waldemar A.; Tomasina, Florencia; Portela, Magdalena; Radí, Rafael; Murgida, Daniel H.

doi:10.1039/c4sc02181a

Cited by 52 publications

(119 citation statements)

References 63 publications

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“…The higher redox potential of HQ moiety in the coating respect to its value in solution could be attributed to the interaction of the HQ with the polymer or phosphate species in the film. Similar positive shifts in the redox potential have been reported for adsorbed proteins on positive surfaces . This supports the idea that it is thermodynamically easier to reduce redox centers (to transfer electrons to them) when they are close to positive charges.…”

Section: Resultssupporting

confidence: 86%

Supramolecular Surface Chemistry: Substrate‐Independent, Phosphate‐Driven Growth of Polyamine‐Based Multifunctional Thin Films

Marmisollé

Irigoyen

Gregurec

et al. 2015

Adv Funct Materials

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The ability to engineer surfaces at the supramolecular level by controlled integration of specific chemical units through substrate‐independent methodologies represents one of the new paradigms of contemporary materials science. Here, a method is reported to form multifunctional supramolecular coatings through simple dip‐coating of substrates in an aqueous solution of polyamine in the presence of phosphate anions. The chemical richness and versatility of polyamines are exploited as phosphate receptors to form thin functional films on a broad variety of substrates, ranging from metal to carbonaceous surfaces. It is shown that the simple derivatization of pendant amino groups of polyallylamine precursors with different chemical groups can endow films with predefined responsiveness or multiple functions—this translates into one‐pot and one‐step preparation of substrate‐adherent films displaying built‐in functions. It is believed that the flexibility, speed, and versatility with which this method provides such robust functional films make it very attractive for preparing samples of fundamental and technological interest.

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Section: Resultssupporting

confidence: 86%

Supramolecular Surface Chemistry: Substrate‐Independent, Phosphate‐Driven Growth of Polyamine‐Based Multifunctional Thin Films

Marmisollé

Irigoyen

Gregurec

et al. 2015

Adv Funct Materials

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“…These values fit within the range between 100 and 205 mV reported for the horse heart Met-SO derivative. 5,12,16,17 The drop in the potential compared to that of WT* (274±4 mV) 21 is consistent with the change in ligation and a more solvent-accessible heme pocket. The differences in the potentials of WT-M80SO and Lys-ligated M80K # (−94±2 mV) 21 are in accord with Met-SO, rather than Lys, being the sixth ligand in the ferrous protein.…”

Section: Resultsmentioning

confidence: 61%

“…15 More recently Murgida et al have considered Lys/His and hydroxide/His as possible ligands to the heme iron in the ferric protein. 12 The Lys/His and hydroxide/His heme species have very similar resonance Raman spectra but the hydroxide/His reference appeared to fit better the spectra of Met-SO cyt c . In addition, the pH dependence of the reduction potential of Met-SO cyt c was similar to that of M80A mutant of cyt c , the variant with hydroxide/His ligation at neutral pH.…”

Section: Introductionmentioning

confidence: 95%

Ligation and Reactivity of Methionine-Oxidized Cytochrome c

Zhong

Pletneva

2018

Inorg. Chem.

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Met80, one of the heme iron ligands in cytochrome c (cyt c) is readily oxidized to Met sulfoxide (Met-SO) by several biologically-relevant oxidants. The modification has been suggested to impact both the electron-transfer (ET) and apoptotic functions of this metalloprotein. The coordination of the heme iron in Met-oxidized cyt c (Met-SO cyt c) is critical for both of these functions but has remained poorly defined. We present electronic absorption, NMR, and EPR spectroscopic investigations as well kinetic studies and mutational analyses to identify the heme iron ligands in yeast iso-1 Met-SO cyt c. Similar to the alkaline form of native cyt c, Lys73 and Lys79 ligate to the ferric heme iron in the Met80-oxidized protein but this coordination takes place at much lower pH. The ferrous heme iron is ligated by Met-SO implying the redox-linked ligand switch in the modified protein. Binding studies with a model peptide microperoxidase-8 provide a rationale for alterations in ligation and for the role of the polypeptide packing in native and Met-SO cyt c. Imidazole binding experiments have revealed that Lys dissociation from the ferric heme in K73A/K79G/M80K (M80K#) and Met-SO is more than three orders of magnitude slower than the opening of the heme pocket that limits Met80 replacement in native cyt c. The Lys-to-Met-SO ligand substitution gates ET of ferric Met-SO cyt c with Co(terpy)22+. Owing to the slow Lys dissociation step, ET reaction is slow but possible, which is not the case for non-switchable M80A and M80K#. Acidic conditions cause Lys replacement by a water ligand in Met-SO cyt c (pKa=6.3±0.1) increasing intrinsic peroxidase activity of the protein. This pH-driven ligand switch may be a mechanism to boost peroxidase function of cyt c specifically in apoptotic cells.

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“…These complexes are known to modulate changes in DNA molecules more effectively than single polyamines . Also, this specific interaction of phosphate anions with amino groups of some membrane components has recently been suggested to play a crucial role in the modulation of the alternative functions of cytochrome in preapoptotic conditions . P‐NMR studies have revealed that interactions with phosphates occur in the whole range of pH where a typical synthetic polyamine, polyallylamine (PAH), is protonated and phosphate is anionic (≈4–9) .…”

Section: Introductionmentioning

confidence: 99%

Phosphate‐Responsive Biomimetic Nanofluidic Diodes Regulated by Polyamine–Phosphate Interactions: Insights into Their Functional Behavior from Theory and Experiment

Pérez-Mitta

Marmisollé

Albesa

et al. 2017

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There is currently high interest in developing nanofluidic devices whose iontronic output is defined by biological interactions. The fabrication of a phosphate responsive nanofluidic diode by using the biological relevant amine-phosphate interactions is shown. The fabrication procedure includes the modification of a track-etched asymmetric (conical) nanochannel with polyallylamine (PAH) by electrostatic self-assembly. PAH is the arcaetypical model of polyamine and it is further used to address the nanochannels with phosphate responsivity. In order to explore the influence that phosphate in solution has in the conductance of the modified nanochannels, current-voltage measurements using different concentrations of phosphates are performed. Furthermore, to have a complete physicochemical understanding of the system, experimental data is analyzed using a continuous model based on Poison-Nernst-Planck equations and compared with results obtained from stochastic Monte Carlo simulations.

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Specific methionine oxidation of cytochrome c in complexes with zwitterionic lipids by hydrogen peroxide: potential implications for apoptosis

Abstract: The rise of H2O2 concentration that characterizes the initiation of apoptosis can specifically oxidize Met80 in cytochrome c bound to zwitterionic phospholipids, yielding a stable peroxidase.

Cited by 52 publications

References 63 publications

Supramolecular Surface Chemistry: Substrate‐Independent, Phosphate‐Driven Growth of Polyamine‐Based Multifunctional Thin Films

Supramolecular Surface Chemistry: Substrate‐Independent, Phosphate‐Driven Growth of Polyamine‐Based Multifunctional Thin Films

Ligation and Reactivity of Methionine-Oxidized Cytochrome c

Phosphate‐Responsive Biomimetic Nanofluidic Diodes Regulated by Polyamine–Phosphate Interactions: Insights into Their Functional Behavior from Theory and Experiment

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