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Angewandte Chemie - International Edition

Volumn 52, Issue 3, 2013, Pages 993-997

Nitrogen inversion barriers affect the N-oxidation of tertiary alkylamines by cytochromes P450

(6) Rydberg, Patrik a Jørgensen, Martin S a Jacobsen, Thomas A b Jacobsen, Anne Marie c Madsen, Kim G d Olsen, Lars a

a UNIVERSITY OF COPENHAGEN (Denmark)

b Aniona (Denmark)

c H LUNDBECK A S (Denmark)

d NOVO NORDISK A S (Denmark)

Author keywords

cytochromes; density functional calculations; N dealkylation; N inversion barrier; N oxidation

Indexed keywords

ALKYL AMINES; ALKYLAMINE; CYTOCHROME P450; CYTOCHROMES P450; DEALKYLATION; N-DEALKYLATION; N-INVERSION BARRIERS; N-OXIDATION; NITROGEN ATOM; NITROGEN INVERSION;

CATALYSIS; CHEMISTRY; PROTEINS;

DENSITY FUNCTIONAL THEORY;

AMINE; CYTOCHROME P450; NITROGEN;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; METABOLISM; OXIDATION REDUCTION REACTION; THERMODYNAMICS;

AMINES; CYTOCHROME P-450 ENZYME SYSTEM; NITROGEN; OXIDATION-REDUCTION; SUBSTRATE SPECIFICITY; THERMODYNAMICS;

EID: 84872328870 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201206207 Document Type: Article

Times cited : (22)

References (40)

1
- 33645050104
- EE 111.
- F. P. Guengerich, AAPS J. 2006, 8, E 101 -E 111.
- (2006) AAPS J. , vol.8 , pp. 101
- Guengerich, F.P.¹

2
- 84860217008
- N. M. DeVore, K. M. Meneely, A. G. Bart, E. S. Stephens, K. P. Battaile, E. E. Scott, FEBS J. 2012, 279, 1621-1631
- (2012) FEBS J. , vol.279 , pp. 1621-1631
- Devore, N.M.¹ Meneely, K.M.² Bart, A.G.³ Stephens, E.S.⁴ Battaile, K.P.⁵ Scott, E.E.⁶

3
- 84859500879
- A. Wang, U. Savas, M. H. Hsu, C. D. Stout, E. F. Johnson, J. Biol. Chem. 2012, 287, 10834-10843.
- (2012) J. Biol. Chem. , vol.287 , pp. 10834-10843
- Wang, A.¹ Savas, U.² Hsu, M.H.³ Stout, C.D.⁴ Johnson, E.F.⁵

4
- 58149157800
- P. Rydberg, U. Ryde, L. Olsen, J. Chem. Theory Comput. 2008, 4, 1369-1377.
- (2008) J. Chem. Theory Comput. , vol.4 , pp. 1369-1377
- Rydberg, P.¹ Ryde, U.² Olsen, L.³

5
- 0022467917
- F. P. Guengerich, D. Müller-Enoch, I. A. Blair, Mol. Pharmacol. 1986, 30, 287-295
- (1986) Mol. Pharmacol. , vol.30 , pp. 287-295
- Guengerich, F.P.¹ Müller-Enoch, D.² Blair, I.A.³

6
- 0020018460
- P. Hlavica, CRC Crit. Rev. Biochem. Mol. 1982, 12, 39-101.
- (1982) CRC Crit. Rev. Biochem. Mol. , vol.12 , pp. 39-101
- Hlavica, P.¹

7
- 84862845373
- J. Zaretzki, P. Rydberg, C. Bergeron, K. P. Bennett, L. Olsen, C. M. Breneman, J. Chem. Inf. Model. 2012, 52, 1637-1659.
- (2012) J. Chem. Inf. Model. , vol.52 , pp. 1637-1659
- Zaretzki, J.¹ Rydberg, P.² Bergeron, C.³ Bennett, K.P.⁴ Olsen, L.⁵ Breneman, C.M.⁶

8
- 0014644925
- M. H. Bickel, Pharmacol. Rev. 1969, 21, 325-355.
- (1969) Pharmacol. Rev. , vol.21 , pp. 325-355
- Bickel, M.H.¹

9
- 19944399431
- A. S. Kalgutkar, I. Gardner, R. S. Obach, C. L. Shaffer, E. Callegari, K. R. Henne, A. E. Mutlib, D. K. Dalvie, J. S. Lee, Y. Nakai, J. P. O'Donnell, J. Boer, S. P. Harriman, Curr. Drug Metab. 2005, 6, 161-225
- (2005) Curr. Drug Metab. , vol.6 , pp. 161-225
- Kalgutkar, A.S.¹ Gardner, I.² Obach, R.S.³ Shaffer, C.L.⁴ Callegari, E.⁵ Henne, K.R.⁶ Mutlib, A.E.⁷ Dalvie, D.K.⁸ Lee, J.S.⁹ Nakai, Y.¹⁰ O'Donnell, J.P.¹¹ Boer, J.¹² Harriman, S.P.¹³

10
- 0037253576
- Q. Xia, M. W. Chou, F. Kadlubar, P. C. Chan, P. P. Fu, Chem. Res. Toxicol. 2003, 16, 66-73.
- (2003) Chem. Res. Toxicol. , vol.16 , pp. 66-73
- Xia, Q.¹ Chou, M.W.² Kadlubar, F.³ Chan, P.C.⁴ Fu, P.P.⁵

11
- 4644275807
- B. Meunier, S. P. de Visser, S. Shaik, Chem. Rev. 2004, 104, 3947-3980
- (2004) Chem. Rev. , vol.104 , pp. 3947-3980
- Meunier, B.¹ De Visser, S.P.² Shaik, S.³

12
- 0035984571
- P. R. Ortiz de Montellano, J. J. De Voss, Nat. Prod. Rep. 2002, 19, 477-493.
- (2002) Nat. Prod. Rep. , vol.19 , pp. 477-493
- Ortiz De Montellano, P.R.¹ De Voss, J.J.²

13
- 0018843513
- G. Powis, L. Wincentsen, Biochem. Pharmacol. 1980, 29, 347-351
- (1980) Biochem. Pharmacol. , vol.29 , pp. 347-351
- Powis, G.¹ Wincentsen, L.²

14
- 0016246195
- M. Sugiura, K. Iwasaki, H. Noguchi, R. Kato, Life Sci. 1974, 15, 1433-1442
- (1974) Life Sci. , vol.15 , pp. 1433-1442
- Sugiura, M.¹ Iwasaki, K.² Noguchi, H.³ Kato, R.⁴

15
- 0035060888
- K. Takekawa, S. Kitamura, K. Sugihara, S. Ohta, Xenobiotica 2001, 31, 11-23.
- (2001) Xenobiotica , vol.31 , pp. 11-23
- Takekawa, K.¹ Kitamura, S.² Sugihara, K.³ Ohta, S.⁴

16
- 34250641915
- K. B. Cho, Y. Moreau, D. Kumar, D. A. Rock, J. P. Jones, S. Shaik, Chem. Eur. J. 2007, 13, 4103-4115
- (2007) Chem. Eur. J. , vol.13 , pp. 4103-4115
- Cho, K.B.¹ Moreau, Y.² Kumar, D.³ Rock, D.A.⁴ Jones, J.P.⁵ Shaik, S.⁶

17
- 77954712561
- K. M. Roberts, J. P. Jones, Chem. Eur. J. 2010, 16, 8096-8107.
- (2010) Chem. Eur. J. , vol.16 , pp. 8096-8107
- Roberts, K.M.¹ Jones, J.P.²

18
- 78449309981
- P. Rydberg, D. E. Gloriam, L. Olsen, Bioinformatics 2010, 26, 2988-2989
- (2010) Bioinformatics , vol.26 , pp. 2988-2989
- Rydberg, P.¹ Gloriam, D.E.² Olsen, L.³

19
- 77953932263
- P. Rydberg, D. E. Gloriam, J. Zaretzki, C. Breneman, L. Olsen, ACS Med. Chem. Lett. 2010, 1, 96-100
- (2010) ACS Med. Chem. Lett. , vol.1 , pp. 96-100
- Rydberg, P.¹ Gloriam, D.E.² Zaretzki, J.³ Breneman, C.⁴ Olsen, L.⁵

20
- 84855867453
- P. Rydberg, L. Olsen, ACS Med. Chem. Lett. 2012, 3, 69-73
- (2012) ACS Med. Chem. Lett. , vol.3 , pp. 69-73
- Rydberg, P.¹ Olsen, L.²

21
- 73449135498
- P. Rydberg, P. Vasanthanathan, C. Oostenbrink, L. Olsen, ChemMedChem 2009, 4, 2070-2079.
- (2009) ChemMedChem , vol.4 , pp. 2070-2079
- Rydberg, P.¹ Vasanthanathan, P.² Oostenbrink, C.³ Olsen, L.⁴

22
- 0031796437
- J. Fang, R. T. Coutts, K. F. McKenna, G. B. Baker, Naunyn- Schmiedeberg′s Arch. Pharmacol. 1998, 358, 592-599
- (1998) Naunyn-Schmiedeberg′s Arch. Pharmacol. , vol.358 , pp. 592-599
- Fang, J.¹ Coutts, R.T.² McKenna, K.F.³ Baker, G.B.⁴

23
- 0032955464
- M. Tugnait, E. M. Hawes, G. McKay, M. Eichelbaum, K. K. Midha, Chem.-Biol. Interact. 1999, 118, 171-189.
- (1999) Chem.-Biol. Interact. , vol.118 , pp. 171-189
- Tugnait, M.¹ Hawes, E.M.² McKay, G.³ Eichelbaum, M.⁴ Midha, K.K.⁵

24
- 0033791657
- W. Jacobsen, U. Christians, L. Z. Benet, Drug Metab. Dispos. 2000, 28, 1343.
- (2000) Drug Metab. Dispos. , vol.28 , pp. 1343
- Jacobsen, W.¹ Christians, U.² Benet, L.Z.³

25
- 0030434501
- E. Koyama, K. Chiba, M. Tani, T. Ishizaki, J. Pharmacol. Exp. Ther. 1996, 278, 21.
- (1996) J. Pharmacol. Exp. Ther. , vol.278 , pp. 21
- Koyama, E.¹ Chiba, K.² Tani, M.³ Ishizaki, T.⁴

26
- 0033810675
- E. Störmer, L. L. von Moltke, R. I. Shader, D. J. Greenblatt, Drug Metab. Dispos. 2000, 28, 1168-1175.
- (2000) Drug Metab. Dispos. , vol.28 , pp. 1168-1175
- Störmer, E.¹ Von Moltke, L.L.² Shader, R.I.³ Greenblatt, D.J.⁴

27
- 0032820022
- L. Becquemont, S. Mouajjah, O. Escaffre, P. Beaune, C. Funck-Brentano, P. Jaillon, Drug Metab. Dispos. 1999, 27, 1068-1073.
- (1999) Drug Metab. Dispos. , vol.27 , pp. 1068-1073
- Becquemont, L.¹ Mouajjah, S.² Escaffre, O.³ Beaune, P.⁴ Funck-Brentano, C.⁵ Jaillon, P.⁶

28
- 0030077735
- B. J. Ring, J. Catlow, T. J. Lindsay, T. Gillespie, L. K. Roskos, B. J. Cerimele, S. P. Swanson, M. A. Hamman, S. A. Wrighton, J. Pharmacol. Exp. Ther. 1996, 276, 658.
- (1996) J. Pharmacol. Exp. Ther. , vol.276 , pp. 658
- Ring, B.J.¹ Catlow, J.² Lindsay, T.J.³ Gillespie, T.⁴ Roskos, L.K.⁵ Cerimele, B.J.⁶ Swanson, S.P.⁷ Hamman, M.A.⁸ Wrighton, S.A.⁹

29
- 0033047284
- K. G. Jensen, L. Dalgaard, Drug Metab. Dispos. 1999, 27, 125.
- (1999) Drug Metab. Dispos. , vol.27 , pp. 125
- Jensen, K.G.¹ Dalgaard, L.²

30
- 0025908449
- C. L. Miranda, R. L. Reed, F. P. Guengerich, D. R. Buhler, Carcinogenesis 1991, 12, 515.
- (1991) Carcinogenesis , vol.12 , pp. 515
- Miranda, C.L.¹ Reed, R.L.² Guengerich, F.P.³ Buhler, D.R.⁴

31
- 0028306340
- B. J. Ring, C. J. Parli, M. C. George, S. A. Wrighton, Drug Metab. Dispos. 1994, 22, 352-357.
- (1994) Drug Metab. Dispos. , vol.22 , pp. 352-357
- Ring, B.J.¹ Parli, C.J.² George, M.C.³ Wrighton, S.A.⁴

32
- 0029880344
- P. Sanwald, M. David, J. Dow, Drug Metab. Dispos. 1996, 24, 602.
- (1996) Drug Metab. Dispos. , vol.24 , pp. 602
- Sanwald, P.¹ David, M.² Dow, J.³

33
- 0027230584
- A. Lemoine, J. C. Gautier, D. Azoulay, L. Kiffel, C. Belloc, F. P. Guengerich, P. Maurel, P. Beaune, J. P. Leroux, Mol. Pharmacol. 1993, 43, 827-832.
- (1993) Mol. Pharmacol. , vol.43 , pp. 827-832
- Lemoine, A.¹ Gautier, J.C.² Azoulay, D.³ Kiffel, L.⁴ Belloc, C.⁵ Guengerich, F.P.⁶ Maurel, P.⁷ Beaune, P.⁸ Leroux, J.P.⁹

34
- 0031691414
- B. C. Jones, R. Hyland, M. Ackland, C. A. Tyman, D. A. Smith, Drug Metab. Dispos. 1998, 26, 875-882.
- (1998) Drug Metab. Dispos. , vol.26 , pp. 875-882
- Jones, B.C.¹ Hyland, R.² Ackland, M.³ Tyman, C.A.⁴ Smith, D.A.⁵

35
- 1642603466
- J. Wõjcikowski, L. Pichard-Garcia, P. Maurel, W. A. Daniel, Eur. Neuropsychopharmacol. 2004, 14, 199-208.
- (2004) Eur. Neuropsychopharmacol. , vol.14 , pp. 199-208
- Wõjcikowski, J.¹ Pichard-Garcia, L.² Maurel, P.³ Daniel, W.A.⁴

36
- 0028171950
- J. C. Bloomer, S. J. Baldwin, G. J. Smith, A. D. Ayrton, S. E. Clarke, R. J. Chenery, Br. J. Clin. Pharmacol. 1994, 38, 557-566.
- (1994) Br. J. Clin. Pharmacol. , vol.38 , pp. 557-566
- Bloomer, J.C.¹ Baldwin, S.J.² Smith, G.J.³ Ayrton, A.D.⁴ Clarke, S.E.⁵ Chenery, R.J.⁶

37
- 0029587052
- T. Ebner, C. O. Meese, M. Eichelbaum, Mol. Pharmacol. 1995, 48, 1078-1086.
- (1995) Mol. Pharmacol. , vol.48 , pp. 1078-1086
- Ebner, T.¹ Meese, C.O.² Eichelbaum, M.³

38
- 69249141050
- C. S. Li, W. Wu, K. B. Cho, S. Shaik, Chem. Eur. J. 2009, 15, 8492-8503.
- (2009) Chem. Eur. J. , vol.15 , pp. 8492-8503
- Li, C.S.¹ Wu, W.² Cho, K.B.³ Shaik, S.⁴

39
- 31544459908
- C. S. Li, W. Wu, D. Kumar, S. Shaik, J. Am. Chem. Soc. 2006, 128, 394-395.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 394-395
- Li, C.S.¹ Wu, W.² Kumar, D.³ Shaik, S.⁴

40
- 0028223613
- P. Hlavica, Drug Metab. Rev. 1994, 26, 325-348.
- (1994) Drug Metab. Rev. , vol.26 , pp. 325-348
- Hlavica, P.¹

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