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Start Over Author "Hasuda T" Journal journal of organic chemistry
2 results on '"Hasuda T"'

1. Synthesis of Antitumor Bicyclic Hexapeptide RA-VII Analogues Possessing an Aromatic Amino Acid at Residue 2.

Author

Kitahara K, Mizushima H, Ogura K, Kato M, Fukaya H, Hasuda T, Sato H, Nakane T, Takeya K, and Hitotsuyanagi Y

Subjects
Humans, Amino Acids, Aromatic chemistry, Amino Acids, Aromatic chemical synthesis, Drug Screening Assays, Antitumor, Molecular Structure, HCT116 Cells, HL-60 Cells, Oligopeptides chemistry, Oligopeptides chemical synthesis, Structure-Activity Relationship, Cell Proliferation drug effects, Peptides, Cyclic chemistry, Peptides, Cyclic chemical synthesis, Peptides, Cyclic pharmacology, Antineoplastic Agents chemistry, Antineoplastic Agents chemical synthesis, Antineoplastic Agents pharmacology
Abstract

RA-III acetate was treated with Lawesson's reagent to afford [Tyr-3-Ψ(CS-NH)-Ala-4]RA-III acetate. Treatment of this product with Hg(OAc) 2 /Li 2 CO 3 and then methanol gave an oxazole intermediate. Acid-catalyzed arylation of the methylene carbon atom on the oxazole ring and subsequent partial hydrolysis of the oxazole ring in the resultant compounds afforded RA-VII analogues having an aromatic amino acid at residue 2. [5-Fluoro-d-Trp-2]RA-VII showed IC 50 values of 0.038 and 0.077 μM against the HL-60 and HCT-116 cell lines, respectively.

Published
2024
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2. Synthesis of [Gly-1]RA-VII, [Gly-2]RA-VII, and [Gly-4]RA-VII. Glycine-containing analogues of RA-VII, an antitumor bicyclic hexapeptide from Rubia plants.

Author

Hitotsuyanagi Y, Hasuda T, Aihara T, Ishikawa H, Yamaguchi K, Itokawa H, and Takeya K

Subjects
Animals, Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic isolation & purification, Bridged Bicyclo Compounds chemistry, Bridged Bicyclo Compounds isolation & purification, Cell Survival drug effects, Cyclization, Mice, Molecular Structure, Peptides, Cyclic chemistry, Peptides, Cyclic isolation & purification, Protein Conformation, Structure-Activity Relationship, Tumor Cells, Cultured, Antineoplastic Agents, Phytogenic chemical synthesis, Bridged Bicyclo Compounds chemical synthesis, Glycine chemistry, Peptides, Cyclic chemical synthesis, Rubia chemistry
Abstract

Three analogues of RA-VII (1), an antitumor bicyclic hexapeptide from Rubia plants, were synthesized. Three analogues, [Gly-1]RA-VII (4), [Gly-2]RA-VII (5), and [Gly-4]RA-VII (6), in which one of the three alanine residues in 1 was replaced by a glycine residue, were prepared by linking of the cycloisodityrosine unit, obtained by degradation of 1, to three different glycine-containing tetrapeptides followed by macrocyclization. Of these three analogues, analogue 4 showed the highest cytotoxic activity. The NMR study revealed that in solution the conformer structures and their ratios of analogue 4 were very similar to those of natural peptide 1, suggesting that the methyl groups at Ala-2 and Ala-4 should be essential for producing the bioactive conformation, whereas that at D-Ala-1 is not essential.

Published
2004
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