Reversible and selective encapsulation of dextromethorphan and β-estradiol using an asymmetric molecular capsule assembled via the weak-link approach

Jose Mendez-Arroyo; Andrea I. D'Aquino; Alyssa B. Chinen; Yashin D. Manraj; Chad A. Mirkin

doi:10.1021/jacs.6b10027

Reversible and selective encapsulation of dextromethorphan and β-estradiol using an asymmetric molecular capsule assembled via the weak-link approach

Jose Mendez-Arroyo, Andrea I. D'Aquino, Alyssa B. Chinen, Yashin D. Manraj, Chad A. Mirkin^*

^*Corresponding author for this work

Chemistry

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

58 Scopus citations

Abstract

An allosterically regulated, asymmetric receptor featuring a binding cavity large enough to accommodate three-dimensional pharmaceutical guest molecules as opposed to planar, rigid aromatics, was synthesized via the Weak-Link Approach. This architecture is capable of switching between an expanded, flexible "open" configuration and a collapsed, rigid "closed" one. The structure of the molecular receptor can be completely modulated in situ through the use of simple ionic effectors, which reversibly control the coordination state of the Pt(II) metal hinges to open and close the molecular receptor. The substantial change in binding cavity size and electrostatic charge between the two configurations is used to explore the capture and release of two guest molecules, dextromethorphan and β-estradiol, which are widely found as pollutants in groundwater.

Original language	English (US)
Pages (from-to)	1368-1371
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	4
DOIs	https://doi.org/10.1021/jacs.6b10027
State	Published - Feb 1 2017

Funding

This material is based upon work supported by the National Science Foundation award CHE-1149314, the Department of Defense National Security Science and Engineering Faculty Fellowship award N00014-15-1-0043, and the U.S. Army award W911NF-15-1-0151. J.M.A. acknowledges a fellowship from Consejo Nacional de Ciencia y Tecnologia (CONACYT). A.B.C. acknowledges a National Defense Science and Engineering Graduate Fellowship, and A.I.D. acknowledges a National Science Foundation Graduate Research Fellowship.

ASJC Scopus subject areas

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/jacs.6b10027

Cite this

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title = "Reversible and selective encapsulation of dextromethorphan and β-estradiol using an asymmetric molecular capsule assembled via the weak-link approach",

abstract = "An allosterically regulated, asymmetric receptor featuring a binding cavity large enough to accommodate three-dimensional pharmaceutical guest molecules as opposed to planar, rigid aromatics, was synthesized via the Weak-Link Approach. This architecture is capable of switching between an expanded, flexible {"}open{"} configuration and a collapsed, rigid {"}closed{"} one. The structure of the molecular receptor can be completely modulated in situ through the use of simple ionic effectors, which reversibly control the coordination state of the Pt(II) metal hinges to open and close the molecular receptor. The substantial change in binding cavity size and electrostatic charge between the two configurations is used to explore the capture and release of two guest molecules, dextromethorphan and β-estradiol, which are widely found as pollutants in groundwater.",

author = "Jose Mendez-Arroyo and D'Aquino, {Andrea I.} and Chinen, {Alyssa B.} and Manraj, {Yashin D.} and Mirkin, {Chad A.}",

note = "Funding Information: This material is based upon work supported by the National Science Foundation award CHE-1149314, the Department of Defense National Security Science and Engineering Faculty Fellowship award N00014-15-1-0043, and the U.S. Army award W911NF-15-1-0151. J.M.A. acknowledges a fellowship from Consejo Nacional de Ciencia y Tecnologia (CONACYT). A.B.C. acknowledges a National Defense Science and Engineering Graduate Fellowship, and A.I.D. acknowledges a National Science Foundation Graduate Research Fellowship. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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Reversible and selective encapsulation of dextromethorphan and β-estradiol using an asymmetric molecular capsule assembled via the weak-link approach. / Mendez-Arroyo, Jose; D'Aquino, Andrea I.; Chinen, Alyssa B. et al.
In: Journal of the American Chemical Society, Vol. 139, No. 4, 01.02.2017, p. 1368-1371.

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

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AU - Manraj, Yashin D.

AU - Mirkin, Chad A.

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Reversible and selective encapsulation of dextromethorphan and β-estradiol using an asymmetric molecular capsule assembled via the weak-link approach

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UN SDGs

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