Cobalamin coenzyme forms are not likely to be superior to cyano- and hydroxyl-cobalamin in prevention or treatment of cobalamin deficiency

Molecular Nutrition and Food Research

Volumn 59, Issue 7, 2015, Pages 1364-1372

  Obeid, Rima ^a,b   Fedosov, Sergey N ^a,c   Nexo, Ebba ^c  

^a AARHUS UNIVERSITY   (Denmark)

^b SAARLAND UNIVERSITY   (Germany)

^c AARHUS UNIVERSITY HOSPITAL   (Denmark)

Author keywords

Adenosylcobalamin; Coenzyme; Cyanocobalamin; Deficiency; Hydroxylcobalamin; Methylcobalamin

Indexed keywords

COBAMAMIDE; CYANOCOBALAMIN; HYDROXOCOBALAMIN; MECOBALAMIN;

ANALOGS AND DERIVATIVES; CHEMISTRY; HUMAN; METABOLISM; TRANSPORT AT THE CELLULAR LEVEL; VITAMIN B 12 DEFICIENCY;

BIOLOGICAL TRANSPORT; COBAMIDES; HUMANS; HYDROXOCOBALAMIN; VITAMIN B 12; VITAMIN B 12 DEFICIENCY;

EID: 84934434859     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.201500019     Document Type: Review

References (65)

1. Hodgkin, D. C., Kamper, J., Mackay, M., Pickworth, J. et al., Structure of vitamin B12. Nature 1956, 178, 64-66.
2. Lenhert, P. G., Hodgkin, D. C., Structure of the 5, 6-dimethyl-benzimidazolylcobamide coenzyme. Nature 1961, 192, 937-938.
3. Thakkar, K., Billa, G., Treatment of vitamin B12 deficiency-Methylcobalamine? Cyancobalamine? Hydroxocobalamin?-clearing the confusion. Eur. J. Clin. Nutr. 2015, 69, 1-2.
4. Zhang, Y. F., Ning, G., Mecobalamin. Expert. Opin. Investig. Drugs 2008, 17, 953-964.
5. Institute of Medicine. Vitamin B12. Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline. USA: Washington, DC, National Academy Press 2000, 306-356.
6. Allen, L. H., Causes of vitamin B12 and folate deficiency. Food Nutr. Bull. 2008, 29, S20-S34.
7. Obeid, R., Schorr, H., Eckert, R., Herrmann, W., Vitamin B12 status in the elderly as judged by available biochemical markers. Clin. Chem. 2004, 50, 238-241.
8. Yetley, E. A., Pfeiffer, C. M., Phinney, K. W., Bailey, R. L. et al., Biomarkers of vitamin B-12 status in NHANES: a roundtable summary. Am. J Clin Nutr. 2011, 94, 313S-321S.
9. Andres, E., Kurtz, J. E., Perrin, A. E., Maloisel, F. et al., Oral cobalamin therapy for the treatment of patients with food- cobalamin malabsorption. Am. J. Med. 2001, 111, 126-129.
10. Andres, E., Affenberger, S., Vinzio, S., Kurtz, J. E. et al., Food-cobalamin malabsorption in elderly patients: clinical manifestations and treatment. Am. J. Med. 2005, 118, 1154-1159.
11. Banerjee, R., The Yin-Yang of cobalamin biochemistry. Chem. Biol. 1997, 4, 175-186.
12. Kräutler B., Organometallic Chemistry of B12-Coenzymes. In: Siegel A, Sigel H, Sigel RKO, eds. Metal-Carbon Bonds in Enzymes and Cofactors. Cambridge, UK: The Royal Society of Chemistry 2009:1-51.
13. Beedholm-Ebsen, R., van de Wetering, K., Hardlei, T., Nexo, E. et al., Identification of multidrug resistance protein 1 (MRP1/ABCC1) as a molecular gate for cellular export of cobalamin. Blood 2010, 115, 1632-1639.
14. Schjonsby, H., Andersen, K. J., The intestinal absorption of vitamin B12. Scand. J. Gastroenterol. Suppl. 1974, 29, 7-11.
15. Mathews, F. S., Gordon, M. M., Chen, Z., Rajashankar, K. R. et al., Crystal structure of human intrinsic factor: cobalamin complex at 2.6-A resolution. Proc. Natl. Acad. Sci USA 2007, 104, 17311-17316.
16. Wuerges, J., Geremia, S., Randaccio, L., Structural study on ligand specificity of human vitamin B12 transporters. Biochem. J. 2007, 403, 431-440.
17. Hippe, E., Olesen, H., Nature of vitamin B 12 binding. 3. Thermodynamics of binding to human intrinsic factor and transcobalamins. Biochim. Biophys. Acta 1971, 243, 83-88.
18. Fedosov, S. N., Berglund, L., Fedosova, N. U., Nexo, E., Petersen, T. E., Comparative analysis of cobalamin binding kinetics and ligand protection for intrinsic factor, transcobalamin, and haptocorrin. J Biol. Chem. 2002, 277, 9989-9996.
19. Fedosov, S. N., Petersen, T. E., Nexo, E., Binding of cobalamin and cobinamide to transcobalamin from bovine milk. Biochemistry 1995, 34, 16082-16087.
20. Wuerges, J., Garau, G., Geremia, S., Fedosov, S. N. et al., Structural basis for mammalian vitamin B12 transport by transcobalamin. Proc. Natl. Acad. Sci USA 2006, 103, 4386-4391.
21. Fedosov, S. N., Fedosova, N. U., Krautler, B., Nexo, E., Petersen, T. E., Mechanisms of discrimination between cobalamins and their natural analogues during their binding to the specific B12-transporting proteins. Biochemistry 2007, 46, 6446-6458.
22. Muir, M., Chanarin, I., Separation of cobalamin analogues in human sera binding to intrinsic factor and to R-type vitamin B12 binders. Br. J. Haematol. 1983, 54, 613-621.
23. Gruber, K., Puffer, B., Krautler, B., Vitamin B12-derivatives-enzyme cofactors and ligands of proteins and nucleic acids. Chem. Soc. Rev. 2011, 40, 4346-4363.
24. Hippe, E., Changes in Stokes radius on binding of vitamin B12 to human intrinsic factor and transcobalamins. Biochim. Biophys. Acta. 1970, 208, 337-339.
25. Fedosov, S. N., Fedosova, N. U., Berglund, L., Moestrup, S. K. et al., Composite organization of the cobalamin binding and cubilin recognition sites of intrinsic factor. Biochemistry 2005, 44, 3604-3614.
26. Halpern, J., Mechanisms of coenzyme B12-dependent rearrangements. Science. 1985, 227, 869-875.
27. Nielsen, M. J., Rasmussen, M. R., Andersen, C. B., Nexo, E., Moestrup, S. K., Vitamin B12 transport from food to the body's cells-a sophisticated, multistep pathway. Nat. Rev. Gastroenterol. Hepatol. 2012, 9, 345-354.
28. Gailus, S., Hohne, W., Gasnier, B., Nurnberg, P. et al., Insights into lysosomal cobalamin trafficking: lessons learned from cblF disease. J. Mol. Med. 2010, 88, 459-466.
29. Rutsch, F., Gailus, S., Miousse, I. R., Suormala, T. et al., Identification of a putative lysosomal cobalamin exporter altered in the cblF defect of vitamin B12 metabolism. Nat. Genet. 2009, 41, 234-239.
30. Banerjee, R., Gherasim, C., Padovani, D., The tinker, tailor, soldier in intracellular B12 trafficking. Curr. Opin. Chem Biol. 2009, 13, 484-491.
31. Watkins, D., Rosenblatt, D. S., Lessons in biology from patients with inborn errors of vitamin B12 metabolism. Biochimie 2013, 95, 1019-1022.
32. Oladipo, O., Rosenblatt, D. S., Watkins, D., Miousse, I. R. et al., Cobalamin F disease detected by newborn screening and follow-up on a 14-year-old patient. Pediatrics 2011, 128, e1636-e1640.
33. Waggoner, D. J., Ueda, K., Mantia, C., Dowton, S. B., Methylmalonic aciduria (cblF): case report and response to therapy. Am. J. Med. Genet. 1998, 79, 373-375.
34. Zhao, H., Ruberu, K., Li, H., Garner, B., Perturbation of neuronal cobalamin transport by lysosomal enzyme inhibition. Bioscience Reports 2014, 34, 43-50.
35. Li, Z., Gherasim, C., Lesniak, N. A., Banerjee, R., Glutathione-dependent One-electron Transfer Reactions Catalyzed by a B12 Trafficking Protein. J Biol. Chem. 2014, 289, 16487-16497.
36. Gherasim, C., Lofgren, M., Banerjee, R., Navigating the B(12) road: assimilation, delivery, and disorders of cobalamin. J. Biol. Chem. 2013, 288, 13186-13193.
37. Koutmos, M., Gherasim, C., Smith, J. L., Banerjee, R., Structural basis of multifunctionality in a vitamin B12-processing enzyme. J. Biol. Chem. 2011, 286, 29780-29787.
38. Ruetz, M., Gherasim, C., Gruber, K., Fedosov, S. et al., Access to organometallic arylcobaltcorrins through radical synthesis: 4-ethylphenylcobalamin, a potential ``antivitamin B(12)''. Angew. Chem. Int. Ed Engl. 2013, 52, 2606-2610.
39. Hannibal, L., Kim, J., Brasch, N. E., Wang, S. et al., Processing of alkylcobalamins in mammalian cells: A role for the MMACHC (cblC) gene product. Mol. Genet. Metab. 2009, 97, 260-266.
40. Banerjee, R., B12 trafficking in mammals: A for coenzyme escort service. ACS Chem. Biol. 2006, 1, 149-159.
41. Andersson, H. C., Shapira, E., Biochemical and clinical response to hydroxocobalamin versus cyanocobalamin treatment in patients with methylmalonic acidemia and homocystinuria (cblC). J. Pediatr. 1998, 132, 121-124.
42. Pezacka, E., Green, R., Jacobsen, D. W., Glutathionylcobalamin as an intermediate in the formation of cobalamin coenzymes. Biochem. Biophys. Res. Commun. 1990, 169, 443-450.
43. Mutti, E., Ruetz, M., Birn, H., Krautler, B., Nexo, E., 4-ethylphenyl-cobalamin impairs tissue uptake of vitamin B12 and causes vitamin B12 deficiency in mice. PLoS. ONE. 2013, 8, e75312.
44. Mah, W., Deme, J. C., Watkins, D., Fung, S. et al., Subcellular location of MMACHC and MMADHC, two human proteins central to intracellular vitamin B(12) metabolism. Mol. Genet. Metab. 2013, 108, 112-118.
45. Coelho, D., Kim, J. C., Miousse, I. R., Fung, S. et al., Mutations in ABCD4 cause a new inborn error of vitamin B(12) metabolism. Nat. Genet. 2012, 44, 1152-1155.
46. Carrillo-Carrasco, N., Chandler, R. J., Venditti, C. P., Combined methylmalonic acidemia and homocystinuria, cblC type. I. Clinical presentations, diagnosis and management. J. Inherit. Metab Dis. 2012, 35, 91-102.
47. Carrillo-Carrasco, N., Venditti, C. P., Combined methylmalonic acidemia and homocystinuria, cblC type. II. Complications, pathophysiology, and outcomes. J. Inherit. Metab Dis. 2012, 35, 103-114.
48. Waly, M. I., Kharbanda, K. K., Deth, R. C., Ethanol lowers glutathione in rat liver and brain and inhibits methionine synthase in a cobalamin-dependent manner. Alcohol Clin. Exp. Res. 2011, 35, 277-283.
49. Xia, L., Cregan, A. G., Berben, L. A., Brasch, N. E. Studies on the formation of glutathionylcobalamin: any free intracellular aquacobalamin is likely to be rapidly and irreversibly converted to glutathionylcobalamin. Inorg. Chem. 2004, 43, 6848-6857.
50. Jeong, J., Park, J., Park, J., Kim, J., Processing of glutathionylcobalamin by a bovine B12 trafficking chaperone bCblC involved in intracellular B12 metabolism. Biochem. Biophys. Res. Commun. 2014, 443, 173-178.
51. Adams, J. F., Ross, S. K., Mervyn, L., Boddy, K., King, P., Absorption of cyanocobalamin, coenzyme B 12, methylcobalamin, and hydroxocobalamin at different dose levels. Scand. J. Gastroenterol. 1971, 6, 249-252.
52. Herbert, V., Sullivan LW., Activity of coenzyme B12 in man. Ann. N. Y. Acad. Sci. 1964, 112, 855-870.
53. Torsvik, I., Ueland, P. M., Markestad, T., Bjorke-Monsen, A. L., Cobalamin supplementation improves motor development and regurgitations in infants: results from a randomized intervention study. Am. J. Clin. Nutr. 2013, 98, 1233-1240.
54. Mellman, I. S., Youngdahl-Turner, P., Willard, H. F., Rosenberg, L. E., Intracellular binding of radioactive hydroxocobalamin to cobalamin-dependent apoenzymes in rat liver. Proc. Natl. Acad. Sci. USA 1977, 74, 916-920.
55. Kolhouse, J. F., Allen, R. H., Recognition of two intracellular cobalamin binding proteins and their identification as methylmalonyl-CoA mutase and methionine synthetase. Proc. Natl. Acad. Sci. USA 1977, 74, 921-925.
56. Hardlei, T. F., Morkbak, A. L., Bor, M. V., Bailey, L. B. et al., Assessment of vitamin B(12) absorption based on the accumulation of orally administered cyanocobalamin on transcobalamin. Clin. Chem. 2010, 56, 432-436.
57. Hall, C. A., Begley, J. A., Green-Colligan, P. D., The availability of therapeutic hydroxocobalamin to cells. Blood 1984, 63, 335-341.
58. Hertz, H., Kristensen, H. P., Hoff-Jorgensen, E., Studies on vitamin B12 retention. Composition of retention following intramuscular injection of cyanocobalamin and hydroxocobalamin. Scand. J. Haematol. 1964, 1, 5-15.
59. Shepherd, G., Velez, L. I., Role of hydroxocobalamin in acute cyanide poisoning. Ann. Pharmacother. 2008, 42, 661-669.
60. Schuh, S., Rosenblatt, D. S., Cooper, B. A., Schroeder, M. L. et al., Homocystinuria and megaloblastic anemia responsive to vitamin B12 therapy. An inborn error of metabolism due to a defect in cobalamin metabolism. N. Engl. J. Med. 1984, 310, 686-690.
61. Adams JF., The urinary excretion and retention of cyaocobalamin by subjects given repeated parenteral doses. J. Clin. Pathol. 1964, 17, 31-38.
62. Shibuya, K., Misawa, S., Nasu, S., Sekiguchi, Y. et al., Safety and Efficacy of Intravenous Ultra-high Dose Methylcobalamin Treatment for Peripheral Neuropathy: A Phase I/II Open Label Clinical Trial. Intern. Med. 2014, 53, 1927-1931.
63. Araki, A., Sako, Y., Ito, H., Plasma homocysteine concentrations in Japanese patients with non-insulin-dependent diabetes mellitus: effect of parenteral methylcobalamin treatment. Atherosclerosis. 1993, 103, 149-157.
64. Guest, J.R., Friedman, S., Dilwort, M. J., Woods, D.D., Methylcobalamin as a source of the methyl group of methionine. Ann. N. Y. Acad. Sci. 1964, 112, 774-790.
65. Pfohl-Leszkowicz, A., Keith, G., Dirheimer, G., Effect of cobalamin derivatives on in vitro enzymatic DNA methylation: methylcobalamin can act as a methyl donor. Biochemistry 1991, 30, 8045-8051.