Synthesis and evaluation of biological activities of vibsanin A analogs

Wataru Matsuki; So Miyazaki; Keisuke Yoshida; Akihiro Ogura; Yukiko Sasazawa; Ken ichi Takao; Siro Simizu

doi:10.1016/j.bmcl.2017.08.059

Synthesis and evaluation of biological activities of vibsanin A analogs

Wataru Matsuki, So Miyazaki, Keisuke Yoshida, Akihiro Ogura, Yukiko Sasazawa, Ken ichi Takao, Siro Simizu

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

Vibsanin A is an 11-membered vibsane diterpenoid and is reported to induce myeloid cell differentiation via activation of protein kinase C (PKC) without tumor-promoting activity. Therefore, vibsanin A is thought to be an attractive compound for acute myeloid leukemia (AML) therapy. In this study, we synthesized vibsanin A analogs and compared the activity of these compounds for PKC activation and myeloid cell differentiation. We found that the hydroxymethyl group in vibsanin A is an important substituent to induce differentiation of AML cells. Collectively, our results showed the biochemical features of vibsanin A and provided new insights into the development of new antileukemic drugs.

Original language	English
Pages (from-to)	4536-4539
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	27
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2017.08.059
Publication status	Published - 2017

Keywords

Acute myeloid leukemia
Differentiation
Protein kinase C
Vibsanin A

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmcl.2017.08.059

Cite this

@article{fb12c5426b334b719cc14e88279e8bf8,

title = "Synthesis and evaluation of biological activities of vibsanin A analogs",

abstract = "Vibsanin A is an 11-membered vibsane diterpenoid and is reported to induce myeloid cell differentiation via activation of protein kinase C (PKC) without tumor-promoting activity. Therefore, vibsanin A is thought to be an attractive compound for acute myeloid leukemia (AML) therapy. In this study, we synthesized vibsanin A analogs and compared the activity of these compounds for PKC activation and myeloid cell differentiation. We found that the hydroxymethyl group in vibsanin A is an important substituent to induce differentiation of AML cells. Collectively, our results showed the biochemical features of vibsanin A and provided new insights into the development of new antileukemic drugs.",

keywords = "Acute myeloid leukemia, Differentiation, Protein kinase C, Vibsanin A",

author = "Wataru Matsuki and So Miyazaki and Keisuke Yoshida and Akihiro Ogura and Yukiko Sasazawa and Takao, {Ken ichi} and Siro Simizu",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.bmcl.2017.08.059",

language = "English",

volume = "27",

pages = "4536--4539",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "19",

}

TY - JOUR

T1 - Synthesis and evaluation of biological activities of vibsanin A analogs

AU - Matsuki, Wataru

AU - Miyazaki, So

AU - Yoshida, Keisuke

AU - Ogura, Akihiro

AU - Sasazawa, Yukiko

AU - Takao, Ken ichi

AU - Simizu, Siro

PY - 2017

Y1 - 2017

N2 - Vibsanin A is an 11-membered vibsane diterpenoid and is reported to induce myeloid cell differentiation via activation of protein kinase C (PKC) without tumor-promoting activity. Therefore, vibsanin A is thought to be an attractive compound for acute myeloid leukemia (AML) therapy. In this study, we synthesized vibsanin A analogs and compared the activity of these compounds for PKC activation and myeloid cell differentiation. We found that the hydroxymethyl group in vibsanin A is an important substituent to induce differentiation of AML cells. Collectively, our results showed the biochemical features of vibsanin A and provided new insights into the development of new antileukemic drugs.

AB - Vibsanin A is an 11-membered vibsane diterpenoid and is reported to induce myeloid cell differentiation via activation of protein kinase C (PKC) without tumor-promoting activity. Therefore, vibsanin A is thought to be an attractive compound for acute myeloid leukemia (AML) therapy. In this study, we synthesized vibsanin A analogs and compared the activity of these compounds for PKC activation and myeloid cell differentiation. We found that the hydroxymethyl group in vibsanin A is an important substituent to induce differentiation of AML cells. Collectively, our results showed the biochemical features of vibsanin A and provided new insights into the development of new antileukemic drugs.

KW - Acute myeloid leukemia

KW - Differentiation

KW - Protein kinase C

KW - Vibsanin A

UR - http://www.scopus.com/inward/record.url?scp=85028745170&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85028745170&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2017.08.059

DO - 10.1016/j.bmcl.2017.08.059

M3 - Article

C2 - 28888819

AN - SCOPUS:85028745170

SN - 0960-894X

VL - 27

SP - 4536

EP - 4539

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 19

ER -

Synthesis and evaluation of biological activities of vibsanin A analogs

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this