Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids
Jianbo Wu
1
,
Xiaofang Wang
1
,
Francis C.K. Chiu
2
,
Cécile Häberli
3, 4
,
D. Shackleford
2
,
Eileen Ryan
2
,
Kamaraj Sriraghavan
1
,
Vivek J Bulbule
1
,
Alexander I Wallick
5
,
Yuxiang Dong
1
,
KAREN E. WHITE
2
,
Paul H Davis
5
,
Susan C Charman
2
,
J Keiser
3, 4
,
Jonathan L. Vennerstrom
1
Publication type: Journal Article
Publication date: 2020-03-05
scimago Q1
wos Q1
SJR: 1.801
CiteScore: 11.5
Impact factor: 6.8
ISSN: 00222623, 15204804
PubMed ID:
32134263
Drug Discovery
Molecular Medicine
Abstract
Semisynthetic artemisinins and other bioactive peroxides are best known for their powerful antimalarial activities, and they also show substantial activity against schistosomes-another hemoglobin-degrading pathogen. Building on this discovery, we now describe the initial structure-activity relationship (SAR) of antischistosomal ozonide carboxylic acids OZ418 (2) and OZ165 (3). Irrespective of lipophilicity, these ozonide weak acids have relatively low aqueous solubilities and high protein binding values. Ozonides with para-substituted carboxymethoxy and N-benzylglycine substituents had high antischistosomal efficacies. It was possible to increase solubility, decrease protein binding, and maintain the high antischistosomal activity in mice infected with juvenile and adult Schistosoma mansoni by incorporating a weak base functional group in these compounds. In some cases, adding polar functional groups and heteroatoms to the spiroadamantane substructure increased the solubility and metabolic stability, but in all cases decreased the antischistosomal activity.
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Total citations:
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Citations from 2024:
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BibTex |
MLA
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GOST
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Wu J. et al. Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids // Journal of Medicinal Chemistry. 2020. Vol. 63. No. 7. pp. 3723-3736.
GOST all authors (up to 50)
Copy
Wu J., Wang X., Chiu F. C., Häberli C., Shackleford D., Ryan E., Sriraghavan K., Bulbule V. J., Wallick A. I., Dong Y., WHITE K. E., Davis P. H., Charman S. C., Keiser J., Vennerstrom J. L. Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids // Journal of Medicinal Chemistry. 2020. Vol. 63. No. 7. pp. 3723-3736.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.jmedchem.0c00069
UR - https://doi.org/10.1021/acs.jmedchem.0c00069
TI - Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids
T2 - Journal of Medicinal Chemistry
AU - Wu, Jianbo
AU - Wang, Xiaofang
AU - Chiu, Francis C.K.
AU - Häberli, Cécile
AU - Shackleford, D.
AU - Ryan, Eileen
AU - Sriraghavan, Kamaraj
AU - Bulbule, Vivek J
AU - Wallick, Alexander I
AU - Dong, Yuxiang
AU - WHITE, KAREN E.
AU - Davis, Paul H
AU - Charman, Susan C
AU - Keiser, J
AU - Vennerstrom, Jonathan L.
PY - 2020
DA - 2020/03/05
PB - American Chemical Society (ACS)
SP - 3723-3736
IS - 7
VL - 63
PMID - 32134263
SN - 0022-2623
SN - 1520-4804
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Wu,
author = {Jianbo Wu and Xiaofang Wang and Francis C.K. Chiu and Cécile Häberli and D. Shackleford and Eileen Ryan and Kamaraj Sriraghavan and Vivek J Bulbule and Alexander I Wallick and Yuxiang Dong and KAREN E. WHITE and Paul H Davis and Susan C Charman and J Keiser and Jonathan L. Vennerstrom},
title = {Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids},
journal = {Journal of Medicinal Chemistry},
year = {2020},
volume = {63},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.jmedchem.0c00069},
number = {7},
pages = {3723--3736},
doi = {10.1021/acs.jmedchem.0c00069}
}
Cite this
MLA
Copy
Wu, Jianbo, et al. “Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids.” Journal of Medicinal Chemistry, vol. 63, no. 7, Mar. 2020, pp. 3723-3736. https://doi.org/10.1021/acs.jmedchem.0c00069.