Rapid Macrocycle Threading by a Fluorescent Dye-Polymer Conjugate in Water with Nanomolar Affinity

Evan M Peck; Wenqi Liu; Graeme T Spence; Scott K Shaw; Anthony P Davis; Harry Destecroix; Bradley D Smith

doi:10.1021/jacs.5b03573

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Rapid Macrocycle Threading by a Fluorescent Dye-Polymer Conjugate in Water with Nanomolar Affinity

Journal article

Open access

Rapid Macrocycle Threading by a Fluorescent Dye-Polymer Conjugate in Water with Nanomolar Affinity

Evan M Peck, Wenqi Liu, Graeme T Spence, Scott K Shaw, Anthony P Davis, Harry Destecroix and Bradley D Smith

Journal of the American Chemical Society, Vol.137(27), pp.8668-8671

07/15/2015

DOI: 10.1021/jacs.5b03573

PMCID: PMC4643739

PMID: 26106948

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Abstract

A macrocyclic tetralactam host is threaded by a highly fluorescent squaraine dye that is flanked by two polyethylene glycol (PEG) chains with nanomolar dissociation constants in water. Furthermore, the rates of bimolecular association are very fast with k(on) ≈ 10(6)-10(7) M(-1) s(-1). The association is effective under cell culture conditions and produces large changes in dye optical properties including turn-on near-infrared fluorescence that can be imaged using cell microscopy. Association constants in water are ∼1000 times higher than those in organic solvents and strongly enthalpically favored at 27 °C. The threading rate is hardly affected by the length of the PEG chains that flank the squaraine dye. For example, macrocycle threading by a dye conjugate with two appended PEG2000 chains is only three times slower than threading by a conjugate with triethylene glycol chains that are 20 times shorter. The results are a promising advance toward synthetic mimics of streptavidin/biotin.

Animals

CHO Cells

Cricetulus

Cyclobutanes - chemistry

Fluorescent Dyes - chemistry

Kinetics

Lactams, Macrocyclic - chemistry

Microscopy, Fluorescence

Optical Imaging

Phenols - chemistry

Polyethylene Glycols - chemistry

Water - chemistry

Details

Title: Subtitle: Rapid Macrocycle Threading by a Fluorescent Dye-Polymer Conjugate in Water with Nanomolar Affinity
Creators: Evan M Peck - †Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States
Wenqi Liu - †Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States
Graeme T Spence - †Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States
Scott K Shaw - †Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States
Anthony P Davis - ‡School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K
Harry Destecroix - ‡School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K
Bradley D Smith - †Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States
Resource Type: Journal article
Publication Details: Journal of the American Chemical Society, Vol.137(27), pp.8668-8671
DOI: 10.1021/jacs.5b03573
PMID: 26106948
PMCID: PMC4643739
NLM abbreviation: J Am Chem Soc
ISSN: 0002-7863
eISSN: 1520-5126
Grant note: R01 GM059078 / NIGMS NIH HHS T32GM075762 / NIGMS NIH HHS T32 GM075762 / NIGMS NIH HHS
Language: English
Date published: 07/15/2015
Academic Unit: Chemistry
Record Identifier: 9984216612202771

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