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At least 19 recordsLinked to original sources
PubMed1983

Cysteinyldopa isomers and dopa in lesions and urine of Japanese patients with malignant melanoma.

Cysteinyldopas and Dopa in the urine and tissues of Japanese melanoma patients were investigated quantitatively by means of high-performance liquid chromatography. Cysteinyldopa isomers were detected in the urine of eumelanic Japanese patients. The amount (X +/- SD%) of each isomer of cysteinyldopa in the urine was 80.26 +/- 4.66% in 5-S-cysteinyldopa, 9.39 +/- 1.64% in 2-S-cysteinyldopa, 7.07 +/- 3.33% in 2, 5-S, S-dicysteinyldopa, and 3.28 +/- 1.43% in 6-S-cysteinyldopa. The amount of cysteinyldopa in melanoma tissues was 26-314 times more than that of Dopa. The amount (X +/- SD%) of cysteinyldopa in the tissues was 80.34 +/- 1.75% in 5-S-cysteinyldopa, 11.06 +/- 1.91% in 2-S-cysteinyldopa, 6.27 +/- 1.43% in 2, 5-S, S-dicysteinyldopa, and 2.34 +/- 0.61% in 6-S-cysteinyldopa. The fact that the percentages of each isomer of cysteinyldopa in the urine and in the tissues were approximately constant suggests that the cysteinyldopas secreted from melanoma cells were excreted into the urine without being metabolized.

Cysteinyldopa↗
PubMed1982

The effect of cysteine on oxidation of tyrosine, dopa, and cysteinyldopas.

The influence of cysteine on the oxidation of tyrosine, dopa, and monocysteinyldopas by mushroom tyrosinase was reexamined. During oxidation of tyrosine in the presence of cysteine the concentration of dopa increased slowly, whereas the concentration of cysteinyldopas increased more rapidly. When the concentration of cysteine decreased the cysteinyldopas were rapidly consumed and dopa concentrations increased sharply. Experiments on the oxidation of dopa by tyrosinase in the presence of cysteine showed that this thiol does not inhibit the oxidation. Dopa concentrations decreased more rapidly in the presence of cysteine because cysteine addition to dopaquinone prevented reformation of dopa from dopaquinone. Both 2-S-cysteinyldopa and 5-S-cysteinyldopa are substrates for tyrosinase. The oxidation of cysteinyldopas was inhibited at high cysteine concentrations. The greater part of 2,5-S,S-dicysteinyldopa formed during the oxidation of monocysteinyldopas in the presence of cysteine is derived from 5-S-cysteinyldopa, which is a better substrate for tyrosinase than 2-S-cysteinyldopa. The fact that cysteine binds more rapidly to 5-S-cysteinyldopaquinone than to 2-S-cysteinyldopaquinone further stresses the importance of 5-S-cysteinyldopa in the formation of 2,5-S,S-dicysteinyldopa. Oxidation of dopa in the presence of cysteine and glutathione or methionine showed that glutathione is added to dopaquinone but less rapidly than cysteine. Methionine showed insignificant addition to dopaquinone. When dopa or 5-OH-dopa is added to an incubate of cysteinyldopa and tyrosinase the oxidation of cysteinyldopa is accelerated owing to oxidation of cysteinyldopa by dopaquinone or 5-OH-dopaquinone.

Ascorbic Acid↗
PubMed1980

[5-S-cysteinyldopa in the urine - a "tumor test" for malignant melanoma? Comparison with the usual laboratory examinations].

In a total of 1,828 determinations, urinary excretion of 5-S-Cysteinyldopa was studied over a period of three years in 384 patients treated for melanoma or with metastases of malignant melanoma. By serial investigations the excretion of 5-S-Cysteinyldopa was compared to the course of the disease. In the case of small and circumscribed metastases which could be eliminated by surgical treatment, the excretion of 5-S-Cysteinyldopa remained normal. When the disease became generalized, an increase of the urinary excretion of 5-S-Cysteinyldopa prior to the clinical manifestation of the metastases was observed in only four out of 26 cases. In the remaining cases, the increase of 5-S-Cysteinyldopa coincided with the manifestation of metastases, or the excretion of the substance became pathological when the metastases were already conspicuous. In five patients, the urinary excretion of 5-S-Cysteinyldopa remained normal inspite of widespread disease. Therefore, its diagnostic value seems to be similar to that of the "common" laboratory investigations the results of which are only pathological when the disease has already become generalized. Our investigations demonstrate that serial investigations of the urinary excretion of 5-S-Cysteinyldopa only rarely indicate melanoma metastases prior to their clinical manifestation. In cases of early metastasing melanoma, all common laboratory investigations are of limited value. BSR and GGT levels which become pathological very early in the course of the disease are so sensitive that slightly pathological levels may be ambiguous. In these cases, however, pathological levels of 5-S-Cysteinyldopa most probably will indicate a widespread disease.

BCG Vaccine↗
PubMed1988

Plasma 5-S-cysteinyldopa differentiates patients with primary and metastatic melanoma from patients with dysplastic nevus syndrome and normal subjects.

To determine whether plasma 5-S-cysteinyldopa levels are useful in following up patients at risk for melanoma, we measured plasma 5-S-cysteinyldopa in patients with dysplastic nevus syndrome and/or malignant melanoma and in control subjects. In patients with dysplastic nevus syndrome, plasma 5-S-cysteinyldopa levels did not differ from those in control subjects. Conversely, patients with malignant melanomas had significantly higher plasma 5-S-cysteinyldopa levels than did controls. Those with localized cutaneous malignant melanoma and no distant metastases (Stage I and II disease) had 5-S-cysteinyldopa levels twofold greater than those of control subjects, whereas the levels of those with regional lymph node involvement (Stage III disease) were fourfold greater than those of control subjects. Levels of those with extraregional metastases (Stage IV disease) were 7- to 450-fold higher than those of control subjects. Moreover, plasma 5-S-cysteinyldopa levels correlated with the spread of disease and were useful in distinguishing primary melanoma and Stages III and IV melanoma. We conclude that plasma 5-S-cysteinyldopa may be an important tool for identifying melanoma at an earlier, more curable stage and for following up patients at risk for the development of melanoma, for example, those with dysplastic nervus syndrome.

Adult↗
PubMed1975

Urinary excretion of 5-S-cysteinyldopa in patients with primary melanoma or melanoma metastasis.

Urinary excretion of 5-S-cysteinyldopa was studied in 9 patients with primary melanoma. All had 5-S-cysteinyldopa excretion in the normal range. In 8 of the patients excretion values decreased after removal of the tumour. Twenty-four patients with clinical signs of melanoma metastasis were examined for 5-S-cysteinyldopa and dopa+dopamine in the urine. 16 of the 24 had pathologically increased excretion of 5-S-cysteinyldopa and 7 of the 24 had pathological excretion of dopa+dopamine. Six of the latter belonged to the group with increased 5-S-cysteinyldopa excretion and one patient had a borderline value of 5-S-cysteinyldopa. Determination of 5-S-cysteinyldopa seems to be of value in the follow-up of patients operated on for primary melanoma.

Adult↗
PubMed1978

The urinary melanogen cysteinyldopa in melanoma and in suntanning: Australian experience.

Determination of urine cysteinyldopa excretion is the most sensitive chemical test for the detection of melanoma metastases and has been successfully applied during the Scandinavian winter, when sun irradiation is low. The value of this determination, under Australian conditions of greater sun irradiation, has been assessed by comparing the cysteinyldopa excretion of patients with that of normal subjects exposed to sunlight. Cysteinyldopa is an intermediate in the biosynthesis of the red-brown phaeomelanin. Of 20 patients without known secondary melanoma, the cysteinyldopa concentration of "spot" urines ranged from 0 to 190 (mean 48) microgram/ml; of six known to have local metastases, 0 to 80 (mean 19) microgram/ml; and of four known to have extensive metastases 80 to 1350 (mean 330) microgram/ml. The effect of sun irradiation alone was assessed in nine healthy subjects followed one to 11 weeks before and after recorded periods of sun exposure. The cysteinyldopa concentrations of 24-hour urines ranged from 40 to 3100 microgram/ml. Increases occurred three to 10 days following sun exposure and were greatest following multiple small exposures in an individual with "Celtic" complexion. It is concluded that measurement of cysteinyldopa concentration would be of value in the follow-up of melanoma patients in Australia only if patients could be persuaded to live under conditions free of all direct sun-irradiation.

Adolescent↗
PubMed1981

5-S-Cysteinyldopa in ganglion stellatum.

5-S-Cysteinyldopa, an amino acid formed by nucleophilic addition of cysteine to dopaquinone, has been detected in the ganglion stellatum of the cow in amounts varying between 21 and 35 ng/g ganglionic tissue. Dopa was present in slightly higher quantities. Cysteinyldopa has previously been regarded as a substance unique for the melanocytes, where it forms melanin after oxidation and polymerization. At present only hypothetical explanations of our finding can be offered. The content of 5-S-cysteinyldopa in ganglion stellatum may be the result of dopa oxidation in ganglionic cells. An uptake mechanism for circulating cysteinyldopa may exist. Localization of cysteinyldopa to aberrant melanocytes or to aged SIF-cells in the ganglia should also be borne in mind.

3,4-Dihydroxyphenylacetic Acid↗
PubMed1976

On the occurrence of cysteinyldopa and dopa in melanocytes and benign nevi cells.

Previous studies have demonstrated a specific cytoplasmic fluorescence in human melanocytes, as well as in pigmented nevi and in malignant melanomas, when the formaldehyde histofluorescence method for visualization of certain catechol and indole derivatives was used. In malignant melanoma two fluorogenic substances, dopa and cysteinyldopa, were found previously. In human melanocytes and benign nevi cells the fluorogenic catechols have so far not been characterized, since chemical analyses are difficult to perform on skin, due to the small amounts of catechols present. However, using split thickness skin quantitative determinations are possible by sensitive fluorometric methods. The chemical analyses of cysteinyldopa showed that in human adult skin most or all was located in the superficial layers. The only specific fluorescence in the thin skin was found in dendritic melanocytes. The findings leave little doubt that cysteinyldopa is stored in melanocytes although the possibility of a concomitant occurrence of other thioethers is not excluded. Nevi and giant nevi were also similarly studied and we found considerable amounts of cysteinyldopa in the nevi. It seems as if the cysteinyldopa is stored in the fluorescent nevi cells. There was no consistent difference in the content of the catechol derivatives between intradermal and compound nevi.

Adolescent↗
PubMed1980

5-S-cysteinyldopa as a substrate for tyrosinase.

Oxidation of 5-S-cysteinyldopa by mushroom tyrosinase was studied by measuring 5-S-cysteinyldopa consumption with HPLC. 5-S-cysteinyldopa was found to be a substrate for tyrosinase, but our results suggests that a self-catalysed oxidation induced by enzymatically formed 5-S-cysteinyl dopaquinone also takes place. Dopa oxidation by tyrosinase was determined by measuring substrate consumption with HPLC. The oxidation of 5-S-cysteinyldopa was markedly accelerated in the presence of dopa. This could be explained by dopaquinone oxidation of 5-S-cysteinyldopa, which has a lower oxidation potential than dopa.

Catechol Oxidase↗
PubMed1981

5-S-Cysteinyldopa and dopa in serum during treatment with 8-methoxypsoralen and UVA light.

5-S-Cysteinyldopa and dopa concentrations in serum were studied by high-performance liquid chromatography (HPLC) in patients with psoriasis treated by 8-methoxypsoralen and UVA light. A marked increase in 5-S-Cysteinyldopa was found after 3 days' treatment, although no increase in pigmentation could yet be observed. The highest concentrations of 5-S-Cysteinyldopa in serum were noted after 1 or 2 weeks' treatment. In one patient who showed no increase in serum 5-S-Cysteinyldopa treatment was unsuccessful. During PUVA treatment of 3 patients with psoriasis confined to the palms and/or soles a delayed increase in serum 5-S-Cysteinyldopa was noted after 5 weeks. This delayed response after treatment of a small area of the body is remarkable, and may indicate the formation of a systemic melanocyte stimulation factor. There was no increase in the serum dopa concentrations during PUVA treatment, and dopa analysis was of no value in assessing the activity of the melanocytes. Some unexpectedly high dopa values recorded before and during PUVA treatment may be explained by the fact that dopa originates in the nervous system or the adrenals.

Adult↗
PubMed1983

Studies on amelanotic melanoma with the fluorescence method (Falck and Hillarp) and biochemical analysis of 5-S-cysteinyldopa in the tissues.

Histochemical findings of primary and metastatic amelanotic melanomas were shown by the formaldehyde-induced fluorescence method (Falck and Hillarp). All or some of the amelanotic melanoma cells were discovered to emit green specific fluorescence. Results of the determination of 5-S-cysteinyldopa and DOPA in amelanotic melanoma tissues indicated that the specific fluorescence emitted by these cells is primarily due to the presence of 5-S-cysteinyldopa. The values of 5-S-cysteinyldopa in these tissues were lower than those in melanotic melanoma, but were approximately the same as those in pigmented nevus. When unpigmented tumors were histopathologically revealed to be malignant, amelanotic melanoma could be definitely diagnosed by the fluorescence method of Falck and Hillarp and the biochemical analysis of 5-S-cysteinyldopa in the tissues.

Adult↗
PubMed1978

The quantitative determination of 5-S-cysteinyldopa and dopa in normal serum and in serum from patients with malignant melanoma by means of high-pressure liquid chromatography.

A method is described for quantitative determination of 5-S-cysteinyldopa and Dopa in serum involving high-pressure liquid chromatographic analysis (HPLC) and electrochemical detection. The chromatographic system allows estimation of injected amounts corresponding to 25 pg of 5-S-cysteinyldopa and Dopa. In normal subjects the mean serum 5-S-cysteinyldopa concentration was 2.8 ng/ml (range 0.4--12 ng/ml) and the mean serum Dopa 6.3 ng/ml (range 4--10 ng/ml). Patients with melanoma metastases showed increased serum concentrations of 5-S-cysteinyldopa.

Chromatography, High Pressure Liquid↗
PubMedDate not supplied

Microdialysis of 5-S-cysteinyldopa from interstitial fluid in cutaneous human melanoma transplanted to athymic mice.

Microdialysis was investigated as a tool for the determination of the extracellular concentration of the pigment metabolite 5-S-cysteinyldopa in human melanoma transplanted to athymic mice. Histology of the tumour with the microdialysis probes in situ showed no tissue damage. With probes equipped with polycarbonate membranes (20 kD) extraction (relative recovery) was approximately 50% at pH 4.0 and flow rates of 1 microliter/min, but at pH 7.0 recoveries were markedly lower, particularly from serum. In a first series of human melanomas transplanted to athymic mice low concentrations of 5-S-cysteinyldopa were detected in only two out of ten dialysates and were not detected in the other eight. Utilizing devices constructed for comparison of membrane characteristics in vitro we found about 4-fold higher recoveries with cuprophane and polyamide membranes than with polycarbonate membranes. Therefore newly constructed microdialysis probes (CMA/11) with cuprophane membranes were tested in vitro and gave recoveries of 38-48% from Ringer-Acetate solutions and 22-31% from serum, and the pH effects were low. When these probes were utilized in a second series of melanomas transplanted to athymic mice, 5-S-cysteinyldopa could easily be quantified in 10/10 experiments. A steady-state level of the dialysate 5-S-cysteinyldopa concentration was reached after 45 min.

Animals↗
PubMed1997

S100B protein, 5-S-cysteinyldopa and 6-hydroxy-5-methoxyindole-2-carboxylic acid as biochemical markers for survival prognosis in patients with malignant melanoma.

Elevated levels of the phaeomelanin metabolite 5-S-cysteinyldopa and the eumelanin metabolite 6-hydroxy-5-methoxyindole-2-carboxylic acid in urine and serum have been shown in previous studies to correlate with disseminated malignant melanoma. Immunohistochemical detection of S100B protein is an acknowledged method for the diagnosis of malignant melanoma, and it has been suggested that rising serum levels of S100B protein are associated with the survival rate of patients with malignant melanoma. In the present study serum levels of S100B protein and urinary concentrations of 5-S-cysteinyldopa and 6-hydroxy-5-methoxyindole-2-carboxylic acid were measured in 91 patients with histopathologically verified malignant melanoma. At the time of sampling 13 patients were in clinical stage I, 13 in stage II and 65 in stage III. The urinary levels of the melanin metabolites were determined by automated high performance liquid chromatography, and the serum levels of S100B protein by an immunoradiometric assay with two monoclonal antibodies. The overall survival rate was most strongly associated with the serum levels of S100B protein (P < 0.001), but there was also a significant correlation to urinary levels of 5-S-cysteinyldopa (P < 0.001). A corresponding association with urinary levels of 6-hydroxy-5-methoxyindole-2-carboxylic acid was found in only a very few patients with extremely high urinary concentrations. A statistically significant increase in relative hazard was found for S100B protein levels exceeding 0.6 microgram/l (P < 0.001), and predictably for patients in clinical stage III (P < 0.001). An analysis of S100B protein levels in patients in clinical stage III showed a significant correlation to survival (P = 0.005). 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.

Adult↗
PubMed1982

Urinary free and conjugated 5-S-cysteinyldopa in normal subjects and in patients with melanoma.

We measured free and total 5-S-cysteinyldopa excretion in 24-h urine specimens from nine patients with malignant melanoma and forty-five controls, and found that the levels of 5-S-cysteinyldopa excretion (measured by a fluorometric method) were greatly increased in the melanoma patients. The conjugates were hydrolysed by enzymatic treatment with beta-glucuronidase/arylsulphatase, and we found that the percentage of conjugated 5-S-cysteinyldopa was higher in urines with a low content of free 5-S-cysteinyldopa than in those with a higher concentration.

Adult↗
PubMed1983

Protein-bound dopa and 5-S-cysteinyldopa in non-melanogenic tissues.

To explore the possibility that dopa and 5-S-cysteinyldopa, precursors of melanin, can be produced in non-melanogenic tissues, this study examined the contents of the free and protein-bound forms of two catechols in non-melanogenic tissues of mice and rats, and compared the urinary excretion of free catechols in black and albino mice. Considerable amounts of protein bound dopa and 5-S-cysteinyldopa were present in the hair of tyrosinase-negative, albino mice and white mice, the latter completely lacking follicular melanocytes. The liver, kidney and brain of mice and the adrenals of rats also contained small amounts of these catechols. Both black and albino mice excreted free dopa and 5-S-cysteinyldopa, the amounts of which did not differ significantly in the two animals. It is suggested that oxidation mechanism(s) other than tyrosinase may participate in the synthesis of these catechols in proteins. Turnover of 5-S-cysteinyldopa-containing proteins may lead to the release of this catechol into blood and eventually to excretion into urine.

Animals↗
PubMed1979

5 years' experience of 5-S-cysteinyldopa in melanoma diagnosis.

Determinations of the urinary excretion of 5-S-cysteinyldopa were performed in 571 patients previously treated by surgery for melanoma or melanoma metastasis. 90% of the 161 patients with metastases showed values exceeding 0.15 mg/24 h, and 9% of the 410 patients without metastases had such values. The increase in 5-S-cysteinyldopa excretion was generally more pronounced in men with metastases than in women, 98% of the men and 77% of the women with metastases showing values exceeding 0.15 mg/24 h. High levels of 5-S-cysteinyldopa are of grave prognostic significan4% died within one month, and only 3% survived for more than a year. In Sweden, determination of 5-S-cysteinyldopa in patients operated on for melanoma gives maximum information in the winter (October--March), when sun exposure does not influence the excretion levels.

Adult↗
PubMed1975

Formation of cysteinyldopa from glutathionedopa in melanoma.

Glutathionedopa injected intravenously into mice is metabolized and excreted in the urine as a compound with the fluorescence characteristics of cysteinyldopa. Glutathionedopa incubated with a guinea-pig kidney homogenate is metabolized to a compound with the fluorescence characteristics of cysteinyldopa. Boiling of the kidney homogenate prevents the metabolism of glutathionedopa. Incubation of glutathionedopa with a homogenate of a melanoma metastasis led to the formation of a compound with the fluorescence characteristics of cysteinyldopa. Boiling of the melanoma homogenate prevented the metabolism of glutathionedopa. Large amounts of glutathione added to the incubate inhibited the reaction. Lung tissue and blood plasma had no detectable ability to metabolize glutathionedopa. The results show that human melanoma contains one or several enzymes capable of metabolizing glutathionedopa to a smaller dopathioether, probably cysteinyldopa. Such enzymes seem to be normally present in mice and guinea-pigs and have been demonstrated in the guinea-pig kidney.

Animals↗