2-Amino-4-hydroxy-6-pteridinecarboxaldehyde

Waller, Coy W.; Goldman, A. A.; Angier, Robert B.; Boothe, James H.; Hutchings, B. L.; Mowat, John H.; Semb, Joseph

doi:10.1021/ja01166a081

Cited by 68 publications

(20 citation statements)

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“…The peak at 1 h 42 min could be either pterin 6aldehyde or 6HMP. UV spectra showed that it was not pterind-aldehyde but 6HMP [24,25]. Additionally because it would release a 3H atom from the C-9 position and this was not found in the void volume.…”

Section: Resultsmentioning

confidence: 96%

A novel chemotaxis regulating enzyme that splits folic acid into 6‐hydroxymethylpterin and P‐aminobenzoylglutamic acid

1980

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Section: Resultsmentioning

confidence: 96%

A novel chemotaxis regulating enzyme that splits folic acid into 6‐hydroxymethylpterin and P‐aminobenzoylglutamic acid

1980

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“…Materials 2-Amino-4-hydroxy-6-pyrophosphorylmethylpteri dine was prepared by the method of Shiota et al (6) from 2-amino-4-hydroxy-6-hydroxymethylpteridine (7). For use as a substrate in the enzymatic reaction, 2 -amino-4-hydroxy-6-pyrophosphorylmethylpteridine was reduced, by treatment with sodium borohydride, to the dihydro-derivative (3).…”

Section: Methodsmentioning

confidence: 99%

The Biosynthesis of Folic Acid Compounds in Plants

Okinaka

Iwai

1970

J. Vitaminol

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“…2 13), which is identical with that of pterin-6-aldehyde (15), and its fluorescent spectrum (excitation 355 nm, fluorescence 450 nm, pH 6.5, determined on a Spex Fluorolog fluorometer).…”

Section: Resultsmentioning

confidence: 81%

Pterin-6-aldehyde, a cancer cell catabolite: identification and application in diagnosis and treatment of human cancer.

Halpern¹,

Halpern²,

Stea³

et al. 1977

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

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Active folic acid degradation with the formation of pterin-6aldehyde is a previously undescribed characteristic of cancer cells in tissue culture. Neither normal adult epithelial and fibroblastic cells nor human amniotic cells nor mouse embryonic fibroblasts degrade folic acid to a measurable degree.Twenty-nine patients whose diagnoses were not revealed until after the test of their first morning urine for pterin-6aldehydewas completed were studied for the presence or absence of pterin-6aldehyde by thin-layer chromatography. (3)(4)(5)(6)(7)(8).Biopterin, a guanosine and not a folate derivative, and its oxidation products (xanthopterin, isoxanthopterin, and leucopterin), are also found in human urine (9, 10). A sluggishly active folate cleavage enzyme has been demonstrated in crude liver extracts of animals (11,12), and an inert folate cleavage enzyme, activated by HCI, has been reported in human red blood cells (13). Cleavage of folic acid occurs between C-9 and N-10, immediately yielding pterin-6-aldehyde and p-aminobenzoylglutamate. When [3H]folic acid was injected into men, [3H]pteridines were found in the urine (14).Moreover, when either we or our gouty patients consumed 50-100 mg of folic acid, the next first morning's freshly voided urine, which was protected from light and oxidation, contained not only folic acid but considerable quantities of pterin-6-aldehyde, pterin-6-carboxylate, and pterin, indicating, we believe, active folate degradation in vivo.Herein, we describe the excretion and identification of pterin-6-aldehyde in the culture media of malignant cells, but its absence in the media of adult normal cells, embryonic cells, and amniotic cells. We also report the demonstration by thinlayer chromatography of pterin-6-aldehyde in the urine of patients with cancer, in concentrations greater than 300 nmol/ml, and its absence in adequately studied patients without malignancies. MATERIALS AND METHODSTissue Culture. We used McCoy's 5a (modified) medium without Bactopeptone and added 15% dialyzed fetal calf serum and gentamicin (50,ug/ml). In the reconstructed medium we varied the folic acid from 10 ag/liter to 10 mg/liter and the vitamin B12 from 0.5 ,g/liter to 2 mg/liter. In some experiments we added N5-methyltetrahydrofolate in place of folic acid. All cultures were shown to be concurrently PPLO (pleuropneumonia-like organism)-negative by culture for 3 weeks on GIBCO broth and pour plates. The cell types studied are listed in Table 1.The fluorescent substance was isolated from two sets of experiments. In the first set the cells were grown in Falcon plastic 75 cm2 flasks containing 10 ml of medium for 2-3 days, depending on the cell doubling time. The medium was discarded and replaced by fresh medium, which was allowed to remain in the flask for the ensuing 36-72 hr in order to ensure collection during logarithmic phase growth of the cells. Controls consisted of simultaneously incubated media without cells. All determinations were done in quadruplicate. In the second set each cell type was gr...

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2-Amino-4-hydroxy-6-pteridinecarboxaldehyde

Cited by 68 publications

References 0 publications

A novel chemotaxis regulating enzyme that splits folic acid into 6‐hydroxymethylpterin and P‐aminobenzoylglutamic acid

A novel chemotaxis regulating enzyme that splits folic acid into 6‐hydroxymethylpterin and P‐aminobenzoylglutamic acid

The Biosynthesis of Folic Acid Compounds in Plants

Pterin-6-aldehyde, a cancer cell catabolite: identification and application in diagnosis and treatment of human cancer.

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