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Journal of Physical Chemistry B

Volumn 113, Issue 38, 2009, Pages 12773-12781

Methylation of 2′-deoxyguanosine by a free radical mechanism

(3) Crean, Conor a Geacintov, Nicholas E a Shafirovich, Vladimir a

a NEW YORK UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMOLECULES; DIMETHYL SULFOXIDE; DNA; FREE RADICALS; GENES; METHYLATION; NUCLEIC ACIDS; OXIDATION; PHOTOLYSIS; POSITIVE IONS;

ALKYL RADICALS; AQUEOUS BUFFER SOLUTION; CARBONATE RADICAL ANION; COMBINATION REACTIONS; DEOXYGUANOSINE (DG); DOUBLE STRANDED DNA; END-PRODUCTS; ENZYMATIC DIGESTIONS; FREE RADICAL MECHANISM; INTERNAL STANDARDS; LC-MS/MS; MECHANISTIC ASPECTS; METHYL RADICAL; NEUTRAL RADICAL; ONE-ELECTRON OXIDATION; PHOTOCHEMICAL METHOD; SELECTIVE OXIDATION; SIMULTANEOUS GENERATION; SULFATE RADICALS;

ALKYLATION;

DEOXYGUANOSINE; FREE RADICAL; GUANINE;

ARTICLE; CHEMISTRY; DNA METHYLATION;

DEOXYGUANOSINE; DNA METHYLATION; FREE RADICALS; GUANINE;

EID: 70349286318 PISSN: 15206106 EISSN: None Source Type: Journal
DOI: 10.1021/jp903554n Document Type: Article

Times cited : (23)

References (63)

1
- 0014672640
- Loveless, A. Nature 1969, 223, 206-207.
- (1969) Nature , vol.223 , pp. 206-207
- Loveless, A.¹

2
- 0016042235
- Goth, R.; Rajewsky, M. F. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 639-643.
- (1974) Proc. Natl. Acad. Sci. U.S.A. , vol.71 , pp. 639-643
- Goth, R.¹ Rajewsky, M.F.²

3
- 2442515307
- Choi, J. Y.; Guengerich, F. P. J. Biol. Chem. 2004, 279, 19217-19229.
- (2004) J. Biol. Chem. , vol.279 , pp. 19217-19229
- Choi, J.Y.¹ Guengerich, F.P.²

4
- 33745891206
- Upton, D. C.; Wang, X.; Blans, P.; Perrino, F. W.; Fishbein, J. C.; Akman, S. A. Mutat Res. 2006, 599, 1-10.
- (2006) Mutat Res. , vol.599 , pp. 1-10
- Upton, D.C.¹ Wang, X.² Blans, P.³ Perrino, F.W.⁴ Fishbein, J.C.⁵ Akman, S.A.⁶

5
- 0003411354
- Cambridge University Press: Cambridge, U.K.
- Lijinsky, W. Chemistry and Biology of N-Nitroso Compounds; Cambridge University Press: Cambridge, U.K., 1992.
- (1992) Chemistry and Biology of N-Nitroso Compounds
- Lijinsky, W.¹

6
- 0003526343
- American Chemical Society: Washington, D.C
- Loeppky, R. N.; Michejda, C. J. Nitrosamines and Related N-Nitroso Compounds.; American Chemical Society: Washington, D.C, 1994.
- (1994) Nitrosamines and Related N-Nitroso Compounds
- Loeppky, R.N.¹ Michejda, C.J.²

7
- 0016441048
- Lawley, P. D.; Orr, D. J.; Jarman, M. Biochem. J. 1975, 145, 73-84.
- (1975) Biochem. J. , vol.145 , pp. 73-84
- Lawley, P.D.¹ Orr, D.J.² Jarman, M.³

8
- 8844267685
- Blans, P.; Fishbein, J. C. Chem. Res. Toxicol. 2004, 17, 1531-1539.
- (2004) Chem. Res. Toxicol. , vol.17 , pp. 1531-1539
- Blans, P.¹ Fishbein, J.C.²

9
- 0027220027
- Augusto, O. Free Radical Biol. Med. 1993, 15, 329-336.
- (1993) Free Radical Biol. Med. , vol.15 , pp. 329-336
- Augusto, O.¹

10
- 0016158648
- Maeda, M.; Nushi, K.; Kawazoe, Y. Tetrahedron 1974, 30, 2677-2682.
- (1974) Tetrahedron , vol.30 , pp. 2677-2682
- Maeda, M.¹ Nushi, K.² Kawazoe, Y.³

11
- 0029845883
- Kohda, K.; Tsunomoto, H.; Minoura, Y.; Tanabe, K.; Shibutani, S. Chem. Res. Toxicol. 1996, 9, 1278-1284.
- (1996) Chem. Res. Toxicol. , vol.9 , pp. 1278-1284
- Kohda, K.¹ Tsunomoto, H.² Minoura, Y.³ Tanabe, K.⁴ Shibutani, S.⁵

12
- 49549128629
- Araki, M.; Maeda, M.; Kawazoe, Y. Tetrahedron 1976, 32, 337-340.
- (1976) Tetrahedron , vol.32 , pp. 337-340
- Araki, M.¹ Maeda, M.² Kawazoe, Y.³

13
- 0025688436
- Augusto, O.; Cavalieri, E. L.; Rogan, E. G.; RamaKrishna, N. V.; Kolar, C. J. Biol. Chem. 1990, 265, 22093-22096.
- (1990) J. Biol. Chem. , vol.265 , pp. 22093-22096
- Augusto, O.¹ Cavalieri, E.L.² Rogan, E.G.³ Ramakrishna, N.V.⁴ Kolar, C.⁵

14
- 0017779854
- Zady, M. F.; Wong, J. L. J. Am. Chem. Soc. 1977, 99, 5096-5101.
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 5096-5101
- Zady, M.F.¹ Wong, J.L.²

15
- 0000339570
- Zady, M. F.; Wong, J. L. J. Org. Chem. 1980, 45, 2373-2377.
- (1980) J. Org. Chem. , vol.45 , pp. 2373-2377
- Zady, M.F.¹ Wong, J.L.²

16
- 0017622271
- Rogers, K. J.; Pegg, A. E. Cancer Res. 1977, 37, 4082-4087.
- (1977) Cancer Res. , vol.37 , pp. 4082-4087
- Rogers, K.J.¹ Pegg, A.E.²

17
- 0019390432
- Herron, D. C.; Shank, R. C. Cancer Res. 1981, 41, 3967-3972.
- (1981) Cancer Res. , vol.41 , pp. 3967-3972
- Herron, D.C.¹ Shank, R.C.²

18
- 0026612456
- Netto, L. E.; RamaKrishna, N. V.; Kolar, C.; Cavalieri, E. L.; Rogan, E. G.; Lawson, T. A.; Augusto, O. J. Biol. Chem. 1992, 267, 21524-21527.
- (1992) J. Biol. Chem. , vol.267 , pp. 21524-21527
- Netto, L.E.¹ Ramakrishna, N.V.² Kolar, C.³ Cavalieri, E.L.⁴ Rogan, E.G.⁵ Lawson, T.A.⁶ Augusto, O.⁷

19
- 0014215579
- Rice, J. M.; Dudek, G. O. J. Am. Chem. Soc. 1967, 89, 2719-2725.
- (1967) J. Am. Chem. Soc. , vol.89 , pp. 2719-2725
- Rice, J.M.¹ Dudek, G.O.²

20
- 0024501624
- Candeias, L. P.; Steenken, S. J. Am. Chem. Soc. 1989, 111, 1094-1099.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 1094-1099
- Candeias, L.P.¹ Steenken, S.²

21
- 0031027125
- Steenken, S.; Jovanovic, S. V. J. Am. Chem. Soc. 1997, 119, 617-618.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 617-618
- Steenken, S.¹ Jovanovic, S.V.²

22
- 41649117108
- Crean, C.; Geacintov, N. E.; Shafirovich, V. Chem. Res. Toxicol. 2008, 21, 358-373.
- (2008) Chem. Res. Toxicol. , vol.21 , pp. 358-373
- Crean, C.¹ Geacintov, N.E.² Shafirovich, V.³

23
- 37049070316
- Kishore, K.; Asmus, K.-D. J. Chem. Soc, Perkin Trans. 2 1989, 2079-2084.
- (1989) J. Chem. Soc, Perkin Trans. , vol.2 , pp. 2079-2084
- Kishore, K.¹ Asmus, K.-D.²

24
- 0001661743
- Neta, P.; Grodkowski, J.; Ross, A. B. J. Phys. Chem. Ref. Data 1996, 25, 709-1050.
- (1996) J. Phys. Chem. Ref. Data , vol.25 , pp. 709-1050
- Neta, P.¹ Grodkowski, J.² Ross, A.B.³

25
- 0030990682
- Ludwig, M. L.; Matthews, R. G. Annu. Rev. Biochem. 1997, 66, 269-313.
- (1997) Annu. Rev. Biochem. , vol.66 , pp. 269-313
- Ludwig, M.L.¹ Matthews, R.G.²

26
- 33845561476
- Endicott, J. F.; Netzel, T. L. J. Am. Chem. Soc. 1979, 101, 4000-4002.
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 4000-4002
- Endicott, J.F.¹ Netzel, T.L.²

27
- 0027502111
- Chen, E.; Chance, M. R. Biochemistry 1993, 32, 1480-1487.
- (1993) Biochemistry , vol.32 , pp. 1480-1487
- Chen, E.¹ Chance, M.R.²

28
- 0001405859
- Shiang, J. J.; Walker, L. A.; Anderson, N. A.; Cole, A. G.; Sension, R. J. J. Phys. Chem. B 1999, 103, 10532-10539.
- (1999) J. Phys. Chem. B , vol.103 , pp. 10532-10539
- Shiang, J.J.¹ Walker, L.A.² Anderson, N.A.³ Cole, A.G.⁴ Sension, R.J.⁵

29
- 33846863589
- Pacher, P.; Beckman, J. S.; Liaudet, L. Physiol. Rev. 2007, 87, 315-424.
- (2007) Physiol. Rev. , vol.87 , pp. 315-424
- Pacher, P.¹ Beckman, J.S.² Liaudet, L.³

30
- 33646583190
- Perrier, S.; Hau, J.; Gasparutto, D.; Cadet, J.; Favier, A.; Ravanat, J. L. J. Am. Chem. Soc. 2006, 128, 5703-5710.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 5703-5710
- Perrier, S.¹ Hau, J.² Gasparutto, D.³ Cadet, J.⁴ Favier, A.⁵ Ravanat, J.L.⁶

31
- 0000793941
- Shafirovich, V.; Dourandin, A.; Huang, W.; Luneva, N. P.; Geacintov, N. E. J. Phys. Chem. B 1999, 103, 10924-10933.
- (1999) J. Phys. Chem. B , vol.103 , pp. 10924-10933
- Shafirovich, V.¹ Dourandin, A.² Huang, W.³ Luneva, N.P.⁴ Geacintov, N.E.⁵

32
- 0001212060
- Ivanov, K. L.; Glebov, E. M.; Plyusnin, V. F.; Ivanov, Y. V.; Grivin, V. P.; Bazhin, N. M. J. Photochem. Photobiol. A 2000, 133, 99-104.
- (2000) J. Photochem. Photobiol. A , vol.133 , pp. 99-104
- Ivanov, K.L.¹ Glebov, E.M.² Plyusnin, V.F.³ Ivanov, Y.V.⁴ Grivin, V.P.⁵ Bazhin, N.M.⁶

33
- 0035816604
- Shafirovich, V.; Dourandin, A.; Huang, W.; Geacintov, N. E. J. Biol. Chem. 2001, 276, 24621-24626.
- (2001) J. Biol. Chem. , vol.276 , pp. 24621-24626
- Shafirovich, V.¹ Dourandin, A.² Huang, W.³ Geacintov, N.E.⁴

34
- 0004815397
- Hickel, B. J. Phys. Chem. 1975, 79, 1054-1059.
- (1975) J. Phys. Chem. , vol.79 , pp. 1054-1059
- Hickel, B.¹

35
- 0013691408
- McElroy, W. J. J. Phys. Chem. 1990, 94, 2435-2441.
- (1990) J. Phys. Chem. , vol.94 , pp. 2435-2441
- McElroy, W.J.¹

36
- 0034653650
- Steenken, S.; Jovanovic, S. V.; Bietti, M.; Bernhard, K. J. Am. Chem. Soc. 2000, 122, 2373-2374.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 2373-2374
- Steenken, S.¹ Jovanovic, S.V.² Bietti, M.³ Bernhard, K.⁴

37
- 0031014406
- Sannes-Lowery, K. A.; Mack, D. P.; Hu, P.; Mei, H.-Y.; Loo, J. A. J. Am. Soc. Mass Spectrom. 1997, 8, 90-95.
- (1997) J. Am. Soc. Mass Spectrom. , vol.8 , pp. 90-95
- Sannes-Lowery, K.A.¹ Mack, D.P.² Hu, P.³ Mei, H.-Y.⁴ Loo, J.A.⁵

38
- 0030786967
- Ni, J.; Mathews, M. A. A.; McCloskey, J. A. Rapid Commun. Mass Spectrom. 1997, 11, 535-540.
- (1997) Rapid Commun. Mass Spectrom. , vol.11 , pp. 535-540
- Ni, J.¹ Mathews, M.A.A.² McCloskey, J.A.³

39
- 0030968113
- Wang, P. P.; Bartlett, M. G.; Martin, L. B. Rapid Commun. Mass Spectrom. 1997, 11, 846-856.
- (1997) Rapid Commun. Mass Spectrom. , vol.11 , pp. 846-856
- Wang, P.P.¹ Bartlett, M.G.² Martin, L.B.³

40
- 0032529265
- Constantinesco, F.; Benachenhou, N.; Motorin, Y.; Grosjean, H. Nucleic Acids Res. 1998, 26, 3753-3761.
- (1998) Nucleic Acids Res. , vol.26 , pp. 3753-3761
- Constantinesco, F.¹ Benachenhou, N.² Motorin, Y.³ Grosjean, H.⁴

41
- 0347629021
- Joffe, A.; Geacintov, N. E.; Shafirovich, V. Chem. Res. Toxicol. 2003, 16, 1528-1538.
- (2003) Chem. Res. Toxicol. , vol.16 , pp. 1528-1538
- Joffe, A.¹ Geacintov, N.E.² Shafirovich, V.³

42
- 23944508507
- Crean, C.; Geacintov, N. E.; Shafirovich, V. Angew. Chem., Int. Ed. 2005, 44, 5057-5060.
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 5057-5060
- Crean, C.¹ Geacintov, N.E.² Shafirovich, V.³

43
- 0000157105
- Candeias, L. P.; Steenken, S. J. Am. Chem. Soc. 1993, 115, 2437-2440.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 2437-2440
- Candeias, L.P.¹ Steenken, S.²

44
- 13844269360
- Singh, R.; Kaur, B.; Farmer, P. B. Chem. Res. Toxicol. 2005, 18, 249-256.
- (2005) Chem. Res. Toxicol. , vol.18 , pp. 249-256
- Singh, R.¹ Kaur, B.² Farmer, P.B.³

45
- 31544440695
- Singh, R.; Farmer, P. B. Carcinogenesis 2006, 27, 178-196.
- (2006) Carcinogenesis , vol.27 , pp. 178-196
- Singh, R.¹ Farmer, P.B.²

46
- 0031819230
- Nakao, L. S.; Augusto, O. Chem. Res. Toxicol. 1998, 11, 888-894.
- (1998) Chem. Res. Toxicol. , vol.11 , pp. 888-894
- Nakao, L.S.¹ Augusto, O.²

47
- 50749132992
- Bachler, V.; Hildenbrand, K. Radiât Phys. Chem. 1992, 40, 59-68.
- (1992) Radiât Phys. Chem. , vol.40 , pp. 59-68
- Bachler, V.¹ Hildenbrand, K.²

48
- 33846039190
- Adhikary, A.; Kumar, A.; Becker, D.; Sevilla, M. D. J. Phys. Chem. B 2006, 110, 24171-24180.
- (2006) J. Phys. Chem. B , vol.110 , pp. 24171-24180
- Adhikary, A.¹ Kumar, A.² Becker, D.³ Sevilla, M.D.⁴

49
- 0023144379
- Hole, E. O.; Sagstuen, E. Radiât Res. 1987, 109, 190-205.
- (1987) Radiât Res. , vol.109 , pp. 190-205
- Hole, E.O.¹ Sagstuen, E.²

50
- 0026506920
- Hole, E. O.; Nelson, W. H.; Sagstuen, E.; Close, D. M. Radiat Res. 1992, 119-138.
- (1992) Radiat Res. , pp. 119-138
- Hole, E.O.¹ Nelson, W.H.² Sagstuen, E.³ Close, D.M.⁴

51
- 0000251808
- Wetmore, S. D.; Boyd, R. J.; Eriksson, L. A. J. Phys. Chem. B 1998, 102, 9332-9343.
- (1998) J. Phys. Chem. B , vol.102 , pp. 9332-9343
- Wetmore, S.D.¹ Boyd, R.J.² Eriksson, L.A.³

52
- 0037206801
- Mundy, J.; Colvin, M. E.; Quong, A. A. J. Phys. Chem. A 2002, 106, 10063-10071.
- (2002) J. Phys. Chem. A , vol.106 , pp. 10063-10071
- Mundy, J.¹ Colvin, M.E.² Quong, A.A.³

53
- 13944273322
- Misiaszek, R.; Crean, C.; Geacintov, N. E.; Shafirovich, V. J. Am. Chem. Soc. 2005, 127, 2191-2200.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 2191-2200
- Misiaszek, R.¹ Crean, C.² Geacintov, N.E.³ Shafirovich, V.⁴

54
- 3543019650
- Misiaszek, R.; Crean, C.; Joffe, A.; Geacintov, N. E.; Shafirovich, V. J. Biol. Chem. 2004, 279, 32106-32115.
- (2004) J. Biol. Chem. , vol.279 , pp. 32106-32115
- Misiaszek, R.¹ Crean, C.² Joffe, A.³ Geacintov, N.E.⁴ Shafirovich, V.⁵

55
- 0031000954
- Wang, W.; Razskazovskii, Y.; Sevilla, M. D. Int. J. Radiat Biol. 1997, 71, 387-399.
- (1997) Int. J. Radiat Biol. , vol.71 , pp. 387-399
- Wang, W.¹ Razskazovskii, Y.² Sevilla, M.D.³

56
- 0034602912
- Candeias, L. P.; Steenken, S. Chem-Eur. J. 2000, 6, 475-484.
- (2000) Chem-Eur. J. , vol.6 , pp. 475-484
- Candeias, L.P.¹ Steenken, S.²

57
- 7544247157
- Kofod, P. J. Inorg. Biochem. 2004, 98, 1978-1980.
- (2004) J. Inorg. Biochem. , vol.98 , pp. 1978-1980
- Kofod, P.¹

58
- 0037743696
- CRC Press: Boca Raton, FL
- Luo, Y. R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003.
- (2003) Handbook of Bond Dissociation Energies in Organic Compounds
- Luo, Y.R.¹

59
- 0035796427
- Steenken, S.; Jovanovic, S. V.; Candeias, L. P.; Reynisson, J. Chem.-Eur. J. 2001, 7, 2829-2833.
- (2001) Chem.-Eur. J. , vol.7 , pp. 2829-2833
- Steenken, S.¹ Jovanovic, S.V.² Candeias, L.P.³ Reynisson, J.⁴

60
- 0028152235
- Riordan, C. G.; Wei, P. J. Am. Chem. Soc. 1994, 116, 2189-2190.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 2189-2190
- Riordan, C.G.¹ Wei, P.²

61
- 42949160738
- Tanaka, M.; Ohkubo, K.; Fukuzumi, S. J. Photochem. Photobiol. A 2008, 197, 94-100.
- (2008) J. Photochem. Photobiol. A , vol.197 , pp. 94-100
- Tanaka, M.¹ Ohkubo, K.² Fukuzumi, S.³

62
- 0028231429
- Milligan, J. R.; Ward, J. F. Radiât Res. 1994, 137, 295-299.
- (1994) Radiât Res. , vol.137 , pp. 295-299
- Milligan, J.R.¹ Ward, J.F.²

63
- 2942590732
- Brown, J. M.; Wilson, W. R. Nat Rev. 2004, 4, 437-447.
- (2004) Nat Rev. , vol.4 , pp. 437-447
- Brown, J.M.¹ Wilson, W.R.²

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