TY - JOUR
T1 - Inverse Correlation between Lethality and Thermodynamic Stability of Contact Insecticide Polymorphs
AU - Yang, Jingxiang
AU - Zhu, Xiaolong
AU - Hu, Chunhua T.
AU - Qiu, Mengdi
AU - Zhu, Qiang
AU - Ward, Michael D.
AU - Kahr, Bart
N1 - Funding Information:
We are grateful for support from the Materials Research Science and Engineering Center (MRSEC) program of the National Science Foundation under Award No. DMR- 1420073. The X-ray facility was supported partially by the NSF under Award Number CRIF/CHE-0840277. Work at UNLV is supported by the National Nuclear Security Administration under the Stewardship Science Academic Alliances program through DOE Cooperative Agreement DE-NA0001982. We thank Professor Claude Desplan and Cleopatra Tsanis (NYU Biology) for the donation of the Drosophila melanogaster, whose progeny produced the results herein.
Funding Information:
We are grateful for support from the Materials Research Science and Engineering Center (MRSEC) program of the National Science Foundation under Award No. DMR-1420073. The X-ray facility was supported partially by the NSF under Award Number CRIF/CHE-0840277. Work at UNLV is supported by the National Nuclear Security Administration under the Stewardship Science Academic Alliances program through DOE Cooperative Agreement DE-NA0001982. We thank Professor Claude Desplan and Cleopatra Tsanis (NYU Biology) for the donation of the Drosophila melanogaster, whose progeny produced the results herein.
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/3/6
Y1 - 2019/3/6
N2 - Contact insecticides often involve the interaction of whole organisms and toxicant crystal surfaces. The crystalline phase of these compounds has not, however, been considered for the optimization of insecticide performance. Lindane (1R,2r,3S,4R,5r,6S-hexachlorocyclohexane) has been one of the most widely used insecticides, but other (inactive) stereoisomers accompanying its manufacture have led to massive chemical waste remediation problems. Crystalline polymorphs are also isomers in the broadest sense, yet only one crystal structure of lindane has been reported. Herein, we report the discovery and characterization of two new polymorphs, Forms II and III. The efficacy of Forms I, II, and III against Drosophila melanogaster revealed an inverse correlation between lethality and thermodynamic stability; the least stable kills fastest. This understanding provides a crystal engineering opportunity wherein formulations containing the most active contact insecticide polymorph can achieve infectious disease prophylaxis while reducing environmental exposure and associated chemical waste.
AB - Contact insecticides often involve the interaction of whole organisms and toxicant crystal surfaces. The crystalline phase of these compounds has not, however, been considered for the optimization of insecticide performance. Lindane (1R,2r,3S,4R,5r,6S-hexachlorocyclohexane) has been one of the most widely used insecticides, but other (inactive) stereoisomers accompanying its manufacture have led to massive chemical waste remediation problems. Crystalline polymorphs are also isomers in the broadest sense, yet only one crystal structure of lindane has been reported. Herein, we report the discovery and characterization of two new polymorphs, Forms II and III. The efficacy of Forms I, II, and III against Drosophila melanogaster revealed an inverse correlation between lethality and thermodynamic stability; the least stable kills fastest. This understanding provides a crystal engineering opportunity wherein formulations containing the most active contact insecticide polymorph can achieve infectious disease prophylaxis while reducing environmental exposure and associated chemical waste.
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U2 - 10.1021/acs.cgd.8b01800
DO - 10.1021/acs.cgd.8b01800
M3 - Article
AN - SCOPUS:85062064539
SN - 1528-7483
VL - 19
SP - 1839
EP - 1844
JO - Crystal Growth and Design
JF - Crystal Growth and Design
IS - 3
ER -