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Cysteinyldopa (0):
Recent article
Cysteinyldopa
Abstract
Serum 5-S-CD levels were significantly increased by therapeutic UVB exposure. Sustained levels of 5-S-CD in serum appear to reflect the degree of skin injury during NB-UVB phototherapy....
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PMID: 18954414
PDF is available here.
PDF is available here.
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Abstract
We study in further detail the apoptotic process activated by this catechol-thioether derivative of dopamine in SH-SY5Y neuroblastoma cells. CysDA activates a cascade of events by an initial perturbation of Calcium homeostasis in the cell. Cell treatment with the catechol-thioether induces an immedi...
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PMID: 17929313
PDF is available here.
PDF is available here.
Inorganic Chemistry (47)3 2008
Abstract
Cysteinyldopas are naturally occurring conjugates of cysteine and dopa (3,4-dihydroxy-l-phenylalanine) that are precursors to red pheomelanin pigments. Metal ions are known to influence pheomelanogenesis in vitro and may be regulatory factors in vivo. Cydo (3-[(2-amino-ethyl)sulfanyl]-4,6-di-tert-bu...
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PMID: 18163613
PDF is available here.
PDF is available here.
Abstract
The characteristic absorption and photochemical properties of pheomelanins are generally attributed to "benzothiazine" structural units derived biogenetically from 5-S-cysteinyldopa. This notion, however, conveys little or no information about the structural chromophores responsible for the photorea...
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PMID: 18435615
PDF is available here.
PDF is available here.
Journal of Chromatography A (1156)1-2 2007
Abstract
5-S-cysteinyldopa is a well-known pigment intermediate and analysis of its plasma concentration is interesting for the early diagnosis, as well as for evaluation of treatment and follow-up of malignant melanoma. A determination method of 5-SCD in human plasma was developed using solid phase extracti...
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PMID: 17229429
PDF is available here.
PDF is available here.
Human Cell (20)2 2007
Abstract
A new human malignant melanoma cell line, designated DEOC-1, was established from the heel lesion of a 59-year-old man. This cell line has grown well for 84 months. The monolayer, cultured cells are polygonal in shape, appear to be spindle-shaped cells or multipolar cells, and have a tendency to pil...
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PMID: 17547717
PDF is available here.
PDF is available here.
Blood Purification (25)5-6 2007
Abstract
The high constitutive levels of free 5SCD, pheomelanin, and PB-DOPA in the blood may be deteriorating in HD patients through the production of reactive oxygen species.
2007 S. Karger AG, Basel...
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PMID: 18089933
PDF is available here.
PDF is available here.
Pigment Cell Research (19)5 2006
Abstract
We measured serum and urine levels of melanin-related metabolites, 5-S-cysteinyldopa (5-S-CD) and 6-hydroxy-5-methoxyindole-2-carboxylic acid (6H5MI2C), in nine subjects exposed to normal sunlight over the course of 12 months. We collected samples in the middle of each month and examined the variati...
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PMID: 16965276
PDF is available here.
PDF is available here.
Inorganic Chemistry (45)16 2006
Abstract
A new cysteinyldopa model ligand Cydo {3-[(2-aminoethyl)sulfanyl]-4,6-di-tert-butylbenzene-1,2-diol} was prepared and its reactivity with Cu(II) explored. Under anaerobic conditions, tetranuclear [Cu4(Cydo)4] is isolated, but in the presence of O2, a benzothiazine intermediate accumulates that is tr...
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PMID: 16878910
PDF is available here.
PDF is available here.
Journal of Physical Chemistry B (110)28 2006
Abstract
We report a detailed photoluminescence study of cysteinyldopa-melanin (CDM), the synthetic analogue of pheomelanin. Emission spectra are shown to be a far more sensitive probe of CDM's spectroscopic behavior than are absorption spectra. Although CDM and dopa-melanin (DM, the synthetic analogue of eu...
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PMID: 16836351
PDF is available here.
PDF is available here.
Abstract
We have investigated a possible correlation between melanin-type and the antioxidant defense system after UV, focusing on the activities of superoxide dismutase and catalase, which correlated with the phototype of epidermal reconstructs. UVA was more effective than UVB in damaging these enzymatic ac...
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PMID: 16417235
PDF is available here.
PDF is available here.
Carbohydrate Research (340)18 2005
Abstract
The reactions of 5-S-cysteinyldopa, L-alpha-methyldopa and DL-m-tyrosine with D-glucose were investigated at 90 degrees C in phosphate buffer at pH ranging from 5.0 to 9.0. Whereas gave mainly the double Maillard condensation product N,N'-bis(1''-deoxy-D-fructos-1''-yl)-5-S-cysteinyldopa, as an inse...
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PMID: 16229826
PDF is available here.
PDF is available here.
Biochemistry (Washington) (44)48 2005
Coating proteins: structure and cross-linking in fp-1 from the green shell mussel Perna canaliculus.
Abstract
The protein family known as fp-1 provides mussel byssus with a protective outer coating and has drawn much attention for its water resistant bioadhesive properties in vitro. A new fp-l isolated from the green shell mussel Perna canaliculus (pcfp-1) reveals a composition dominated by only four amino...
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PMID: 16313194
PDF is available here.
PDF is available here.
Clinical Cancer Research (11)22 2005
Abstract
SPARC or its combination with GPC3 is thus considered a potentially useful tumor marker, especially for melanoma at an early stage....
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PMID: 16299239
PDF is available here.
PDF is available here.
Cancer Letters (221)2 2005
Abstract
We here show that 5-S-cysteinyldopa significantly protects melanocytes from membrane damage (permeability) induced by ultraviolet A radiation. Thus, 5-S-cysteinyldopa, may at the same time sensitise DNA and protect membranes from damage induced by ultraviolet radiation....
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PMID: 15808398
PDF is available here.
PDF is available here.
Journal of Biological Chemistry (280)16 2005
Abstract
We show here that the o-quinone dopaminochrome (DACHR), a relatively stable DA oxidation product, promotes concentration (0.1-0.2 mum)- and respiration-dependent generation of H(2)O(2) at Complex I in brain mitochondria, with further stimulation by low concentrations of rotenone (5-30 nm). The roten...
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PMID: 15710606
PDF is available here.
PDF is available here.
Pigment Cell Research (17)5 2004
Abstract
These results suggest that A/A epidermal melanoblasts are influenced by the A gene from the dermis of neonatal mice, and are capable of synthesizing pheomelanin in the culture. Pheomelanin production in the epidermis from 3.5- and 5.5-d-old A/A mice may be induced by the expression of the agouti gen...
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PMID: 15357837
PDF is available here.
PDF is available here.
Abstract
Abstract
5-S-L-Cysteinyl-L-dopa is a well-known pigment intermediate and analysis of its serum concentration is well suited for evaluation of treatment and follow-up of stage III and IV malignant melanoma. A simplified analytical method is described using organic extraction followed by clean-up on a boronate...
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PMID: 15370461
PDF is available here.
PDF is available here.
Neurologia Medico-Chirurgica (43)12 2003
Abstract
A 35-year-old male presented with a variant of neurocutaneous melanosis with leptomeningeal malignant melanoma. He had three pigmented nevi from birth. He suffered diplopia followed by headache. T1-weighted magnetic resonance (MR) imaging revealed hydrocephalus and a small linear hyperintense lesion...
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PMID: 14723271
PDF is available here.
PDF is available here.
Pigment Cell Research (16)6 2003
Abstract
These results suggest that the proliferation of p/p melanoblasts-melanocytes is stimulated by L-Tyr, and that the differentiation of melanocytes is induced by L-Tyr as the age of the donor mice advanced, although eumelanin and pheomelanin fail to accumulate in p/p melanocytes and are released from t...
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PMID: 14629719
PDF is available here.
PDF is available here.
Pigment Cell Research (16)5 2003
Abstract
A sensitive and specific high performance liquid chromatography (HPLC) method was developed to quantify 4-amino-3-hydroxyphenylalanine (4-AHP) and 3-amino-4-hydroxyphenylalanine (3-AHP) in urine. In degradation studies of melanin pigment, 4-AHP and 3-AHP are derived from benzothiazine units of pheom...
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PMID: 12950724
PDF is available here.
PDF is available here.
Melanoma Research (13)4 2003
Abstract
We have shown that the serum level of 5-S-CD is a sensitive and specific marker in predicting distant metastases. In melanocytes and melanoma cells, cysteinyldopa isomers are oxidized to phaeomelanin, the yellow to reddish melanin pigment. In this study we have developed a new method to measure leve...
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PMID: 12883361
PDF is available here.
PDF is available here.
Abstract
These results thus suggest that vitamin C administration during chelation with DMSA/MiADMSA was significantly beneficial in reducing oxidative stress however, it had little or no additive effect on the depletion of lead compared with the effect of chelators alone. Thus, the co-administration of vita...
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PMID: 12732454
PDF is available here.
PDF is available here.
Abstract
We can confirm that changes in both marker concentrations correlated with the stages of the patient. The markers are most sensitive in Stage IV patients and also have a high specificity in these patients. In Stage IV melanoma patients, 5-S-CD and S-100B protein levels are independent significant pro...
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PMID: 12509947
PDF is available here.
PDF is available here.
Melanoma Research (12)5 2002
Abstract
We investigated the clinical utility of a new and optimized method to detect 5-S-CD by analysing 207 plasma samples derived from 138 patients with clinical stage I/II ( = 60), III ( = 32) or IV ( = 46) melanoma. Control groups consisted of 27 patients with non-melanoma skin diseases and 30 healthy v...
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PMID: 12394189
PDF is available here.
PDF is available here.
Melanoma Research (12)4 2002
Abstract
We compared the usefulness of two serum markers for melanoma, 5-S-cysteinyldopa (5-S-CD) and melanoma inhibitory activity (MIA), in the monitoring of postsurgical melanoma patients. A total of 154 serum samples taken from 45 melanoma patients, who underwent surgery of the primary tumour and were und...
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PMID: 12170180
PDF is available here.
PDF is available here.
Biochimica et Biophysica Acta (1571)2 2002
Abstract
In the presence of iron or copper ions, the course of the oxidation in air of 5-S-cysteinyldopa (1), the main biosynthetic precursor of pheomelanins and trichochromes, was markedly changed affording two main products. One of these was identified as the oxobenzothiazine 8, previously obtained under n...
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PMID: 12049796
PDF is available here.
PDF is available here.
Melanoma Research (12)3 2002
Abstract
We measured serum levels of 5-S-CD in 2648 samples taken from 218 patients in order to evaluate the usefulness of this parameter in following melanoma progression and prognosis. 5-S-CD levels were significantly elevated above the upper limit of the normal range (10 nmol/l) in stage IV melanoma patie...
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PMID: 12140381
PDF is available here.
PDF is available here.
Abstract
We show that exposure of neurons (CSM 14.1) to 5-S-cysteinyl conjugates of dopamine, L-DOPA, DOPAC or DHMA causes neuronal damage, increases in oxidative DNA base modification and an elevation of caspase-3 activity in cells. Damage to neurons was apparent 12-48 h of post-exposure and there were incr...
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PMID: 12067224
PDF is available here.
PDF is available here.
Abstract
5-S-cysteinyldopa is a precursor of pheomelanin. S-100B protein is a low molecular weight, acidic, calcium binding, cytoplasmatic protein. LDH was defined as the most important serum parameter in disseminated melanoma. The aim of the present study was to compare the prognostic values of serum 5-S-Cy...
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PMID: 12515998
PDF is available here.
PDF is available here.
Abstract
5-S-cysteinyldopa is a precursor of melanin. Its serum and urinary level can reflect melanoma progression. In this study the concentration changes of 5-S-CD in melanomas of all stages were examined, and patients were monitored during and after treatment. Serum samples were taken from 479 melanoma pa...
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PMID: 12088105
PDF is available here.
PDF is available here.
Abstract
The contributions of pulse radiolysis towards characterisation of unstable ortho-quinones relevant to melanogenesis are reviewed. The quinones discussed include dopaquinone, the precursor of both eumelanogenesis and phaeomelanogenesis, and 5-S-cysteinyldopaquinone, an early component of the phaeomel...
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PMID: 11744399
PDF is available here.
PDF is available here.
Journal of Organic Chemistry (66)21 2001
Abstract
We investigated the oxidation of 5 in air or with chemical and enzymatic agents under biomimetic conditions. In the presence of zinc ions, which occur in epidermal tissues at significant concentrations, the reaction course is diverted toward the formation of a labile 3-carboxy-2H-1,4-benzothiazine i...
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PMID: 11597214
PDF is available here.
PDF is available here.
Pigment Cell Research (14)3 2001
Abstract
We evaluated the clinical relevance of TF expression in melanocytic tumors and TF serum level in patients with malignant melanoma. TF expression in benign and malignant melanocytic lesions was examined by immunoperoxidase staining in 20 nevi, 41 primary, and 24 metastatic melanoma lesions. TF was de...
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PMID: 11434567
PDF is available here.
PDF is available here.
Kidney International (59)5 2001
Abstract
A significant fraction of exogenously administered dopamine reacts with -SH groups of cysteine and probably also with -SH groups on peptides and proteins. During brief dopamine treatment of endotoxic shock in rats, neither dopamine nor cysteinyl-dopamine crossed the blood-brain barrier....
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PMID: 11318961
PDF is available here.
PDF is available here.
Abstract
The value of 5-S-CD in patients with primary melanoma and in patients without symptoms ranged around the normal level. There was a significant difference between the values of patients with or without symptoms. There was also a significant difference between the 5-S-CD values at clinical Stage I and...
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PMID: 11029605
PDF is available here.
PDF is available here.
Pigment Cell Research (13)4 2000
Abstract
We have examined quantitatively the role of dopaquinone in the non-enzymatic oxidation of 5-S-cysteinyldopa using pulse radiolysis and have demonstrated that the redox exchange reaction between dopaquinone and 5-S-cysteinyldopa occurs spontaneously with a rate constant of 8.8 x 10(5) M(-1) sec(-1)....
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PMID: 10952395
PDF is available here.
PDF is available here.
Melanoma Research (10)4 2000
Abstract
We recommend the use of 5SCD in urine as a valuable, reliable and simple biochemical marker to use in the clinical follow-up of melanoma patients with advanced disease....
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PMID: 10985671
PDF is available here.
PDF is available here.
Abstract
Human glutathione transferase M2-2 prevents the formation of neurotoxic aminochrome and dopachrome by catalyzing the conjugation of dopamine and dopa o-quinone with glutathione. NMR analysis of dopamine and dopa o-quinone-glutathione conjugates revealed that the addition of glutathione was at C-5 to...
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PMID: 10903891
PDF is available here.
PDF is available here.
Journal of Organic Chemistry (65)14 2000
Abstract
HPLC evidence is reported demonstrating the occurrence in some human urine samples of a novel catecholic metabolite, (3R,7S)-3, 7-dicarboxy-10,11-dihydroxy-2,3,4,5,6,7,8,9-octahydropyrido[ 4,3-g][1, 4]benzothiazepine (2). The compound was shown to arise by a double Pictet-Spengler condensation of th...
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PMID: 10891125
PDF is available here.
PDF is available here.
Clinical Chemistry (46)7 2000
Abstract
The results obtained with different RNA extraction methods illustrate the importance of quantitative methods for validation of methods. The use of QIAamp RNA improved the extraction efficiency considerably. Data from a case study suggest the assay is suitable in the follow-up of patients with high r...
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PMID: 10894834
PDF is available here.
PDF is available here.
Biochimica et Biophysica Acta (1475)1 2000
Abstract
We have now examined the course of the oxidation of CD at physiological pHs, under different reaction conditions. Surprisingly, a consumption of CD far exceeding the stoichiometry of the oxidant was observed at low oxidant-to-substrate ratios, low temperatures and high substrate concentrations. The...
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PMID: 10806337
PDF is available here.
PDF is available here.
Abstract
5-S-Cysteinyldopa in melanoma is not formed from glutathione in vivo to any appreciable extent. The intracellular amount of cysteine is probably not a limiting factor for cysteinyldopa formation. It seems that both NAC and OTC can be used as cysteine deliverers to melanoma cells in vivo to produce r...
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PMID: 10663636
PDF is available here.
PDF is available here.
Abstract
These results suggest that the balance between CysH and GSH, which is partly determined by the rate of utilization of CysH for GSH biosynthesis, regulates not only the levels of 5-S-CD and DOPA but also the melanogenic activity of pigment cells. Since DOPA functions as a cofactor in the monophenolas...
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PMID: 10644002
PDF is available here.
PDF is available here.
Abstract
5-S-Cysteinyldopa (5-SCD) in plasma and urine was determined by means of a newly developed method. This method incorporates optimized conditions for blood collection and storage, as well as a new extraction and separation technique, required for the strong oxidation and light sensitive 5-SCD. The ne...
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PMID: 10360420
PDF is available here.
PDF is available here.
Gynecologic Oncology (72)1 1999
Abstract
A 75-year-old Japanese woman, who had an enlarged uterus and two nodules on the anterior vaginal wall, underwent wide excision of the anterior vaginal wall, bilateral inguinal lymphadenectomy, modified radical hysterectomy, and pelvic lymph node dissection. Her serum level of 5-S-cysteinyldopa (5-S-...
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PMID: 9889040
PDF is available here.
PDF is available here.
Abstract
We examined the concentration changes of serum S-100 protein and 5-S-CD in 252 melanoma patients of different clinical stages. Serum samples were taken from 252 melanoma patients at 860 times, from June 1996 to July 1998. The serum S-100 protein was measured by the immunoluminometric assay, levels o...
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PMID: 10491021
PDF is available here.
PDF is available here.
Nippon Ganka Gakkai zasshi (102)5 1998
Abstract
These results suggest that 5-S-CD in the intraocular fluid may serve as a useful biochemical marker for the diagnosis of uveal melanoma....
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PMID: 9619024
PDF is available here.
PDF is available here.
Abstract
We investigated the urinary excretion of these pigment precursor metabolites from 136 children, 5 to 15 years of age. The mean 5SCD excretion was 38.1 mumol/mol creatinine. A significant age-related decrease from a mean of 60.4 mumol/mol creatinine at 5 years of age to 28.0 mumol/mol creatinine at a...
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PMID: 9498023
PDF is available here.
PDF is available here.
Cancer Research (57)22 1997
Abstract
The melanin metabolite 5-S-cysteinyldopa (5-S-CD) has been reported to be helpful in detecting occult melanoma metastases and as a prognostic marker in B16 melanoma-bearing mice. The goal of our study was to analyze the significance of the serum 5-S-CD level for the biochemical detection of metastas...
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PMID: 9371505
PDF is available here.
PDF is available here.
Abstract
The cellular concentration of reduced glutathione (GSH) modulates the sensitivity of human melanoma cells to alkylating drugs in vitro. To investigate whether the membrane-associated enzyme gamma-glutamyl transpeptidase (gamma-GTP) involved in GSH breakdown was expressed in melanoma cells, the enzym...
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PMID: 9415231
PDF is available here.
PDF is available here.
Melanoma Research (7)5 1997
Abstract
Our study suggests that of the three biochemical tumour markers, S100B and to a lesser extent 5-S-cysteinyldopa have the greatest potential to be used as predictors of survival prognosis in patients with malignant melanoma....
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PMID: 9429222
PDF is available here.
PDF is available here.
Abstract
We measured the urinary excretion of 5-S-CD on at least three different occasions in 50 patients with melanoma. No significant increase was found in 26 patients without metastases, in 10 patients with regional lymph node metastasis and 2 patients with amelanotic melanoma. However, all the 12 patient...
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PMID: 9298132
PDF is available here.
PDF is available here.
Melanoma Research (7)4 1997
Abstract
We have shown that interstitial glutathione levels decreased during treatment with buthionine sulphoximine (BSO) and recovered after cessation of treatment. The cysteine concentrations also decreased, while 5-S-cysteinyldopa tended to increase during BSO treatment. Restoration of the glutathione lev...
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PMID: 9293482
PDF is available here.
PDF is available here.
Abstract
These results indicate that insulin inhibits the formation of 5-S-cysteinyldopa and that of melanin via the inhibition of tyrosinase activity....
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PMID: 9228219
PDF is available here.
PDF is available here.
Melanoma Research (7)3 1997
Abstract
We simultaneously assayed their serum levels in 30 Japanese melanoma patients. Pre-surgical serum levels of 5-S-CD, cICAM-1 and sIL-2R were elevated in six, 13 and five patients respectively. These abnormal values returned to normal after curative surgery in most of the patients, suggesting a direct...
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PMID: 9195564
PDF is available here.
PDF is available here.
Biochimica et Biophysica Acta (1346)1 1997
Abstract
We report now evidence that DHI, DHICA and CD exert potent inhibitory effects in different in vitro models of lipid peroxidation. The compounds, at 100 microM concentration, substantially decreased malondialdehyde (MDA) formation by lipid peroxidation in rat brain cortex homogenates. At 1.2 microM c...
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PMID: 9187303
PDF is available here.
PDF is available here.
Melanoma Research (7)1 1997
Abstract
The serum levels of the soluble form of intercellular adhesion molecule-1 (sICAM-1) and 5-S-cysteinyldopa (5-S-CD) were determined by double determinant immunoassay and high-performance liquid chromatography, respectively. Fifty-three melanoma patients (stage 1, 12 patients; stage II, 11; stage III,...
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PMID: 9067966
PDF is available here.
PDF is available here.
Abstract
Our results indicate that the direct addition of cysteine to dopaquinone is the main source of 5-S-CD in human epidermal melanocytes. It is proposed that the synthesis of 5-S-CD is a mechanism regulating dopaquinone levels during pigment formation and/or a defence mechanism against oxidative stress....
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PMID: 8931873
PDF is available here.
PDF is available here.