Fluorescent Molecular Sensory System Based on Bis Pyrene-Modified γ-Cyclodextrin Dimer for Steroids and Endocrine Disruptors

Narita, Minoru; Mima, Satoshi; Ogawa, Norio; Hamada, Fumio

doi:10.2116/analsci.17.379

Cited by 35 publications

(5 citation statements)

References 28 publications

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“…To test this hypothesis, the fluorophore functionalized CD‐Ps were investigated as differential receptors for ten bile acids. Numerous β‐ and γ‐CD constructs have been used for the chemosensing of bile salts with fluorescence based readouts . As such, this class of analytes is ideal for validation of CD 4 and CD‐Ps for sensing applications.…”

Section: Resultsmentioning

confidence: 99%

Highly Functionalized β‐Cyclodextrins by Solid‐Supported Synthesis

Vurgun

Nitz

2018

Chemistry A European J

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Using covalent capture, a high yielding selective mono-functionalization of heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-CD with a 5-mercaptopentyl functional group has been achieved. Here, we demonstrate the immobilization of the mono-thiol functionalized β-CD on PEGA resin via a disulfide bond, enabling solid-phase elaboration of the remaining six primary amines. To showcase the potential of this method, the amines were elaborated to tripeptides through standard Fmoc-peptide chemistry. A small library of CD-tripeptide conjugates was generated which, when reduced from the solid support, could be tagged at the released thiol with an environmentally sensitive fluorophore. The resulting library of sensors showed potential for the differential sensing of various bile salts. The described methodology provides a rapid and versatile route to synthesize highly functionalized libraries of CD derivatives that may be tailored towards applications in sensing, catalysis, and multivalent displays.

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Section: Resultsmentioning

confidence: 99%

Highly Functionalized β‐Cyclodextrins by Solid‐Supported Synthesis

Vurgun

Nitz

2018

Chemistry A European J

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“…[35][36][37][38][39][40][41][42][43] We have employed pyrene (PY) as the donor in this study because PY has been employed as donor in several PET reactions. [44][45][46][47][48][49] Our strategy for assembling the D-β-CD-A system which employed both the rim-binding and inclusion binding abilities of β-CD, is outlined in Scheme 1. Addition of tert-butylPMDI to an aqueous solution of native β-CD would result in the formation of the binary rim-binding complex (designated as β-CD PMDI).…”

Section: Resultsmentioning

confidence: 99%

Self-assembly and photoinduced electron transfer in a donor- $$\upbeta $$ β -cyclodextrin-acceptor supramolecular system $$^{\S }$$ §

Krishnan

Balan

et al. 2018

J Chem Sci

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Equimolar amounts of native β-cyclodextrin (β-CD), pyrene-linked adamantane (PYAD) and tert-butylpyromellitic diimide (PMDI) when dissolved in water self-assembled to form the supramolecular donor-acceptor system PYAD β-CD PMDI. The high affinity of adamantane derivatives for inclusion binding in the β-CD cavity and the propensity of PMDI to undergo rim-binding at the narrow rim of β-CD led to the formation of PYAD β-CD PMDI. The ternary complex PYAD β-CD PMDI was thoroughly characterized using various spectroscopic techniques. β-CD performs three functions in the self-assembled complex: (1) encapsulate the adamantane unit and keep the pyrene (PY) moiety above the secondary rim, (2) rim-bind PMDI and keep it at the primary rim, and (3) act as a spacer between pyrene and PMDI. Thus, the ternary complex can function as a donor-spacer-acceptor system capable of undergoing photoinduced electron transfer (PET). Upon excitation of the pyrene moiety in PYAD β-CD PMDI an electron is transferred from the excited pyrene to the PMDI ground state. Steady state and time resolved fluorescence experiments were carried out to study the PET in PYAD β-CD PMDI. Existence of the ternary system and PET processes taking place within it are further supported by laser flash photolysis experiments.

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“…Some other bis-CD sensors appear also in literature [28]. Thus, we have synthetised the 1,3-[bis-N-6A-deoxy-β-cyclodextrin-6A-yl-aminocarbonyl]-7-pyridin-4-yl indolizine (Scheme 2) as a part of our outgoing research program to develop a new range of fluorescent β-CD sensors [29].…”

Section: Resultsmentioning

confidence: 99%

Fluorescent Indolizine-b-Cyclodextrin Derivatives for the Detection of Volatile Organic Compounds

Bécuwe

Landy

Delattre

et al. 2008

Sensors

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This paper presents the synthesis, the structural determination and the sensing capabilities toward Volatile Organic Compounds (VOCs) of a new class of fluorescent indolizine-cyclodextrin sensors. Two different pathways, both involving bipyridinium ylides and 6-amino-b-cyclodextrin, have been used to carry out the synthesis of these sensors. The macrocycle structures were dominantly established by 1H-NMR spectra and systematically studied by molecular modelling (MM3, AM1, AM1-COSMO methods). The sensing capabilities of the sensors were evaluated by emission of fluorescence, during the inclusion of the guest (adamantanol or aromatic derivatives) into the cyclodextrin (CD) host cavity. The host/guest complex formation was investigated by formation constant determinations, using experimental methods, coupled with theoretical calculations of formation energies using a specific docking procedure. Both experimental and theoretical results suggest that some compounds would make very attractive sensors for VOC detection. Some compounds could also be taken into consideration as biological markers.

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Fluorescent Molecular Sensory System Based on Bis Pyrene-Modified γ-Cyclodextrin Dimer for Steroids and Endocrine Disruptors

Abstract: To a cooled solution (-10˚C) of 4-(1-pyrenyl)butanoic acid (165 mg, 0.57 mM) in 8 mL of DMF were added dicyclohexylcarbodiimido (DCC, 118 mg, 0.57 mM) and 1-hydroxybenzotriazole (HOBt, 77 mg, 0.57 mM). The reaction 379 ANALYTICAL SCIENCES MARCH

Cited by 35 publications

References 28 publications

Highly Functionalized β‐Cyclodextrins by Solid‐Supported Synthesis

Highly Functionalized β‐Cyclodextrins by Solid‐Supported Synthesis

Self-assembly and photoinduced electron transfer in a donor- $$\upbeta $$ β -cyclodextrin-acceptor supramolecular system $$^{\S }$$ §

Fluorescent Indolizine-b-Cyclodextrin Derivatives for the Detection of Volatile Organic Compounds

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