Recent Progress on C-4-Modified Podophyllotoxin Analogs as Potent Antitumor Agents

Podophyllotoxin (PPT), as well as its congeners and derivatives, exhibits pronounced biological activities, especially antineoplastic effects. Its strong inhibitory effect on tumor cell growth led to the development of three of the most highly prescribed anticancer drugs in the world, etoposide, ten...

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Published inMedicinal research reviews Vol. 35; no. 1; pp. 1 - 62
Main Authors Liu, Ying-Qian, Tian, Jing, Qian, Keduo, Zhao, Xiao-Bo, Morris-Natschke, Susan L., Yang, Liu, Nan, Xiang, Tian, Xuan, Lee, Kuo-Hsiung
Format Journal Article
LanguageEnglish
Published United States Blackwell Publishing Ltd 01.01.2015
Wiley Subscription Services, Inc
Subjects
Animals
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
C-4 position
Cancer
cytotoxic agents
Drug therapy
Humans
podophyllotoxin
Podophyllotoxin - analogs & derivatives
Podophyllotoxin - chemistry
Podophyllotoxin - pharmacology
reviews
Structure-Activity Relationship
podophyllotoxin
cytotoxic agents
C-4 position
reviews
Online AccessGet full text

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Abstract Podophyllotoxin (PPT), as well as its congeners and derivatives, exhibits pronounced biological activities, especially antineoplastic effects. Its strong inhibitory effect on tumor cell growth led to the development of three of the most highly prescribed anticancer drugs in the world, etoposide, teniposide, and the water‐soluble prodrug etoposide phosphate. Their clinical success as well as intriguing mechanism of action stimulated great interest in further modification of PPT for better antitumor activity. The C‐4 position has been a major target for structural derivatization aimed at either producing more potent compounds or overcoming drug resistance. Accordingly, numerous PPT derivatives have been prepared via hemisynthesis and important structure–activity relationship (SAR) correlations have been identified. Several resulting compounds, including GL‐331, TOP‐53, and NK611, reached clinical trials. Some excellent reviews on the distribution, sources, applications, synthesis, and SAR of PPT have been published. This review focuses on a second generation of new etoposide‐related drugs and provides detailed coverage of the current status and recent development of C‐4‐modified PPT analogs as anticancer clinical trial candidates.
AbstractList Podophyllotoxin (PPT), as well as its congeners and derivatives, exhibits pronounced biological activities, especially antineoplastic effects. Its strong inhibitory effect on tumor cell growth led to the development of three of the most highly prescribed anticancer drugs in the world, etoposide, teniposide, and the water-soluble prodrug etoposide phosphate. Their clinical success as well as intriguing mechanism of action stimulated great interest in further modification of PPT for better antitumor activity. The C-4 position has been a major target for structural derivatization aimed at either producing more potent compounds or overcoming drug resistance. Accordingly, numerous PPT derivatives have been prepared via hemisynthesis and important structure-activity relationship (SAR) correlations have been identified. Several resulting compounds, including GL-331, TOP-53, and NK611, reached clinical trials. Some excellent reviews on the distribution, sources, applications, synthesis, and SAR of PPT have been published. This review focuses on a second generation of new etoposide-related drugs and provides detailed coverage of the current status and recent development of C-4-modified PPT analogs as anticancer clinical trial candidates.
Podophyllotoxin (PPT), as well as its congeners and derivatives, exhibits pronounced biological activities, especially antineoplastic effects. Its strong inhibitory effect on tumor cell growth led to the development of three of the most highly prescribed anticancer drugs in the world, etoposide, teniposide, and the water-soluble prodrug etoposide phosphate. Their clinical success as well as intriguing mechanism of action stimulated great interest in further modification of PPT for better antitumor activity. The C-4 position has been a major target for structural derivatization aimed at either producing more potent compounds or overcoming drug resistance. Accordingly, numerous PPT derivatives have been prepared via hemisynthesis and important structure-activity relationship (SAR) correlations have been identified. Several resulting compounds, including GL-331, TOP-53, and NK611, reached clinical trials. Some excellent reviews on the distribution, sources, applications, synthesis, and SAR of PPT have been published. This review focuses on a second generation of new etoposide-related drugs and provides detailed coverage of the current status and recent development of C-4-modified PPT analogs as anticancer clinical trial candidates.Podophyllotoxin (PPT), as well as its congeners and derivatives, exhibits pronounced biological activities, especially antineoplastic effects. Its strong inhibitory effect on tumor cell growth led to the development of three of the most highly prescribed anticancer drugs in the world, etoposide, teniposide, and the water-soluble prodrug etoposide phosphate. Their clinical success as well as intriguing mechanism of action stimulated great interest in further modification of PPT for better antitumor activity. The C-4 position has been a major target for structural derivatization aimed at either producing more potent compounds or overcoming drug resistance. Accordingly, numerous PPT derivatives have been prepared via hemisynthesis and important structure-activity relationship (SAR) correlations have been identified. Several resulting compounds, including GL-331, TOP-53, and NK611, reached clinical trials. Some excellent reviews on the distribution, sources, applications, synthesis, and SAR of PPT have been published. This review focuses on a second generation of new etoposide-related drugs and provides detailed coverage of the current status and recent development of C-4-modified PPT analogs as anticancer clinical trial candidates.
Author Qian, Keduo
Zhao, Xiao-Bo
Lee, Kuo-Hsiung
Morris-Natschke, Susan L.
Liu, Ying-Qian
Tian, Jing
Yang, Liu
Nan, Xiang
Tian, Xuan
AuthorAffiliation 1 School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
5 Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung, Taiwan
2 Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina
4 State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, P.R. China
3 Environmental and Municipal Engineering School, Lanzhou Jiaotong University, Lanzhou, P.R. China
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  surname: Nan
  fullname: Nan, Xiang
  organization: School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
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  organization: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, P.R. China
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  surname: Lee
  fullname: Lee, Kuo-Hsiung
  email: : Ying-Qian Liu, School of Pharmacy, Lanzhou University, Lanzhou 730000, P.R. China. Kuo-Hsiung Lee, Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599. , yqliu@lzu.edu.cnkhlee@unc.edu
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Issue 1
Keywords podophyllotoxin
cytotoxic agents
C-4 position
reviews
Language English
License http://onlinelibrary.wiley.com/termsAndConditions#vor
2014 Wiley Periodicals, Inc.
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National Natural Science Foundation of China - No. 30800720; No. 31371975
ark:/67375/WNG-V04WF27Q-D
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istex:79BDE8247109ABE40EACDBB26A8743D90716E9BF
Fundamental Research Funds for the Central Universities - No. lzujbky-2013-69
Young Scholars Science Foundation of Lanzhou Jiaotong University - No. 2011011
30800720, 31371975
Fundamental Research Funds for the Central Universities
Contract grant number
CA177584‐01.
Contract grant sponsor
National Natural Science Foundation of China
lzujbky‐2013‐69
2011011
NIH
Contract grant numbers
Young Scholars Science Foundation of Lanzhou Jiaotong University
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PublicationTitle Medicinal research reviews
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Snippet Podophyllotoxin (PPT), as well as its congeners and derivatives, exhibits pronounced biological activities, especially antineoplastic effects. Its strong...
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SubjectTerms Animals
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
C-4 position
Cancer
cytotoxic agents
Drug therapy
Humans
podophyllotoxin
Podophyllotoxin - analogs & derivatives
Podophyllotoxin - chemistry
Podophyllotoxin - pharmacology
reviews
Structure-Activity Relationship
Title Recent Progress on C-4-Modified Podophyllotoxin Analogs as Potent Antitumor Agents
URI https://api.istex.fr/ark:/67375/WNG-V04WF27Q-D/fulltext.pdf
https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fmed.21319
https://www.ncbi.nlm.nih.gov/pubmed/24827545
https://www.proquest.com/docview/1634480317
https://www.proquest.com/docview/1635005800
https://pubmed.ncbi.nlm.nih.gov/PMC4337794
Volume 35
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