Structural investigations of pyridin-4-yl indolizine modified β-cyclodextrin derivatives as fluorescent chemosensors for organic guest molecules

Delattre, François; Woisel, Patrice; Bria, Marc; Surpateanu, Gheorghe

doi:10.1016/j.carres.2005.05.001

Cited by 17 publications

(6 citation statements)

References 24 publications

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“…With the aim of optimizing the properties of cyclodextrins for a particular use, many substituted CDs have been prepared and new derivatives continue to be reported . It has been shown that macrocyclic amphiphiles of hydrophobically modified CDs can form a variety of supramolecular assemblies, including monolayers, multilayers, and Langmuir−Blodgett films at the air−water interface .…”

Section: Introductionmentioning

confidence: 99%

On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n-Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study

et al. 2007

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The formation of reverse micelles (RMs) of sodium 1,4-bis(2-ethylhexyl)sulfosuccinate (AOT) in n-heptane including two different beta-cyclodextrin (beta-CD) derivatives (hydroxypropyl-beta-CD, hp-beta-CD, and decenyl succinyl-beta-CD, Mod-beta-CD) is reported. Both cyclodextrins can be incorporated into AOT RMs in different zones within the aggregate, while beta-CD cannot. Using UV-vis and induced circular dichroism (ICD) spectroscopy and different achiral molecular probes (some azo dyes, p-nitroaniline and ferrocene), it was possible to determine that Mod-beta-CD is located with its cavity at the oil side of the AOT RM interface, while for hp-beta-CD the cavity is inside the RM water pool. Among the molecular probes used, methyl orange (MO) was the only one which gave the ICD signal when dissolved in the AOT RMs with hp-beta-CD, so a detailed study of MO behavior in homogeneous media was also performed to compare with the microheterogeneous media. The solvatochromic behavior of the dye depends not only on the polarity of the media but also on other specific solvent properties. A Kamlet-Taft analysis shows that the MO absorption spectrum shifts to longer wavelength with an increase in the solvent polarity-polarizability (pi*) and the hydrogen donor ability (alpha) of the medium. MO appears to be almost 3 times more sensitive to the pi* parameter than to the alpha parameter. In addition, from the MO absorption spectral changes with the hp-beta-CD concentration, the association equilibrium constants in pure water (K11W) and inside the RMs (K11RM) were computed. The results show that K11W is almost 10 times larger than the value inside the RMs. The latter can be explained considering that MO resides anchored to the RM interface through hydrogen bond interaction with the hydration bound water. This study shows for the first time that the cyclodextrin chiral cavity is available for a guest in an organic medium such as the RMs; therefore, we have created a potentially powerful nanoreactor with two different confined regions in the same aggregate: the polar core of the RMs and the chiral hydrophobic cavity of cyclodextrin.

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Section: Introductionmentioning

confidence: 99%

On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n-Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study

et al. 2007

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“…were successfully introduced on the scaffold by combining pre- or postfunctionalization reactions, ensuring the versatility of this platform. Another interesting aspect is linked to the intrinsic fluorescence of the indolizine ring ,,, that allows the easy monitoring of the molecules not only during synthesis, but also in the course of biochemical and biological assays. In the present work, fluorescence properties were applied to assess the stability of biotin-tagged molecules.…”

Section: Discussionmentioning

confidence: 99%

“…In a previous work, we considered the use of pyridinium ylide-alkyne cycloaddition forming indolizine as fluorogenic coupling methodology . Indeed, bioactive indolizines are well-known (for a recent review on their chemical synthesis and biological evaluation, see Singh and Mmatli), but new applications have emerged in the fields of fluorescent markers in biology, − detection of organic compounds, , or material sciences . Among the different synthetic strategies, we selected the two-step preparation of 1,3,7-trisubstituted indolizines (illustrated in Scheme ) from easily accessible reactants (pyridine, alkylating agent, and propiolic ester or amide) and simple reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Indolizine-Based Scaffolds as Efficient and Versatile Tools: Application to the Synthesis of Biotin-Tagged Antiangiogenic Drugs

et al. 2017

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We describe the design and optimization of polyfunctional scaffolds based on a fluorescent indolizine core derivatized with various orthogonal groups (amines, esters, oximes, alkynes, etc.). To show one application as tools in biology, the scaffold was used to prepare drug–biotin conjugates that were then immobilized onto avidin-agarose for affinity chromatography. More specifically, the antiangiogenic drug COB223, whose mechanism of action remained unclear, was chosen as a proof-of-concept drug. The drug-selective discrimination of proteins observed after elution of the cell lysates through the affinity columns, functionalized either with the biologically active COB223 or a structurally related inactive analogue (COB236), is a clear indication that the presence of the indolizine core does not limit drug–protein interaction and confirms the usefulness of the indolizine scaffold. Furthermore, the separation of COB223-interacting proteins from human placental extracts unveiled unanticipated protein targets belonging to the family of regulatory RNA-binding proteins, which opens the way to new hypotheses on the mode of action of this antiangiogenic drug.

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“…4 In a continuing program on the design and synthesis of chemosensors for recognition of environmentally important molecular species, 5 we have investigated the synthesis and emission properties of a new tripod fluorescent system, which bears a triazine core with cyclomaltooligosaccharide (cyclodextrin, CD) units as wellknown molecular receptors. While the design and synthesis of target-selective receptors with luminescent signaling systems have attained a significant position in supramolecular b-cyclodextrin chemistry for alcohol, 6 volatile organic compound, or metal-ion detection, 7,8 these systems are less frequently employed in the case of pesticides. While relatively few reports in the literature have been devoted to the spectrofluorimetric study of CD complexes with pesticides, none, to the best of our knowledge, was dedicated to the direct determination of a pesticide guest by a fluorescent macrocycle-b-CD complex.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of a fluorescent tripod detection system for pesticides by microwave-assisted click chemistry

Mallard-Favier

Blach

Cazier

et al. 2009

Carbohydrate Research

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Structural investigations of pyridin-4-yl indolizine modified β-cyclodextrin derivatives as fluorescent chemosensors for organic guest molecules

Cited by 17 publications

References 24 publications

On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n-Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study

On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n-Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study

Indolizine-Based Scaffolds as Efficient and Versatile Tools: Application to the Synthesis of Biotin-Tagged Antiangiogenic Drugs

Efficient synthesis of a fluorescent tripod detection system for pesticides by microwave-assisted click chemistry

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