Solvation of anionic water‐soluble porphyrins: A computational study

Cuya, Teobaldo; Louro, Sônia R.W.; Pascutti, Pedro Geraldo; Anteneodo, Celia

doi:10.1002/qua.22700

Cited by 11 publications

(8 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…At 310 K and within simulation time, only the second barrier could be overcome, meaning that the substituents had restricted rotation ability. The SDF of water molecules revealed a moderate hydration of the central porphyrin ring, especially of the nitrogen atoms, in agreement with the trends reported by Guizado et al − Hydration was more pronounced for the Mpyr+ as compared to the Phe groups. In fact, experimental measurements of n -butanol/water partition coefficients (see Table ) demonstrate that the affinity of the different photosensitizers for water is improved as the number of strongly hydrated Mpyr+ groups increases in relation to the number of Phe groups. , …”

Section: Resultssupporting

confidence: 90%

Photodynamic Efficiency of Cationicmeso-Porphyrins at Lipid Bilayers: Insights from Molecular Dynamics Simulations

2012

View full text Add to dashboard Cite

Porphyrin derivatives have applications as photoactive drugs in photodynamic therapy. However, little is known about their interactions with phospholipid membranes at the molecular level. We employed molecular dynamics simulations to model the binding between a series of cationic meso-(N-methyl-4-pyridinium)phenylporphyrins and anionic phosphatidylglycerol lipid bilayers. This was done in the presence of molecular oxygen within the membrane. The ability of various porphyrins to cause photodamage was quantified in terms of their immersion depth and degree of exposition to a higher oxygen concentration inside the membrane. Simulations showed that the photodynamic efficiency could be improved as the number of hydrophobic phenyl substituents attached to the porphyrinic ring increased. In the specific case of porphyrins containing two hydrophobic and two charged substituents, the cis isomer was significantly more efficient than the trans. These results correlate well with previous experimental observations. They highlight the importance of both the total charge and amphiphilicity of the photosensitizer for its performance in photodynamic therapy.

show abstract

Section: Resultssupporting

confidence: 90%

Photodynamic Efficiency of Cationicmeso-Porphyrins at Lipid Bilayers: Insights from Molecular Dynamics Simulations

2012

View full text Add to dashboard Cite

show abstract

“…The process of ion solvation has been deeply studied, employing mostly water as solvent. Some examples of this kind of studies are the halide ions hydrated by a variable number of water molecules, [16][17][18][19][20][21] the solvation of the hydronium and hydroxide ions, [22][23][24] of anionic porphyrins 25 or the hydration of the perchlorate, perbromate, selenate, arsenate and vanadate anions. 26 Moreover, some authors have recently applied this strategy to the study of acid and base dissociation in water.…”

Section: Introductionmentioning

confidence: 99%

A computational study of the protonation of simple amines in water clusters

Sánchez‐Lozano

Cabaleiro‐Lago

Hermida-Ramón

et al. 2013

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

The microsolvation study of a group of amines with a variable number of water molecules was performed by conducting a theoretical analysis of the properties of the clusters formed by the amines with up to seven molecules of water. We describe the microsolvation of several amines focusing on the dissociation of a water molecule that transfers a proton to the amine and forms a hydroxide ion. Ab initio calculations were performed on these clusters employing the DFT/B3LYP and MP2 methods with the 6-311++G(2d,p) basis set. Several stationary points for each cluster were thus located and characterized as minima from frequency calculations. Intermolecular BSSE corrected interaction energies were obtained. The protonation mechanism of the amines was examined in terms of some parameters that include the lengths of the bonds involved in the process of proton transfer and the frequencies associated with certain O-H and N-H stretching modes. On the basis of the calculations, all studied amines present similar behavior but trimethylamine, whose limitations to be integrated in the water hydrogen bond network cause the instability of some of their complexes. The cyclic configurations are the most stable structures up to five water molecules due to the presence of cooperative effects associated with the hydrogen bonds of water molecules. However, when the number of water molecules increases the spatial forms become the most stable configurations. The dissociated forms were not found to have the most stable configuration in any of the studied systems but energetic differences between the dissociated and non-dissociated forms decrease with the number of water molecules.

show abstract

“…hydrophilic profile. 4,5 However, RDFs provide only averaged information and miss important details of the water structure around a solute. In the present work, from the outcomes of molecular dynamics (MD) simulations in a classical approximation, spatial distribution functions were analyzed to obtain detailed information on the water structure surrounding PPIX and heme.…”

Section: Introductionmentioning

confidence: 99%

Hydration of hydrophobic biological porphyrins

Cuya

Louro

Anteneodo³

2011

The Journal of Chemical Physics

View full text Add to dashboard Cite

Explicit solvent, single solute molecular dynamics simulations of protoporphyrin IX and its Fe(2+) complex (heme) in water were performed. The relation of solute-solvent was examined through the spatial distribution functions of water molecules around the centroid of the porphyrin ring. A detailed description of the time-averaged structure of water surrounding the solutes as well as of its fluctuations is presented.

show abstract

Solvation of anionic water‐soluble porphyrins: A computational study

Cited by 11 publications

References 14 publications

Photodynamic Efficiency of Cationicmeso-Porphyrins at Lipid Bilayers: Insights from Molecular Dynamics Simulations

Photodynamic Efficiency of Cationicmeso-Porphyrins at Lipid Bilayers: Insights from Molecular Dynamics Simulations

A computational study of the protonation of simple amines in water clusters

Hydration of hydrophobic biological porphyrins

Contact Info

Product

Resources

About