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Inclusion complexes of cyclodextrins with 4-amino-1,8-naphthalimides (part 2)

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Abstract

Fluorescence spectroscopy was used to characterize inclusion compounds between 4-amino-1,8-naphthalimides (ANI) derivatives and different cyclodextrins (CDs). The ANI derivatives employed were N-(12-aminododecyl)-4-amino-1,8-naphthalimide (mono-C12ANI) and N,N′-(1,12-dodecanediyl)bis-4-amino-1,8-naphthalimide (bis-C12ANI). The CDs used here were α-CD, β-CD, γ-CD, HP-α-CD, HP-β-CD and HP-γ-CD. The presence of CDs resulted in pronounced blue-shifts in the emission spectra of the ANI derivatives, with increases in emission intensity. This behavior was parallel to that observed for the dyes in apolar solvents, indicating that inclusion complexes were formed between the ANI and the CDs. Mono-C12ANI formed inclusion complexes of 1:1 stoichiometry with all the CDs studied. Complexes with the larger CDs (HP-β-CD, HP-γ-CD and γ-CD) were formed by inclusion of the chromophoric ANI ring system, whereas the smaller CDs (α-CD, HP-α-CD and β-CD) formed complexes with mono-C12ANI by inclusion of the dodecyl chain. Bis-C12ANI formed inclusion complexes of 1:2 stoichiometry with HP-β-CD, HP-γ-CD and γ-CD, but did not form inclusion complexes with α-CD, HP-α-CD and β-CD. The data were treated in the case of the large CDs using a Benesi-Hildebrand like equation, giving the following equilibrium constants: mono-C12ANI:HP-β-CD (K 11 = 50 M−1), mono-C12ANI:HP-γ-CD (K 11 = 180 M−1), bis-C12ANI:HP-β-CD (K 12 = 146 M−2), bis-C12ANI:HP-γ-CD (K 12 = 280 M−2).

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Acknowledgments

This work was supported by grants from Brazilian agency FAPESP (grant No. 05/51104-4 and 08/57940-7). S.B. thanks CNPq for a PQ scholarship. B.P.G.S. and R.O.M. are grateful to FAPESP for doctoral fellowships.

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  1. Universidade Federal do ABC, Rua Santa Adélia, 166, Santo André, SP, 09210-170, Brazil

    Barbara Perez Gonçalves Silva & Sergio Brochsztain

  2. Centro Interdisciplinar de Investigação Bioquímica, Universidade de Mogi das Cruzes, Av. Dr. Cândido Xavier de Almeida Souza, 200, Mogi das Cruzes, SP, 08780-911, Brazil

    Rodrigo Oliveira Marcon

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  1. Barbara Perez Gonçalves Silva
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Correspondence to Sergio Brochsztain.

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Silva, B.P.G., Marcon, R.O. & Brochsztain, S. Inclusion complexes of cyclodextrins with 4-amino-1,8-naphthalimides (part 2). J Incl Phenom Macrocycl Chem 68, 313–322 (2010). https://doi.org/10.1007/s10847-010-9790-8

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