Interactions of zinc octacarboxyphthalocyanine with selected amino acids and with albumin

Kliber, Marta; Broda, Małgorzata A.; Nackiewicz, Joanna

doi:10.1016/j.saa.2015.11.003

Cited by 9 publications

(8 citation statements)

References 43 publications

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“…However, unsubstituted metallophthalocyanines, including ZnPc, are practically not soluble in water [17]. In this case, the desired solubility could be achieved by introducing several polar groups (for example, carboxylic or sulfonic) to the external benzene rings [18]. The other way of increased water dispersibility, with solubility increased from 16 to 120 mg/l, was recently reported as a result of ZnPc nanowire formation, directly grown from powdered ZnPc [17].…”

Section: Introductionmentioning

confidence: 99%

“…The other way of increased water dispersibility, with solubility increased from 16 to 120 mg/l, was recently reported as a result of ZnPc nanowire formation, directly grown from powdered ZnPc [17]. On the other hand, a basic (unsubstituted) ZnPc molecule could be selected as a good computational model, mimicking a less or more distorted structure of its more complex derivatives [18].…”

Section: Introductionmentioning

confidence: 99%

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Solvent impact on the planarity and aromaticity of free and monohydrated zinc phthalocyanine: a theoretical study

2017

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A theoretical investigation on the planarity of molecular structure of zinc phthalocyanine (ZnPc) and its aromaticity has been performed using B3LYP and M06-2X density functionals combined with selected Pople-type basis sets. The effect of the applied calculation method on the optimized structure of ZnPc and ZnPc•••H 2 O, both in the gas phase and in the polar solvent, was analyzed. To quantify the aromaticity of the ZnPc and ZnPc•••H 2 O complexes, both the geometric and magnetic criteria, i.e., Harmonic Oscillator Model of Aromaticity (HOMA) index and the nucleus-independent chemical shift (NICS) values at the centers or 1 Å above the centers of structural subunits, were calculated. The energies of highest energy occupied molecular orbital (HOMO) and lowest energy unoccupied molecular orbital (LUMO) and energy gaps were also estimated. The results show that the free ZnPC molecule is flat in the gas phase and nonplanar in the polar environments (DMSO and water). ZnPC•••H 2 O is nonpolar in the gas phase and polar solvent which is in agreement with recent X-ray reports. Both HOMA and NICS indexes indicate the presence of highly aromatic macrocycle and benzene rings while these parameters for pyrrolic ring are significantly smaller than in free pyrrole. The presence of polar solvents practically does not change aromaticity of the ring subunits of the studied compounds.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Solvent impact on the planarity and aromaticity of free and monohydrated zinc phthalocyanine: a theoretical study

2017

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“…The rate constant of the irradiation of ZnPcOC complex under LED illumination was determined; its value was 0.1870 1/min. The value of the rate constant for this complex is much higher than was presented in [34] because a different dose of radiation was used. In the case of Al(OH)PcOC, complex dependence A = f(t) was linear (Fig.…”

Section: Resultsmentioning

confidence: 83%

“…The presence of selected amino acids or albumin does not have an impact on the position of the bands in the Soret region (λ max = 360 nm) or in the Q region (λ max = 621.5 and 691.5 nm), just as in the case of zinc octacarboxyphthalocyanine [34]. Nevertheless, after adding albumin or amino acids to the Al(OH)PcOC solution, the intensity of B and Q bands slightly increased (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…The received values of k e comparing the photostability of the studied octacarboxyphthalocyanines are shown in Table 2. The photolysis of ZnPcOC complex occur by the mechanism of first-order reaction and the resulting k e shown in [34]. Also, Schnurpfeil and co-workers presented the photo-oxidative stability of many complexes of zinc phthalocyanine; their k e values were determined on the basis of the kinetics of the first-order reactions [36].…”

Section: Resultsmentioning

confidence: 99%

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Interactions of amino acids with aluminum octacarboxyphthalocyanine hydroxide. Experimental and DFT studies

et al. 2017

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The influence of albumin and amino acids (l-serine, glycine, l-histidine, l-tryptophan, l-cysteine) on the properties of aluminum octacarboxyphthalocyanine hydroxide (Al(OH)PcOC) was investigated in a phosphate buffer (pH 8.0). Particular attention was paid to the spectroscopic properties and photostability of Al(OH)PcOC. The effect of albumin or amino acids on the photodegradation of Al(OH)PcOC was examined in water using red light: 685 nm and daylight irradiation. Analysis of kinetic curves indicated that interaction with those molecules increases the photostability of Al(OH)PcOC. The molecular structure of Al(OH)PcOC complexes (in vacuum and in water) with axially or equatorially coordinated amino acids was studied by the B3LYP/6-31G* method, and the effects on molecular structure and electronic absorption spectrum were investigated on the basis of the density functional theory. The calculation results revealed that axial coordination significantly reduces the non-planarity of the phthalocyanine ring, and, thus, alters the electronic structure. On the other hand, hydrogen bonding of phthalocyanine side COOH groups with amino acids, in equatorial complexes, does not change the structure within the center of the phthalocyanine, and causes only a slight increase in UV–vis bands intensity, which is in perfect agreement with experimental data. Graphical abstractStructure of equatorial complex of Al(OH)PcOC with l-histidine calculated byB3LYP/6-31G(d) method. Dotted lines H-bonds Electronic supplementary materialThe online version of this article (doi:10.1007/s00894-017-3222-2) contains supplementary material, which is available to authorized users.

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Spectral Manifestation of the Aggregation of Molecules of Octacarboxyphthalocyanine and its Zinc Complex in a Nanoporous Silicate Gel Matrix

et al. 2020

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Interactions of zinc octacarboxyphthalocyanine with selected amino acids and with albumin

Cited by 9 publications

References 43 publications

Solvent impact on the planarity and aromaticity of free and monohydrated zinc phthalocyanine: a theoretical study

Solvent impact on the planarity and aromaticity of free and monohydrated zinc phthalocyanine: a theoretical study

Interactions of amino acids with aluminum octacarboxyphthalocyanine hydroxide. Experimental and DFT studies

Spectral Manifestation of the Aggregation of Molecules of Octacarboxyphthalocyanine and its Zinc Complex in a Nanoporous Silicate Gel Matrix

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