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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supplementary Information Mechanistic Study of Hydrolytic Degradation and Protonation of Temozolomide Saber Mirzaei a, M. H. Khalilian a, and Avat (Arman) Taherpour a,b* a Faculty of Chemistry, Razi University, P.O.Box: , Kermanshah, Iran. b Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran. avatarman.taherpour@gmail.com S1
2 Table of Contents Page No. Figure S1. The path-1 relative energy profile of TMZ decomposition for rotamer B. S3 Figure S2. The path-2 relative energy profile of TMZ decomposition for rotamer B..... S4 Table S1. Calculated relative free energies for both TMZ-B degradation paths..... S5 Figure S3. The overall mechanism of TMZ decomposition.... S5 Figure S4. The base-catalysed degradation of TMZ... S6 Figure S5. Atom numbering assignment of TMZ S7 Table S2. Protonation free energies for all protonated atoms.. S7 Table S3. NPA partial atomic charges for TMZ.. S8 Table S4. Absolute free energies (a.u.) for both TMZ degradation paths of rotamer A S8 Table S5. Absolute free energies (a.u.) for the gas and water-mediated interconversion between N9 and O13 protonated forms of Temozolomide..... S9 Table S6. Absolute free energies (a.u.) for all protonated atoms. S9 S1. pk a calculations procedure and methods.. S10 S2. Figure and Cartesian coordinates of all optimized protonated species at the B3LYP/ G(2d,p) level of theory.... S11 S3. Cartesian coordinates of all optimized structures of Temozolomide degradation at the B3LYP/6-31+G(d) level of theory. S20 S4. Cartesian coordinates of optimized transition states of Temozolomide reaction with different nucleophiles at the CBS-4M level of theory S32 S2
3 G (kcal.mol -1 ) Figure S1. The path-1 relative energy profile of TMZ decomposition for rotamer B (also see table s1). 60 TS-I TS-II CBS-4M B3LYP I II -15 TMZ+water III TMZ+water TS-I I III TS-II II S3
4 G (kcal.mol -1 ) Figure S2. The path-2 relative energy profile of TMZ decomposition for rotamer B (also see table s1). 60 TS-I TS-II CBS-4M B3LYP I II -15 TMZ+water III TMZ+water TS-I I III TS-II II S4
5 G (kcal.mol -1 ) Table S1. Calculated relative free energies (ΔG) for both TMZ-B degradation paths (in kcal.mol -1 ) PATH-1 PATH-2 Structure a CBS-4M B3LYP/6-31+G(d) CBS-4M B3LYP/6-31+G(d) SR b TS-I I II TS-II III a The TMZ+water structure has been optimized as a reactant and all other energies were compared to this structure relatively. b Separated reactants. Figure S3. The overall mechanism of TMZ decomposition TS-I of Path-1 Tautomerisation TS* TS-II of Path-2 *The energy of tautomerization TS is adopted from ref.36 (Doucet, K. G.; Glister, J. F.; Pye, C. C., Can. J. Chem. 2010). S5
6 Figure S4. The base-catalysed degradation of TMZ. TS-I Intermediate I II TS-II III G (kcal.mol -1 )* 7.23 (20.58) ** *Calculated at CBS-4M. **For second detected transition state. TMZ+OH - TS-I Intermediate TS-II II I MTIC+CO 2 S6
7 Figure S5. Atom numbering assignment of TMZ. Table S2. Protonation free energies for all protonated atoms. B3LYP/ g(2d,p) CBS-4M Position TMZA TMZB TMZA TMZB O N N N N N O N S7
8 Table S3. NPA partial atomic charges for TMZ. Atom TMZ-A TMZ-B O13-A O13-B N9-B O C C N N N N C N C C C O N Table S4. Absolute free energies (a.u.) for both TMZ degradation paths of rotamer A. PATH-1 PATH-2 Structure CBS-4M (gas) B3LYP/6-31+g* (gas) B3LYP/6-31+g* (PCM) B3LYP/6-31+g* (SM8) CBS-4M (gas) B3LYP/6-31+g* (gas) B3LYP/6-31+g* (PCM) B3LYP/6-31+g* (SM8) TMZ+water TS-I I II TS-II III S8
9 Table S5. Absolute free energies (a.u.) for the gas and water-mediated interconversion between N9 and O13 protonated forms of Temozolomide. Structure G3MP2 CBS-4M B3LYP/ G(2d,p) O TS N O13w TSw N9w Table S6. Absolute free energies (a.u.) for all protonated atoms. B3LYP/ g(2d,p) CBS-4M Position TMZA TMZB TMZA TMZB O N N N N N O N position O13 N9 N5 O1 G3MP2 / TMZA G3MP2 / TMZB S9
10 S1. pk a calculations procedure and methods. The reported pk a values were obtained using the direct thermodynamic cycle (as follows). 1 On the basis of this cycle the G obtained by this formula: Eventually, from the G, the pk a could be achieved. Following methods were used for this calculation: The B3LYP/6-31+G(d,p) level was used for both solvation and gas phase calculations. The kcal.mol -1 value was used for free energy of solvation of H + from Tissandier and coworkers. 2 It should be mentioned that the mono-hydrated TMZs were used for these computations to give better results. As there is no experimental data available for pk a of TMZ, imidazole ring is selected to see the certainty of the used methods. The calculated imidazole pk a is 7.35, which is in notable agreement to the experimental, 6.97, value. Exp. pk a Calc. pk a Imidazole TMZ * * Average value of O13 and N9 protonated species. 1 R. Casasnovas, J. Ortega-Castro, J. Frau, J. Donoso, F. Muñoz. Int. J. Quantum Chem., M.D. Tissandier, K.A. Cowen, W.Y. Feng, E. Gundlach, M.H. Cohen, A.D. Earhart, J.V. Coe, J. Phys. Chem. A., S10
11 S2. Figure and Cartesian coordinates of all optimized protonated species at the B3LYP/ G(2d,p) level of theory. O13A V1=74.22 * cm -1 O C C N N N N C N C C C O N H H H H H H H O13B V1=73.73 cm -1 O C C N N N N C N C C C O N H H H H H H H *The lowest frequency from the optimized structure. S11
12 N9 A V1=39.34 cm -1 O C C N N N N C N C C C O N H H H H H H H N9 B V1=70.15 cm -1 O C C N N N N C N C C C O N H H H H H H H S12
13 N5-A V1=70.96 cm -1 O C C N N N N C N C C C O N H H H H H H H N5-B V1=56.98 cm -1 O C C N N N N C N C C C O N H H H H H H H S13
14 N6-A V1=46.13 cm -1 O C C N N N N C N C C C O N H H H H H H H N14-A V1=67.49 cm -1 O C C N N N N C N C C C O N H H H H H H H S14
15 N14-B V1=63.06 cm -1 O C C N N N N C N C C C O N H H H H H H H N4-A V1=50.26 cm -1 O C C N N N N C N C C C O N H H H H H H H S15
16 O1-A V1=47.79 cm -1 O C C N N N N C N C C C O N H H H H H H H O1B V1=31.94 cm -1 O C C N N N N C N C C C O N H H H H H H H S16
17 N7-A V1=50.31 cm -1 O C C N N N N C N C C C O N H H H H H H H N7-B V1=13.65 cm -1 O C C N N N N C N C C C O N H H H H H H H S17
18 O13w V1=41.93 cm -1 O C C N N N N C N C C C N O O H H H H H H H H H N9w V1=56.65 cm -1 O C C N N N N C N C C C O N O H H H H H H H H H S18
19 TS-1 V1= cm -1 O C C N N N N C N C C C O N H H H H H H H TSw V1= cm -1 O C C N N N N C N C C C O N O H H H H H H H H H S19
20 S3. Cartesian coordinates of all optimized structures of Temozolomide degradation at the B3LYP/6-31+G(d) level of theory. TMZ+water (rotamer A) V1= cm -1 C N C N C C N N N C O C N O H H H H H H H O H TS-I of path-1(rotamer A) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H S20
21 I of path-1(rotamer A) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H II of path-1(rotamer A) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H S21
22 TS-II of path-1(rotamer A) V1= cm -1 C N C N C N N C O O C O H H N H C H H H N H H III of path-1(rotamer A) V1= cm -1 C N C N C N N C O O C O H H N H C H H H N H H S22
23 TMZ+water (rotamer B) V1= 8.69 cm -1 C N C N C C O C N O N N N C H H H H H H H O H TS-I of path-1(rotamer B) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H S23
24 I of path-1 (rotamer B) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H II of path-1 (rotamer B) V1= cm -1 C N C N C N N N C C O O C O N H H H H H H H H S24
25 TS-II of path-1(rotamer B) V1= cm -1 C N C N C N N N C C O O C O N H H H H H H H H III of path-1(rotamer B) V1= cm -1 C N C N C N N N C C O O C O N H H H H H H H H S25
26 TMZ+water (rotamer A) V1= cm -1 C N C N C C N N N C O C N O H H H H H H H O H TS-I of path-2(rotamer A) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H S26
27 I of path-2(rotamer A) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H II of path-2(rotamer A) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H S27
28 TS-II of path-2(rotamer A) V1= cm -1 N N N C C N C N C O C C O N O H H H H H H H H III of path-2(rotamer A) V1= cm -1 N N N C C N C N C O C C O N O H H H H H H H H S28
29 TMZ+water (rotamer B) V1= 8.69 cm -1 C N C N C C O C N O N N N C H H H H H H H O H TS-I of path-2(rotamer B) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H S29
30 I of path-2(rotamer B) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H II of path-2(rotamer B) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H S30
31 TS-II of path-2(rotamer B) V1= cm -1 N N N C C N C N C O C C O N H H H H H H H O H III of path-2(rotamer B) V1= 3.53 cm -1 N N N C C N C N C O C C O N H H H H H H H O H S31
32 S4. Cartesian coordinates of all optimized transition states of Temozolomide reaction with different nucleophiles at the CBS-4M level of theory. OH - first detected transition state V1= cm -1 G (kcal.mol -1 ) = 7.23 C N C N C C N N N C O C N O H H H H H H O H OH - second detected transition state V1= cm -1 G (kcal.mol -1 ) = C N C N C C N N N C O C N O H H H H H H O H S32
33 MeOH V1= cm -1 G (kcal.mol -1 ) = N N N C C N C N C O C C O N H H H H H H H O C H H H MeNH 2 V1= cm -1 G (kcal.mol -1 ) = N N N C C N C N C O C C O N H H H H H H H N H C H H H S33
34 CH 3 COOH V1= cm -1 G (kcal.mol -1 ) = N N N C N C C N C C N O C O C O O C H H H H H H H H H H CH 3 COOH product V1= cm -1 G (kcal.mol -1 ) = N N N C N C C N C C N O C O C O O C H H H H H H H H H H S34
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