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Investigating the inclusion of the Ag(I)-nimesulide complex into β-cyclodextrin: studies in solution and in the solid state

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Abstract

The present work describes the preparation and characterization of inclusion systems involving β-CD and the silver(I) nimesulide coordination complex (Ag-NMS), prepared by kneading (K) and co-evaporation (CE) methods. Solid state characterization by DSC, XRD and IR vibrational spectroscopic measurements provided remarkable evidences of the formation of true inclusion systems. Solution measurements provided information about the inclusion mode. The UV–Vis spectroscopy was used to obtain the association constants by the Scatchard method, and the value obtained was 370 ± 2 L mol−1. The 1H NMR spectroscopic measurements indicate a total inclusion of the guest into the cavity. A 2D NOESY experiment was carried out for the inclusion complex. The spectrum shows that hydrogens 3–6 of the cyclodextrin clearly correlate with the protons of the phenoxy ring of nimesulide in the Ag-NMS coordination compound, which confirms the formation of the inclusion complex. The antibacterial activities of the Ag-NMS and CE-[(Ag-NMS)·β-CD] inclusion system were evaluated by the well diffusion method over Escherichia coli and Pseudomonas aeruginosa (Gram-negative) and Staphylococcus aureus (Gram-positive) pathogenic bacterial strains. The observed data shows the significant antibacterial activity of the Ag-NMS coordination complex, and no activity for the inclusion complex under the same considered conditions.

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Abbreviations

NMS:

Nimesulide

Ag-NMS:

Silver(I) coordination complex with nimesulide

CD:

Cyclodextrin

DSC:

Differential scanning calorimetry

XRD:

X-ray diffractometry

IR:

Infrared

NMR:

Nuclear magnetic resonance

NOESY:

Nuclear overhauser effect spectroscopy NMR spectroscopy

UV–Vis:

Ultraviolet–Visible spectroscopy

TMS:

Tetramethylsilane

DMSO:

Dimethyl sulfoxide

DMF:

Dimethylformamide

HG:

Host–guest inclusion complex

ϵ :

Molar extinction coefficient

ϵ H :

Molar extinction coefficient of the host molecule

ϵ G :

Molar extinction coefficient of the guest molecule

ϵ HG :

Molar extinction coefficient of the host–guest inclusion complex

ATCC:

American type collection cell

MH:

Mueller-Hinton agar

BHI:

Brain-heart infusion medium

CFU:

Colony forming unit

MIC:

Minimum inhibitory concentration

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Acknowledgments

This study was supported by grants from the Brazilian Agencies FAPESP (São Paulo State Research Foundation, Brazil—proc. 2012/08230-2), CAPES and CNPq. Professor Corbi is also grateful to Professors Celso A. Bertran and André L. B. Formiga from the Campinas State University, UNICAMP, Brazil, for technical support.

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Authors and Affiliations

  1. Inorganic Chemistry Department, Institute of Chemistry, University of Campinas—UNICAMP, P.O. Box 6154, Campinas, SP, 13083-970, Brazil

    Raphael E. F. de Paiva, Camilla Abbehausen, Fernando R. G. Bergamini, Andre L. Thompson & Pedro P. Corbi

  2. Laboratory of Biotechnology, Institute of Biology, University of Campinas, UNICAMP, Campinas, SP, 13083-970, Brazil

    Danilo A. Alves & Marcelo Lancellotti

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  1. Raphael E. F. de Paiva
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  2. Camilla Abbehausen
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  3. Fernando R. G. Bergamini
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Correspondence to Pedro P. Corbi.

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de Paiva, R.E.F., Abbehausen, C., Bergamini, F.R.G. et al. Investigating the inclusion of the Ag(I)-nimesulide complex into β-cyclodextrin: studies in solution and in the solid state. J Incl Phenom Macrocycl Chem 79, 225–235 (2014). https://doi.org/10.1007/s10847-013-0348-4

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