Alizarin derivatives as inhibitors of calcium transport

Rozin, Yu. A.; Tat’yanenko, L. V.; Buryndina, E. I.; Barybin, A. S.; Popova, V. G.

doi:10.1007/bf02334638

Cited by 10 publications

(4 citation statements)

References 2 publications

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“…It is capable of marking structures containing calcium; this element has been shown to occur in CA glands of Schistosoma mansoni in a high concentration [ 14 ], most likely in an ionic form [ 13 ]. However, it is known that while being a weak complex-forming agent with respect to the free Ca 2+ ions, alizarin exhibits affinity to calcium in biological structures, forming heteroligand complexes with biological objects [ 32 ]. Similarly to S. mansoni , the presence of a significant amount of calcium in CA glands of T. regenti was proven previously [ 11 ].…”

Section: Discussionmentioning

confidence: 99%

Secretory glands in cercaria of the neuropathogenic schistosome Trichobilharzia regenti - ultrastructural characterization, 3-D modelling, volume and pH estimations

et al. 2011

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BackgroundCercariae of schistosomes employ bioactive molecules for penetration into their hosts. These are released from specialized unicellular glands upon stimuli from host skin. The glands were previously well-described in the human pathogen Schistosoma mansoni. As bird schistosomes can also penetrate human skin and cause cercarial dermatitis, our aim was to characterize the architecture and ultrastructure of glands in the neurotropic bird schistosome Trichobilharzia regenti and compare it with S. mansoni. In the context of different histolytic enzymes used by these two species, we focused also on the estimations of gland volumes and pH in T. regenti.ResultsThe architecture and 3-D models of two types of acetabular penetration glands, their ducts and of the head gland are shown here. We characterized secretory vesicles in all three gland types by means of TEM and confirmed accuracy of the models obtained by confocal microscopy. The results of two independent approaches showed that the glands occupy ca. one third of cercarial body volume (postacetabular glands ca. 15%, circumacetabular 12% and head gland 6%). The inner environment within the two types of acetabular glands differed significantly as evidenced by dissimilar ability to bind fluorescent markers and by pH value which was higher in circumacetabular (7.44) than in postacetabular (7.08) glands.ConclusionsAs far as we know, this is the first presentation of a 3-D model of cercarial glands and the first exact estimation of the volumes of the three gland types in schistosomes. Our comparisons between T. regenti and S. mansoni implied that the architecture and ultrastructure of the glands is most likely conserved within the family. Only minor variations were found between the two species. It seems that the differences in molecular composition have no effect on general appearance of the secretory cells in TEM. Fluorescent markers employed in this study, distinguishing between secretory vesicles and gland types, can be useful in further studies of mechanisms used by cercariae for host invasion. Results of the first attempts to estimate pH within schistosome glands may help further understanding of regulation of enzymatic activities present within the glands.

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Section: Discussionmentioning

confidence: 99%

Secretory glands in cercaria of the neuropathogenic schistosome Trichobilharzia regenti - ultrastructural characterization, 3-D modelling, volume and pH estimations

et al. 2011

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“…Experimentally, however, the bicyclopentadione was found as the major product. This contradiction can be simply explained by that from the epoxide radical 24, the CC cleavage of the epoxide unit could occur through a low barrier (TS [24][25][26][27] ) resulting in the very stable vinylethercyclopentadione radical (27) while the 24 → 25 → 26 pathway had a more complicated rearrangement including outer sphere hydrogen transfers which could be kinetically controlled. However, from 27, a much less favored radical species (28) was found after a hydrogen atom transfer from the -OH group to the oxygen atom of the quinonic ring which seems to be much easier than the H transfers predicted for the 24 → 25 transition including H transfers from and to the carbon atoms of the cyclopentadione ring.…”

Section: Autoxidation Of Curcuminmentioning

confidence: 99%

“…Clinical applications (bio-labeling, etc.) are typical research topics involving alizarin (AR) compounds as well [ 24 , 25 ]. AR is a well-known pH indicator due to the changes in its color in terms of (de)protonation of the –OH group at the C2 position (see Scheme 1 ).…”

Section: Introductionmentioning

confidence: 99%

Radical scavenger competition of alizarin and curcumin: a mechanistic DFT study on antioxidant activity

Sadatsharifi

Purgel

2021

J Mol Model

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In vivo hydroxyl, peroxyl, and superoxide free radicals caused by oxidative stress can be toxic to molecules that are essential for the human body. However, there are natural compounds that can decrease the amount of these harmful species. In this work, we are focusing on two well-known compounds, alizarin (red) and curcumin, to study their interactions with these small radicals for a comparison between a rigid and a flexible structure. We made a mechanistic study and found the major and minor degradation products of curcumin as well as the autoxidation products of it based on a wide range of literature. We found several more favored pathways than those that were previously proposed. On the contrary, for degradation/oxidation of alizarin, only a few proposed mechanisms can be found which were performed in specific conditions. Our calculations predicted some favored rearrangements for the alizarin by peroxyl and superoxide radicals. Graphical abstract

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“…In particular, its clinical and industrial applications (textile dyes, biolabeling, optical device manufacturing, etc.) are major topics of recent researches [1][2][3][4][5][6][7][8]. It is also a popular pH indicator with color changes related to the (de)protonation of the -OH group in the C2 position.…”

Section: Introductionmentioning

confidence: 99%

Performance of exchange–correlation functionals on describing ground state geometries and excitations of Alizarin Red S: Effect of complexation and degree of deprotonation

Fehér

Purgel

Joó

2014

Computational and Theoretical Chemistry

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Ground state optimizations and excited state calculations were performed to analyze the possible anionic forms of Alizarin Red S(ulphonated) and its ML 2 type metal complexes formed with palladium(II). Six functionals have been tested (B3LYP, M06-2X, M06, BH&HLYP, PBE0, LC-wPBE, and CAM-B3LYP) with two basis sets (6-311+g(d,p) and TZVP). The relative errors of these functionals in reproducing the experimental UV-Vis absorption wavelengths are reported for the energetically lowest lying isomers. It was found that the degree of deprotonation affects several functionals in a systematic way. M06 and CAM-B3LYP xc-functionals gave the best estimates according to the average relative errors.These two functionals were then used to explore the coordination mode (hydroxy-keto or catechol) of the palladium(II) complexes and the effect of (de)protonation.

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Alizarin derivatives as inhibitors of calcium transport

Cited by 10 publications

References 2 publications

Secretory glands in cercaria of the neuropathogenic schistosome Trichobilharzia regenti - ultrastructural characterization, 3-D modelling, volume and pH estimations

Secretory glands in cercaria of the neuropathogenic schistosome Trichobilharzia regenti - ultrastructural characterization, 3-D modelling, volume and pH estimations

Radical scavenger competition of alizarin and curcumin: a mechanistic DFT study on antioxidant activity

Performance of exchange–correlation functionals on describing ground state geometries and excitations of Alizarin Red S: Effect of complexation and degree of deprotonation

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