Studies on the mechanism of drug-binding to melanin

Larsson, Bengt; Tjälve, Hans

doi:10.1016/0006-2952(79)90326-5

Cited by 211 publications

(80 citation statements)

References 19 publications

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“…Nevertheless, promising results have been obtained with synthetic melanin-like polymers, e.g., polydopamine. [10,103] L-dopa [43,55] Natural (Sepia, [48,56] bovine eye [41] ) 5,6-Dihydroxyindole (DHI)-melanin (QI) [57] Mg 2+ Natural (Sepia [58] ) Natural (bovine eye, [41,45] Sepia, [48,56,59] squid [60] ), dopa-melanin [45] Ca 2+ Natural (bovine eye, [41,45] Sepia, [48,56,59,61] squid [60] ), dopa-melanin [45] Fe 3+ Natural (Sepia, [56,59,62] human hair, [63] black rabbit hair [64] ), neuromelanin, [65][66][67] dopa, [68][69][70] catechols, [71] polydopamine, [72][73][74] DHI-melanin, [63] melanin from cys-dopamine, [75] diethylaminedopamine-melanin [74] Neuromelanin, [76] dopa-melanin, [74] natural (Sepia), [74] diethylamine-dopaminemelanin [74] Natural (Sepia), …”

Section: Melanin/metal Oxides Interfaces: Adhesion Biocompatibilitymentioning

confidence: 99%

“…[84] Neuromelanin has been reported to have a dichotomous role (adverse or protective): beneficial when it reduces the oxidative stress in the brain due to its ability to bind cations; detrimental when it exacerbates the oxidative stress releasing H 2 O 2 or by reducing redox-active metals to a more reactive state. [85][86][87] Particular efforts have been made in understanding the binding of iron to neuromelanin, [76,[88][89][90][91][92][93][94][95] as iron was reported in dopaminergic neurons of Parkinsonian brains. [8] Recently, Sepia melanin has been identified as a suitable model to describe the binding characteristics of neuromelanin.…”

Section: Introductionmentioning

confidence: 99%

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Natural melanin pigments and their interfaces with metal ions and oxides: emerging concepts and technologies

Mauro

Soliveri

et al. 2017

MRS Communications

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Melanin (from the Greek μέλας, mélas, black) is a biopigment ubiquitous in flora and fauna, featuring broadband optical absorption, hydration-dependent electrical response, ion-binding affinity as well as antioxidative and radical-scavenging properties. In the human body, photoprotection in the skin and ion flux regulation in the brain are some biofunctional roles played by melanin. Here we discuss the progress in melanin research that underpins emerging technologies in energy storage/conversion, ion separation/water treatment, sunscreens, and bioelectronics. The melanin research aims at developing approaches to explore natural materials, well beyond melanin, which might serve as a prototype benign material for sustainable technologies.

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Section: Melanin/metal Oxides Interfaces: Adhesion Biocompatibilitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Natural melanin pigments and their interfaces with metal ions and oxides: emerging concepts and technologies

Mauro

Soliveri

et al. 2017

MRS Communications

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“…Association of [ 14 C]TRX radioactivity with the uvea resulted from the affinity of melanin-rich tissues for organic amines and polycyclic aromatic hydrocarbons. The retention or accumulation of xenobiotics having cationic properties by ocular tissues impregnated with melanin seems to be common (Larsson and Tjalve, 1979). Mean plasma concentrations of unchanged TRX at the first time point were slightly higher in females than in males for both rats and dogs.…”

Section: Discussionmentioning

confidence: 90%

Metabolism, Distribution and Excretion of a Selective N-Methyl-d-Aspartate Receptor Antagonist, Traxoprodil, in Rats and Dogs

Prakash¹,

Cui²,

Potchoiba³

et al. 2007

Drug Metab Dispos

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Excretion of radioactivity was rapid and nearly complete within 48 h after dosing in both species. Whole-body autoradioluminography study suggested that TRX radioactivity was retained more by uveal tissues, kidney, and liver than by other tissues. TRX is extensively metabolized in rats and dogs since only 8 to 15% of the administered radioactivity was excreted as unchanged drug in the urine of these species. The metabolic pathways included aromatic hydroxylation at the phenylpiperidinol moiety, hydroxylation at the hydroxyphenyl ring, and O-glucuronidation. There were notable species-related qualitative and quantitative differences in the metabolism of TRX in rats and dogs. The hydroxylation at the 3-position of the phenol ring followed by methylation of the resulting catechol intermediate and subsequent conjugation were identified as the main metabolic pathways in dogs. In contrast, formation of the major metabolites in rats was due to oxidation at the 4-position of the phenylpiperidinol moiety followed by further oxidation and phase II conjugation. TRX glucuronide conjugate was identified as the major circulating component in rats, whereas the glucuronide and sulfate conjugates of O-methyl catechol metabolite were the major metabolites in dog plasma. The site of conjugation of regioisomeric glucuronides was established from the differences in the collision-induced dissociation product ion spectra of their methylated products.Accumulating evidence suggests that in cerebral ischemic or hypoxic conditions such as stroke and head trauma, the NMDA receptor is overstimulated by an increased amount of endogenous glutamate (Bullock et al

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“…DOPA--melanin (DOPA-eumelanin) is a synthetic melanin, which is very similar to natural eumelanin. Melanins reveal the ability of binding to drugs [1][2][3][4], and metal ions [5,6]. Binding the drug with melanin has the character of electrostatic interactions between positive charged drug molecules and carboxylic or orto-semiquinone groups of melanin which have a negative charge at normal pH = 7.…”

Section: Introductionmentioning

confidence: 99%

Triplet States in DOPA-Melanin and in Its Complexes with Kanamycin and Copper Cu(II) Ions

et al. 2010

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The mono-and biradical forms of DOPA-melanin (DOPA-eumelanin) were studied by EPR spectroscopy in 100-300 K temperature range. The existence of triplet states in DOPA-melanin was proved. The analysis of EPR spectra has shown that in DOPA-melanin and its complexes with kanamycin and Cu 2+ ions, two kinds of paramagnetic centres exist. The first of them are in doublet ground state with spin S = 1/2 and they obey the Curie law. The paramagnetic centres of the second group are in thermally excited triplet state with spin S = 1 and in this case the Curie law is not fulfilled.

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Studies on the mechanism of drug-binding to melanin

Cited by 211 publications

References 19 publications

Natural melanin pigments and their interfaces with metal ions and oxides: emerging concepts and technologies

Natural melanin pigments and their interfaces with metal ions and oxides: emerging concepts and technologies

Metabolism, Distribution and Excretion of a Selective N-Methyl-d-Aspartate Receptor Antagonist, Traxoprodil, in Rats and Dogs

Triplet States in DOPA-Melanin and in Its Complexes with Kanamycin and Copper Cu(II) Ions

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