Towards species-specific antifolates

Current Medicinal Chemistry

Volumn 13, Issue 4, 2006, Pages 377-398

  Chan, D C M ^a   Anderson, Amy C ^a  

^a Dartmouth College   (United States)

Author keywords

Antifolate; DHFR; Plasmodium; Pneumocystis; Pteridine; Pyrimethamine; Pyrimidine; Trimethoprim

Indexed keywords

ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTIMALARIAL AGENT; ANTINEOPLASTIC AGENT; ANTIPARASITIC AGENT; CHLOROQUINE; COTRIMOXAZOLE; CYCLOGUANIL; DIHYDROFOLATE REDUCTASE; DIHYDROFOLATE REDUCTASE INHIBITOR; EPIROPRIM; FANSIDAR; FOLIC ACID ANTAGONIST; FURO[2,3 D]PYRIMIDINE DERIVATIVE; ICLAPRIM; METHOTREXATE; PTERIDINE DERIVATIVE; PURINE DERIVATIVE; PYRIDO[2,3 D]PYRIMIDINE DERIVATIVE; PYRIMETHAMINE; PYRIMETHAMINE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRROLO[2,3 D]PYRIMIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE; QUININE; THIENO[2,3 D]PYRIMIDINE DERIVATIVE; TRIAZINE DERIVATIVE; TRIMETHOPRIM; TRIMETREXATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; DRUG DERIVATIVE;

ANTIBIOTIC RESISTANCE; BIOCHEMISTRY; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG TARGETING; ENZYME STRUCTURE; MALARIA FALCIPARUM; NONHUMAN; PLASMODIUM FALCIPARUM; PNEUMOCYSTIS JIROVECI; PNEUMOCYSTIS PNEUMONIA; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REVIEW; SEQUENCE ALIGNMENT; SPECIES DIFFERENCE; AMINO ACID SEQUENCE; ANIMAL; CHEMISTRY; ENZYMOLOGY; GENETICS; HUMAN; METABOLISM; MOLECULAR GENETICS; PNEUMOCYSTIS CARINII;

AMINO ACID SEQUENCE; ANIMALS; ANTIMALARIALS; DRUG DESIGN; FOLIC ACID ANTAGONISTS; HUMANS; MOLECULAR SEQUENCE DATA; PLASMODIUM FALCIPARUM; PNEUMOCYSTIS CARINII; PTERIDINES; PYRIMETHAMINE; PYRIMIDINES; SEQUENCE ALIGNMENT; SPECIES SPECIFICITY; TETRAHYDROFOLATE DEHYDROGENASE; TRIMETHOPRIM; TRIMETREXATE;

EID: 33644868469     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986706775527938     Document Type: Review

References (168)

1. Helweg-Larsen, J. Dan. Med. Bull. 2004, 51, 251-273.
2. Thomas, C.; Limper, A. New Engl. J. Med. 2004, 350, 2487-2498.
3. Allegra, C. J.; Kovacs, J. A.; Drake, J. C.; Swan, J. C.; Chabner, B, A.; Masur, H. J. Exp. Med. 1987, 165, 926-931.
4. Kovacs, J. A.; Hiemenz, J. W.; Macher, A. M.; Stover, D.; Murray, H. W.; Shelhamer, J.; Lane, H. C.; Urmacher, C.; Honig, C.; Longo, D. L.; Parker, M. W.; Natanson, C.; Parrillo, J. E.; Fauci, A. S.; Pizzo, P. A.; Masur, H. Ann. Int. Med. 1984, 100, 663-671.
5. Ma, L.; Borio, L.; Masur, H.; Kovacs, J. J. Inf. Dis. 1999, 180, 1969-1978.
6. Nahimana, A.; Rabodonirina, M.; Bille, J.; Francioli, P.; Hauser, P. M. Antimicrob. Agents Ch. 2004, 48, 4301-4305.
7. CDC Malaria Facts. http://www.cdc.gov/malaria/facts.htm
8. Fidock, D. A.; Rosenthal, P. J.; Croft, S. L.; Brun, R.; Nwaka, S. Nat. Rev. Drug Disc. 2004, 3, 509-520.
9. Gregson, A.; Plowe, C. V. Pharm. Rev. 2005, 57, 117-145.
10. Kongsaeree, P.; Khongsuk, P.; Leartsakulpanich, U.; Chitnumsub, P.; Tarnchompoo, B.; Walkinshaw, M.; Yuthavong, Y. Proc. Natl. Acad. Sci. 2005, 102, 13046-13051.
11. Schwartz, I.; Lackrtiz, E.; Patchen, L. New Engl. J. Med. 1991, 324, 927.
12. Schuurkamp, G.; Spiener, P.; Karen, R.; Bulungol, P. Trans R. Soc. Trop. Med. Hyg. 1989, 83, 607.
13. Miller, L.; Baruch, D.; Marsh, K.; Doumbo, O. Nature 2002, 415, 673-679.
14. Sachs, J.; Malaney, P. Nature 2002, 415, 680-685.
15. Ridley, R. Nature 2002, 415, 686-693.
16. Richie, T.; Saul, A. Nature 2002, 415, 694-701.
17. Hoffman, S.; Subramanian, G.; Collins, F.; Venter, J. Nature 2002, 415, 702-709.
18. Rogers, D.; Randolph, S.; Snow, R.; Hay, S. Nature 2002, 415, 710-715.
19. Hentschel, C. Nature 2002, 415, 715.
20. Le Bras, J.; Durand, R. Fund. Clin. Pharm. 2003, 17, 147-153.
21. Yuthavong, Y. Microbes Infec. 2002, 4, 175-182.
22. Yuthavong, Y.; Yuvaniyama, J.; Chitnumsub, P.; Vanichtanankul, J.; Chusacultanachai, S.; Tarnchompoo, B.; Vilaivan, T.; Kamchonwongpaisan, S. Parasitology 2005, 130, 249.
23. Sibley, C. H.; Hyde, J. E.; Sims, P. F. G.; Plowe, C. V.; Kublin, J. G.; Mberu, E. K.; Cowman, A. F.; Winstanley, P. A.; Watkins, W. M.; Nzila, A. M. Trends Parasitol 2001, 17, 582-588.
24. Winstanley, P. A. Parasitol. Today 2000, 16, 146-153.
25. Kisliuk, R. The biochemistry of folates. In Folate Antagonist as Therapeutic Agents: Sirotnak, F.; Burchall, J.; Ensminger, W.; Montgomery, J., Eds., Academic Press Inc.: London, 1984; Vol. 1, pp. 1-68.
26. MacKenzie, R. Biogenesis and interconversion of substituted tetrahydrofolates. In Folates and Pterins: Blakley, R.; Benkovic, S., Eds., John Wiley & Sons Inc.: New York, 1984; Vol. 1, pp 255-306.
27. Kovacs, J.; Allegra, C.; Beaver, J.; Boarman, D.; Lewis, M.; Parrillo, J.; Chabner, B.; Masur, H. J. Infect. Dis. 1989, 160, 312-319.
28. Warhurst, D. C. Drug Disc. Today 1998, 3, 538-546.
29. Rosowsky, A. Prog. Med. Chem. 1989, 26, 1-252.
30. Feeney, J. Angew. Ch. Int. Ed. 2000, 39, 290-312.
31. McGuire, J. J. Curr. Pharm. Des. 2003, 9, 2593-2613.
32. Gangjee, A.; Jain, H. Curr. Med. Chem. Anti-Canc. Agents, 2004, 4, 405.
33. Then, R. L. J. Chemotherapy 2004, 16, 3.
34. Kompis, I. M.; Islam, K.; Then, R. L. Chem. Rev. 2005, 105, 593.
35. Anderson, A. C. Drug Disc. Today 2005, 10, 121.
36. Howell, E. E. ChemBioChem 2005, 6, 590-600.
37. Cody, V.; Chisum, K.; Pope, C.; Queener, S. F. Protein Expres. Purif. 2005, 40, 417.
38. Santos-Filho, O.; de Alencastro, R.; Figueroa-Villar, J. Biophys. Chem. 2001, 91, 305-317.
39. Delfino, R.; Santos, O.; Figueroa-Villar, J. Biophys. Chem. 2002, 98, 287-300.
40. Southerland, W. M. J. Comput-Aid. Mol. Des. 1994, 8, 113-122.
41. Rosowsky, A.; Cody, V.; Galitsky, N.; Fu, H. N.; Papoulis, A. T.; Queener, S. F. J. Med. Chem. 1999, 42, 4853-4860.
42. Wang, Y.; Bruenn, J.; Queener, S.; Cody, V. Antimicrob. Agents Ch. 2001, 45, 2517-2523.
43. Champness, J.; Achari, A.; Ballantine, S.; Bryant, P.; Delves, C.; Stammers, D. Structure 1994, 2, 915-924.
44. Cody, V.; Galitsky, N.; Luft, J.; Pangborn, W.; Gangjee, A.; Devraj, R.; Queener, S.; Blakley, R. Acta Cryst. 1997, D53, 638-649.
45. Cody, V.; Galitsky, N.; Rak, D.; Luft, J.; Pangborn, W.; Queener, S. Biochemistry 1999, 38, 4303-4312.
46. Cody, V.; Chan, D.; Galitsky, N.; Rak, D.; Luft, J.; Pangborn, W.; Queener, S. F.; Laughton, C.; Stevens, M. Biochemistry 2000, 39, 3556-3564.
47. Cody, V.; Galitsky, N.; Luft, J. R.; Pangborn, W.; Blakley, R.; Gangjee, A. Anti-Cancer Drug Des. 1998, 13, 307-315.
48. Cody, V.; Galitsky, N.; Luft, J. R.; Pangborn, W.; Queener, S. F.; Gangjee, A. Acta Cryst. 2002, D58, 1393.
49. Cody, V.; Galitsky, N.; Luft, J.; Pangborn, W.; Rosowsky, A.; Queener, S. Acta Cryst. 2002, D58, 946.
50. Cody, V.; Luft, J. R.; Pangborn, W.; Gangjee, A.; Queener, S. F. Acta Cryst. 2004, D60, 646.
51. Cody, V.; Luft, J. R.; Pangborn, W. Acta Cryst. 2005, D61, 147.
52. Cody, V.; Galitsky, N.; Luft, J. R.; Pangborn, W.; Gangjee, A. Acta Cryst. 2003, D59, 654.
53. Cody, V.; Galitsky, N.; Luft, J. R.; Pangborn, W.; Rosowsky, A.; Blakley, R. L. Biochemistry 1997, 36, 13897-13903.
54. Lewis, W. S.; Cody, V.; Galitsky, N.; Luft, J. R.; Pangborn, W.; Chunduru, S. K.; Spencer, H. T.; Appleman, J. R.; Blakley, R. L. J. Biol. Chem. 1995, 270, 5057-5064.
55. Gangjee, A.; Vidwans, A.; Vasudevan, A.; Queener, S.; Kisliuk, R.; Cody, V.; Li, R.; Galitsky, N.; Luft, J.; Pangborn, W. J. Med. Chem. 1998, 41, 3426-3434.
56. Klon, A. E.; Heroux, A.; Ross, L. J.; Pathak, V.; Johnson, C. A.; Piper, J. R.; Borhani, D. W. J. Mol Biol. 2002, 320, 677-693.
57. Davies, J. F.; Delcamp, T. J.; Prendergast, N. J.; Ashford, V. A.; Freisheim, J. H.; Kraut, J. Biochemistry 1990, 29, 9467-9479.
58. Oefner, C.; Darcy, A.; Winkler, F. K. Eur. J. Biochem. 1988, 174, 377-385.
59. Yuvaniyama, J.; Chitnumsub, P.; Kamchonwongpaisan, S.; Vanichtanankul, J.; Sirawaraporn, W.; Taylor, P.; Walkinshaw, M. D.; Yuthavong, Y. Nat. Struct. Biol. 2003, 10, 357-365.
60. Whitlow, M.; Howard, A. J.; Stewart, D.; Hardman, K. D.; Kuyper, L. F.; Baccanari, D. P.; Fling, M. E.; Tansik, R. L. J. Biol. Chem. 1997, 272, 30289-30298.
61. Whitlow, M.; Howard, A. J.; Stewart, D.; Hardman, K. D.; Chan, J. H.; Baccanari, D. P.; Tansik, R. L.; Hong, J. S.; Kuyper, L. F. J. Med. Chem. 2001, 44, 2928-2932.
62. Li, R. B.; Sirawaraporn, R.; Chitnumsub, P.; Sirawaraporn, W.; Wooden, J.; Athappilly, F.; Turley, S.; Hol, W. G. J. J. Mol. Biol. 2000, 295, 307-323.
63. O'Neil, R. H.; Lilien, R. H.; Donald, B. R.; Stroud, R. M.; Anderson, A. C. J. Biol. Chem. 2003, 278, 52980.
64. Anderson, A. C. Acta Cryst. 2005, F61, 258-262.
65. Berman, H.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T.; Weissig, H.; Shindyalov, I.; Bourne, P. Nucleic Acids Res. 2000, 28, 235-242.
66. Bairoch, A.; Apweiler, R.; Wu, C.; Barker, W.; Boeckmann, B.; Ferro, S.; Gasteiger, E.; Huang, H.; Lopez, R.; Magrane, M.; Martin, M.; Natale, D.; O'Donovan, C.; Redaschi, N.; Yeh, L. Nucleic Acids Res. 2005, 33, D154-159.
67. Thompson, J. D.; Gibson, T. J.; Plewniak, F.; Jeanmougin, F.; Higgins, D. G. Nucleic Acids Res. 1997, 25, 4876-4882.
68. Gouet, P.; Courcelle, E.; Stuart, D. I.; Metoz, F. Bioinformatics 1999, 15, 305-308.
69. Queener, S. F. J. Med. Chem. 1995, 38, 4739-4759.
70. Fishman, J. A. Antimicrob. Agents Ch. 1998, 42, 995-1004.
71. Fishman, J. A. Antimicrob. Agents Ch. 1998, 42, 1309-1314.
72. Gangjee, A.; Elzein, E.; Kothare, M.; Vasudevan, A. Curr. Pharm. Des. 1996, 2, 263-280.
73. Rosowsky, A.; Hynes, J. B.; Queener, S. F. Antimicrob. Agents Ch. 1995, 39, 79-86.
74. Locher, H.; Sclunegger; H.; Hartman, P.; Angehrn, P.; Then, R. Antimicrob. Agents Ch. 1996, 40, 1376-1381.
75. Stevens, M.; Phillip, K.; Rathbone, D.; O'Shea, D.; Queener, S.; Schwalbe, C.; Lambert, P. J. Med. Chem. 1997, 40, 1886-1893.
76. Robson, C.; Meek, M. A.; Grunwaldt, J. D.; Lambert, P. A.; Queener, S. F.; Schmidt, D.; Griffin, R. J. J. Med. Chem. 1997, 40, 3040-3048.
77. Masciadri, R. Diamino Pyrimidines. 5,773,446, 30 June, 1998.
78. Rosowsky, A.; Queener, S.; Cody, V. Drug Des. Disc. 1999, 16, 25-40.
79. Rosowsky, A.; Papoulis, A.; Queener, S. J. Heterocyclic Chem. 1999, 36, 723-728.
80. Chan, D.; Laughton, C.; Queener, S.; Stevens, M. J. Med. Chem. 2001, 44, 2555-2564.
81. Chan, D.; Laugh ton, C.; Queener, S.; Stevens, M. Bioorg. Med. Chem. 2002, 10, 3001.
82. Rosowsky, A.; Forsch, R.; Queener, S. J. Med. Chem. 2002, 45, 233.
83. Rosowsky, A.; Forsch, R.; Queener, S. J. Med. Chem. 2003, 46, 1726.
84. Rosowsky, A.; Forsch, R.; Sibley, C.; Inderlied, C.; Queener, S. J. Med. Chem. 2004, 47, 1475.
85. Forsch, R.; Queener, S.; Rosowsky, A. Bioorg. Med. Chem. Lett. 2004, 14, 1811.
86. Chan. D.; Fu, H.; Forsch, R.; Queener, S.; Rosowsky, A. J. Med. Chem. 2005, 48, 4420-4431.
87. Jackson, H. C.; Biggadike, K.; McKilligin, E.; Kinsman, O.; Queener, S. F.; Lane, A.; Smith, J. E. Antimicrob. Agents Ch. 1996, 40, 1371-1375.
88. Piper, J: R.; Johnson, C. A.; Krauth, C. A.; Carter, R. L.; Hosmer, C. A.; Queener, S. F.; Borotz, S. E.; Pfefferkorn, E. R. J. Med. Chem. 1996, 39, 1271-1280.
89. Rosowsky, A.; Forsch, R.; Queener, S.; Bertino, J. Pteridines 1997, 8, 173-187.
90. Rosowsky, A.; Fu, H.; Chan, D.; Queener, S. J. Med. Chem. 2004, 47, 2475.
91. Rosowsky, A.; Papoulis, A.; Queener, S. J. Med. Chem. 1998, 41, 913-918.
92. Gangjee, A.; Zhu, Y.; Queener, S. J. Med. Chem. 1998, 41, 4533-4543.
93. Gangjee, A.; Zhu, Y.; Queener, S. F.; Francom, P.; Broom, A. D. J. Med. Chem. 1996, 39, 1836-1845.
94. Gangjee, A.; Vasudevan, A.; Queener, S.; Kisliuk, R. J. Med. Chem. 1996, 39, 1438-1446.
95. Gangjee, A.; Devraj, R.; Queener, S. J. Med. Chem. 1997, 40, 470-478.
96. Gangjee, A.; Vasudevan, A.; Queener, S. F. J. Med. Chem. 1997, 40, 479-485.
97. Gangjee, A.; Adair, O.; Queener, S. J. Med. Chem. 1999, 42, 2447-2455.
98. Rosowsky, A.; Fu, H.; Queener, S. J. Heterocyclic Chem. 2000, 37, 921-926.
99. Gangjee, A.; Mavandadi, F.; Queener, S. F. J. Med. Chem. 1997, 40, 1173-1177.
100. Rosowsky, A.; Fu, H.; Queener, S. J. Heterocyclic Chem. 2001, 38, 1197-1202.
101. Rosowsky, A.; Mota, C.; Queener, S. J. Heterocyclic Chem. 1996, 33, 1959-1966.
102. Rosowsky, A.; Papoulis, A.; Queener, S. J. Med. Chem. 1997, 40, 3694-3699.
103. Donkor, I. O.; Li, H.; Queener, S. F. Eur. J. Med. Chem. 2003, 38, 605-611.
104. Gangjee, A.; Vasudevan, A.; Queener, S. F. J. Med. Chem. 1997, 40, 3032-3039.
105. Gangjee, A.; Elzein, E.; Queener, S.; McGuire, J. J. Med. Chem. 1998, 41, 1409-1416.
106. Gangjee, A.; Guo, X.; Queener, S.; Cody, V.; Galitsky, N.; Luft, J.; Pangborn, W. J. Med. Chem. 1998, 41, 1263-1271.
107. Wahid, F.; Monneret, C.; Dauzonne, D. Chem. Pharm. Bull. 1999, 47, 156-164.
108. Donkor, I.; Devraj, R.; Queener, S.; Barrows, L.; Gangjee, A. J. Heterocyclic Chem. 1996, 33, 1653-1661.
109. Rosowsky, A.; Papoulis, A.; Forsch, R.; Queener, S. J. Med. Chem. 1999, 42, 1007-1017.
110. Graffner-Nordberg, M.; Kolmodin, K.; Åqvist, J.; Queener, S. F.; Hallberg, A. J. Med. Chem. 2001, 44, 2391-2402.
111. Rosowsky, A.; Chen, H., Fu, H. M.; Queener, S. F. Bioorg. Med. Chem. 2003, 11, 59-67.
112. Graffner-Nordberg, M.; Kolmodin, K.; Åqvist, J.; Queener, S. F.; Hallberg, A. Eur. J. Pharm. Sci. 2004, 22, 43.
113. Gangjee, A.; Shi, J. F.; Queener, S. F. J. Med. Chem. 1997, 40, 1930-1936.
114. DeLano, W. The PyMOL Molecular Graphics System, San Carlos, CA, USA, 2002.
115. Gschwend, D. A.; Sirawaraporn, W.; Santi, D. V.; Kuntz, I. D. Proteins 1997, 29, 59-67.
116. Mattioni, B. E.; Jurs, P. C. J. Mol. Graph. Model. 2003, 21, 391-419.
117. Sutherland, J.; Weaver, D. J. Comput-Aid. Mol. Des. 2004, 18, 309.
118. Gangjee, A.; Lin, X. J. Med. Chem. 2005, 48, 1448.
119. Then, R. L.; Hartman, P. G.; Kompis, I.; Santi, D. Selective Inhibition of Dihydrofolate Reductase from Problem Human Pathogens. In Chemistry and Biology of Pteridines and Folates: Ayling, J. E., Ed. Plenum Press: New York, 1993; pp. 533-536.
120. Broughton, M. C.; Queener, S. F. Antimicrob. Agents Ch. 1991, 35, 1348-1355.
121. Schneider, P.; Hawser, S.; Islam, K. Bioorg. Med. Chem. Lett. 2003, 13, 4217-4221.
122. Arpida, Arpida Granted IND for Oral Iclaprim from US FDA. In 2005.
123. Sorbera, L. A.; Castañer, J.; Rabasseda, X. Drug Future 2004, 29, 220-225.
124. Kuyper, L. F.; Roth, B.; Baccanari, D. P.; Ferone, R.; Beddell, C. R.; Champness, J. N.; Stammers, D. K.; Dann, J. G.; Norrington, F. E. A.; Baker, D. J.; Goodford, P. J. J. Med. Chem. 1982, 25, 1120-1122.
125. Kuyper, L. F.; Roth, B.; Baccanari, D. P.; Ferone, R.; Beddell, C. R.; Champness, J. N.; Stammers, D. K.; Dann, J. G.; Norrington, F. E.; Baker, D. J.; Goodford, P. J. J. Med. Chem. 1985, 28, 303-311.
126. Gangjee, A.; Lin, X.; Queener, S. F. J. Heterocyclic Chem. 2003, 40, 507-512.
127. Queener, S. F. J. Protozool. 1991, 38, 154S-157S.
128. Preussmann, R.; Druckrey, H.; Ivankovic, S.; Hodenberg, A. V. Ann. New York Acad. Sci. 1969, 163, 697-714.
129. Stevens, M. F. G.; Griffin, R. J.; Wong, S. K. Anti-Cancer Drug Des. 1987, 2, 311-318.
130. Bliss, E. A.; Griffin, R. J.; Stevens, M. F. G. J. Chem. Soc. Perk. T1 1987, 1, 2217-2228.
131. Queener, S. F.; Bartlett, M. S.; Jay, M. A.; Durkin, M. M.; Smith, J. W. Antimicrob. Agents Ch. 1987, 31, 1323-1327.
132. Rosowsky, A.; Chen, H. J. Org. Chem. 2001, 66, 7522-6.
133. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belewm, R. K.; Olson, A. J. J. Comput. Chem. 1998, 19, 1639-1662.
134. Grivsky, E. M.; Lee, S.; Sigel, C. W.; Duch, D. S.; Nichol, C. A. J. Med. Chem. 1980, 23, 327-329.
135. Elslager, E. F.; Johnson, J. L.; Werbel, L. M. J. Med. Chem. 1983, 26, 1753-1760.
136. Zink, M.; Lanig, H.; Troschütz, R. Eur. J. Med. Chem. 2004, 39, 1079-1088.
137. Gangjee, A.; Adair, O.; Queener, S. J. Med. Chem. 2003, 46, 5074.
138. Gangjee, A.; Adair, O.; Queener, S. Bioorg. Med. Chem. 2001, 9, 2929-35.
139. Piper, J. R.; Johnson, C. A.; Hosmer, C. A.; Carter, R. L.; Pfefferkorn, E. R.; Borotz, S. E.; Queener, S. F. Lipophilic Antifolates as Candidates against Opportunistic Infections. In Chemistry and Biology of Pteridines and Folates: Ayling, J. E., Ed. Plenum Press: New York, 1993.
140. Gangjee, A.; Vidwans, A.; Elzein, E.; McGuire, J.; Queener, S.; Kisliuk, R.J. Med. Chem. 2001, 44, 1993-2003.
141. Gangjee, A.; Lin, X.; Queener, S. F. J. Med. Chem. 2004, 47, 3689.
142. Gangjee, A.; Jain, H.; Queener, S. J. Heterocyclic Chem. 2005, 42, 589-594.
143. Bzik, D.J.; Li, W.-B.; Horii, T.; Inselburg, J. Proc. Natl. Acad. Sci. 1987, 84, 8360-8364.
144. Lemcke, T.; Cristensen, I. T.; Jorgensen, F. S. Bioorg. Med. Chem. 1999, 7, 1003- 1011.
145. Sirawaraporn, W.; Sathitkul, T.; Sirawaraporn, R.; Yuthavong, Y.; Santi, D. Proc. Natl. Acad. Sci. 1997, 94, 1124-1129.
146. Sirawaraporn, W.; Sirawaraporn, R.; Yongiettrakul, S.; Anuwatwora, A.; Rastelli, G.; Kamchonwongpaisan, S.; Yuthavong, Y. Mol. Biochem. Parasitol. 2002, 121, 185-193.
147. Sirawaraporn, W.; Yongkiettrakul, S.; Sirawaraporn, R.; Yuthavong, Y.; Santi, D. Exp. Parasitol. 1997, 87, 245-252.
148. Sirawaraporn, W.; Prapunwattana, P.; Sirawaraporn, R.; Yuthavong, Y.; Santi, D. V. J. Biol. Chem. 1993, 268, 21637-21644.
149. Chitnumsub, P.; Yavaniyama, J.; Vanichtanankul, J.; Kamchonwongpaisan, S.; Walkinshaw, M. D.; Yuthavong, Y. Acta Cryst. 2004, D60, 780-783.
150. McKie, J.; Douglas, K.; Chan, C.; Roser, S.; Yates, R.; Read, M.; Hyde, J.; Dascombe, M.; Yuthavong, Y.; Sirawaraporn, W. J. Med. Chem. 1998, 41, 1367-1370.
151. Toy T.; Brobey, R.; Sano, G.; Horii, T.; Tomioka, N.; Itai, A. Biochem. Biophys. Res. Comm. 1997, 235, 515-519.
152. Reynolds, M. G.; Roos, D. S. J. Biol. Chem. 1998, 73, 3461-3469.
153. França, T. C. C.; de Medeiros, A. L. R.; dos Santos, E. C. P.; Santos, O. A.; Figueroa-Villar, J. D. J. Brazil. Chem. Soc. 2004, 15, 450-454.
154. Rasli, G.; Sirawaraporn, W.; Sompornpisut, P.; Vilaivan, T.; Kamchonwongpaisan, S.; Quarrell, R.; Lowe, G.; Thebtaranonth, Y.; Yuthavong, Y. Bioorg. Med. Chem. 2000, 8, 1117-1128.
155. Yuthavong, Y.; Vilaivan, T.; Chareonsethakul, N.; Kamchonwongpaisan, S.; Sirawaraporn, W.; Quarrell, R.; Lowe, G. J. Med. Chem. 2000, 43, 2738-2744.
156. Vilaivan, T.; Saesaengseerung, N.; Jarprung, D.; Kamchonwongpaisan, S.; Sirawaraporn, W.; Yuthavong, Y. Bioorg. Med. Chem. 2003, 11, 217-224.
157. Kamchonwongpaisan, S.; Quarrell, R.; Charoensetakul, N.; Ponsinet, R.; Vilaivan, T.; Vanichtanankul, J.; Tarnchompoo, B.; Sirawaraporn, W.; Lowe, G.; Yuthavong, Y. J. Med. Chem. 2004, 47, 673-680.
158. Sardarian, A.; Douglas, K.; Read, M.; Sims, P.; Hyde, J.; Chitnumsub, P.; Sirawaraporn, R.; Sirawaraporn, W. Org. Biomol. Chem. 2003, 1, 960-964.
159. Tarnchompoo, B.; Sirichaiwat, C.; Phupong, W.; Intaraudom, C.; Sirawaraporn, W.; Kamchonwongpaison, S.; Vanichtanankul, J.; Thebtaranonth, Y.; Yuthavong, Y. J. Med. Chem. 2002, 45, 1244-1252.
160. Sirichaiwat, C.; Intaraudom, C.; Kamchonwongpaisan, S.; Vanichtanankul, J.; Thebtaranonth, Y.; Yuthavong, Y. J. Med. Chem. 2004, 47, 345-354.
161. Rastelli, G.; Pacchioni, S.; Sirawaraporn, W.; Sirawaraporn, R.; Parenti, M.; Ferrari, A. J. Med. Chem. 2003, 46, 2834-2845.
162. Jensen, N. P.; Ager, A. L.; Bliss, R. A.; Canfield, C.J.; Kotecka, B. M.; Rieckmann, K. H.; Terpinski, J.; Jacobus, D. P. J. Med. Chem. 2001, 44, 3925-3931.
163. Shearer, T. W.; Kozar, M. P.; O'Neil, M. T.; Smith, P. L.; Schiehser, G. A.; Jacobus, D. P.; Diaz, D. S.; Yang, Y. S.; Millions, W. K.; Skillman, D. R. J. Med. Chem. 2005, 48, 2805-2813.
164. Agarwal, A.; Srivastava, K.; Puri, S. K.; Chauhan, P. M. S. Bioorg. Med. Chem. Lett. 2005, 15, 531-533.
165. Lee, H. K.; Rana, T. M. J. Comb. Chem. 2004, 6, 504-508.
166. Kidwai, M.; Mothsra, P.; Mohan, R.; Biswas, S. Bioorg. Med. Chem, Lett. 2005, 15, 915-917.
167. Parenti, M. D.; Pacchioni, S.; Ferrari, A. M.; Rastelli, G. J. Med. Chem. 2004, 47, 4258-4267.
168. Kamchonwongpaisan, S.; Vanichtanankul, J.; Tarnchompoo, B.; Yuvaniyama, J.; Taweechai, S.; Yuthavong, Y. Anal. Chem. 2005, 77, 1222-1227.