The 3D structure of the anticancer prodrug CPT-11 with Torpedo californica acetylcholinesterase rationalizes its inhibitory action on AChE and its hydrolysis by butyrylcholinesterase and carboxylesterase

Chemico-Biological Interactions

Volumn 157-158, Issue , 2005, Pages 153-157

  Harel, Michal ^a   Hyatt, Janice L ^b   Brumshtein, Boris ^a   Morton, Christopher L ^b   Wadkins, Randy M ^c   Silman, Israel ^a   Sussman, Joel L ^a   Potter, Philip M ^b  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b ST JUDE CHILDREN S RESEARCH HOSPITAL   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Alzheimer; Anticancer prodrug; Cholinergic syndrome; Colon cancer; X ray crystallography

Indexed keywords

ACETYLCHOLINE; ACETYLCHOLINESTERASE; ANTINEOPLASTIC AGENT; CAMPTOTHECIN DERIVATIVE; CARBOXYLESTERASE; CHOLINESTERASE; DONEPEZIL; IRINOTECAN; PRODRUG;

COLON CANCER; CONFERENCE PAPER; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG BINDING; DRUG HYDROLYSIS; DRUG STRUCTURE; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; INHIBITION KINETICS; NONHUMAN; STRUCTURE ANALYSIS; TORPEDO CALIFORNICA;

ACETYLCHOLINESTERASE; ANIMALS; ANTINEOPLASTIC AGENTS; BUTYRYLCHOLINESTERASE; CAMPTOTHECIN; CARBOXYLESTERASE; CHOLINESTERASE INHIBITORS; CRYSTALLOGRAPHY, X-RAY; HYDROLYSIS; LIVER; MODELS, MOLECULAR; PROTEIN STRUCTURE, TERTIARY; RABBITS; TORPEDO;

MAMMALIA; TORPEDO CALIFORNICA;

EID: 28744446117     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2005.10.016     Document Type: Conference Paper

References (18)

1. A. Tanizawa, A. Fujimori, Y. Fujimori, and Y. Pommier Comparison of topoisomerase I inhibition, DNA damage, and cytotoxicity of camptothecin derivatives presently in clinical trials J. Natl. Cancer Inst. 86 1994 836 842
2. W.L. Furman Direct translation of a protracted irinotecan schedule from a xenograft model to a Phase I trial in children J. Clin. Oncol. 17 1999 1815 1824
3. N. Saijo Progress in treatment of small-cell lung cancer: role of CPT-11 Br. J. Cancer 89 2003 2178 2183
4. C.J. Langer The global role of irinotecan in the treatment of lung cancer: 2003 update Oncology 17 2003 30 40
5. M. Simon, A. Argiris, and J.R. Murren Progress in the therapy of small cell lung cancer Crit. Rev. Oncol. Hematol. 49 2004 119 133
6. D. Gandia CPT-11-induced cholinergic effects in cancer patients [letter] J. Clin. Oncol. 11 1993 196 197
7. D. Abigerges Phase I and pharmacologic studies of the camptothecin analog irinotecan administered every 3 weeks in cancer patients J. Clin. Oncol. 13 1995 210 221
8. R. Bugat Efficacy of irinotecan HCl (CPT11) in patients with metastatic colorectal cancer after progression while receiving a 5-FU-based chemotherapy Proc. Annu. Meet. Am. Soc. Clin. Oncol. 14 1995 A567 (meeting abstract)
9. 2 irinotecan (CRT-11) given every two weeks Proc. Annu. Meet. Am. Soc. Clin. Oncol. 16 1997 A953 (meeting abstract)
10. C.L. Morton, R.M. Wadkins, M.K. Danks, and P.M. Potter CPT-11 is a potent inhibitor of acetylcholinesterase but is rapidly catalyzed to SN-38 by butyrylcholinesterase Cancer Res. 59 1999 1458 1463
11. H.M. Dodds, and L.P. Rivory The mechanism for the inhibition of acetylcholinesterases by irinotecan (CPT-11) Mol. Pharmacol. 56 1999 1346 1353
12. Y. Kawato Inhibitory activity of camptothecin derivatives against acetylcholinesterase in dogs and their binding activity to acetylcholine receptors in rats J. Pharm. Pharmacol. 45 1993 444 448
13. W.L. DeLano, PyMOL is a user-sponsored molecular modeling system, http://pymol.sourceforge.net.
14. A.T. Brunger Crystallography & NMR system: a new software suite for macromolecular structure determination Acta Cryst. 54 Pt 5 1998 905 921
15. S. Bencharit Structural insights into CPT-11 activation by mammalian carboxylesterases Nat. Struct. Biol. 9 2002 337 342
16. Z. Radic, E. Reiner, and P. Taylor Role of the peripheral anionic site on acetylcholinesterase: inhibition by substrates and coumarin derivatives Mol. Pharmacol. 39 1991 98 104
17. W. Kabsch Automatic processing of rotation diffraction data from crystals of initially unknown symmetry and cell constants J. Appl. Cryst. 26 1993 795 800
18. T.A. Jones, J.Y. Zou, S.W. Cowan, and Kjeldgaard Improved methods for building protein models in electron density maps and the location of errors in these models Acta Cryst. 47 Pt 2 1991 110 119