Retarded Photooxidation of Cyamemazine in Biomimetic Microenvironments

Limones-Herrero, Daniel; Pérez‐Ruiz, Raúl; Jiménez, M. Consuelo; Miranda, Miguel A.

doi:10.1111/php.12303

Cited by 10 publications

(13 citation statements)

References 30 publications

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“…2 The fields of photochemistry and photocatalysis, among others, have also capitalized on the benefits of spatial confinement, [3][4][5][6] which are related to changes in key properties such as light absorption, formation of redox intermediates, lifetime of excited species, thermodynamics of reacting mixtures, kinetics of competitive steps and adsorption/desorption of chemical species. 3,7,8 Literature precedents of confined photoinduced reactions involve the use of mesoporous inorganic materials, 9 microemulsions, 10 micelles, 11 vesicles, 12 polyelectrolyte multilayered capsules, 13 proteins 14 and photocatalyst-loaded liquid foams, 15 among others. 16 Furthermore, we have recently reviewed an emerging research field focused on the use of viscoelastic gels 17 as tunable and processable reaction vessels for photochemical and photophysical transformations of embedded reactants, providing similar or superior results than those obtained in solution.…”

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confidence: 99%

Intragel photoreduction of aryl halides by green-to-blue upconversion under aerobic conditions

et al. 2015

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confidence: 99%

Intragel photoreduction of aryl halides by green-to-blue upconversion under aerobic conditions

et al. 2015

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“…The same trend has been observed in other biomimetic media; the extent of photoprotection in the gel is higher than within cyclodextrins but lower than in the protein cavities. [4]…”

Section: Discussionmentioning

confidence: 99%

“…Our group has recently examined the photobehavior of CMZ within different microenvironments. The results show that, in sodium dodecyl sulphate micelles and in 1-acid glycoproteins, the local hydrophobicity prevents CMZ photoionization, resulting in a retarded phootoxidation [4].…”

Section: Chart 1 Chemical Structures Of the Investigated Drug And Itmentioning

confidence: 90%

“…Concerning its photophysical properties, the CMZ fluorescence spectrum displays a maximum at  = 530 nm, with a fluorescence quantum yield (F) of 0.11 in PBS (phosphate buffered saline solution, pH = 7.4); the absorption spectrum obtained upon laser flash photolysis (LFP) exhibits contributions from two transient species: the triplet excited state ( 3 CMZ*) and the radical cation (CMZ +• ). Both species overlap in the 400-550 nm region; at shorter wavelengths, 3 CMZ* peaks at 320 nm, while CMZ +• does at 290 nm [3,4].…”

Section: Introductionmentioning

confidence: 98%

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Photobehavior of the antipsychotic drug cyamemazine in a supramolecular gel protective environment

Vendrell-Criado

Miravet

Miranda

et al. 2020

Journal of Photochemistry and Photobiology B: Biology

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“…CYAM absorbs UV light and emits green-orange fluorescence, making it detectable by fluorescence microscopy (5). Furthermore, photooxidation of CYAM is reduced in biomimetic microenvironments (6), raising the possibility of imaging CYAM in neurons. CYAM has a log P (partition coefficient) of 4.4 and a pK a of 9.3, suggesting that it could act as a membrane-permeant weak base.…”

Section: Resultsmentioning

confidence: 99%

Action potentials and amphetamine release antipsychotic drug from dopamine neuron synaptic VMAT vesicles

Tucker

Block

Levitan

2015

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

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Based on lysotracker red imaging in cultured hippocampal neurons, antipsychotic drugs (APDs) were proposed to accumulate in synaptic vesicles by acidic trapping and to be released in response to action potentials. Because many APDs are dopamine (DA) D2 receptor (D2R) antagonists, such a mechanism would be particularly interesting if it operated in midbrain DA neurons. Here, the APD cyamemazine (CYAM) is visualized directly by two-photon microscopy in substantia nigra and striatum brain slices. CYAM accumulated slowly into puncta based on vacuolar H + -ATPase activity and dispersed rapidly upon dissipating organelle pH gradients. Thus, CYAM is subject to acidic trapping and released upon deprotonation. In the striatum, Ca 2+ -dependent reduction of the CYAM punctate signal was induced by depolarization or action potentials. Striatal CYAM overlapped with the dopamine transporter (DAT). Furthermore, parachloroamphetamine (pCA), acting via vesicular monoamine transporter (VMAT), and a charged VMAT, substrate 1-methyl-4-phenylpyridinium (MPP + ), reduced striatal CYAM. In vivo CYAM administration and in vitro experiments confirmed that clinically relevant CYAM concentrations result in vesicular accumulation and pCA-dependent release. These results show that some CYAM is in DA neuron VMAT vesicles and suggests a new drug interaction in which amphetamine induces CYAM deprotonation and release as a consequence of the H + countertransport by VMAT that accompanies vesicular uptake, but not by inducing exchange or acting as a weak base. Therefore, in the striatum, APDs are released with DA in response to action potentials and an amphetamine. This synaptic corelease is expected to enhance APD antagonism of D2Rs where and when dopaminergic transmission occurs.M ost antipsychotic drugs (APDs) are competitive dopamine (DA) D2 receptor (D2R) antagonists (1, 2). The standard view is that APDs, by being weak bases that are in equilibrium with an uncharged form, cross the blood-brain barrier to access extracellular receptor binding sites from the circulation. However, because APDs are weak bases, they have been proposed to accumulate also in acidic intracellular organelles by acidic trapping (i.e., the less abundant uncharged basic hydrophobic form enters organelles passively and then is protonated to become membrane-impermeant). This hypothesis was first explored by examining a D2 antagonist with a covalently added fluorophore and APD displacement of acridine orange (3). More recently, APDs were found to be released from brain tissue by depolarization, which is expected for any positively charged drug. However, follow-up experiments in hippocampal neuron cultures showed that APDs displace the acidophilic dye lysotracker red, implying there is overlap in intracellular distribution between APDs and lysotracker red. Furthermore, lysotracker red was found to accumulate in hippocampal neuron synaptic vesicles by acidic trapping without displacing native neurotransmitter and to be released in response to electrical stimulation. Thus, b...

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Retarded Photooxidation of Cyamemazine in Biomimetic Microenvironments

Cited by 10 publications

References 30 publications

Intragel photoreduction of aryl halides by green-to-blue upconversion under aerobic conditions

Intragel photoreduction of aryl halides by green-to-blue upconversion under aerobic conditions

Photobehavior of the antipsychotic drug cyamemazine in a supramolecular gel protective environment

Action potentials and amphetamine release antipsychotic drug from dopamine neuron synaptic VMAT vesicles

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