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

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.

[1]  A. Ueno.  Review: fluorescent cyclodextrins for molecule sensing , 1996 .

[2]  H. Ikeda,et al.  Fluorescent cyclodextrins for molecule sensing: Fluorescent properties, NMR characterization, and inclusion phenomena of N-dansylleucine-modified cyclodextrins , 1996 .

[3]  M. Fernández,et al.  Stabilization of α-chymotrypsin by chemical modification with monoamine cyclodextrin , 2005 .

[4]  R. Zare,et al.  Capillary electrochromatography: operating characteristics and enantiomeric separations , 1996 .

[5]  F. Hamada,et al.  Fluorescent molecular sensory system based on bis pyrene-modified gamma-cyclodextrin dimer for steroids and endocrine disruptors. , 2001, Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.

[6]  François Delattre,et al.  1,3-Dipolar cycloaddition reaction of bipyridinium ylides with the propynamido-β-cyclodextrin. A regiospecific synthesis of a new class of fluorescent β-cyclodextrins , 2004 .

[7]  A. Ueno,et al.  A Molecule Detection Sensor of Modified Cyclodextrin Based on Guest-responsive Intramolecular Fluorescence Quenching , 2001 .

[8]  U. Resch‐Genger,et al.  Fluorescence and UV/Vis spectroscopic behaviour of novel biindolizines , 2000 .

[9]  M. Salome,et al.  Analytical Improvement in Measuring Formation Constants of Inclusion Complexes between β-Cyclodextrin and Phenolic Compounds , 2000 .

[10]  G. Vergoten,et al.  A comparative study by AM1, PM3 and ab initio HF/3-21G methods on the structure and reactivity of monosubstituted carbanion 1,2,4-triazolium ylides , 2000 .

[11]  G. Surpateanu,et al.  Sulfobutyl Ether‐β‐Cyclodextrins: Promising Supramolecular Carriers for Aqueous Organometallic Catalysis , 2005 .

[12]  D. Landy,et al.  Experimental and Theoretical Study on the Inclusion Compounds of Aroma Components with β-Cyclodextrins , 2006 .

[13]  F. Hamada,et al.  Fluorescent Pyrrolinone-modified Cyclodextrins as a Chemo-sensor for Organic Guests , 1999 .

[14]  François Delattre,et al.  1-(4-Nitrophenoxycarbonyl)-7-pyridin-4-yl indolizine: a new versatile fluorescent building block. Application to the synthesis of a series of fluorescent β-cyclodextrins , 2005 .

[15]  François Delattre,et al.  Synthesis of a new fluorinated fluorescent β-cyclodextrin sensor , 2005 .

[16]  G. Surpateanu,et al.  Synthesis and Characterisation of Extended p-Bonding Systems in Cycloimmonium Ylides Derived from the 4,4’-Bipyridine , 2002 .

[17]  K. Uekama,et al.  Recent Aspects of Pharmaceutical Application of Cyclodextrins , 2002 .

[18]  L. Szente,et al.  Cyclodextrins as food ingredients , 2004 .

[19]  L. Gundersen,et al.  Indolizines as novel potent inhibitors of 15-lipoxygenase. , 2003, Bioorganic & medicinal chemistry.

[20]  J. Szejtli.  Cyclodextrins and their inclusion complexes , 1982 .

[21]  S. Bhosale.  β-Cyclodextrin as supramolecular catalyst in organic synthesis , 2007 .

[22]  David Landy,et al.  New fluorescent bis‐β‐cyclodextrin‐indolizine sensor. Synthesis and sensing ability , 2007 .

[23]  G. Garçon,et al.  SYNTHESIS OF NEW FLUORESCENT β-CYCLODEXTRIN SENSOR , 2005 .

[24]  H. S. Wolff,et al.  iRun: Horizontal and Vertical Shape of a Region-Based Graph Compression , 2022, Sensors.

[25]  K. Hattori,et al.  Detection of environmental chemicals by SPR assay using branched cyclodextrin as sensor ligand , 2007 .

[26]  J. Szejtli.  Utilization of cyclodextrins in industrial products andprocesses , 1997 .

[27]  G. Surpateanu,et al.  Solubilisation of chlorinated solvents by cyclodextrin derivatives: a study by static headspace gas chromatography and molecular modelling. , 2007, Journal of hazardous materials.

[28]  F. Cazier,et al.  Tuneable fluorescent marker appended to β-cyclodextrin : a pH-driven molecular switch , 2007 .

[29]  U. Banerjee,et al.  Biotechnological applications of cyclodextrins. , 2002, Biotechnology advances.

[30]  J. Szejtli.  Introduction and General Overview of Cyclodextrin Chemistry. , 1998, Chemical reviews.