The antiplasmodial activity of norcantharidin analogs

Joanna Bajsa; Adam McCluskey; Christopher P. Gordon; Scott G. Stewart; Timothy A. Hill; Rajnish Sahu; Stephen O. Duke; Babu L. Tekwani

doi:10.1016/j.bmcl.2010.09.004

The antiplasmodial activity of norcantharidin analogs

Joanna Bajsa
, Adam McCluskey
, Christopher P. Gordon
, Scott G. Stewart
, Timothy A. Hill
, Rajnish Sahu
, Stephen O. Duke
, Babu L. Tekwani

School of Science

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

27 Citations (Scopus)

Abstract

The antiplasmodial activities of sixty norcantharidin analogs were tested in vitro against a chloroquine sensitive (D6, Sierra Leone) and chloroquine resistant (W2) strains of Plasmodium falciparum. Forty analogs returned IC50 values <500 μM against at least one of the P. falciparum strains examined. The ring open compound 24 ((1S,4R)-3-(allylcarbamoyl)-7- oxabicyclo[2.2.1]heptane-2-carboxylic acid) is the most active aliphatic analog (D6 IC50 = 3.0 Â± 0.0 and W2 IC50 = 3.0 Â± 0.8 μM) with a 20-fold enhancement relative to norcantharidin. Surprisingly, seven norcantharimides also displayed good antiplasmodial activity with the most potent, 5 returning D6 = 8.9 Â± 0.9 and W2 IC50 = 12.5 Â± 2.2 μM, representing a fivefold enhancement over norcantharidin.

Original language	English
Pages (from-to)	6688-6695
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	22
DOIs	https://doi.org/10.1016/j.bmcl.2010.09.004
Publication status	Published - 2010

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10.1016/j.bmcl.2010.09.004

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@article{89ae7c9ba70348f4af3e8e8b71d06f95,

title = "The antiplasmodial activity of norcantharidin analogs",

abstract = "The antiplasmodial activities of sixty norcantharidin analogs were tested in vitro against a chloroquine sensitive (D6, Sierra Leone) and chloroquine resistant (W2) strains of Plasmodium falciparum. Forty analogs returned IC50 values <500 μM against at least one of the P. falciparum strains examined. The ring open compound 24 ((1S,4R)-3-(allylcarbamoyl)-7- oxabicyclo[2.2.1]heptane-2-carboxylic acid) is the most active aliphatic analog (D6 IC50 = 3.0 {\^A}± 0.0 and W2 IC50 = 3.0 {\^A}± 0.8 μM) with a 20-fold enhancement relative to norcantharidin. Surprisingly, seven norcantharimides also displayed good antiplasmodial activity with the most potent, 5 returning D6 = 8.9 {\^A}± 0.9 and W2 IC50 = 12.5 {\^A}± 2.2 μM, representing a fivefold enhancement over norcantharidin.",

author = "Joanna Bajsa and Adam McCluskey and Gordon, \{Christopher P.\} and Stewart, \{Scott G.\} and Hill, \{Timothy A.\} and Rajnish Sahu and Duke, \{Stephen O.\} and Tekwani, \{Babu L.\}",

year = "2010",

doi = "10.1016/j.bmcl.2010.09.004",

language = "English",

volume = "20",

pages = "6688--6695",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier",

number = "22",

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TY - JOUR

T1 - The antiplasmodial activity of norcantharidin analogs

AU - Bajsa, Joanna

AU - McCluskey, Adam

AU - Gordon, Christopher P.

AU - Stewart, Scott G.

AU - Hill, Timothy A.

AU - Sahu, Rajnish

AU - Duke, Stephen O.

AU - Tekwani, Babu L.

PY - 2010

Y1 - 2010

N2 - The antiplasmodial activities of sixty norcantharidin analogs were tested in vitro against a chloroquine sensitive (D6, Sierra Leone) and chloroquine resistant (W2) strains of Plasmodium falciparum. Forty analogs returned IC50 values <500 μM against at least one of the P. falciparum strains examined. The ring open compound 24 ((1S,4R)-3-(allylcarbamoyl)-7- oxabicyclo[2.2.1]heptane-2-carboxylic acid) is the most active aliphatic analog (D6 IC50 = 3.0 Â± 0.0 and W2 IC50 = 3.0 Â± 0.8 μM) with a 20-fold enhancement relative to norcantharidin. Surprisingly, seven norcantharimides also displayed good antiplasmodial activity with the most potent, 5 returning D6 = 8.9 Â± 0.9 and W2 IC50 = 12.5 Â± 2.2 μM, representing a fivefold enhancement over norcantharidin.

AB - The antiplasmodial activities of sixty norcantharidin analogs were tested in vitro against a chloroquine sensitive (D6, Sierra Leone) and chloroquine resistant (W2) strains of Plasmodium falciparum. Forty analogs returned IC50 values <500 μM against at least one of the P. falciparum strains examined. The ring open compound 24 ((1S,4R)-3-(allylcarbamoyl)-7- oxabicyclo[2.2.1]heptane-2-carboxylic acid) is the most active aliphatic analog (D6 IC50 = 3.0 Â± 0.0 and W2 IC50 = 3.0 Â± 0.8 μM) with a 20-fold enhancement relative to norcantharidin. Surprisingly, seven norcantharimides also displayed good antiplasmodial activity with the most potent, 5 returning D6 = 8.9 Â± 0.9 and W2 IC50 = 12.5 Â± 2.2 μM, representing a fivefold enhancement over norcantharidin.

UR - http://handle.uws.edu.au:8081/1959.7/546807

U2 - 10.1016/j.bmcl.2010.09.004

DO - 10.1016/j.bmcl.2010.09.004

M3 - Article

C2 - 20888768

SN - 0960-894X

VL - 20

SP - 6688

EP - 6695

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 22

ER -

The antiplasmodial activity of norcantharidin analogs

Abstract

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