Structure-activity relationships within a family of selectively cytotoxic macrolide natural products

Arthur R. Salomon; Yongbo Zhang; Haruo Seto; Chaitan Khosla

doi:10.1021/ol006767d

Structure-activity relationships within a family of selectively cytotoxic macrolide natural products

Arthur R. Salomon, Yongbo Zhang, Haruo Seto, Chaitan Khosla^*

^*Corresponding author for this work

Chemistry

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

46 Scopus citations

Abstract

(equation presented) We describe a semi-synthetic deglycosylated derivative of apoptolidin that retains considerable activity against the mitochondrial ATPase but has greatly reduced cellular cytotoxicity. We also demonstrate that a related antifungal natural product, cytovaricin, inhibits the same molecular target. Structural comparison of these macrolides provides insights into their conserved features that are presumably important for biological activity and identifies promising avenues at the interface of organic synthesis and biosynthesis for the generation of new selective cytotoxic agents.

Original language	English (US)
Pages (from-to)	57-59
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	1
DOIs	https://doi.org/10.1021/ol006767d
State	Published - Jan 11 2001

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol006767d

Cite this

@article{d9226240bb1f4260b3a82532b69329e4,

title = "Structure-activity relationships within a family of selectively cytotoxic macrolide natural products",

abstract = "(equation presented) We describe a semi-synthetic deglycosylated derivative of apoptolidin that retains considerable activity against the mitochondrial ATPase but has greatly reduced cellular cytotoxicity. We also demonstrate that a related antifungal natural product, cytovaricin, inhibits the same molecular target. Structural comparison of these macrolides provides insights into their conserved features that are presumably important for biological activity and identifies promising avenues at the interface of organic synthesis and biosynthesis for the generation of new selective cytotoxic agents.",

author = "Salomon, {Arthur R.} and Yongbo Zhang and Haruo Seto and Chaitan Khosla",

year = "2001",

month = jan,

day = "11",

doi = "10.1021/ol006767d",

language = "English (US)",

volume = "3",

pages = "57--59",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Structure-activity relationships within a family of selectively cytotoxic macrolide natural products

AU - Salomon, Arthur R.

AU - Zhang, Yongbo

AU - Seto, Haruo

AU - Khosla, Chaitan

PY - 2001/1/11

Y1 - 2001/1/11

N2 - (equation presented) We describe a semi-synthetic deglycosylated derivative of apoptolidin that retains considerable activity against the mitochondrial ATPase but has greatly reduced cellular cytotoxicity. We also demonstrate that a related antifungal natural product, cytovaricin, inhibits the same molecular target. Structural comparison of these macrolides provides insights into their conserved features that are presumably important for biological activity and identifies promising avenues at the interface of organic synthesis and biosynthesis for the generation of new selective cytotoxic agents.

AB - (equation presented) We describe a semi-synthetic deglycosylated derivative of apoptolidin that retains considerable activity against the mitochondrial ATPase but has greatly reduced cellular cytotoxicity. We also demonstrate that a related antifungal natural product, cytovaricin, inhibits the same molecular target. Structural comparison of these macrolides provides insights into their conserved features that are presumably important for biological activity and identifies promising avenues at the interface of organic synthesis and biosynthesis for the generation of new selective cytotoxic agents.

UR - http://www.scopus.com/inward/record.url?scp=0035843327&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035843327&partnerID=8YFLogxK

U2 - 10.1021/ol006767d

DO - 10.1021/ol006767d

M3 - Article

C2 - 11429871

AN - SCOPUS:0035843327

SN - 1523-7060

VL - 3

SP - 57

EP - 59

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Structure-activity relationships within a family of selectively cytotoxic macrolide natural products

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this