title: Development of a reduction-responsive amino acid that induces peptide bond cleavage in hypoxic cells.
abstract: Hypoxia-responsive amino acids are indispensable in the preparation of hypoxic tumor-specific peptidyl prodrugs. In this paper, the design and synthesis of a reduction-responsive amino acid that induces peptide bond cleavage after reduction of the nitro group are described. Application to hypoxia-responsive peptide bond cleavage system is also reported.
authors.affiliation: Department of Bioorganic Synthetic Chemistry, Institute of Health Biosciences and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505, Japan. ashige@ph.tokushima-u.ac.jp
authors.forename: Akira
authors.initials: A
authors.lastname: Shigenaga
authors.forename: Keiji
authors.initials: K
authors.lastname: Ogura
authors.forename: Hiroko
authors.initials: H
authors.lastname: Hirakawa
authors.forename: Jun
authors.initials: J
authors.lastname: Yamamoto
authors.forename: Koji
authors.initials: K
authors.lastname: Ebisuno
authors.forename: Licht
authors.initials: L
authors.lastname: Miyamoto
authors.forename: Keisuke
authors.initials: K
authors.lastname: Ishizawa
authors.forename: Koichiro
authors.initials: K
authors.lastname: Tsuchiya
authors.forename: Akira
authors.initials: A
authors.lastname: Otaka
mesh_terms: D000577:Amides / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D015687:Cell Hypoxia / Q000502:physiology; D031541:Fluorescence Resonance Energy Transfer; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011355:Prodrugs / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000577:Amides; D000596:Amino Acids; D010455:Peptides; D011355:Prodrugs