Abstract
A more convenient and facile approach for the synthesis and production of camptothecin–amino acids carbamate linkers, that can be used in the synthesis of bioconjugate peptides JF-10-81, JF-10-71, and other peptide analogs designed to target somatostatin receptors has been described.
Similar content being viewed by others
References
Bezerra Y, Fuselier JA, Peyman JA, Oner H, Drouant G, Coy DH (2005) Study of inhibitory effects of an antiangiogenic somatostatin–camptothecin conjugate on laser-induced choroidal neovascularization in rats. Retina 25:345–354
Bolin DR, Sytwu I-I, Humiec F, Meinhofer J (1989) Preparation of oligomer-free N α-Fmoc and N α-urethane amino acids. Int. J. Peptide Protein Res. 33:353–359
Burke PJ, Senter PD, Meyer DW et al (2009) Design, synthesis, and biological evaluation of antibody-drug conjugates comprised of potent camptothecin analogues. Bioconjugate Chem. 20:1242–1250
Chari RVJ (1998) Targeted delivery of chemotherapeutics: tumor-activated prodrug therapy. Adv Drug Deliv Rev 31:89–104
Chen Q, Gabathuler R (2004) Synthesis of camptothecin melantotransferrin (p97) conjugate through a carbamate bond. Synth Commun 34:2414–2424
Czerwinski G, Tarasova NI, Michejda CJ (1998) Cytotoxic agents directed to peptide hormone receptors: defining requirements for a successful drug. Proc Natl Acad Sci USA 95:11520–11525
de Groot FMH, Busscher GF, Aben RWM, Scheeren HW (2002) Novel 20-carbonate linked prodrugs of camptothecin and 9-aminocamptothecin designed for activation by tumour-associated plasmin. Bioorg. Med. Chem. Lett. 12:2371–2376
Ducry L, Stump B (2010) Antibody-drug conjugates: linking cytotoxic payloads to monoclonal antibodies. Bioconjugate Chem. 21:5–13
Fuselier JA, Sun L, Woltering SN, Murphy WA, Vasilevich N, Coy DH (2003) An adjustable release rate linking strategy for cytotoxin-peptide conjugates. Bioorg. Med. Chem. Lett. 13:799–803
Gomes P, Vale N, Moreira R (2007) Cyclization-activated prodrugs. Molecules 12:2484–2506
Granett MC (2001) Targeted drug conjugates: principles and progress. Adv Drug Deliv Rev 53:171–216
Henne WA, Doorneweerd DD, Hilgenbrink AR, Kularatne SA, Low PS (2006) Synthesis and activity of a folate peptide camptothecin prodrug. Bioorg. Med. Chem. Lett. 16:5350–5355
Kratz F, Muller IA, Ryppa C, Warnecke A (2008) Prodrug strategies in anticancer chemotherapy. Chem Med Chem 3:20–53
Kumar SK, Williams SA, Isaacs JT, Denmeade SR, Khan SR (2007) Modulating paclitaxel bioactivity for targeting prostate cancer. Bioorg. Med. Chem. 15:4973–4984
Lee B-S, Nalla AK, Stock IR, Shear TC, Black KL, Yu JS (2010) Oxidative stimuli-responsive nanoprodrug of camptothecin kills glioblastoma cells. Bioorg. Med. Chem. Lett. 20:5262–5268
Leu Y-L, Roffler SR, Chern J-W (1999) Design and synthesis of water-soluble glucuronide derivatives of camptothecin for cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy (ADEPT). J Med Chem 42:3623–3628
Martins ET, Baruah H, Kramarczyk J, Saluta G, Day CS, Kucera GL, Bierbach U (2001) Design, synthesis, and biological activity of a novel non-cisplatin-type platinum-acridine pharmacophore. J Med Chem 44:4492–4496
McKenna MD, Grabchev I, Bosch P (2009) The synthesis of a novel 1,8-napthalimide based PAMAM-type dendron and its potential for light-harvesting. Dyes Pigments 81:180–186
Moody TW, Fuselier JA, Coy DH, Mantey S, Pradham T, Nakagawa T, Jensen RT (2005) Camptothecin–somatostatin conjugates inhibit the growth of small cell lung cancer cells. Peptides 26:1560–1566
Neilson PE (1999) Peptide nucleic acids as therapeutic agents. Curr Opin Struct Biol 9:353–357
Ohwada J, Ozawa S, Kohchi M et al (2009) Synthesis and biological activities of a pH-dependently activated water-soluble prodrug of a novel hexacyclic camptothecin analog. Bioorg. Med. Chem. Lett. 19:2772–2776
Papot S, Tranoy I, Tillequin F, Florent JC, Gesson JP (2002) Design of selectively activated anticancer prodrugs: elimination and cyclization strategies. Curr Med Chem Anti-Cancer Agents 2:115–185
Pessah N, Reznik M, Shamis M et al (2004) Bioactivation of carbamate-based 20(S)-camptothecin prodrugs. Bioorg. Med. Chem. 12:1859–1866
Reubi JC (2003) Peptide receptors as molecular targets for cancer diagnosis and therapy. Endocr Rev 24:389–427
Saari WS, Schwering JE, Lyle PA, Smith SJ, Engelhardt EL (1990) Cylization-activated prodrugs. Basic carbamates of 4-hydroxyanisole. J. Med Chem 33:97–101
Shan D, Nicolaou MG, Borchardt RT, Wang B (1997) Prodrug strategies based on intramolecular cyclization reactions. J Pharm Sci 86:765–767
Sun L, Coy DH (2008) Cytotoxic conjugates of peptide hormones for cancer chemotherapy. Drugs Future 33:217–223
Sun L, Fuselier JA, Coy DH (2004) Effects of camptothecin conjugated to a somatostatin analog vector on growth of tumor cell lines in culture related tumors in rodents. Drug Delivery 11:231–238
Tranoy-Opalinski I, Fernades A, Thomas M, Gesson JP, Papot S (2008) Design of self-immolative linkers for tumour-activated prodrug therapy. Anti-Cancer Agents Med Chem 8:618–637
Vigroux A, Bergon M, Zedde C (1995) Cylicization-activated prodrugs:N-(substituted 2-hydroxyphenyl and 2-hydroxypropyl) carbamates based on ring-opened derivatives of active benzoxazolones and oxazolidinones as mutual prodrugs of acetaminophen. J Med Chem 38:3983–3994
Viirre RD, Hudson RHE (2002) A convenient and scalable synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride. Key intermediates for peptide nucleic acid synthesis. J. Org. Chem. 68:1630–1632
Zhao H, Lee C, Sai P et al (2000) 20-O-Acylcamptothecin derivatives: evidence for lactone stabilization. J Org Chem 65:4601–4606
Acknowledgments
We thank LSU Mass Spectrometry Facility for ESI-MS analysis and technical assistance.
Conflict of interest
M.A. Etienne, M. Kostochka, J.A. Fuselier, D. H. Coy, and Tulane University have proprietary rights to amino acid carbamate linkers and somatostatin conjugates described herein.
Author information
Authors and Affiliations
Corresponding author
Additional information
M.A. Etienne and M. Kostochka contributed equally to this manuscript.
Rights and permissions
About this article
Cite this article
Etienne, M.A., Kostochka, M., Fuselier, J.A. et al. Synthesis of camptothecin–amino acid carbamate linkers. Amino Acids 42, 1727–1733 (2012). https://doi.org/10.1007/s00726-011-0884-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00726-011-0884-4