Inactivation of O6-alkylguanine-DNA alkyltransferase. 1. Novel O6- (hetarylmethyl)guanines having basic rings in the side chain

Journal of Medicinal Chemistry

Volumn 41, Issue 26, 1998, Pages 5265-5271

  McElhinney, R Stanley ^a   Donnelly, Dorothy J ^a   McCormick, Joan E ^a   Kelly, Jane ^a   Watson, Amanda J ^a   Rafferty, Joseph A ^a   Elder, Rhoderick H ^a   Middleton, Mark R ^a   Willington, Mark A ^a   McMurry, T Brian H ^a   Margison, Geoffrey P ^a  

^a CHRISTIE HOSPITAL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

6 O ALKYLGUANINE DNA ALKYLTRANSFERASE; GUANINE DERIVATIVE; DRUG DERIVATIVE; ENZYME INHIBITOR; GUANINE; METHYLATED DNA PROTEIN CYSTEINE METHYLTRANSFERASE; O(6) BENZYLGUANINE; O(6)-BENZYLGUANINE; RECOMBINANT PROTEIN;

ARTICLE; DRUG ACTIVITY; DRUG EFFECT; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INACTIVATION; HUMAN; HUMAN CELL; CELL CULTURE; CHEMISTRY; DRUG ANTAGONISM; SYNTHESIS;

ENZYME INHIBITORS; GUANINE; HUMANS; O(6)-METHYLGUANINE-DNA METHYLTRANSFERASE; RECOMBINANT PROTEINS; TUMOR CELLS, CULTURED;

EID: 0032542080     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9708644     Document Type: Article

References (69)

1. 6-alkylguanine alkyltransferase (AT) in cancer chemotherapy. Cancer Treat. Rev. 1988, 15, 279-292.
2. Margison, G. P.; O'Connor, P. J. Biological consequences of reactions with DNA: Role of specific lesions. Handbook Exp. Pharmacol. 94/1.
3. 6-alkylguanine-DNA alkyltransferase: regulation and importance in response to alkylating carcinogenic and therapeutic agents. Cancer Res. 1990, 50, 6119-6129.
4. Margison, G. P.; O'Connor, P. J.; Cooper, D. P.; Davis, J.; Hall, N.; Redmond, S. M. S.; Buser, K.; Cerny, T.; Citti, L.; D'Incalci, M. Triazenes: Chemical, Biological and Structural Aspects; In Giraldi, T., Connors, T. A., Cartei, G., Eds.; Plenum Press: New York, 1990; pp 195-206.
5. 6-Methylguanine-DNA methyltransferase in human normal and tumor tissue from brain, lung and ovary. Cancer Res. 1991, 51, 4131-4134.
6. 6-Benzylguanine and its role in chemotherapy. Clin. Cancer Res. 1997, 3, 8837-847.
7. Zlotogorski, E.; Erickson, L. C. Pretreatment of human colon tumor cells with DNA methylating agents inhibits their activity to repair chloroethyl monoadducts. Carcinogenesis (London) 1984, 5, 83-87.
8. 6-alkylguanines. Cancer Res. 1985, 45, 6413-6417.
9. 6-methylguanine as a free base. Cancer Res. 1986, 46, 1663-1668.
10. 6-benzylguanine provides a means to evaluate the role of this protein in protection against carcinogenic and therapeutic alkylating agents. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 5368-5372.
11. 6-alkylguanine-DNA alkyltransferase. J. Med. Chem. 1992, 35, 4486-4491.
12. 6-alkylguanine-DNA alkyltransferase. J. Med. Chem. 1994, 37, 342-347.
13. 6-arylmethylguanines. Biol. Pharm. Bull. 1995, 18, 424-430.
14. 6-alkylguanine-DNA alkyltransferase. J. Med. Chem. 1995, 38, 359-365.
15. 6-substituted guanines). Anti-Cancer Drug Des. 1994, 9, 401-408.
16. 6-methylguanine-DNA methyltransferase from E. coli. EMBO J. 1994, 13, 1495-1501.
17. 6-alkylguanine-DNA alkyltransferase based on the crystal structure of the C-terminal domain of the Ada protein from Escherichia coli. Anti-Cancer Drug Des. 1995, 10, 75-95.
18. N2 transition states. Can. J. Chem. 1982, 60, 2500-2520.
19. Arcoria, A.; Maccarone, E.; Musumarra, G.; Tomaselli, G. A. Nucleophilic substitution in the side-chain of five-membered heterocycles - I. Reactions of furfuryl, 2-thenyl and benzyl chlorides with aniline in acetonitrile and in benzene. Tetrahedron 1975, 31, 2523-2527.
20. Östman, B. Secondary α-deuterium isotope effects and relative rates in the halogen exchange reactions of benzyl and thenyl chlorides. J. Am. Chem. Soc. 1965, 87, 3163-3166.
21. Losse, G.; Jeschkeit, H.; Willenberg, E. Der Furfuryloxycarbonyl-Rest, eine acidolytisch leicht abspaltbare N-Schutzgruppe für Peptidsynthesen. (The furfuryloxycarbonyl residue, an N-protective group for peptide synthesis readily cleaved by acidolysis.) Angew. Chem. 1964, 76, 271. Jeschkeit, H.; Losse, G.; Neubert, K. Peptidsynthesen mit den Furfuryloxycarbonylrest als Aminoschutzgruppe. (Peptide synthesis using the furfuryloxycarbonyl residue for protection of the amino group.) Chem. Ber. 1966, 99, 2803-2812.
22. Losse, G.; Jeschkeit, H.; Willenberg, E. Der Furfuryloxycarbonyl-Rest, eine acidolytisch leicht abspaltbare N-Schutzgruppe für Peptidsynthesen. (The furfuryloxycarbonyl residue, an N-protective group for peptide synthesis readily cleaved by acidolysis.) Angew. Chem. 1964, 76, 271. Jeschkeit, H.; Losse, G.; Neubert, K. Peptidsynthesen mit den Furfuryloxycarbonylrest als Aminoschutzgruppe. (Peptide synthesis using the furfuryloxycarbonyl residue for protection of the amino group.) Chem. Ber. 1966, 99, 2803-2812.
23. Bláha, K.; Rudinger, J. Amino acids and peptides. XLVII. Rates of fission of some substituted benzyloxycarbonylglycines and two heterocyclic analogues with hydrogen bromide in acetic acid. Collect. Czech. Chem. Commun. 1965, 30, 585-598.
24. 6-substituted guanine derivatives as antitumor agents. Int. Pat. Appl. WO 94/29312, 1994; Chem. Abstr. 1995, 122, 239458e.
25. (a) Bowles, W. A.; Schneider, F. H.; Lewis, L. R.; Robins, R. K. Synthesis and antitumor activity of 9-(tetrahydro-2-furyl)purine analogues of biologically important deoxynucleosides. J. Med. Chem. 1963, 6, 471-480.
26. 6 to C-8 in the guanine series. J. Am. Chem. Soc. 1973, 95, 7174-7175.
27. 2-methyl derivatives. J. Org. Chem. 1969, 34, 2160-2163.
28. (a) Spassova, M.; Dvoráková, H.; Holy, A.; Budesínky, M.; Masojídková, M. Synthesis of N-(3-azido-2-hydroxypropyl), N-(3-phthalimido-2-hydroxypropyl) and N-(3-amino-2-hydroxypropyl) derivatives of heterocyclic bases. Collect. Czech. Chem. Commun. 1994, 59, 1153-1174.
29. 2-benzylguanine in the reaction of 2-amino-6-chloropurine with sodium benzyloxide, and benzylation of nucleic acid bases. Chem. Pharm. Bull. 1996, 44, 1395-1399.
30. McCoss, M.; Chen, A.; Tolman, R. L. Synthesis of the chiral acyclonucleoside antiherpetic agent (S)-9-(2,3-dihydroxy-1-propoxymethyl)guanine. Tetrahedron Lett. 1985, 26, 1815-1818.
31. Kiburis, J.; Lister, J. H. Nucleophilic displacement of the trimethylammonio-group as a new route to fluoropurines. J. Chem. Soc. C 1971, 3942-3947.
32. Lembicz, N. K.; Grant, S.; Clegg, W.; Griffin, R. J.; Heath, S. L.; Golding, B. T. Facilitation of displacements at the 6-position of purines by the use of 1,4-diazabicyclo[2.2.2]octane as leaving group. J. Chem. Soc., Perkin Trans. 1 1997, 185-186.
33. Linn, J. A.; McLean, E. W.; Kelley, J. L. 1,4-Diazabicyclo[2.2.2]-octane (DABCO) - catalysed hydrolysis and alcoholysis reactions of 2-amino-9-benzyl-6-chloro-9H-purine. J. Chem. Soc., Chem. Commun. 1994, 913-914.
34. Fallab, S. Über Thiazolyl-(5)-carbinol. (On Thiazolyl-5-carbinol.) Helv. Chim. Acta 1952, 35, 215-216.
35. Cama, L. D.; Wildonger, K. J.; Guthikonda, R.; Ratcliffe, R. W.; Christensen, B. G. Total synthesis of thienamycin analogs. III. Tetrahedron 1983, 39, 2531-2549.
36. Ziegler, F. E.; Sweeny, J. G. Synthetic studies related to the yohimbine alkaloids. J. Org. Chem. 1969, 34, 3545-3548.
37. De Wet, C. R.; De Villiers, P. A. New synthesis of 2-hydroxyisonicotinic acid and its ethyl ester. Tydskr. Natuurwet. 1974, 14, 70-72; Chem. Abstr. 1976, 84, 30822w.
38. De Wet, C. R.; De Villiers, P. A. New synthesis of 2-hydroxyisonicotinic acid and its ethyl ester. Tydskr. Natuurwet. 1974, 14, 70-72; Chem. Abstr. 1976, 84, 30822w.
39. Kelly, T. R.; Howard, H. R.; Koe, B. K.; Sarges, R. Synthesis and dopamine autoreceptor activity of a 5-(methylmercapto)-methyl-substituted derivative of (±)-3-PPP (3-(3-hydroxyphenyl)-1-n-propylpiperidine). J. Med. Chem. 1985, 28, 1368-1371.
40. Kauffmann, T.; Fischer, H. Hetarine,XVI. Seitenkettencyclisierung bei 3,4-Dehydropyridin-Derivaten. (Side chain cyclization in 3,4-dehydropyridine derivatives.) Chem. Ber. 1973, 106, 220-227.
41. Hamana, M.; Yamazaki, M. Tertiary amine oxides. IX. Reaction of 2-substituted pyridine-1-oxides with acetic anhydride. J. Pharm. Soc. Jpn. 1961, 81, 574-578; Chem. Abstr. 1961, 55, 24743.
42. Hamana, M.; Yamazaki, M. Tertiary amine oxides. IX. Reaction of 2-substituted pyridine-1-oxides with acetic anhydride. J. Pharm. Soc. Jpn. 1961, 81, 574-578; Chem. Abstr. 1961, 55, 24743.
43. Dallacker, F.; Fechter, P.; Mues, V. 1,3-Dioxolohetarenes, 3. Preparation and reactions of pyrido [2,3-d]- and pyrido[3,4-d]-[1,3]dioxoles. Z. Naturforsch. 1979, 34b, 1729-1736. This paper is not recorded in Chem. Abstr. but is quoted in Dallacker, F.; Jouck, W. Derivatives of 1,3-benzdioxoles, 53. Z. Naturforsch. 1984, 35b, 1598-1606; Chem. Abstr. 1985, 102, 166561h.
44. Dallacker, F.; Fechter, P.; Mues, V. 1,3-Dioxolohetarenes, 3. Preparation and reactions of pyrido [2,3-d]- and pyrido[3,4-d]-[1,3]dioxoles. Z. Naturforsch. 1979, 34b, 1729-1736. This paper is not recorded in Chem. Abstr. but is quoted in Dallacker, F.; Jouck, W. Derivatives of 1,3-benzdioxoles, 53. Z. Naturforsch. 1984, 35b, 1598-1606; Chem. Abstr. 1985, 102, 166561h.
45. Dallacker, F.; Fechter, P.; Mues, V. 1,3-Dioxolohetarenes, 3. Preparation and reactions of pyrido [2,3-d]- and pyrido[3,4-d]-[1,3]dioxoles. Z. Naturforsch. 1979, 34b, 1729-1736. This paper is not recorded in Chem. Abstr. but is quoted in Dallacker, F.; Jouck, W. Derivatives of 1,3-benzdioxoles, 53. Z. Naturforsch. 1984, 35b, 1598-1606; Chem. Abstr. 1985, 102, 166561h.
46. Dallacker, F.; Fechter, P.; Mues, V. 1,3-Dioxolohetarenes, 3. Preparation and reactions of pyrido [2,3-d]- and pyrido[3,4-d]-[1,3]dioxoles. Z. Naturforsch. 1979, 34b, 1729-1736. This paper is not recorded in Chem. Abstr. but is quoted in Dallacker, F.; Jouck, W. Derivatives of 1,3-benzdioxoles, 53. Z. Naturforsch. 1984, 35b, 1598-1606; Chem. Abstr. 1985, 102, 166561h.
47. Trofimenko, S. Dihalomalonaldehydes. J. Org. Chem. 1963, 28, 3243-3245.
48. Sawhney, I.; Wilson, J. R. H. Preparation of 5-(benzoylmethyl)-thiazoles and related compounds as agrochemical fungicides. Eur. Pat. Appl. EP 395,174, 1990; Chem. Abstr. 1991, 114, 143410s.
49. Hagen, H.; Markert, J.; Ziegler, H. 1,2-Benzisothiazoles. Ger. Pat. DE 3,018,108, 1981; Chem. Abstr. 1982, 96, 68980g. The reaction in dimethylformamide at 70 °C proceeds very satisfactorily without an autoclave; cf. Markert, J.; Hagen, H. Preparation of 1,2-benzisothiazoles and some secondary reactions. Liebigs Ann. Chem. 1980, 768-778.
50. Hagen, H.; Markert, J.; Ziegler, H. 1,2-Benzisothiazoles. Ger. Pat. DE 3,018,108, 1981; Chem. Abstr. 1982, 96, 68980g. The reaction in dimethylformamide at 70 °C proceeds very satisfactorily without an autoclave; cf. Markert, J.; Hagen, H. Preparation of 1,2-benzisothiazoles and some secondary reactions. Liebigs Ann. Chem. 1980, 768-778.
51. Adams, A.; Slack, R. Isothiazole: a new mononuclear heterocyclic system. J. Chem. Soc. 1959, 3061-3072.
52. Hatanaka, M.; Ishimaru, T. Synthetic penicillins. Heterocyclic analogs of ampicillin. Structure - activity relationships. J. Med. Chem. 1973, 16, 978-984.
53. Maquestiau, A.; Flammang, R.; Ben Abdelouahab, F.-B. Flash-vacuum pyrolysis of 1,2,4-triazolides: a new synthesis of functionalized azoles. Heterocycles 1989, 29, 103-114.
54. Wolf, F. J.; Weijlard, J. n-Butyl glyoxylate. Organic Syntheses; John Wiley: New York, 1963; Coll. Vol. 4, pp 124-125.
55. Van Leusen, A. M.; Hoogenboom, B. E.; Siderius, H. A novel and efficient synthesis of oxazoles from tosylmethyl isocyanide and carbonyl compounds. Tetrahedron Lett. 1972, 2369-2372.
56. Kende, A. S.; Kawamura, K.; DeVita, R. J. Enantioselective total synthesis of neooxazolomycin. J. Am. Chem. Soc. 1990, 112, 4070-4072.
57. Panizzi, L. Investigations of β-dialdehydes. I. Carbethoxymalonaldehyde. Gazz. Chim. Ital. 1946, 76, 56-65. Panizzi, L. Heterocyclic syntheses. VIII. 4-Isoxazolecarboxylic acid and its isomers. Gazz. Chim. Ital. 1947, 77, 206-214; Chem. Abstr. 1946, 40, 7163-7164; 1948, 42, 903-904.
58. Panizzi, L. Investigations of β-dialdehydes. I. Carbethoxymalonaldehyde. Gazz. Chim. Ital. 1946, 76, 56-65. Panizzi, L. Heterocyclic syntheses. VIII. 4-Isoxazolecarboxylic acid and its isomers. Gazz. Chim. Ital. 1947, 77, 206-214; Chem. Abstr. 1946, 40, 7163-7164; 1948, 42, 903-904.
59. Panizzi, L. Investigations of β-dialdehydes. I. Carbethoxymalonaldehyde. Gazz. Chim. Ital. 1946, 76, 56-65. Panizzi, L. Heterocyclic syntheses. VIII. 4-Isoxazolecarboxylic acid and its isomers. Gazz. Chim. Ital. 1947, 77, 206-214; Chem. Abstr. 1946, 40, 7163-7164; 1948, 42, 903-904.
60. Panizzi, L. Investigations of β-dialdehydes. I. Carbethoxymalonaldehyde. Gazz. Chim. Ital. 1946, 76, 56-65. Panizzi, L. Heterocyclic syntheses. VIII. 4-Isoxazolecarboxylic acid and its isomers. Gazz. Chim. Ital. 1947, 77, 206-214; Chem. Abstr. 1946, 40, 7163-7164; 1948, 42, 903-904.
61. Kusumi, T.; Chang, C. C.; Wheeler, M.; Kubo, I.; Nakanishi, K. Isolation, structure and synthesis of 4-hydroxyisoxazole (triumferol), a seed germination inhibitor from an African plant. Tetrahedron Lett. 1981, 22, 3451-3454.
62. Kirchlechner, R.; Casutt, M.; Heywang, U.; Schwarz, M. W. New synthesis of 1,5-disubstituted imidazoles. Synthesis 1994, 247-248.
63. Link, H.; Bernauer, K. Über die Synthese der Pilocarpus-Alkaloide Isopilosin und Pilocarpin, sowie die absolute Konfiguration des (+)-Isopilosins. (Synthesis of the Pilocarpus alkaloids isopilosine and pilocarpine, and the absolute configuration of (+)-isopilosine.) Helv. Chim. Acta 1972, 55, 1053-1062.
64. 4-triheterapentalenes from isothiazole-5-carbaldehyde. J. Chem. Soc., Perkin Trans. 1 1979, 2340-2345.
65. Doyle, F. P.; Mehta, M. D.; Sach, G. S.; Pearson, J. L. Pharmacodynamic compounds. Part I. Some antispasmodics derived from substituted 2-pyrrolidinylalkanols. J. Chem. Soc. 1958, 4458-4466.
66. 6-alkylguanine-DNA-alkyltransferase cDNA in human cells and transgenic mice. Nucleic Acids Res. 1990, 18, 5723-5727.
67. 6-alkylguanine-DNA-alkyltransferase. Nucleic Acids Res. 1990, 18, 13-16.
68. 6-alkylguanine-DNA-alkyltransferase. Nucleic Acids Res. 1990, 18, 13-16.
69. 6-alkylguanine alkyltransferase activity in Chinese hamster V79 cells following selection with chloroethylating agents. Carcinogenesis (London) 1988, 9, 45-49.