Folate chemistry and metabolism

Clinical Research and Regulatory Affairs

Volumn 18, Issue 3, 2001, Pages 137-159

  Shane, Barry ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85015515871     PISSN: 10601333     EISSN: 15322521     Source Type: Journal    
DOI: 10.1081/CRP-100108170     Document Type: Article

References (97)

1. Wills L. Treatment of “Pernicious Anemia of Pregnancy” and “Tropical Anemia” with Special Reference to Yeast Extract as a Curative Agent. Br. Med. J. 1931; 1: 1059 – 1064
2. Stokstad E. L.R. Historical Perspective on Key Advances in the Biochemistry and Physiology of Folates. Contemporary Issues in Clinical Nutrition, M. F. Picciano, E. L.R. Stokstad, J. F. Gregory. Folic Acid Metabolism in Health and disease. Wiley-Liss, New York 1990; 13: 1 – 21
3. Shane B., Stokstad E. L.R. Vitamin B12-Folate Interrelationships. Ann. Rev. Nutr. 1985; 5: 115 – 141
4. MRC Vitamin Study Research Group. Prevention of Neural Tube Defects: Results of the Medical Research Council Vitamin Study. Lancet 1991; 338: 131 – 137
5. Czeizel A. E., Dudas I. Prevention of the First Occurrence of Neural-tube Defects by Periconceptional Vitamin Supplementation. N. Engl. J. Med. 1992; 327: 1832 – 1835
6. McGuire J. J., Coward J. K. Pteroylpolyglutamates: Biosynthesis, Degradation, and Function. Folates and Pterins, R. L. Blakley, S. J. Benkovik. John Wiley & Sons, New York 1984; 1: 135 – 190
7. Shane B. Folylpolyglutamate Synthesis and Role in the Regulation of One Carbon Metabolism. Vit. Horm. 1989; 45: 263 – 335
8. Gregory J. F. Chemical and Nutritional Aspects of Folate Research: Analytical Procedures, Methods of Folate Synthesis, Stability, and Bioavailability of Dietary Folates. Adv. Food Nutr. Res. 1989; 33: 1 – 101
9. Herbert V., Das K. C. Folic Acid and Vitamin B12. Modern Nutrition in Health and Disease, M. E. Shils, J. A. Olson, M. Shike. 8th ed., Philadelphia:Lea and Fabiger. 1993; 402 – 425
10. Eichner E. R., Hillman R. S. The Evolution of Anemia in Alcoholic Patients. Am. J. Med. 1971; 50: 218 – 232
11. Ratnam M., Freisheim J. H. Proteins Involved in the Transport of Folates and Antifolates by Normal and Neoplastic Cells. Contemporary Issues in Clinical Nutrition, M. F. Picciano, E. L.R Stokstad, J. F. Gregory. Folic Acid Metabolism in Health and Disease. Wiley-Liss, New York 1990; 13: 91 – 120
12. Fernandes-Costa F., Metz J. Role of Serum Folate Binders in the Delivery of Folate to Tissues and the Fetus. Br. J. Haematol. 1979; 41: 335 – 342
13. Henderson G. B. Transport of Folate Compounds into Cells. Folates and Pterins, R. L. Blakley, V. M. Whitehead. Nutritional, Pharmacological, and Physiological Aspects. John Wiley & Sons, New York 1986; 3: 207 – 250
14. Henderson G. B., Tsuji J. M. Methotrexate Efflux in L1210 Cells. Kinetic and Specificity Properties of the Efflux System Sensitive to Bromosulfophthalein and its Possible Identity with a System which Mediates the Efflux of 3′,5′-Cyclic AMP. J. Biol. Chem. 1987; 262: 3571 – 13578
15. Horne D. W., Briggs W. T., Wagner C. Transport of 5-Methyltetrahydrofolic Acid and Folic Acid in Freshly Isolated Hepatocytes. J. Biol. Chem. 1978; 253: 3529 – 3535
16. Horne D. W., Reed K. A., Said H. M. Transport of 5-Methyltetrahydrofolic Acid in Basolateral Membrane Vesicles of Rat Liver. Am. J. Physiol. 1992; 262: G150 G158
17. Home D. W., Reed K. A., Hoefs J., Said H. M. 5-Methyltetrahydrofolic Acid Transport in Basolateral Membrane Vesicles from Human Liver. Am. J. Clin. Nutr. 1993; 58: 80 – 84
18. Said H. M., Redha R. A Carrier-Mediated Transport for Folate in Basolateral Membrane Vesicles of Rat Small Intestine. Biochem. J. 1987; 247: 141 – 146
19. Cybulski R. L., Fisher R. R. Uptake of Oxidized Folates by Rat Liver Mitochondria. Biochim. Biophys. Acta 1981; 646: 329 – 333
20. Horne D. W., Holloway R. S., Said H. M. Uptake of 5-Formyltetrahydrofolate in Isolated Rat Liver Mitochondria is Carrier-Mediated. J. Nutr. 1992; 122: 2204 – 2209
21. Kim J-S., Lowe K. E., Shane B. Regulation of Folate and One Carbon Metabolism in Mammalian Cells. 4. Role of Folylpolyglutamate Synthetase in Antifolate Metabolism and Cytotoxicity. J. Biol. Chem. 1993; 268: 21680 – 21685
22. Antony A. C., Kane M. A., Portillo R. M., Elwood P. C., Kolhouse J. F. Studies of the Role of a Particulate Folate-Binding Protein in the Uptake of 5-methyltetrahydrofolate by Cultured Human KB Cells. J. Biol. Chem. 1985; 260: 14911 – 14917
23. Selhub J., Franklin W. A. The Folate-Binding Protein of Rat Kidney. Purification, Properties, and Cellular Distribution. J. Biol. Chem. 1984; 259: 6601 – 6606
24. Kane M. A., Elwood P. C., Portillo R. M., Antony A. C., Kolhouse J. F. The Interrelationship of the Soluble and Membrane-Associated Folate-binding Proteins in Human KB Cells. J. Biol. Chem. 1986; 261: 15625 – 15631
25. Wagner C. Proteins Binding Pterins and Folates. Folates and Pterins, R. L. Blakley, V. M. Whitehead. Nutritional, Pharmacological, and Physiological Aspects. John Wiley & Sons, New York 1986; 3: 251 – 296
26. Lee H-C., Shoda R., Krall J. A., Foster J. D., Selhub J., Rosenberry T. L. Folate Binding Protein from Kidney Brush Border Membranes Contains Components of a Glycoinositol Phospholipid Anchor. Biochemistry 1992; 31: 3236 – 3243
27. Weitman S. D., Weinberg A. G., Coney L. R., Zarawski V. R., Jennings D. S., Kamen B. A. Cellular Localization of the Folate Receptor: Potential Role in Drug Toxicity and Folate Homeostasis. Cancer Res. 1992; 52: 6708 – 6711
28. Kamen B. A., Capdevila A. Receptor-Mediated Folate Accumulation is Regulated by the Cellular Folate Content. Proc. Natl. Acad. Sci. USA 1986; 83: 5983 – 5987
29. Weitman S. D., Lark R. H., Coney L. R., Fort D. W., Frasca V., Zarawski V. R., Kamen B. A. Distribution of the Folate Receptor GP38 in Normal and Malignant Cell Lines and Tissues. Cancer Res. 1992; 52: 3396 – 3401
30. Sirotnak F. M., Jacobsen D. M., Yang C-H. Alteration of Folate Analogue Transport Following Induced Maturation of HL-60 Leukemia Cells. Early Decline in Mediated Influx, Relationship to Commitment, and Functional Dissociation of Entry and Exit Routes. J. Biol. Chem. 1986; 261: 11150 – 11155
31. Antony A. C., Bruno E., Briddell R. A., Brandt J. E., Verma R. S., Hoffman R. Effect of Perturbation of Specific Folate Receptors during In Vitro Erythropoiesis. J. Clin. Invest. 1987; 80: 1618 – 1623
32. Birn H., Selhub J., Christensen E. I. Internalization and Intracellular Transport of Folate-binding Protein in Rat Kidney Proximal Tubule. Am. J. Physiol. 1993; 264: C302 – C310
33. Rothberg K. G., Ying Y., Kolhouse J. F., Kamen B. A., Anderson R. G.W. The Glycophosphoilpid-Linked Folate Receptor Internalizes Folate without Entering the Clathrin-Coated Pit Endocytic Pathway. J. Cell. Biol. 1990; 110: 637 – 649
34. Krumdieck C. L., Tamura T., Eto I. Synthesis and Analysis of the Pteroylpolyglutamates. Vitam Horm 1983; 40: 45 – 104
35. Cossins E. A. Folates in Biological Materials. Folates and Pterins, R. L. Blakley, S. J. Benkovik. John Wiley & Sons, New York 1984; 1: 1 – 59
36. Thenen S. W., Shin Y. S., Stokstad E. L.R. The Turnover of Rat-Liver Folate Pools. Proc. Soc. Exp. Biol. Med. 1973; 142: 638 – 631
37. Lowe K. E., Osborne C. B., Lin B-F., Kim J-S., Hsu J-C., Shane B. Regulation of Folate and One Carbon Metabolism in Mammalian Cells. 2. Effect of Folylpolyglutamate Synthetase Substrate Specificity and Level on Folate Metabolism and Folylpolyglutamate Specificity of Metabolic Cycles of One Carbon Metabolism. J. Biol. Chem. 1993; 268: 21665 – 21673
38. Horne D. W., Patterson D., Cook R. J. Effect of Nitrous Oxide Inactivation of Vitamin B12 Dependent Methionine Synthetase on the Subcellular Distribution of Folate Coenzymes in Rat Liver. Arch. Biochem. Biophys. 1989; 270: 729 – 733
39. Lin B-F., Huang R-F.S., Shane B. Regulation of Folate and One Carbon Metabolism in Mammalian Cells. 3. Role of Mitochondrial Folylpolyglutamate Synthetase. J. Biol. Chem. 1993; 268: 21674 – 21679
40. Appling D. R. Compartmentation of Folate-Mediated One-Carbon Metabolism in Eukaryotes. FASEB J. 1991; 5: 2645 – 2651
41. McBurney M. W., Whitmore G. F. Isolation and Biochemical Characterization of Folate Deficient Mutants of Chinese Hamster Cells. Cell 1974; 2: 173 – 182
42. Taylor R. T., Hanna M. L. Folate-Dependent Enzymes in Cultured Chinese Hamster Ovary Cells: Folylpolyglutamate Synthetase and its Absence in Mutants Auxotrophic for Glycine + Adenosine + Thymidine. Arch. Biochem. Biophys. 1977; 181: 331 – 344
43. Osborne C. B., Lowe K. E., Shane B. Regulation of Folate and One Carbon Metabolism in Mammalian Cells. 1. Folate Metabolism in Chinese Hamster Ovaly Cells Expressing Escherichia Coli or Human Folylpoly-γ-Glutamate Synthetase Activity. J. Biol. Chem. 1993; 268: 21657 – 21664
44. Moran R. G., Colman P. D. Measurement of Folylpolyglutamate Synthetase in Mammalian Tissues. Anal. Biochem. 1984; 140: 326 – 342
45. Von der Porten A. E., Gregory J. F., Toth J. P., Cerda J. J., Curry S. H., Bailey L. B. Vivo Folate Kinetics during Chronic Supplementation of Human Subjects with Deuterium-Labeled Folic Acid. J. Nutr. 1992; 122: 1293 – 1299
46. Garrow T. A., Admon A., Shane B. Expression Cloning of a Human cDNA Encoding Folylpoly-γ-Glutamate Synthetase and Determination of its Primary Structure. Proc.Natl. Acad. Sci. USA 1992; 89: 9151 – 9155
47. Cichowicz D. J., Shane B. Mammalian Folylpoly-γ-Glutamate Synthetase. 1. Purification and General Properties of the Hog Liver Enzyme. Biochemistry 1987; 26: 504 – 512
48. Cichowicz D. J., Shane B. Mammalian Folylpoly-γ-Glutamate Synthetase. 2. Substrate Specificity and Kinetic Properties. Biochemistry 1987; 26: 513 – 521
49. Cook J. D., Cichowicz D. J., George S., Lawler A., Shane B. Mammalian Folylpoly-γ-Glutamate Synthetase. 4. In Vitro and In Vivo Metabolism of Folates and Analogues and Regulation of Folate Homeostasis. Biochemistry 1987; 26: 530 – 539
50. McGuire J. J., Hsieh P., Coward J. K., Bertino J. R. Enzymatic Synthesis of Folylpoly-Glutamates. Characterization of the Reaction and its Products. J. Biol. Chem. 1980; 255: 5776 – 5788
51. Moran R. G., Colman P. D. Mammalian Folyl Polyglutamate Synthetase: Partial Purification and Properties of the Mouse Liver Enzyme. Biochemistry 1984; 23: 4580 – 4589
52. George S., Cichowicz D. J., Shane B. Mammalian Folylpoly-γ-Glutamate Synthetase. 3. Specificity for Folate Analogues. Biochemistry 1987; 26: 522 – 529
53. Coll R. J., Cesar D., Hynes J. B., Shane B. Vitro Metabolism of 5,8-Dideazafolates and 5,8-Dideazaisofolates by Mammalian Folylpoly-Γ-Glutamate Synthetase. Biochem Pharmacol 1991; 42: 833 – 838
54. Wittwer A. J., Wagner C. Identification of the Folate-Binding Proteins of Rat Liver Mitochondria as Dimethylglycine Dehydrogenase and Sarocosine Dehydrogenase. Purification and Folate-Binding Characteristics. J. Biol. Chem. 1981; 256: 4102 – 4108
55. Cook R. J., Wagner C. Glycine-N-Methyltransferase is a Folate Binding Protein of Rat Liver Cytosol. Proc. Natl. Acad. Sci. USA 1984; 81: 3631 – 3634
56. Wagner C., Briggs W. T., Cook R. J. Inhibition of Glycine N-Methyltrarnsferase Activity by Folate Derivatives: Implications for Regulation of Methyl Group Metabolism. Biochem. Biophys. Res. Commun. 1985; 127: 746 – 752
57. Min H., Shane B., Stokstad E. L.R. Identification of 10-Formyl-Tetrahydrofolate Dehydrogenase-Hydrolase as a Major Folate Binding Protein in Liver Cytosol. Biochim. Biophys. Acta. 1988; 967: 348 – 353
58. Schirch L. Folates in Serine and Glycine Metabolism. Folates and Pterins, R. L. Blakley, S. J. Benkovik. John Wiley & Sons, New York 1984; 1: 399 – 432
59. Zamierowski M. M., Wagner C. Effect of Folacin Deficiency on Folacin-Binding Proteins in the Rat. J. Nutr. 1977; 107: 1937 – 1945
60. Fort D. W., Lark R. H., Smith A. K., Marling-Cason M., Weitman S. D., Shane B., Kamen B. A. Accumulation of 5-Methyltetrahydrofolic Acid and Folylpolyglutamate Synthetase Expression by Mitogen Stimulated Human Lymphocytes. Br. J. Haematol. 1993; 84: 595 – 601
61. Houghton J. A., Williams L. G., de Graaf S. S. et al. Relationship Between Dose Rate of [6RS]Leucovorin Administration, Plasma Concentrations of Reduced Folates and Pools of 5,10-Methylenetetrahydrofolates and Tetrahydrofolates in Human Colon Adenocarcinoma Xenografts. Cancer Res. 1990; 50: 3493 – 3502
62. Galivan J., Nimec Z., Balinska M. Regulation of Methotrexate Polyglutamate Accumulation In Vitro: Effects of Cellular Folate Content. Biochem. Pharm. 1983; 32: 3244 – 3247
63. Egan M. G., Sirlin S., Rumberger B. G., Shane B., Sirotnak F. M. Decreasing Levels of Folylpolyglutamate Synthetase Gene Expression During Induction of Differentiation of HL-60 Cells. Proc. Am. Assoc. Cancer Res. 1993; 34: 275
64. Marchetti M., Tolomelli B., Formiggini G., Bovina C., Barbiroli B. Distribution of Pteroylpolyglutamates in Rat Liver after Partial Hepatectomy. Biochem. J. 1980; 188: 553 – 556
65. Eto I., Krumdieck C. L. Changes in the Chain Length of Folylpolyglutamates During Liver Regeneration. Life Sci. 1982; 30: 183 – 189
66. Whitehead V. M., Rosenblatt D. S., Vuchich M-J., Shuster J. J., Witte A., Beaulieu D. Accumulation of Methotrexate and Methotrexate Polyglutamates in Lymphoblasts at Diagnosis of Childhood Acute Iymphoblastic Leukemia: A Pilot Prognostic Study. Blood 1990; 76: 44 – 49
67. Lenz H-J., Schneiders B., Danenberg K., Goker E., Shane B., Bertino J. R., Danenberg P. V. A Polymerase Chain Reaction (PCR) Assay for Folylpolyglutamate Synthetase (FPGS) Gene Expression: Marked Variation in Human Leukemia Blast Samples. Proc. Am. Assoc. Cancer. Res. 1993; 34: 504
68. Pizzorno G. P., Mini E., Coronella M. et al. Impaired Polyglutamylation of Methotrexate as a Cause of Resistance in CCRF-CEM Cells After Short-Term High-Dose Treatment with this Drug. Cancer Res. 1988; 48: 2149 – 2155
69. McCloskey D. E., McGuire J. J., Russell C. A. et al. Decreased Folylpolyglutamate Synthetase Activity as a Mechanism of Methotrexate Resistance in CCRF-CEM Human Leukemia Sublines. J. Biol. Chem. 1991; 266: 6181 – 6187
70. Pizzorno G., Chang Y-M., McGuire J. J., Bertino J. R. Inherent Resistance of Human Squamous Carcinoma Cell Lines to Methotrexate as a Result of Decreased Polyglutamylation of this Drug. Cancer Res. 1989; 49: 5275 – 5280
71. Cassady I. A., Budge M. M., Healy M. J., Nixon P. F. An Inverse Relationship of Rat Liver Folate Polyglutamate Chain Length to Nutritional Folate Sufficiency. Biochem. Biophys. Acta. 1980; 633: 258 – 268
72. Matthews R. G. Methionine Biosynthesis. Folates and Pterins, R. L. Blakley, S. J. Benkovik. John Wiley & Sons, New York 1984; 1: 497 – 554
73. Wilson S. D., Horne D. W. Effect of Nitrous Oxide Inactivation of Vitamin B12 on the Levels of Folate Coenzymes in Rat Bone Marrow, Kidney, Brain, and Liver. Arch. Biochem. Biophys. 1986; 244: 248 – 253
74. Kutzbach C., Stokstad E. L.R. Mammalian Methylenetetrahydrofolate Reductase. Partial Purification, Properties, and Inhibition by S-Adenosylmethionine. Biochem. Biophys. Acta. 1971; 250: 45 – 477
75. Green J. M., Ballou D. P., Matthews R. G. Examination of the Role of Methylenetetrahydrofolate Reductase in Incorporation of Methylenetetrahydrofolate into Cellular Metabolism. FASEB J. 1988; 2: 299 – 302
76. Chanarin I., Deacon R., Lumb M., Perry J. Cobalamin-Folate Interrelations. Blood Rev. 1989; 3: 211 – 215
77. Chanarin I., Deacon R., Lumb M., Perry J. Cobalamin and Folate: Recent Developments. J. Clin. Path. 1992; 45: 277 – 283
78. Hoffbrand A. V., Jackson B. F.A. Correction of the DNA Synthesis Defect in Vitamin B12 Deficiency by Tetrahydrofolate: Evidence in Favour of the Methyl-Trap Hypothesis as the Cause of Megaloblastic Anaemia in Vitamin B12 Deficiency. Br. J. Haematol 1993; 83: 643 – 647
79. Samuels L. L., Moccio D. M., Sirotnak F. M. Similar Differential for Total Polyglutamylation and Cytotoxicity Among Various Folate Analogues in Human and Murine Tumor Cells In Vitro. Cancer Res. 1985; 45: 1488 – 1495
80. Murphy M., Keating M., Boyle P., Weir D. G., Scott J. M. The Elucidation of the Mechanism of Folate Catabolism in the Rat. Biochem. Biophys. Res. Commun. 1976; 71: 1017 – 1024
81. Scott J. M. Catabolism of Folates. Folates and Pterins, R. L. Blakley, S. J. Benkovik. John Wiley & Sons, New York 1984; 1: 307 – 327
82. McPartlin J., Halligan A., Scott J. M., Darling M., Weir D. G. Accelerated Folate Break Down in Pregnancy. Lancet 1993; 341: 148 – 149
83. Vickers P. J., Di Cecco R., Pristupa Z. B., Scrimgeour K. G. Folylpolyglutamate Hydrolase from Beef Liver. Chemistry and Biology of Pteridines 1986, B. A. Cooper, V. M. Whitehead. Walter de Gruyter & Co, Berlin 1986; 933 – 936
84. Brody T., Stokstad E. L.R. Folate Oligoglutamate: Amino Acid Transpeptidase. J. Biol. Chem. 1982; 257: 14271 – 14279
85. Priest D. G., Veronee D. C., Mangum M., Bednarek J. M., Doig M. T. Comparison of Folylpolyglutamate Hydrolases of Mouse Liver, Kidney, Muscle and Brain. Mol. Cell. Biochem. 1982; 43: 81 – 87
86. Elsenhans B., Ahmad O., Rosenberg I. H. Isolation and Characterization of Pteroylpolyglutamate Hydrolase from Rat Intestinal Mucosa. J. Biol. Chem. 1984; 259: 6364 – 6368
87. Wang T. T.Y., Chandler C. J., Halsted C. H. Intracellular Pteroylpolyglutamate Hydrolase from Human Jejunal Mucosa. Isolation and Characterization. J. Biol. Chem. 1986; 261: 13551 – 13555
88. Chandler C. J., Wang T. T.Y., Halsted C. H. Pteroylpolyglutamate Hydrolase from Human Jejunal Brush Borders. Purification and Characterization. J. Biol. Chem. 1986; 261: 928 – 933
89. Whitehead V. M., Kalman T. I., Vuchich M-J. Inhibition of Gamma-Glutamyl Hydrolases in Human Cells by 2-Mercaptomethylglutaric Acid. Biochem Biophys. Res. Commun. 1987; 144: 292 – 297
90. O'Connor B. M., Rotundo R. F., Nimec Z., McGuire J. M., Galivan J. Secretion of γ-Glutamyl Hydrolase In Vitro. Cancer Res. 1991; 51: 3874 – 3881
91. Barrueco J. R., O'Leary D. F., Sirotnak F. M. Metabolic Turnover of Methotrexate Polyglutamates in Lysosomes Derived from S180 cells. J. Biol. Chem. 1992; 267: 19986 – 19991
92. Rhee M. S., Wang Y., Nair M. G., Galivan J. Acquisition of Resistance to Antifolates caused by Enhanced γ-Glutamyl Hydrolase Activity. Cancer Res. 1993; 53: 1 – 3
93. Whitehead V. M. Pharmacokinetics and Physiological Disposition of Folate and its Derivatives. Folates and Pterins, R. L. Blakley, V. M. Whitehead. John Wiley & Sons, New York 1986; 3: 177 – 205
94. Williams W. M., Huang K. C. Renal Tubular Transport of Folic Acid and Methotrexate in the Monkey. Am. J. Physiol. 1982; 242: F484 – F490
95. Selhub J., Emmanouel D., Stavropoulos T., Arnold R. Renal Folate Absorption and the Kidney Folate Binding Protein. Am. J. Physiol. 1987; 252: F750 – F756
96. Eisenga B. H., Collins T. D., McMartin K. E. Effect of Acute Ethanol on Urinary Excretion of 5-Methyltetrahydrofolic Acid and Folate Derivatives in the Rat. J. Nutr. 1989; 119: 1498 – 1505
97. Rong N., Selhub J., Goldin B. R., Rosenberg I. H. Bacterially Syntheized Folate in Rat Large Intestine is Incorporated into Host Tissue Folyl Polyglutamates. J. Nutr. 1991; 121: 1955 – 1959