Complexation of achiral calixarenes with chiral pharmaceutical substances: A circular dichroism study

Current Pharmaceutical Analysis

Volumn 9, Issue 1, 2013, Pages 121-129

  Chamseddin, Chamseddin ^a   Jira, Thomas ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Active Pharmaceutical Ingredients (APIs); Calixarenes (CA); Circular Dichroism (CD); Cyclodextrins; Host guest omplexation; Macrocyclic molecules

Indexed keywords

ACETONITRILE; ALPHA CYCLODEXTRIN; AMPHETAMINE; BETA CYCLODEXTRIN; CALIXARENE DERIVATIVE; CHELATING AGENT; EPHEDRINE; GAMMA CYCLODEXTRIN; HYOSCYAMINE; LEVOMEPROMAZINE; LEVONORGESTREL; MACROCYCLIC COMPOUND; METHANOL; MOXIFLOXACIN; NAPROXEN; OLIGOMER; PROPRANOLOL; TIMOLOL; UNCLASSIFIED DRUG; VALSARTAN; WATER;

ARTICLE; BINDING AFFINITY; CHEMICAL COMPOSITION; CHIRAL ACTIVE PHARMACEUTICAL INGREDIENT; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; CONTROLLED STUDY; DRUG DETERMINATION; DRUG SOLUBILITY; HYDROPHILICITY; HYDROPHOBICITY; MOLECULAR INTERACTION; MOLECULE; PRIORITY JOURNAL;

EID: 84873126277     PISSN: 15734129     EISSN: 1875676X     Source Type: Journal    
DOI: 10.2174/157341213804806160     Document Type: Article

References (19)

1. Gutsche, C.D. Calixarenes in monographs in supramolecular chemistry; Royal Society of Chemistry: Cambridge, 1989.
2. Morozumi, T.; Shinkai, S. A novel "reading-out" system for amino acid chirality with induced chirality in water-soluble calix[n]arenes, Chem. Lett., 1994, 1515-1518.
3. Morozumi, T.; Shinkai, S. Induced circular dichroism detection of chiral ammonium guests through inclusion in calix[n]arene cavities, J. Chem. Soc. Chem. Commun., 1994, 1219-1220.
4. Kikuchi, Y.; Kobayashi, K.; Aoyama, Y. Complexation of chiral glycols, steroidal polyols, and sugars with a multibenzenoid, achiral host as studied by induced circular dichroism spectros-copy: exciton chirality induction in resorcinol-aldehyde cyclotetramer and its use as a supramolecular probe for the assignments of stereochemistry of chiral guests, J. Am. Chem. Soc., 1992, 114, 1351-1358.
5. Arimura, T.; Shinkai, S. Formation of molecular complexes with calixarenes as detected by induced circular dichroism, Bull. Chem. Soc. Jpn., 1991, 64, 1896-1900.
6. Gutsche, C.D. Calixarenes Revisited, The Royal Society of Chemistry: Cambridge, 1998.
7. Millership, J.S. A preliminary investigation of the solution complexation of 4-sulphonic calix[n]arenes with testosterone, J. Inclusion Phenom. Macromol. Chem., 2001, 39, 327-331.
8. Yang, W.; de Villiers, M.M. The solubilization of the poorly water soluble drug nifedipine by water soluble 4-sulphonic calix[n]arenes, Eur. J. Pharm. Biopharm., 2004, 58, 629-636.
9. Yang, W.; de Villiers, M.M. Aqueous solubilization of furosemide by supramolecular complexation with 4-sulphonic calix[n]arenes, J. Pharm. Pharmacol., 2004, 56, 703-708.
10. Yang, W.; de Villiers, M.M. Effect of 4-sulphonato-calix[n]arenes and cyclodextrins on the solubilization of niclosamide, a poorly water soluble anthelmintic, The AAPS Journal, 2005, 7, 241-248.
11. Berova, N.; Nakanishi, K.; Woody, R.W. Circular Dichroism: Principles and Applications, Wiley: New York, 2000; pp. 431-845.
12. Urbanová, M.; Malon, P. Analytical Methods in Supramolecular Chemistry, Schalley, C. A., Ed., Wiley: New York, 2007; pp 265-305.
13. Mason, S.F. Molecular optical activity and the chiral discriminations, Cambridge: Cambridge University Press, 1982.
14. Harada, N.; Nakanishi, K. Circular dichroic spectroscopy: exciton coupling in organic stereochemistry, University Science Books, 1983.
15. Arimura, T.; Edamitsu, S.; Shinkai, S.; Manabe, O.; Muramatsu, T.; Tashiro, M. Induced circular dichroism in calixarene complexes, Chem. Lett., 1987, 2269-2272.
16. Allenmark, S. Induced circular dichroism by chiral molecular inter-action, Chirality, 2003, 15, 409-422.
17. Böhmer, V.; McKervey, M.A. Calixarene neue Möglichkeiten der supramolekularen Chemie, Chemie in unserer Zeit, 1991, 25, 195-207.
18. U.S. National Library of Medicine. http://www.nlm.nih.gov/
19. Kamogawa, K; Kitagawa, T. Solute/solvent and solvent/solvent interactions in methanol solutions: quantitative separation by Raman difference spectroscopy, J. Phys. Chem., 1985, 89, 1531-1537.