The natural bicyclic hexapeptide RA-VII is a novel inhibitor of the eukaryotic translocase eEF2

Miyoshi, Tomohiro; Nomura, Toshihiro; Takeya, Koich; Uchiumi, Toshio

doi:10.1016/j.bbrc.2022.05.035

Biochemical and Biophysical Research Communications

2022

DOI: 10.1016/j.bbrc.2022.05.035

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The natural bicyclic hexapeptide RA-VII is a novel inhibitor of the eukaryotic translocase eEF2

Tomohiro Miyoshi

Toshihiro Nomura

Koich Takeya

et al.

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Cited by 9 publications

(1 citation statement)

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“…4 The antitumor activity is believed to result from the inhibition of protein synthesis through interactions with eukaryotic ribosomes. 5,6 Peptide 1 inhibits eukaryotic translocase eEF2 7 and causes the conformational change in F-actin and the stabilization of actin filaments to induce G2 arrest. 8 The cycloisodityrosine moiety and the aromatic ring moiety of Tyr-3 with a para-methoxy group are indispensable for the potent cytotoxic activity of this series of peptides.…”

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confidence: 99%

Synthesis and Cytotoxicity Evaluation of Tyrosine-5 Fluorinated Analogues of RA-VII, An Antitumor Bicyclic Hexapeptide

Hitotsuyanagi,

Yoshida,

Nagaishi

et al. 2023

Synlett

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RA-VII analogues fluorinated at each ε-position of Tyr-5 were designed. The synthesis of these peptide analogues commenced with the preparation of atropisomeric fluorocycloisodityrosines from protected 3-fluoro-L-tyrosyl-3-boronyl-L-tyrosine mediated by copper(II) acetate and 4-(dimethylamino)pyridine. After N-methylation, the tetrapeptide segment was coupled with the N-terminus of each fluorocycloisodityrosine to afford a hexapeptide. After removal of the C- and N-terminal protecting groups, each peptide was subjected to macrocyclization to produce an analogue. The analogue with a β-oriented fluorine atom was equipotent to RA-VII with regard to cytotoxicity toward human mammary carcinoma MCF-7 cells, and showed 2.1-fold and 1.4-fold lower cytotoxicities than RA-VII toward human promyelocytic leukemia HL-60 and human colorectal cancer HCT-116 cells, respectively, whereas the analogue with an α-oriented fluorine atom showed 7.7-fold, 6.0-fold, and 14-fold lower cytotoxicities than RA-VII toward those cells, respectively.

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confidence: 99%

Synthesis and Cytotoxicity Evaluation of Tyrosine-5 Fluorinated Analogues of RA-VII, An Antitumor Bicyclic Hexapeptide

Hitotsuyanagi,

Yoshida,

Nagaishi

et al. 2023

Synlett

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Structures of new cytotoxic bicyclic hexapeptides with a phenylpropanoid unit from Rubia cordifolia

Fukaya,

Kitamura,

Hasuda

et al. 2025

Phytochemistry Letters

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Synthesis and cytotoxicity evaluation of retro-inverso analogue of antitumor bicyclic hexapeptide RA-VII

Suzuki,

Masuda,

Yamamoto

et al. 2024

Tetrahedron Letters

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The natural bicyclic hexapeptide RA-VII is a novel inhibitor of the eukaryotic translocase eEF2

Cited by 9 publications

References 30 publications

Synthesis and Cytotoxicity Evaluation of Tyrosine-5 Fluorinated Analogues of RA-VII, An Antitumor Bicyclic Hexapeptide

Synthesis and Cytotoxicity Evaluation of Tyrosine-5 Fluorinated Analogues of RA-VII, An Antitumor Bicyclic Hexapeptide

Structures of new cytotoxic bicyclic hexapeptides with a phenylpropanoid unit from Rubia cordifolia

Synthesis and cytotoxicity evaluation of retro-inverso analogue of antitumor bicyclic hexapeptide RA-VII

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