Design of novel hypoxia-targeting IDO hybrid inhibitors conjugated with an unsubstituted L-TRP as an IDO affinity moiety

Advances in Experimental Medicine and Biology

Volumn 662, Issue , 2010, Pages 415-421

  Nakashima, Hitomi ^a   Ikkyu, Kazuhiro ^a   Nakashima, Kouichiro ^a   Sano, Keiichiro ^a   Uto, Yoshihiro ^a   Nakata, Eiji ^a   Nagasawa, Hideko ^a   Sugimoto, Hiroshi ^a   Shiro, Yoshitsugu ^a   Nakagawa, Yoshinori ^a   Hori, Hitoshi ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 (1 OXIDO 1,2,4 BENZOTRIAZIN 3 YL)AMINOBUTYL N TERT BUTOXYCARBONYL 2 AMINO INDOLE 3 YL PROPANAMIDE; 4 (1,4 DIOXIDO 1,2,4 BENZOTRIAZIN 3 YL)AMINOBUTYL N TERT BUTOXYCARBONYL 2 AMINO INDOLE 3 YL PROPANAMIDE; 5 (1 OXIDO 1,2,4 BENZOTRIAZIN 3 YL)AMINOPENTYL N TERT BUTOXYCARBONYL 2 AMINO INDOLE 3 YL PROPANAMIDE; 5 (1,4 DIOXIDO 1,2,4 BENZOTRIAZIN 3 YL)AMINOPENTYL N TERT BUTOXYCARBONYL 2 AMINO INDOLE 3 YL PROPANAMIDE; INDOLEAMINE 2,3 DIOXYGENASE; INDOLEAMINE 2,3 DIOXYGENASE INHIBITOR; TX 2274; UNCLASSIFIED DRUG; UTX 2; UTX 3; UTX 4; ENZYME INHIBITOR; TIRAPAZAMINE; TRIAZINE DERIVATIVE; TRYPTOPHAN;

CONFERENCE PAPER; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BINDING; DRUG BINDING SITE; DRUG CONJUGATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; HYPOXIA; PRIORITY JOURNAL; ARTICLE; CELL HYPOXIA; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; DRUG SCREENING; HUMAN; KINETICS; METABOLISM; SYNTHESIS;

CELL HYPOXIA; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HUMANS; INDOLEAMINE-PYRROLE 2,3,-DIOXYGENASE; KINETICS; TRIAZINES; TRYPTOPHAN;

EID: 77949904798     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4419-1241-1_60     Document Type: Conference Paper

References (7)

1. H. Sugimoto, S. Oda, T. Otsuki, T. Hino, T. Yoshida, Y. Shiro, Crystal structure of human indoleamine 2,3-dioxygenase: Catalytic mechanism of O2 incorporation by a heme-containing dioxygenase, Proc. Nat. Acad. Sci. USA. 103, 2611-2616 (2006).
2. C. Uyttenhove, L. Pilotte, I. Theate, V. Stroobant, D. Colau, N. Parmentier, T. Boon, B. Eynde, Evidence for a tumoral immune resistance mechanism based on tryptophan degradation by indoleamine 2,3-dioxygenase, Nat. Med. 9, 1269-1274 (2003). (Pubitemid 37279849)
3. D. Y. Hou, A. J. Muller, M. D. Sharma, J. DuHadaway, T. Banerjee, M. Johnson, A. L. Mellor, G. C. Prendergast, D, H. Munn, Inhibition of Indoleamine 2,3-Dioxygenase in Dendritic cells by Stereoisomers of 1-Methyl-Tryptophan Correlates with Antitumor Responses, Cancer Res. 67, 792-801 (2007). (Pubitemid 46192220)
4. G. J. Maghzal, S. R. Thomas, N. H. Hunt, R. Stocker, Cytochrome b5, not superoxide anion radicals, is a major reductant of indoleamine 2,3-dioxygenase in human cells, J. Biol. Chem. 283, 12014-12025 (2008).
5. M. P. Hay, K. O. Hicks, F. B. Pruijn, K. Pchalek, B. G. Siim, W. R. Willson, W. A. Denny, Pharmacokinetic/Pharmacodynamic Model-Guided Identification of Hypoxia-Selective 1,2,4-Benzotriazine 1,4-Dioxides with Antitumor Activity: The Role of Extravascular Transport, J. Med. Chem. 50, 6392-6404 (2007). (Pubitemid 350250426)
6. H. Nagasawa, Y. Uto, H. Hori, Design of Hypoxia-Targeting Drugs as New Cancer Therapeutics. Biol. Pharm. Bull. 29, 2335-2342 (2006). (Pubitemid 44885846)
7. H. Nakashima, Y. Uto, E. Nakata, H. Nagasawa, K. Ikkyu, N. Hiraoka, K. Nakashima, Y. Sakaki, H. Sugimoto, Y. Shiro, T. Hashimoto, Y. Okamoto, Y. Asakawa, H. Hori, Synthesis and biological activity of 1-methyl-tryptophan- tirapazamine hybrids as hypoxiatargeting indoleamine 2,3-dioxygenase inhibitors, Bioorg. Med. Chem. 16, 8661-8669 (2008).