Mechanisms and kinetics of Thiotepa and tepa hydrolysis: DFT study

Journal of Molecular Modeling

Volumn 18, Issue 8, 2012, Pages 3563-3576

  Torabifard, Hedieh ^a   Fattahi, Alireza ^a  

^a SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Anticancer drugs; DFT; Hydrolysis; Kinetic study; Thiotepa and Tepa

Indexed keywords

AZIRIDINE; GUANINE; TEPA; THIOTEPA; WATER;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; CONJUGATION; DENSITY; DENSITY FUNCTIONAL THEORY; DISSOCIATION; DRUG HYDROLYSIS; ELECTRON; ENERGY; MATHEMATICAL MODEL; PHASE TRANSITION; POLARIZATION; PRIORITY JOURNAL; PROTON TRANSPORT; QUANTUM THEORY; REACTION ANALYSIS; SOLVENT EFFECT; TAUTOMERIZATION;

TEPA;

EID: 84961977356     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-012-1354-y     Document Type: Article

References (70)

1. Sykes M, Karnofsky D, Phillips F, Burchenal JH (1953) Clinical studies of triethylene-phosphoramide and diethylene-phosphoramide compounds with nitrogen mustard-like activity. Cancer 6:142-148
2. Jones HC, Swinney J (1961) Thiotepa in the treatment of tumors of the bladder. Lancet 2:615-618
3. Perloff M, Hart RD, Holland JF (1977) Vinblastine, adriamycin, thiotepa and halotestin (VATH): therapy for advanced breast cancer refractory to prior therapy. Cancer 39:1289-1293
4. Gutin PH, Levi JA, Wiernik PH, Walker MD (1977) Treatment of malignant meningeal disease with intrathecal thiotepa: a phase II study. Cancer Treat Rep 61:885-887 (Pubitemid 8167617)
5. Herzig GP (1987) High-dose ThioTEPA and autologous marrow transplantation: advances in cancer chemotherapy. Wiley, New York
6. Van Maanen MJ, Smeets CJM, Beijnen JH (2000) Chemistry, pharmacology and pharmacokinetics of N, N', N' - triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev 26:257-268 (Pubitemid 30604037)
7. Van Maanen MJ, Tijhof IM, Damen JMA et al (1999) A search for new metabolites of N, N', N'-triethylenethiophosphoramide. Cancer Res 59:4720-4724
8. Van Maanen MJ, Doesburg Smits K, Damen JMA et al (2000) Stability of Thiotepa and its metabolites, TEPA, monochloroTEPA and thioTEPA-mercapturate, in plasma and urine. Int J Pharm 200:187-194 (Pubitemid 30364905)
9. Van der Wall E, Beijnen JH, Ro D, Enhuis S (1995) High-dose chemotherapy regimens for solid tumors. Cancer Treat Rev 21:105-132
10. Bestian H (1950) Uber einige reaktionen des aethylen-imins. Liebig's Annin Chemie 566:210-229
11. Maxwell J, Kaushik DS, Butler CG (1974) Behavior of an aziridine alkylating agent in acid solution. Biochem Pharmacol 23:168-170
12. Pyatigorskaya TL, Zhilkova OY, Shelkovsky VS et al (1987) Hydrolysis of 1, 1, 1'-phosphinothioylidine trisaziridine (thioTEPA) in aqueous solution. Biomed Environm Mass Spectrom 14:143-148 (Pubitemid 17056188)
13. Murray KM, Erkkila D, Gombotz WR et al (1997) Stability of thioTEPA (lyophilised) in 0.9% sodium chloride injection. Am J Health-Syst Pharm 54:2588-2591 (Pubitemid 27511867)
14. Kolman A, Chovanec M, Osterman Golkar S (2002) Genotoxic effects of ethylene oxide, propylene oxide and epichlorohydrin in humans: update review (1990-2001) Mutat Res/Rev. Mutat Res 512:173-194 (Pubitemid 35441053)
15. Farmer PB, Shuker DEG (1999) What is the significance of increases in background levels of carcinogen-derived protein and DNA adducts? Some considerations for incremental risk assessment Mutat Res/Fundam Mol Mech Mutagen 424:275-286 (Pubitemid 29101624)
16. Kranjc A, Mavri J (2006) Guanine alkylation by ethylene oxide: calculation of chemical reactivity. J Phys Chem A 110:5740-5744 (Pubitemid 43798616)
17. Benigni R, Bossa C (2010) Mechanisms of chemical carcinogenicity and mutagenicity: a review with implications for predictive toxicology. Chem Rev 111:2507-2536
18. Pullman B (1980) Carcinogenesis: fundamental mechanisms and environmental effects. D Reidel, Dordrecht, The Netherlands, pp 51-55
19. La DK, Swenberg JA (1996) DNA adducts: biological markers of exposure and potential applications to risk assessment. Mutat Res 365:129-146 (Pubitemid 26344743)
20. LoPachin RM, DeCaprio AP (2005) Protein adduct formation as a molecular mechanism in neurotoxicity. Toxicol Sci 86:214-225 (Pubitemid 41418633)
21. Ho TL (1975) Hard soft acids bases (HSAB) principle and organic chemistry. Chem Rev 75:1-20
22. Carlson RM (1990) Assessment of the propensity for covalent binding of electrophiles to biological substrates. Environ Health Perspect 87:227-232 (Pubitemid 20316921)
23. Dunn JA, Bardos TJ (1991) Comparative chemical and biological studies of four prototype phosphoraziridine antineoplastic agents. Biochem Pharmacol 41:885-892
24. Hargreaves RHJ, Hartley JA, Butler J (2000) Mechanism of action of Quinone-containing alkylating agents: DNA alkylation by Aziridinylquinones. Front Biosci 172:172-180
25. Musser SM, Pan SS, Egorin MJ et al (1992) Alkylation of DNA with aziridine produced during the hydrolysis of N, N', N'- triethylenethiophosphoramide. Chem Res Toxicol 5:95-99
26. Hemminki K (1984) Reactions of ethyleneimine with guanosine and deoxyguanosine. Chem Biol Interact 48:249-260 (Pubitemid 14144054)
27. Egorin MJ, Snyder SW, Pan SS, Daly C (1989) Cellular transport and accumulation of thiotepa in murine, human, and avian cells. Cancer Res 49:5611-5617 (Pubitemid 19256440)
28. Phillips RM, Bibby MC, Double JA (1988) Experimental correlations of in vitro drug sensitivity with in vivo responses to thiotepa in a panel of murine colon tumors. Cancer Chemother Pharmacol 21:168-172 (Pubitemid 18087032)
29. Miller B, Tenenholz T, Egorin MJ et al (1988) Cellular pharmacology of N, N', N'-Triethylenethiophosphor amide. Cancer Lett 41:157-168
30. Abraham TW, Kalman TI, McIntee EJ, Wagner CR (1996) Synthesis and biological activity of aromatic aminoacid phosphoramidates of 5-fluoro-20-deoxyuridine and 1-β-arabinofuranosylcytosine: evidence of phosphor-amidase activity. J Med Chem 39:4569-4575 (Pubitemid 26382841)
31. Galesa K, Bren U, Kranjc A, Mavri J (2008) Determination carcinogenicity of acrylamide: a computational study. J Agric Food Chem 56:8720-8727
32. Warshel A (1991) Computer modeling of chemical reactions in enzymes and solutions. Wiley, New York
33. Mertus S, Scrocco E, Tomasi J (1981) Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Chem Phys 55:117-129
34. Pliego JR, Riveros JM (2001) The cluster-continuum model for the calculation of the solvation free energy of ionic species. J Phys Chem A 105:7241-7247 (Pubitemid 35373203)
35. Spartan (2006) Spartan V102'; Wavefunction, Inc. Irvine, CA
36. Becke AD (1993) Density-functional thermochemistry. III The role of exact exchange J Chem Phys 98:5648-5652
37. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785-789
38. Cossi M, Barone V, Mennucci B, Tomasi J (1998) Ab initio study of ionic solutions by a polarizable continuum dielectric model. Chem Phys Lett 286:253-260 (Pubitemid 128181148)
39. Cossi M, Rega N, Scalmani G, Barone V (2003) Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J Comput Chem 24:669-681
40. Namazian M, Halvani S, Noorbala MR (2004) Density functional theory response to the calculations of pKa values of some carboxylic acids in aqueous solution. J Mol Struct THEOCHEM 711:13-18 (Pubitemid 40247346)
41. Sevastik R, Himo F (2007) Quantum chemical modeling of enzymatic reactions: the case of 4-oxalocrotonate tautomerase. J Bioorg Chem 35:444-457 (Pubitemid 47633436)
42. Georgieva P, Himo F (2008) Density functional theory study of the reaction mechanism of the DNA repairing enzyme alkylguanine alkyltransferase. Chem Phys Lett 463:214-218
43. Chen S, Fang w, Himo F (2008) Technical aspects of quantum chemical modeling of enzymatic reactions: the case of phosphotriesterase. Theor Chem Account 120:515-522
44. Himo F, Guo J, Rinaldo-Matthis A, Nordlund P (2005) Reaction mechanism of deoxyribonucleotidase: a theoretical study. J Phys Chem B 109:20004-20008 (Pubitemid 41598515)
45. Pliego JR (2004) Basic hydrolysis of formamide in aqueous solution: a reliable theoretical calculation of the activation free energy using the cluster-continuum model. Chem Phys 306:273-280
46. Stare J, Henson NJ, Eckert J (2009) Mechanistic aspects of propene epoxidation by hydrogen peroxide. Catalytic role of water molecules, external electric field, and zeolite framework of TS-1. J Chem Inf Model 49:833-846
47. Nguyen MT, Raspoet G, Vanquickenborne LG (1999) Necessity to consider a three-water chain in modelling the hydration of ketene imines and carbodiimides. J Chem Soc 4:813-820 (Pubitemid 129639880)
48. Reed AE, Weinhold F (1985) Natural localized molecular orbitals. J Chem Phys 83:1736-1740
49. Reed AE, Weinstock RB, Weinhold F (1985) Natural population analysis. J Chem Phys 83:735-746
50. Reed AE, Weinhold F (1983) Natural bond orbital analysis of near-Hartree-Fock water dimer. J Chem Phys 78:4066-4073
51. Foster JP, Weinhold F (1980) Natural hybrid orbitals. J Am Chem Soc 102:7211-7218
52. Chocholousova J, Vladimir Spirko V, Hobza P (2004) First local minimum of the formic acid dimer exhibits simultaneously redshifted O-HO and improper blue-shifted C-HO hydrogen bonds. Phys Chem Chem Phys 6:37-41
53. Reed AE, Curtiss LA, Weinhold F (1988) Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev 88:899-926
54. Bader RFW (2002) AIM2000 program package, Ver. 2.0, McMaster University: Hamilton, Ontario, Canada
55. Bader RFW (1998) Bond Path: a universal indicator of bonded interactions. J Phys Chem A 102:7314-7323 (Pubitemid 128578168)
56. Bader RFW (1990) Atoms in molecules. A quantum theory. Clarendon, Oxford, UK
57. Pakiari AH, Eskandari K (2006) The chemical nature of very strong hydrogen bonds in some categories of compounds. J Mol Struct THEOCHEM 759:51-60
58. Abboud JLM, Mó O, De Paz JLG et al (1993) Thiocarbonyl versus carbonyl compounds: A comparison of intrinsic reactivities. J Am Chem Soc 115:12468-12476 (Pubitemid 24078347)
59. Hocquet A (2001) Intramolecular hydrogen bonding in 2'- deoxyribonucleosides: an AIM topological study of the electronic density. Phys Chem/Chem Phys 3:3192-3199 (Pubitemid 32881386)
60. Rozas I, Alkorta I, Elguero J (2000) Behavior of ylides containing N, O, and C atoms as hydrogen bond acceptors. J Am Chem Soc 122:11154-11161
61. Rahil J, Haake P (1981) Reactivity and mechanism of hydrolysis of phosphonamides. J Am Chem Soc 103(1723):1734
62. Ganta S, Devalapally H, Shahiwala A, Amiji M (2008) A review of stimuli-responsive nanocarriers for drug and gene delivery. J Con Rel 126:187-204
63. Chanley JD, Feageson E (1963) A study of hydrolysis of phosphoramides. II Solvolysis of phosphoramidic acid and comparison with phosphate esters J Am Chem Soc 85:1181-1190
64. Garrison AW, Boozer CE (1968) The acid-catalyzed hydrolysis of a series of phosphoramidates. J Am Chem Soc 90:3486-3494
65. Koizumi T, Haake P (1973) Acid-catalyzed and alkaline hydrolyses of phosphinamides. The lability of phosphorusnitrogen bonds in acid and mechanisms of reaction J Am Chem Soc 95:8073-8079
66. Richter S, Teopelmann W, Lehmann HA (1976) Hydrolysis of phosphoric acid amides. Z Anorg Allg Chem 424:133-143
67. Haake P, Koizumi T (1970) Hydrolysis of phosphinamides and nature of P-N bond. Tetrahedron Lett 55:4845-4848
68. Murray JS, Lane P, Politzer P (2009) Expansion of the-hole concept. J Mol Model 15:723-729
69. Rozeboom MD, Houk KN, Searles S, Seyederzai SE (1982) Photoelectron spetroscopy of N-aryl cyclic amines. Variable conformations and relationships to gas and solution phase basicities. J Am Chem Soc 104:3448-3453
70. Lias SG, Liebman JF, Levin RD (1984) Evaluated gas phase basicities and proton affinities of molecules; heats of formation of protonated molecules. J Phys Chem (ref data) 13:695-808