Design and synthesis of analogues of RA-VII—an antitumor bicyclic hexapeptide from Rubiae radix

Author:

Hitotsuyanagi YukioORCID

Abstract

AbstractThe 14-membered cycloisodityrosine is the core structure of RA-series antitumor bicyclic peptides obtained from Rubia plants (Rubiaceae). In this study, an efficient method for the synthesis of cycloisodityrosines from commercially available l-tyrosine derivatives was developed. Using synthetic cycloisodityrosines and cycloisodityrosines with modified structures, several RA-VII analogues were designed and synthesized to explore structure–activity relationships of the cycloisodityrosine moiety of the RA-series peptides, and newly isolated natural peptides were synthesized to establish their structures. Graphic abstract

Publisher

Springer Science and Business Media LLC

Subject

Molecular Medicine

Reference39 articles.

1. Itokawa H, Takeya K, Mihara K, Mori N, Hamanaka T, Sonobe T, Iitaka Y (1983) Studies on the antitumor cyclic hexapeptides obtained from Rubiae radix. Chem Pharm Bull 31:1424–1427

2. Itokawa H, Takeya K, Hitotsuyanagi Y, Morita H (1997) Macrocyclic peptide alkaloids from plants. In: Cordell GA (ed) The Alkaloids, vol 49. Academic Press, New York, pp 301–387

3. Jolad SD, Hoffman JJ, Torrance SJ, Wiedhopf RM, Cole JR, Arora SK, Bates RB, Gargiulo RL, Kriek GR (1977) Bouvardin and deoxybouvardin, antitumor cyclic hexapeptides from Bouvardia ternifolia (Rubiaceae). J Am Chem Soc 99:8040–8044

4. Majima H, Tsukagoshi S, Furue H, Suminaga M, Sakamoto K, Wakabayashi R, Kishino S, Niitani H, Murata A, Genma A, Nukariya N, Uematsu K, Furuta T, Kurihara M, Yoshida F, Isomura S, Takemoto T, Hirashima M, Izumi T, Nakao I, Ohashi Y, Ito K, Asai R (1993) Phase I study of RA-700. Jpn J Cancer Chemother 20:67–78

5. Yoshida F, Asai R, Majima H, Tsukagoshi S, Furue H, Suminaga M, Sakamoto K, Niitani H, Murata A, Kurihara M, Izumi T, Nakao I, Ohashi Y, Ito K (1994) Study of cardiac function in first stage examination of RA-700. Jpn J Cancer Chemother 21:199–207

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3