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Trollope L, Cruickshank DL, Noonan T, et al. Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures. Beilstein J Org Chem. 2014;10:3136-51doi: 10.3762/bjoc.10.331.
Trollope, L., Cruickshank, D. L., Noonan, T., Bourne, S. A., Sorrenti, M., Catenacci, L., & Caira, M. R. (2014). Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures. Beilstein journal of organic chemistry, 103136-51. https://doi.org/10.3762/bjoc.10.331
Trollope, Lee, et al. "Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures." Beilstein journal of organic chemistry vol. 10 (2014): 3136-51. doi: https://doi.org/10.3762/bjoc.10.331
Trollope L, Cruickshank DL, Noonan T, Bourne SA, Sorrenti M, Catenacci L, Caira MR. Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures. Beilstein J Org Chem. 2014 Dec 29;10:3136-51. doi: 10.3762/bjoc.10.331. eCollection 2014. PMID: 25670983; PMCID: PMC4311586.
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Beilstein J Org Chem. 2014 Dec 29;10:3136-51. doi: 10.3762/bjoc.10.331. eCollection 2014.

Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures.

Beilstein journal of organic chemistry

Lee Trollope, Dyanne L Cruickshank, Terence Noonan, Susan A Bourne, Milena Sorrenti, Laura Catenacci, Mino R Caira

Affiliations

  1. Centre for Supramolecular Chemistry Research (CSCR), Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa.
  2. Department of Drug Sciences, University of Pavia, Via Taramelli 12, 27100 Pavia, Italy.

PMID: 25670983 PMCID: PMC4311586 DOI: 10.3762/bjoc.10.331

Abstract

The phytoalexin trans-resveratrol, 5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol, is a well-known, potent antioxidant having a variety of possible biomedical applications. However, its adverse physicochemical properties (low stability, poor aqueous solubility) limit such applications and its inclusion in cyclodextrins (CDs) has potential for addressing these shortcomings. Here, various methods of the attempted synthesis of inclusion complexes between trans-resveratrol and three methylated cyclodextrins (permethylated α-CD, permethylated β-CD and 2,6-dimethylated β-CD) are described. Isolation of the corresponding crystalline 1:1 inclusion compounds enabled their full structure determination by X-ray analysis for the first time, revealing a variety of guest inclusion modes and unique supramolecular crystal packing motifs. The three crystalline inclusion complexes were also fully characterized by thermal analysis (hot stage microscopy, thermogravimetric analysis and differential scanning calorimetry). To complement the solid-state data, phase-solubility studies were conducted using a series of CDs (native and variously derivatised) to establish their effect on the aqueous solubility of trans-resveratrol and to estimate association constants for complex formation.

Keywords: X-ray structures; cyclodextrin; inclusion complexes; thermal analysis; trans-resveratrol

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