Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study

Botta B, Fraschetti C, Novara FR, Tafi A, Sacco F, Mannina L, Sobolev AP, Mattay J, Letzel M, Speranza M (2009)
Organic & Biomolecular Chemistry 7(9): 1798-1806.

Download
Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Zeitschriftenaufsatz | Veröffentlicht | Englisch
Autor
; ; ; ; ; ; ; ; ;
Abstract / Bemerkung
The stereoselectivity of the reaction between (R)-(-)-2-butylamine and the diastereomeric proton-bound complexes of (+)-catharanthine (C) or (-)-vindoline (V) with some chiral amido[4]resorcinarenes has been investigated in the gas phase by ESI-FT-ICR-MS. The reaction stereoselectivity (0.56 < k(homo)/k(hetero) < 16.9) is found to depend critically on the functional groups present in the chiral pendants of the hosts. Rationalisation of the kinetic results is based on careful computational and spectroscopic studies of the most stable conformations of (+)-catharanthine and its protonated form in the isolated state and in water, as well as in a representative host structure. The emerging picture points to the relevant diastereomeric proton-bound complexes as quasi-degenerate, thus suggesting that their stereoselectivity in the guest exchange reaction is mostly due to kinetic factors. The results of this study may represent a starting point for a deeper comprehension of the intrinsic factors that endow these molecules, and their dimeric forms, with their biochemical properties.
Erscheinungsjahr
Zeitschriftentitel
Organic & Biomolecular Chemistry
Band
7
Ausgabe
9
Seite(n)
1798-1806
ISSN
eISSN
PUB-ID

Zitieren

Botta B, Fraschetti C, Novara FR, et al. Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study. Organic & Biomolecular Chemistry. 2009;7(9):1798-1806.
Botta, B., Fraschetti, C., Novara, F. R., Tafi, A., Sacco, F., Mannina, L., Sobolev, A. P., et al. (2009). Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study. Organic & Biomolecular Chemistry, 7(9), 1798-1806. doi:10.1039/b900735k
Botta, B., Fraschetti, C., Novara, F. R., Tafi, A., Sacco, F., Mannina, L., Sobolev, A. P., Mattay, J., Letzel, M., and Speranza, M. (2009). Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study. Organic & Biomolecular Chemistry 7, 1798-1806.
Botta, B., et al., 2009. Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study. Organic & Biomolecular Chemistry, 7(9), p 1798-1806.
B. Botta, et al., “Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study”, Organic & Biomolecular Chemistry, vol. 7, 2009, pp. 1798-1806.
Botta, B., Fraschetti, C., Novara, F.R., Tafi, A., Sacco, F., Mannina, L., Sobolev, A.P., Mattay, J., Letzel, M., Speranza, M.: Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study. Organic & Biomolecular Chemistry. 7, 1798-1806 (2009).
Botta, Bruno, Fraschetti, Caterina, Novara, Francesca R., Tafi, Andrea, Sacco, Fabiola, Mannina, Luisa, Sobolev, Anatoli P., Mattay, Jochen, Letzel, Matthias, and Speranza, Maurizio. “Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study”. Organic & Biomolecular Chemistry 7.9 (2009): 1798-1806.

5 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Stereochemical preference of 2'-deoxycytidine for chiral bis(diamido)-bridged basket resorcin[4]arenes.
D'Acquarica I, Calcaterra A, Sacco F, Balzano F, Aiello F, Tafi A, Pesci N, Uccello-Barretta G, Botta B., Chirality 25(12), 2013
PMID: 24038320
Cyclochiral resorcin[4]arenes as effective enantioselectors in the gas phase.
Fraschetti C, Letzel MC, Paletta M, Mattay J, Speranza M, Filippi A, Aschi M, Rozhenko AB., J Mass Spectrom 47(1), 2012
PMID: 22282092
Chirality effects on the IRMPD spectra of basket resorcinarene/nucleoside complexes.
Filippi A, Fraschetti C, Piccirillo S, Rondino F, Botta B, D'Acquarica I, Calcaterra A, Speranza M., Chemistry 18(27), 2012
PMID: 22696428

18 References

Daten bereitgestellt von Europe PubMed Central.

Inhibition of tubulin-microtubule polymerization by drugs of the Vinca alkaloid class.
Owellen RJ, Hartke CA, Dickerson RM, Hains FO., Cancer Res. 36(4), 1976
PMID: 1260766
Interaction of drugs with microtubule proteins.
Wilson L, Bamburg JR, Mizel SB, Grisham LM, Creswell KM., Fed. Proc. 33(2), 1974
PMID: 4855812
Synthesis and host-guest studies of chiral N-linked peptidoresorc[4]arenes.
Botta B, D'Acquarica I, Monache GD, Subissati D, Uccello-Barretta G, Mastrini M, Nazzi S, Speranza M., J. Org. Chem. 72(24), 2007
PMID: 17958449

Botta, Eur. J. Org. Chem. (), 2007
Enantioselective guest exchange in a chiral resorcin[4]arene cavity.
Botta B, Botta M, Filippi A, Tafi A, Delle Monache G, Speranza M., J. Am. Chem. Soc. 124(26), 2002
PMID: 12083910

Tafi, Chem.–Eur. J. 10(), 2004

Botta, Angew. Chem., Int. Ed. 43(), 2004

Botta, Chem.–Eur. J. 12(), 2006

Botta, Angew. Chem., Int. Ed. 45(), 2006

Botta, Int. J. Mass Spectrom. 267(), 2007
A kinetic study of guest displacement reactions on a host-guest complex with a photoswitchable calixarene.
Letzel MC, Schafer C, Novara FR, Speranza M, Rozhenko AB, Schoeller WW, Mattay J., J Mass Spectrom 43(11), 2008
PMID: 18698554

Su, J. Phys. Chem. 88(4102), 1988

Su, J. Phys. Chem. 89(), 1988

Gal, Int. J. Mass Spectrom. 222(), 2003
The gas-phase chemistry of cyclodextrin inclusion complexes.
Lebrilla CB., Acc. Chem. Res. 34(8), 2001
PMID: 11513573

Botta, Chem.–Eur. J. 14(), 2008

Bayly, J. Phys. Chem. 97(), 1993

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 19590774
PubMed | Europe PMC

Suchen in

Google Scholar