Synthesis of Novel and Stable 5-Aminolevulinic Acid Derivatives for the Efficient Synthesis of 5-Aminolevulinic Acid Based Prodrugs

Ramakrishnan Vallinayagam; Hugo Bertschy; Yann Berger; Virginie Wenger; Reinhard Neier

doi:10.1055/s-2007-990825

PAPER

Synthesis of Novel and Stable 5-Aminolevulinic Acid Derivatives for the Efficient Synthesis of 5-Aminolevulinic Acid Based Prodrugs

Ramakrishnan Vallinayagam^a, Hugo Bertschy^b, Yann Berger^c, Virginie Wenger^a, Reinhard Neier*^a
^a Institut de Chimie, Université de Neuchâtel, Rue Emile-Argand, 11, PO 158, 2009 Neuchatel, Switzerland
Fax: +41(32)7182511; e-Mail: reinhard.neier@unine.ch;
^b c/o F. Hoffmann-La Roche AG, Grenzacherstrasse 124, 4070 Basel, Switzerland
^c c/o Laboratoire cantonal contrôle denrées alimentaires, Les Croisettes, Case postale 68, 1066 Epalinges, Switzerland

Abstract

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Abstract

The efficient synthesis of two stable, easily handled precursors of 5-aminolevulinate is reported. These precursors are stable to the chemical transformation needed for the synthesis of bioconjugates and can be readily deprotected in good yields.

Key words

amino acid - activated ester - protecting group - prodrug - porphyrin

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References

<A NAME="RZ19107SS-1A">1a</A> Fukuda H. Casas A. Batlle A. Int. J. Biochem. Cell Biol. 2005, 37: 272

<A NAME="RZ19107SS-1B">1b</A> Dickson EFG. Kennedy JC. Pottier RH. Comprehensive Series in Photochemistry & Photobiology Vol. 2: Patrice T. Royal Society of Chemistry; Cambridge: 2003. p.83

<A NAME="RZ19107SS-1C">1c</A> Friesen SA. Hjortland GO. Madsen SJ. Hirschberg H. Engebraten O. Nesland JM. Peng Q. Int. J. Oncol. 2002, 21: 577

<A NAME="RZ19107SS-1D">1d</A> Peng Q. Warloe T. Berg K. Moan J. Kongshaug M. Giercksky KE. Nesland JM. Cancer (New York) 1997, 79: 2282

<A NAME="RZ19107SS-2A">2a</A> Kriegmair M. Baumgartner R. Knuchel R. Stepp H. Hofstadter F. Hofstetter A. J. Urol. 1996, 155: 105

<A NAME="RZ19107SS-2B">2b</A> Jeffes EW. Mccullough JL. Weinstein GD. Fergin PE. Nelson JS. Shull TF. Simpson KR. Bukaty LM. Hoffman WL. Fong NL. Arch. Dermatol. 1997, 133: 727

<A NAME="RZ19107SS-2C">2c</A> Szeimies RM. Dermatol. Clin. 2007, 25: 89

<A NAME="RZ19107SS-2D">2d</A> Morton CA. Dermatol. Clin. 2007, 25: 81

<A NAME="RZ19107SS-2E">2e</A> Lopez RFV. Lange N. Guy R. Bentley MVLB. Adv. Drug Delivery Rev. 2004, 56: 77

<A NAME="RZ19107SS-2F">2f</A> Fotinos N. Campo MA. Popowycz F. Gurny R. Lange N. Photochem. Photobiol. 2006, 82: 994

<A NAME="RZ19107SS-3A">3a</A> Baumgartner R. Stepp HG. Proc. SPIE-Int. Soc. Opt. Eng. 1999, 4166: 122

<A NAME="RZ19107SS-3B">3b</A> . Drugs R&D 2005, 6: 235

<A NAME="RZ19107SS-4A">4a</A> Kloek J. Beijersbergen VH. Photochem. Photobiol. 1996, 64: 994

<A NAME="RZ19107SS-4B">4b</A> Peng Q. Moan J. Warloe T. Iani V. Steen HB. Bjorseth A. Nesland JM. J. Photochem. Photobiol., B. 1996, 34: 95

<A NAME="RZ19107SS-4C">4c</A> Uehlinger P. Zellweger M. Wagnieres G. Juillerat-Jeanneret L. Van den Bergh H. Lange N. J. Photochem. Photobiol., B. 2000, 54: 72

<A NAME="RZ19107SS-5A">5a</A> Berger Y. Greppi A. Siri O. Neier R. Juillerat-Jeanneret L. J. Med. Chem. 2000, 43: 4738

<A NAME="RZ19107SS-5B">5b</A> Berger Y. Ingrassia L. Neier R. Juillerat-Jeanneret L. Bioorg. Med. Chem. 2003, 11: 1343

<A NAME="RZ19107SS-5C">5c</A> Greppi A. Ph.D. Thesis University of Neuchâtel; Switzerland: 1999.

<A NAME="RZ19107SS-6A">6a</A> Benedikt E. Koest HP. Z. Naturforsch. B: Chem. Sci. 1986, 41: 1593

<A NAME="RZ19107SS-6B">6b</A> Moens L. Chemicals and Materials from Renewable Resources ACS Symposium Series 784: Bozell JJ. American Chemical Society; Washington DC: 2001. p.37

<A NAME="RZ19107SS-6C">6c</A> Shrestha-dawadi PB. Lugtenburg J. Eur. J. Org. Chem. 2003, 4654

<A NAME="RZ19107SS-7A">7a</A> MacDonald SF. Can. J. Chem. 1974, 52: 3257

<A NAME="RZ19107SS-7B">7b</A> Ha H.-J. Lee S.-K. Ha Y.-J. Park J.-W. Synth. Commun. 1994, 24: 2557

<A NAME="RZ19107SS-8A">8a</A> Afonso CAM. Tetrahedron Lett. 1995, 36: 8857

<A NAME="RZ19107SS-8B">8b</A> Saito S. Nakajima H. Inaba M. Moriwake T. Tetrahedron Lett. 1989, 30: 837

<A NAME="RZ19107SS-9A">9a</A> Itoh M. Hagiwara D. Kamiya T. Bull. Chem. Soc. Jpn. 1977, 50: 718

<A NAME="RZ19107SS-9B">9b</A> Harris RB. Wilson IB. Tetrahedron Lett. 1983, 24: 231

<A NAME="RZ19107SS-10">10</A> Brunner H. Hausmann F. Knuechel R. Photochem. Photobiol. 2003, 78: 481

Ramakrishnan, V.; Schmitt, F.; Barge, J.; Wagnieres, G.; Wenger, V.; Neier, R.; Juillerat-Jeannerat, L. manuscript submitted.

<A NAME="RZ19107SS-11B">11b</A> Vallinayagam R. Ph.D. Thesis University of Neuchatel; Switzerland: 2007.