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Vitamin B12 in drug delivery: breaking through the barriers to a B12 bioconjugate pharmaceutical

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Pages 127-140 | Published online: 04 Dec 2010

Bibliography

  • Banerjee R, Gherasim C, Padovani D. The tinker, tailor, soldier in intracellular B12 trafficking. Curr Opin Chem Biol 2009;13:484-91
  • Alpers D, Russell-Jones G. Intrinsic factor, haptocorrin and their receptors. In: Banerjee R, editor, Chemistry and biochemistry of B12. New York: John Wiley & Sons; 1999. p. 411-40
  • Rothenberg S, Quadros E, Regec A. Transcobalamin II. In: Banerjee R, editor. Chemistry and biochemistry of B12. New York: John Wiley & Sons; 1999. p. 441-73
  • Randaccio L, Geremia S, Wuerges J, Vitamin B12: Unique metalorganic compounds and the most complex vitamins. Molecules 2010;15:3228-59
  • Waibel R, Treichler H, Schaefer N, New derivatives of vitamin B12 show preferential targeting of tumors. Cancer Res 2008;68:2904-11
  • Coudroy G, Gburek J, Verroust P, Contribution of cubilin and amnionless to processing and membrane targeting of cubilin–amnionless complex. J Am Soc Nephrol 2005;16:2330-37
  • Morkbak A, Pedersen J, Nexo E. Glycosylation independent measurement of the cobalamin binding protein haptocorrin. Clinica Chimica Acta 2005;356:184-90
  • Andersen C, Madsen M, Strm T, Structural basis for receptor recognition of vitamin-B12–intrinsic factor complexes. Nature 2010;464:445-9
  • Mathews F, Gordon M, Chen Z, Crystal structure of human intrinsic factor: Cobalamin complex at 2.6-Å resolution. Proc Natl Acad Sci USA 2007;104:17311-16
  • Wuerges J, Garau G, Geremia S, Structural basis for mammalian vitamin B12 transport by transcobalamin. P Natl Acad Sci USA 2006;103:4386-91
  • Adkins Y, Lonnerdal B. Potential host-defense role of a human milk vitamin B-12-binding protein, haptocorrin, in the gastrointestinal tract of breastfed infants, as assessed with porcine haptocorrin in vitro1-3. Am J Clin Nutr 2003;77:1234-40
  • Marques H, Ngoma B, Egan T, Parameters for the amber force field for the molecular mechanics modeling of the cobalt corrinoids. J Mol Struct 2001;561:71-91
  • Marques H, Brown K. Molecular mechanics and molecular dynamics simulations of porphyrins, metalloporphyrins, heme proteins and cobalt corrinoids. Coord Chem Rev 2002;225:123-58
  • Brown K, Zou X, Marques H. NMR-restrained molecular modeling of cobalt corrinoids: cyanocobalamin (vitamin B12) and methylcobalt corrinoids. Theochem 1998;453:209-24
  • Allis D, Fairchild T, Doyle R. The binding of vitamin B12 to transcobalamin (II); structural considerations for bioconjugate design – a molecular dynamics study. Mol BioSyst 2010;6:1611-18
  • Kandt C, Xu Z, Tieleman D. Opening and closing motions in the periplasmic vitamin B12 binding protein BtuF. Biochemistry 2006;45:13284-92
  • Gumbart J, Wiener M, Tajkhorshid E. Coupling of calcium and substrate binding through loop alignment in the outer-membrane transporter BtuB. J Mol Biol 2009;393:1129-42
  • Wuerges J, Fedosov S, Randaccio L, Vitamin B12 transport proteins: Crystallographic analysis of beta-axial ligand substitutions in cobalamin bound to transcobalamin. Life 2007;59:722-29
  • Alsenz J, Russell-Jones G-J, Westwood S. Oral absorption of peptides through the cobalamin (vitamin B12) pathway in the rat intestine. Pharm Res 2000;17:825-32
  • Petrus A, Fairchild T, Doyle R. Vitamin B12 as a carrier for the oral delivery of insulin. ChemMedChem 2007;2:1-5
  • Wang X, Wei L, Kotra L. Cyanocobalamin (vitamin B12) conjugates with enhanced solubility. Bioorg Med Chem 2007;15:1780-87
  • Ruiz-Sanchez P, Mundwiler S, Alberto R. Syntheses and characterization of vitamin B12–Pt(II) conjugates and their adenosylation in an enzymatic assay. J Biol Inorg Chem 2008;13:335-47
  • Carmel R. Extreme elevation of serum transcobalamin I in patients with metastatic cancer. N Engl J Med 1975;292:282-4
  • Leuner C, Dressman J. Improving drug solubility for oral delivery using solid dispersions. Eur J Pharm Biopharm 2000;50:47-60
  • Fasano A. Novel approaches for oral delivery of macromolecules. J Pharm Sci 1998;87:1351-6
  • Gaucher G, Satturwar P, Jones M-C, Polymeric micelles for oral drug delivery. Eur J Pharm Biopharm 2010;76:147-58
  • Fedosov S, Grissom C, Fedosova N, Application of a fluorescent cobalamin analogue for analysis of the binding kinetics. FEBS J 2006;273:4742-53
  • Cooperman J. Distribution of radioactive and nonradioactive vitamin Bl2 in normal and malignant tissues of an infant with neuroblastoma. Cancer Res 1972;32:167-72
  • Bose S, Seetharam S, Seetharam B, In vitro and in vivo inactivation of transcobalamin II receptor by its antiserum. J Biol Chem 1996;271:4195-200
  • Wooley K, Collins D, Morton K. Uptake of Co-57-vitaminB-12 by murine tumors of many histologic types. Clin Res 1993;41:73
  • Collins D, Hogenkamp H. Transcobalamin II receptor imaging via radiolabeled diethylene-triaminepentaacetate cobalamin analogs. J Nucl Med 1997;38:717-23
  • Collins D, Hogenkamp H, Gebhard M. Tumor imaging via indium 111-labeled DTPA-adenosylcobalamin. Mayo Clin Proc 1999;74:687-91
  • Ruiz-Sanchez P, Mundwiler S, Alberto R, Iodination of cisplatin adduct of vitamin B12 [{B12}-CN-{cis-PtCl(NH3)2}]+. J Organomet Chem 2007;692:1358-62
  • Mundwiler S, Waibel R, Alberto R, Picolylamine-methylphosphonic acid esters as tridentate ligands for the labeling of alcohols with the fac-[M(CO)3]+ core (M = 99 mTc, Re): synthesis and biodistribution of model compounds and of a 99 mTc-labeled cobinamide. Nucl Med Biol 2005;32:473-84
  • Siega P, Wuerges J, Randaccio L, Release of toxic Gd3+ Ions to tumour cells by vitamin B12 bioconjugates. Chem Eur J 2009;15:7980-89
  • Bauer J, Morrison B, Grane R, Effects of interferon on transcobalamin II-receptor expression and antitumor activity of nitrosylcobalamin. J Natl Cancer I 2002;94:1010-19
  • Levy M, Spino M, Read S. Colchicine: a state-of-the-art review. Pharmacotherapy 1991;11:196-211
  • Bagnato J, Eilers A, Grissom C, Synthesis and characterization of a cobalamin-colchicine conjugate as a novel tumor-targeted cytotoxin. J Org Chem 2004;69:8988-96
  • Mundwiler S, Kunze S, Alberto R, Cyanide-bridged vitamin B12–cisplatin conjugates. Chem Eur J 2005;11:4089-95
  • Ruiz-Sanchez P, Mundwiler S, Alberto R. Syntheses of fluorescent vitamin B12-Pt(II) conjugates and their Pt(II) release in a spectroelectrochemical assay. Chimia 2007;61:190-3
  • Ruiz-Sanchez P, Ferrari S, Alberto R, Vitamin B12 as a carrier for targeted platinum delivery: in vitro cytotoxicity and mechanistic studies. J Biol Inorg Chem 2010 DOI 10.1007/s00775-010-0697-z
  • Petrus A, Fairchild T, Doyle R. Traveling the vitamin B12 pathway: oral delivery of protein and peptide drugs. Angew Chem Int Ed 2008;47:1022-28
  • Pathare P, Wilbur D, Heusser S, Synthesis of cobalamin-biotin conjugates that vary in the position of cobalamin coupling. evaluation of cobalamin derivative binding to transcobalamin II. Bioconjugate Chem 1996;7:217-32
  • Petrus A, Allis D, Doyle R. Exploring the implications of vitamin B12 conjugation to insulin on insulin receptor binding. ChemMedChem 2009;4:421-6
  • Carkeet C, Dueker S, Lango J, Human vitamin B12 absorption measurement by accelerator mass spectrometry using specifically labeled 14C-cobalamin. P Natl Acad Sci USA 2006;103:5694-99
  • Hogenkamp H, Collins D, Live D, Synthesis and characterization of nido-carborane-cobalamin conjugates. Nuc Med Biol 2000;27:89-92
  • McGreevy J, Cannon M, Grissom C. Minimally invasive lymphatic mapping using fluorescently labeled vitamin B12. J Surg Res 2003;111:38-44
  • Kunze S, Zobi F, Alberto R, Vitamin B12 as a ligand for technetium and rhenium complexes. Angew Chem 2004;116:5135-39
  • Mukherjee R, Donnay E, Radomski M, Vanadium–vitamin B12 bioconjugates as potential therapeutics for treating diabetes. Chem Commun 2008:3783-85
  • Lee M, Grissom C. Design, synthesis, and characterization of fluorescent cobalamin analogues with high quantum efficiencies. Org Lett 2009;11:2499-502
  • Russell-Jones G, McEwan J, McTavish K. Preliminary studies on the selective accumulation of vitamin-targeted polymers within tumours. J Drug Target 2010; published ahead of print May 6th, PMID: 20446757
  • Olesen H, Hippe E, Haber E, Nature of vitamin B12 binding: II. Steric orientation of vitamin B12 on binding and number of combining sites of human intrinsic factor and the transcobalamins. Biochim Biophys Acta Protein Struct 1971;243:66
  • Ahrenstedt S, Thorell J. The production of antibodies to vitamin B-12. Clin Chim Acta 1979;95:419-23
  • Habberfield A, Kinstler O, Pitt C. Conjugates of vitamin B12 and proteins Patent. WOW09428015; 1994
  • Russell-Jones G, Westwood S, Habberfield A. Vitamin B12 mediated oral delivery systems for granulocyte-colony stimulating factor and erythropoietin. Bioconjugate Chem 1995;6:459-65
  • Russell-Jones G, Westwood S, Farnworth P, Synthesis of LHRH antagonists suitable for oral administration via the vitamin B12 uptake system. Bioconjugate Chem 1995;6:34-42
  • Alsenz J, Russell-Jones G, Westwood S, Oral absorption of peptides through the cobalamin pathway in the rat intestine. Pharmaceutical research 2000;17:825
  • Chalasani K, Russell-Jones G, Jain A, Effective oral delivery of insulin in animal models using vitamin B12-coated dextran nanoparticles. J Control Release 2007;122:141-50

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