Physicochemical investigation of the influence of saccharide-based parenteral formulation excipients on l-p-boronphenylalanine solubilisation for boron neutron capture therapy

Journal of Pharmaceutical Sciences

Volumn 101, Issue 1, 2012, Pages 223-232

  Schmidt, Elke ^a   Dooley, Neil ^a   Ford, Steven J ^a   Elliott, Moira ^a   Halbert, Gavin W ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Boron neutron capture therapy (BNCT); Boronphenylalanine (BPA); Complexation; Cyclodextrins; Excipients; Formulation; Physicochemical; Solubility

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; BORONIC ACID DERIVATIVE; CARBOHYDRATE; FRUCTOSE; MANNITOL; PHENYLALANINE; TREHALOSE;

ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; HUMAN; NEUTRON CAPTURE THERAPY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSICAL CHEMISTRY; PKA; SOLUBILITY; ULTRAVIOLET RADIATION;

EID: 82255179375     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22761     Document Type: Article

References (29)

1. Barth RF, Coderre JA, Vicente MGH, Blue TE. 2005. Boron neutron capture therapy of cancer: Current status and future prospects. Clin Cancer Res 11(11):3987-4002.
2. Joensuu H, Kankaanranta L, Seppala T, Auterinen I, Kallio M, Kulvik M, Laakso J, Vahatalo J, Kortesniemi M, Kotiluoto P, Seren T, Karila J, Brander A, Jarviluoma E, Ryynanen P, Paetau A, Ruokonen I, Minn H, Tenhunen M, Jaakelainen J, Farkkila M, Savolainen S. 2003. Boron neutron capture therapy of brain tumors: Clinical trials at the Finnish facility using boronophenylalanine. J Neurooncol 62(1):123-134.
3. Liberman SJ, Dagrosa A, Rebagliati RAJ, Bonomi MR, Roth BM, Turjanski L, Castiglia SI, Gonzalez SJ, Menendez PR, Cabrini R, Roberti MJ, Batistoni DA. 2004. Biodistribution studies of boronophenylalanine-fructose in melanoma and brain tumor patients in Argentina. Appl Radiat Isot 61(5):1095-1100.
4. Nawashiro H, Otani N, Shinomiya N, Fukui S, Ooigawa H, Shima K, Matsuo H, Kanai Y, Endou H. 2006. L-type amino acid transporter 1 as a potential molecular target in human astrocytic tumors. Int J Cancer 119(3):484-492.
5. Detta A, Cruickshank GS. 2009. L-amino acid transporter-1 and boronophenylalanine-based boron neutron capture therapy of human brain tumors. Cancer Res 69(5):2126-2132.
6. Snyder HR, Reedy AJ, Lennarz WJ. 1958. Synthesis of aromatic boronic acids, aldehydo boronic acids and a boronic acid analog of tyrosine. J Am Chem Soc 80:835-838.
7. Soloway AH, Wright RL, Messer JR. 1961. Evaluation of boron compounds for use in neutron capture therapy of brain tumours. 1. Animal investigations. J Pharmacol Exp Ther 134:117-122.
8. Yoshino K, Suzuki A, Mori Y, Kakihana H, Honda C, Mishima Y, Kobayashi T, Kanda K. 1989. Improvement of solubility of p-boronophenylalanine by complex formation with monosaccharides. Strahlenther Onkol 165(2-3):127-129.
9. Mori Y, Suzuki A, Yoshino K, Kakihana H. 1989. Complex formation of p-boronophenylalanine with some monosaccharides. Pigment Cell Res 2(4):273-277.
10. Bendel P, Wittig A, Basilico F, Mauri PL, Sauerwein W. 2010. Metabolism of borono-phenylalanine-fructose complex (BPA-fr) and borocaptate sodium (BSH) in cancer patients-Results from EORTC trial 11001. J Pharm Biomed Anal 51(1):284-287.
11. Henriksson R, Capala J, Michanek A, Lindahl SA, Satford LG, Franzen L, Blomquist E, Westlin JE, Bergenheim AT. 2008. Boron neutron capture therapy (BNCT) for glioblastoma multiforme: A phase II study evaluating a prolonged high-dose of boronophenylalanine (BPA). Radiother Oncol 88(2):183-191.
12. Collins J. 1993. Metabolic disease. Time for fructose solutions to go. Lancet 341(8845):600.
13. Laakso J, Ruokonen I, Lapatto R, Kallio M. 2003. Inborn errors in metabolism and 4-boronophenylalanine-fructose- based boron neutron capture therapy. Radiat Res 160(5):606-609.
14. Coderre JA, Elowitz EH, Chadha M, Bergland R, Capala J, Joel DD, Liu HYB, Slatkin DN, Chanana AD. 1997. Boron neutron capture therapy for glioblastoma multiforme using p-boronophenylalanine and epithermal neutrons: Trial design and early clinical results. J Neurooncol 33(1-2):141-152.
15. van Rij CM, Sinjewel A, van Loenen AC, Sauerwein WAG, Wittig A, Kriz O, Wilhelm AJ. 2005. Stability of B-10-l-boronophenylaianine-fructose injection. Am J Health Syst Pharm 62(24):2608-2610.
16. Barth RF, Yang WL, Rotaru JH, Moeschberger ML, Boesel CP, Soloway AH, Joel DD, Nawrocky MM, Ono K, Goodman JH. 2000. Boron neutron capture therapy of brain tumors: Enhanced survival and cure following blood-brain barrier disruption and intracarotid injection of sodium borocaptate and boronophenylalanine. Int J Rad Oncol Biol Phys 47(1):209-218.
17. Box K, Comer JE, Gravestock T, Stuart M. 2009. New ideas about the solubility of drugs. Chem Biodivers 6(11):1767-1788.
18. Anonymous 2010. ACD/Labs Online, I-Lab (http://www.acdlabs.com/resources/ilab/).
19. Yan J, Springsteen G, Deeter S, Wang BH. 2004. The relationship among pK(a), pH, and binding constants in the interactions between boronic acids and diols-It is not as simple as it appears. Tetrahedron 60(49):11205-11209.
20. Springsteen G, Wang BH. 2002. A detailed examination of boronic acid-diol complexation. Tetrahedron 58(26):5291-5300.
21. Shull BK, Spielvogel DE, Gopalaswamy R, Sankar S, Boyle PD, Head G, Devito K. 2000. Evidence for spontaneous, reversible paracyclophane formation. Aprotic solution structure of the boron neutron capture therapy drug, l-p-boronophenylalanine. J Chem Soc-Perkin Trans 2(3):557-561.
22. Shull BK, Spielvogel DE, Head G, Gopalaswamy R, Sankar S, Devito K. 2000. Studies on the structure of the complex of the boron neutron capture therapy drug, l-p-boronophenylalanine, with fructose and related carbohydrates: Chemical and C-13 NMR evidence for the beta-D-fructofuranose 2, 3, 6-(p-phenylalanylorthoboronate) structure. J Pharm Sci 89(2):215-222.
23. Islam TMB, Yoshino K, Sasane A. 2003. B-11 NMR study of p-carboxybenzeneboronic acid ions for complex formation with some monosaccharides. Anal Sci 19(3):455-460.
24. Sivaev IB, Bregadze VI. 2008. l-4-Boronophenylalanine (all around the one molecule). ARKIVOC iv:47-61.
25. Box K, Bevan C, Comer J, Hill A, Allen R, Reynolds D. 2003. High-throughput measurement of pKa values in a mixed-buffer linear pH gradient system. Anal Chem 75(4):883-892.
26. Hatanaka H, Komada F, Mishima Y, Okumura K. 1993. Improved bioavailability of para-boronophenylalanine by cyclodextrin complexation. J Pharm Sci 82(10):1054-1057.
27. Ward CJ, Patel P, Ashton PR, James TD. 2000. A molecular colour sensor for monosaccharides. Chem Commun 2000 (3):229-230.
28. Matsumoto M, Ueba K, Kondo K. 2005. Separation of sugar by solvent extraction with phenylboronic acid and trioctylmethylammonium chloride. Sep Purif Technol 43(3):269-274.
29. Mishima Y, Ichihashi M, Hatta S, Honda C, Yamamura K, Nakagawa T, Obara H, Shirakawa J, Hiratsuka J, Taniyama K, Tanaka C, Kanda K, Kobayashi T, Sato T, Ishida MR, Ujeno Y, Takahashi M, Abe M, Nozaki T, Aizawa O, Matsumoto T, Sato T, Karashima H, Yoshino K, Fukuda H. 1989. First human clinical trial of melanoma neutron capture. Diagnosis and therapy. Strahlenther Onkol 165(2-3):251-254.