Influence of alcohols on the .beta.-cyclodextrin/acridine complex

Schuette, Jodi M.; Ndou, Thilivhali T.; Peña, Arsenio Muñoz de la; Mukundan, Srinivasan; Warner, Isiah M.

doi:10.1021/ja00054a042

Cited by 71 publications

(51 citation statements)

References 3 publications

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“…[5][6][7][8][9][10][11][12][13]30 For pyrene, an enhancement of the association efficiency was observed, whereas for naphthalene, azulene, and acridine a decrease of the equilibrium constant was reported. The main feature of these ternary complexation agents was that they have a hydrophobic moiety and on one extremity have hydrogen-bonding atoms.…”

Section: Discussionmentioning

confidence: 98%

Effect of Amino Acid Coinclusion on the Complexation of Pyrene with β-Cyclodextrin

Yang

Bohne

1996

J. Phys. Chem.

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The possibility of amino acids acting as ternary complexation agents for the binding of pyrene with -cyclodextrin ( -CD) was investigated. UV-vis absorption measurements combined with steady-state and time-resolved fluorescence studies were employed to characterize ternary complex formation. From the 18 amino acids tested it was determined that tryptophan, leucine, phenylalanine, methionine, and isoleucine form ternary complexes. The first three also significantly enhance the association constant of pyrene with -CD. Amino acids are less efficient than alcohols in enhancing the association constants of host-guest complexes, but a higher degree of steric constraint in the complexes including these zwitterionic molecules was observed. In addition, two types of pyrene--CD complexes were shown to exist, which were assigned to complexes with 1:1 and 1:2 pyrene: -CD stoichiometries.

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Section: Discussionmentioning

confidence: 98%

Effect of Amino Acid Coinclusion on the Complexation of Pyrene with β-Cyclodextrin

Yang

Bohne

1996

J. Phys. Chem.

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“…This partitioning of Acr was reported in the microheterogeneous environment of micelles, reverse micelles, and also inside the cavity of b-cyclodextrin. [32,33,[50][51][52] The partitioning constant (K p ) calculated from the pseudophase model for 30 mm SDS solution was found to be more than 780 m À1 . [52] The bases Ade and d-Ade, on the other hand, are more likely to be positioned in the interfacial region of the SDS microenvironment.…”

Section: Quenching Of Acr In Sds Micelles By Ade and D-adementioning

confidence: 97%

Influence of 2′‐Deoxy Sugar Moiety on Excited‐State Protonation Equilibrium of Adenine and Adenosine with Acridine inside SDS Micelles: A Time‐Resolved Study with Quantum Chemical Calculations

2012

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The protonation dynamics of the DNA base adenine (Ade) and its nucleoside 2'-deoxyadenosine (d-Ade) are investigated by monitoring the deprotonation kinetics of an N-heterocyclic DNA intercalator, acridine (Acr), in the confined environment of sodium dodecyl sulfate (SDS) micelles. Protonation of acridine (AcrH(+)) occurs at the hydrophilic interface and this species remains in dynamic equilibrium with its deprotonated counterpart (Acr) inside the hydrophobic core of SDS micelles. Quenching of the fluorescence of AcrH(+)* at 478 nm is observed after addition of Ade and d-Ade with Stern-Volmer constant (K(SV)) 298 and 75 M(-1), respectively, with a concomitant increment in Acr* at 425 nm. Time-resolved fluorescence studies reveal quenching in the lifetime of AcrH(+)*. The relative amplitude of AcrH(+)* decreases from 0.97 to 0.51 and 0.97 to 0.89 with equimolar addition of Ade and d-Ade, respectively. These observations are explained by excited-state proton transfer (ESPT) from AcrH(+)* to the bases. The reduced K(SV) value and negligible change in the relative amplitudes of AcrH(+)* with d-Ade infer that ESPT is hindered substantially by the presence of a 2'-deoxy sugar unit. Transient time-resolved absorption spectra of Acr reflect that Ade reduces the absorbance of (3)AcrH(+)*; however, d-Ade keeps it unaltered for more than a time delay of 2 μs. The optimized geometries calculated by quantum chemical methods reflect deprotonation of AcrH(+)* with protonation at the N1 position of Ade, while it remains protonated with d-Ade. The hindered ESPT between AcrH(+)* and d-Ade singles out the significance of the 2'-deoxy sugar moiety in controlling the deprotonation kinetics.

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“…Cyclodextrins, cyclic non-reducing oligosaccharides, have been extensively used to obtain these inclusion complexes. In particular, many studies have focused on the ability of CDs to include guests of varying sizes in different stoichiometric ratios and several analytical applications of these complexes have been reported [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30].…”

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confidence: 99%

Room temperature phosphorescence in cyclodextrins. Analytical applications

Peña¹,

Mahedero²,

Sánchez³

2000

Analusis

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Surfactants which form micelles and cyclodextrins are two of the most common forms of organized media. Surfactants are known for their ability to self-assemble in water and/or organic solvents and form normal/reverse micelles above the critical micelle concentration (CMC). Micellar solubilization in surfactant solutions has been widely exploited in analytical chemistry. The formation of inclusion compounds, by using cyclodextrins as hosts, has been also frequently used to enhance the analytical responses of analytes by incorporation of guest molecules into the cyclodextrins hydrophobic cavity [1].The first observation of room temperature phosphorescence (RTP), using a microscopically organized media, used sodium dodecylsulfate (SDS) micelles in the presence of tallium [2]. Since then, several media have been investigated to stabilize the triplet-state in fluid solution at room temperature. Normal micelles, mainly sodium dodecylsulfate [3][4][5][6], cetyltrimethylammonium bromide (CTB) [7][8][9] and Triton X-100 [10] micelles, have been used in RTP analytical applications. As an alternative to the use of normal micelles, microemulsions, formed in heptane-SDS-1-pentanol, have been also reported for RTP obtention [11][12][13][14].Cyclodextrins (CDs) can form complexes with phosphors and heavy atom containing additives and these host-guest aggregates serve to populate and stabilize the fragile tripletstate, producing characteristic room temperature phosphorescence. These inclusion complexes induce an intense phosphorescence emission which is partially insensitive to Cyclodextrins are composed of D-glucose residues joined by α(1→4) linkages. α-, β-and γ-CDs, which are made up of six, seven and eight D-glucose residues, are the most common members of a CD family. These CDs are shaped like a truncated cone with a hollow, hydrophobic cavity in which a hydrophobic guest can be incorporated.Molecular encapsulation by means of molecular inclusion complex formation offers a new approach in analytical chemistry. Generally, the inclusion complex involves the spatial entrapment of a single guest molecule in the cavity of the host molecule, without the formation of any covalent bonds. Cyclodextrins, cyclic non-reducing oligosaccharides, have been extensively used to obtain these inclusion complexes. In particular, many studies have focused on the ability of CDs to include guests of varying sizes in different stoichiometric ratios and several analytical applications of these complexes have been reported [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30].It is well documented that, depending upon the host CD (i.e. α-, β-or γ-CD) and the size of the guest, different

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Influence of alcohols on the .beta.-cyclodextrin/acridine complex

Cited by 71 publications

References 3 publications

Effect of Amino Acid Coinclusion on the Complexation of Pyrene with β-Cyclodextrin

Effect of Amino Acid Coinclusion on the Complexation of Pyrene with β-Cyclodextrin

Influence of 2′‐Deoxy Sugar Moiety on Excited‐State Protonation Equilibrium of Adenine and Adenosine with Acridine inside SDS Micelles: A Time‐Resolved Study with Quantum Chemical Calculations

Room temperature phosphorescence in cyclodextrins. Analytical applications

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