Camptothecin and thiocamptothecin: The role of sulfur in shifting the hydrolysis equilibrium towards the closed lactone form

ChemMedChem

Volumn 6, Issue 9, 2011, Pages 1706-1714

  Pistolozzi, Marco ^a   Varchi, Greta ^b   Degli Esposti, Alessandra ^b   Guerrini, Andrea ^b   Sotgiu, Giovanna ^b   Ballestri, Marco ^b   Ferroni, Claudia ^b   Venturini, Alessandro ^b   Bertucci, Carlo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b CNR   (Italy)

Author keywords

Absorption spectroscopy; Camptothecins; Computational chemistry; Density functional theory; Liquid chromatography

Indexed keywords

20 THIOCAMPTOTHECIN; BUFFER; CAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; HUMAN SERUM ALBUMIN; LACTONE; SULFUR; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ANTINEOPLASTIC ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CELL STRAIN HT29; CONTROLLED STUDY; DRUG HALF LIFE; DRUG HYDROLYSIS; DRUG STABILITY; EQUILIBRIUM CONSTANT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ALGORITHMS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAMPTOTHECIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; HYDROLYSIS; LACTONES; OXYGEN; SERUM ALBUMIN; SOLUTIONS; SULFUR; THIONES; WATER; X-RAY ABSORPTION SPECTROSCOPY;

EID: 80052101216     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201100206     Document Type: Article

References (55)

1. M. E. Wall, M. C. Wani, C. E. Cook, K. H. Palmer, A. T. McPhail, G. A. Sim, J. Am. Chem. Soc. 1966, 88, 3888-3890.
2. D. Sriram, P. Yogeeswari, R. Thirumurugan, T. R. Bal, Nat. Prod. Res. 2005, 19, 393-412.
3. D. R. Parkinson, S. G. Arbuck, T. Moore, J. M. Pluda, M. C. Christian, Stem Cells 1994, 12, 30-43.
4. H. Ulukan, P. W. Swaan, Drugs 2002, 62, 2039-2057.
5. J. J. Champoux, J. Mol. Biol. 1978, 118, 441-446.
6. Y. H. Hsiang, L. F. Liu, Cancer Res. 1988, 48, 1722-1726.
7. M. A. Bjornsti, P. Benedetti, G. A. Viglianti, J. C. Wang, Cancer Res. 1989, 49, 6318-6323.
8. Y. H. Hsiang, M. G. Lihou, L. F. Liu, Cancer Res. 1989, 49, 5077-5082.
9. R. Garcia-Carbonero, J. G. Supko, Clin. Cancer Res. 2002, 8, 641-661.
10. P. J. Creaven, L. M. Allen, Cancer Chemother. Rep., Part 2 1973, 57, 175-184.
11. J. A. Gottlieb, A. M. Guarino, J. B. Call, V. T. Oliverio, J. B. Block, Cancer Chemother. Rep., Part 2 1970, 54, 461-470.
12. A. Ardizzoni, Oncologist 2004, 9, 4-13.
13. U. Vanhoefer, A. Harstrick, W. Achterrath, S. S. Cao, S. Seeber, Y. M. Rustum, J. Clin. Oncol. 2001, 19, 1501-1518.
14. C. F. Verschraegen, E. A. Natelson, B. C. Giovanella, J. J. Kavanagh, A. P. Kudelka, R. S. Freedman, C. L. Edwards, K. Ende, J. S. Stehlin, Anticancer Drugs 1998, 9, 36-44.
15. S. Dallavalle, A. Ferrari, B. Biasotti, L. Merlini, S. Penco, G. Gallo, M. Marzi, C. Pisano, R. Martinelli, P. Carminati, N. Carenini, P. Perego, M. DeCesare, G. Capranico, G. Pratesi, F. Zunino, J. Med. Chem. 2001, 44, 3264-3274.
16. S. Q. Gao, Z. R. Lu, P. Kopecková, J. Kopecek, J. Controlled Release 2007, 117, 179-185.
17. J. A. Ajani, C. Takimoto, C. R. Becerra, A. Silva, L. Baez, A. Cohn, P. Major, M Kamida, K. Feit, R. DeJager, Invest. New Drugs 2005, 23, 479-484.
18. L. C. Scott, J. C. Yao, A. B. Benson III, A. L. Thomas, S. Falk, R. R. Mena, J. Picus, J. Wright, M. F. Mulcahy, J. A. Ajani, T. R. J. Evans, Cancer Chemother. Pharmacol. 2009, 63, 363-370.
19. G. M. Springett, C. Takimoto, M. McNamara, J. H. Doroshow, S. Syed, E. Eastham, D. Spriggs, S. Pezzulli, G. Michelson, J. Dupont, J. Clin. Oncol. 2004, 22 (14, Suppl.), 3127.
20. D. Bissett, J. Cassidy, J. S. deBono, F. Muirhead, M. Main, L. Robson, D. Fraier, M. L. Magnè, C. Pellizzoni, M. G. Porro, R. Spinelli, W. Speed, C. Twelves, Br. J. Cancer 2004, 91, 50-55.
21. C. Samorì, A. Guerrini, G. Varchi, F. Zunino, G. L. Beretta, C. Femoni, E. Bombardelli, G. Fontana, A. Battaglia, J. Med. Chem. 2008, 51, 3040-3044.
22. C. Samorì, A. Guerrini, G. Varchi, F. Zunino, G. L. Beretta, S. DiMicco, S. Basili, G. Bifulco, R. Riccio, S. Moro, E. Bombardelli, G. Fontana, ChemMedChem 2010, 5, 2006-2015.
23. R. P. Hertzberg, M. J. Caranfa, K. G. Holden, D. R. Jakas, G. Gallagher, M. R. Mattern, S. M. Mong, J. O. Bartus, R. K. Johnson, W. D. Kingsbury, J. Med. Chem. 1989, 32, 715-720.
24. T. G. Burke, Z. Mi, J. Med. Chem. 1994, 37, 40-46.
25. Z. Mi, H. Malak, T. G. Burke, Biochemistry 1995, 34, 13722-13728.
26. J. Supko, L. Malspeis, J. Liq. Chromatogr. 1991, 14, 1779-1803.
27. H. Rosing, E. Doyle, B. E. Davies, J. H. Beijnen, J. Chromatogr. B: Biomed. Appl. 1995, 668, 107-115.
28. P. Opanasopit, M. Yokoyama, M. Watanabe, K. Kawano, Y. Maitani, T. Okano, J. Controlled Release 2005, 104, 313-321.
29. J. Fassberg, V. J. Stella, J. Pharm. Sci. 1992, 81, 676-684.
30. Z. Mi, T. G. Burke, Biochemistry 1994, 33, 10325-10336.
31. P. Sadílek, D. Šatínský, P. Solich, TrAC Trends Anal. Chem. 2007, 26, 375-384.
32. I. Nabiev, F. Fleury, I. Kudelina, Y. Pommier, F. Charton, J. F. Riou, A. J. P. Alix, M. Manfait, Biochem. Pharmacol. 1998, 55, 1163-1174.
33. F. Fleury, A. Ianoul, M. Berjot, A. Feofanov, A. J. P. Alix, I. Nabiev, FEBS Lett. 1997, 411, 215-220.
34. T. Wybranowski, M. Cyrankiewicz, B. Ziomkowska, S. Kruszewski, BioSystems 2008, 94, 258-262.
35. R. Bauernschmitt, R. Ahlrichs, Chem. Phys. Lett. 1996, 256, 454-464.
36. R. E. Stratmann, G. E. Scuseria, M. J. Frisch, J. Chem. Phys. 1998, 109, 8218-8224.
37. M. E. Casida, C. Jamorski, K. C. Casida, D. R. Salahub, J. Chem. Phys. 1998, 108, 4439-4449.
38. C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158-6169.
39. N. Sanna, G. Chillemi, A. Grandi, S. Castelli, A. Desideri, V. Barone, J. Am. Chem. Soc. 2005, 127, 15429-15436.
40. W. J. Hehre, R. Ditchfield, L. Radom, J. A. Pople, J. Am. Chem. Soc. 1970, 92, 4796-4801.
41. Y. Apeloig, P. R. Schleyer, J. A. Pople, J. Am. Chem. Soc. 1977, 99, 1291-1296.
42. F. Bernardi, A. Bottoni, A. Venturini, J. Am. Chem. Soc. 1986, 108, 5395-5400.
43. N. Sanna, G. Chillemi, L. Gontrani, A. Grandi, G. mancini, S. Castelli, G. Zagotto, C. Zazza, V. Barone, and A. Desideri, J. Phys. Chem. B 2009, 113, 5369-5375.
44. It must be mentioned that the transition to the first excited state, which is calculated at low energy with a small oscillator strength using the TD-DF method so that it is outside the wavelength range plotted, does not contribute to the first plotted band of the calculated spectra; this is true for all enolic and ionic forms of both CPT (Figure5) and TCPT (Figure6).
45. Gaussian 09, Revision A.1, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford CT (USA), 2009.
46. V. Wathelet, J. Preat, M. Bouhy, M. Fontaine, E. A. Perpète, J.-M. Andrè, D. Jacquemin, Int. J. Quantum Chem. 2006, 106, 1853-1859.
47. I. Ciofini, C. Adamo, J. Phys. Chem. A 2007, 111, 5549-5556.
48. D. Jacquemin, V. Wathelet, E. A. Perpète, C. Adamo, J. Chem. Theory Comput. 2009, 5, 2420-2435.
49. J. Preat, D. Jacquemin, E. A. Perpète, Int. J. Quantum Chem. 2010, 110, 2147-2154.
50. W. J. Hehre, R. Ditchfield, J. A. Pople, J. Chem. Phys. 1972, 56, 2257-2261.
51. P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213-222.
52. A. T. McPhail, G. A. Sim, J. Chem. Soc. B 1968, 923-928.
53. T. Clark, J. Chandrasekhar, G. W. Spitznagel, P. V. R. Schleyer, J. Comput. Chem. 1983, 4, 294-301.
54. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999-3094.
55. M. Cossi, V. Barone, J. Chem. Phys. 2001, 115, 4708-4718.