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Polyhedral boron derivatives of porphyrins and phthalocyanines

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, Moscow 119991, Russia

Corresponding author, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, Moscow 119991, Russia.

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IGOR B. SIVAEV

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, Moscow 119991, Russia

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DETLEF GABEL

Universität Bremen, PO Box 330440, D-28334 Bremen, Germany

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, and

DIETER WÖHRLE

Universität Bremen, PO Box 330440, D-28334 Bremen, Germany

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https://doi.org/10.1002/jpp.544Cited by:74 (Source: Crossref)

Abstract

The synthesis of compounds containing polyhedral boron cages and porphyrin or phthalocyanine units connected covalently in one molecule is reviewed. The importance of these compounds arises, on the one hand, from the use of polyhedral boron derivatives in neutron capture therapy for cancer; on the other hand, porphyrins and phthalocyanines are known as photosensitizers in photodynamic tumor therapy. Current interest in the binding of polyhedral boron compounds to porphyrins and phthalocyanines is due to the observation that porphyrins and phthalocyanines show improved uptake and good persistence in tissues. Medical applications of compounds containing polyhedral boron cages and porphyrin or phthalocyanine units in one molecule are briefly discussed.

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References

J. G. Moser (ed.) , Photodynamic Tumor Therapy ( Harwood Academic Publishers , Amsterdam , 1998 ) . Google Scholar
H. Ali and J. E. van Lier, Chem. Rev. 99, 2379 (1999), DOI: 10.1021/cr980439y. Crossref, Web of Science, Google Scholar
M. F. Hawthorne, Angew. Chem., Int. Ed. Engl. 32, 950 (1993), DOI: 10.1002/anie.199309501. Crossref, Web of Science, Google Scholar
A. H. Solowayet al., Chem. Rev. 98, 515 (1998). Google Scholar
V. Morin, Tetrahedron 44, 12521 (1994). Google Scholar
R. C. Haushalter and R. W. Rudolph, J. Am. Chem. Soc. 100, 4628 (1978), DOI: 10.1021/ja00482a068. Crossref, Web of Science, Google Scholar
R. C. Haushalter, W. M. Butler and R. W. Rudolph, J. Am. Chem. Soc. 103, 2620 (1981), DOI: 10.1021/ja00400a023. Crossref, Web of Science, Google Scholar
R. C. Haushalter and R. W. Rudolph, J. Am. Chem. Soc. 101, 7080 (1979), DOI: 10.1021/ja00517a058. Crossref, Web of Science, Google Scholar
L. I. Zakharkinet al., Russ. Chem. Bull. 47, 340 (1998), DOI: 10.1007/BF02498962. Crossref, Web of Science, Google Scholar
M. G. H. Vicenteet al., Tetrahedron Lett. 41, 7623 (2000), DOI: 10.1016/S0040-4039(00)01346-0. Crossref, Web of Science, Google Scholar
M. G. H. Vicenteet al., Chem. Commun. 483 (2001), DOI: 10.1039/b100231g. Google Scholar
D. Gabel, Clinical Aspects of Neutron Capture Therapy, eds. R. G. Fairchild, V. P. Bond and A. D. Woodhead (Plenum Press, New York, 1989) p. 233. Crossref, Google Scholar
M. Miuraet al., Tetrahedron Lett. 31, 2247 (1990), DOI: 10.1016/0040-4039(90)80197-T. Crossref, Web of Science, Google Scholar
G. Oenbrink, P. Jürgenlimke and D. Gabel, Photochem. Photobiol. 48, 451 (1988), DOI: 10.1111/j.1751-1097.1988.tb02844.x. Crossref, Web of Science, Google Scholar
M. Miuraet al., Br. J. Radiol. 71, 773 (1998). Crossref, Web of Science, Google Scholar
M. Miuraet al., Cancer Neutron Capture Therapy, ed. Y. Mishima (Plenum Press, New York, 1996) p. 137. Crossref, Google Scholar
M. Miuraet al., Advances in Neutron Capture Therapy, Chemistry and Biology II, eds. B. Larsson, J. Crawford and R. Weinreich (Elsevier, Amsterdam, 1997) p. 56. Google Scholar
M. Miuraet al., Int. J. Cancer 68, 114 (1996). Crossref, Web of Science, Google Scholar
S. B. Kahl, Proc. First Int. Symp. Neutron Capture Therapy, eds. R. G. Fairchild and G. L. Brownell (Brookhaven National Laboratory, BNL 51730, New York, 1983) p. 294. Google Scholar
S. B. Kahlet al., Clinical Aspects of Neutron Capture Therapy, eds. R. G. Fairchild, V. P. Bond and A. D. Woodhead (Plenum Press, New York, 1989) p. 193. Crossref, Google Scholar
S. B. Kahl, Neutron Capture Therapy, ed. H. Hatanaka (Nishimura Co, Ltd, Niigata, 1986) p. 1. Google Scholar
S. B. Kahl and P. Micca, Neutron Capture Therapy, ed. H. Hatanaka (Nishimura Co, Ltd, Niigata, 1986) p. 61. Google Scholar
S. B. Kahlet al., Proc. Natl. Acad. Sci. USA 87, 7265 (1990), DOI: 10.1073/pnas.87.18.7265. Crossref, Web of Science, Google Scholar
R. P. Evstigneevaet al., Proc. Russ. Acad. Sci. 357, 637 (1997). Web of Science, Google Scholar
V. Z. Paschenkoet al., J. Photochem. Photobiol. 54, 162 (2000). Crossref, Web of Science, Google Scholar
D. Gabelet al., Neutron Capture Therapy, ed. H. Hatanaka (Nishimura Co, Ltd., Niigata, 1986) p. 37. Google Scholar
M. Miuraet al., Strahlenther. Onkol. 165, 131 (1989). Web of Science, Google Scholar
S. B. Kahl and M.-S. Koo, J. Chem. Soc., Chem. Commun. 24, 1769 (1990). Google Scholar
S. B. Kahl and M.-S. Koo, Progress in Neutron Capture Therapy for Cancer, eds. B. J. Allen, D. E. Moore and B. V. Harrington (Plenum Press, New York, 1992) p. 223. Crossref, Google Scholar
D. L. DeCampet al., J. Med. Chem. 35, 3426 (1992), DOI: 10.1021/jm00096a020. Crossref, Web of Science, Google Scholar
S. B. Kahlet al., Advances in Neutron Capture Therapy, eds. A. H. Soloway, R. F. Barth and D. E. Carpenter (Plenum Press, New York, 1993) p. 301. Crossref, Google Scholar
L. I. Zakharkinet al., Russ. Chem. Bull. 48, 2312 (1999), DOI: 10.1007/BF02498279. Crossref, Web of Science, Google Scholar
A. S. Phadke and A. R. Morgan, Tetrahedron Lett. 34, 1725 (1993), DOI: 10.1016/S0040-4039(00)60762-1. Crossref, Web of Science, Google Scholar
K. Woodburn, A. S. Phadke and A. R. Morgan, Bioorg. Med. Chem. Lett. 3, 2017 (1993), DOI: 10.1016/S0960-894X(01)81006-4. Crossref, Web of Science, Google Scholar
D. Gabelet al., Current Topics in the Chemistry of Boron, ed. G. Kabalka (Royal Society of Chemistry, Cambridge, 1994) p. 161. Google Scholar
A. Raitzig, S. Ruf and D. Gabel, Advances in Neutron Capture Therapy, Chemistry and Biology II, eds. B. Larsson, J. Crawford and R. Weinreich (Elsevier, Amsterdam, 1997) p. 62. Google Scholar
J. Osterloh et al. , Abstr. First Int. Conf. on Porphyrins and Phthalocyanines (ICPP-1) . Google Scholar
J. Osterlohet al., Abstr. Ninth Int. Symp. on Neutron Capture Therapy for Cancer p. 307. Google Scholar
A. Matsumuraet al., Cancer Neutron Capture Therapy, ed. Y. Mishima (Plenum Press, New York, 1996) p. 245. Crossref, Google Scholar
F. Alamet al., Strahlenther. Onkol. 165, 121 (1989). Web of Science, Google Scholar
F. Alamet al., Clinical Aspects of Neutron Capture Therapy, eds. R. G. Fairchild, V. P. Bond and A. D. Woodhead (Plenum Press, New York, 1989) p. 107. Crossref, Google Scholar
S. B. Kahl and J. Li, Inorg. Chem. 35, 3878 (1996), DOI: 10.1021/ic9600240. Crossref, Web of Science, Google Scholar
K. Yu. Zhizhinet al., Proc. Russ. Acad. Sci. 357, 206 (1997). Web of Science, Google Scholar
R. Spryshkovaet al., Abstr. Eighth Int. Symp. on Neutron Capture Therapy for Cancer p. 43. Google Scholar
J. S. Hillet al., Progress in Neutron Capture Therapy for Cancer, eds. B. J. Allen, D. E. Moore and B. V. Harrington (Plenum Press, New York, 1992) p. 501. Crossref, Google Scholar
S. B. Kahlet al., Strahlenther. Onkol. 165, 134 (1989). Web of Science, Google Scholar
S. B. Kahlet al., Clinical Aspects of Neutron Capture Therapy, eds. R. G. Fairchild, V. P. Bond and A. D. Woodhead (Plenum Press, New York, 1989) p. 205. Crossref, Google Scholar
B. H. Lasteret al., Clinical Aspects of Neutron Capture Therapy, eds. R. G. Fairchild, V. P. Bond and A. D. Woodhead (Plenum Press, New York, 1989) p. 213. Crossref, Google Scholar
R. G. Fairchildet al., Cancer Res. 50, 4860 (1990). Web of Science, Google Scholar
J. S. Hillet al., Proc. Natl. Acad. Sci. USA 89, 1785 (1992), DOI: 10.1073/pnas.89.5.1785. Crossref, Web of Science, Google Scholar
T. Nguyenet al., Radiat. Res. 133, 33 (1993), DOI: 10.2307/3578254. Crossref, Web of Science, Google Scholar
B. H. Lasteret al., Advances in Neutron Capture Therapy, eds. A. H. Soloway, R. F. Barth and D. E. Carpenter (Plenum Press, New York, 1993) p. 535. Crossref, Google Scholar
J. L. Malleschet al., Advances in Neutron Capture Therapy, eds. A. H. Soloway, R. F. Barth and D. E. Carpenter (Plenum Press, New York, 1993) p. 505. Crossref, Google Scholar
S. B. Kahl, J. Tibbitts and J. Fike, Cancer Neutron Capture Therapy, ed. Y. Mishima (Plenum Press, New York, 1996) p. 605. Crossref, Google Scholar
C. P. Ceberget al., J. Neurosurg. 83, 86 (1995). Crossref, Web of Science, Google Scholar
A. D. Mundayet al., Biochim. Biophys. Acta 1311, 1 (1996). Crossref, Web of Science, Google Scholar
P. G. Spizziriet al., Photochem. Photobiol. 64, 975 (1996), DOI: 10.1111/j.1751-1097.1996.tb01864.x. Crossref, Web of Science, Google Scholar
T. Ozawaet al., Proc. Am. Assoc. Cancer Res.39 p. 586. Google Scholar
J. S. Hillet al., Proc. Natl. Acad. Sci. USA 92, 1226 (1995). Web of Science, Google Scholar
J. Tibbittset al., Photochem. Photobiol. 69, 587 (1999), DOI: 10.1111/j.1751-1097.1999.tb03332.x. Crossref, Web of Science, Google Scholar
M. Miuraet al., Progress in Neutron Capture Therapy for Cancer, eds. B. J. Allen, D. E. Moore and B. V. Harrington (Plenum Press, New York, 1992) p. 455. Crossref, Google Scholar
M. Miuraet al., Biochem. Pharmacol. 43, 467 (1992), DOI: 10.1016/0006-2952(92)90565-Z. Crossref, Web of Science, Google Scholar
B. Edwardset al., Abstr. Ninth Int. Symp. on Neutron Capture Therapy for Cancer p. 61. Google Scholar
M. J. Combset al., Cancer Neutron Capture Therapy, ed. Y. Mishima (Plenum Press, New York, 1996) p. 239. Crossref, Google Scholar
T. Yamamotoet al., Advances in Neutron Capture Therapy, Chemistry and Biology II, eds. B. Larsson, J. Crawford and R. Weinreich (Elsevier, Amsterdam, 1997) p. 267. Google Scholar