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Solid-state Sn-119 NMR and antitumor activity of bis[1,3-bis(3-oxapentamethylene-carbamoylthioacetato)-1,1,3,3-tetrabutyl-1,3-distannoxane], and the crystal structure of its bis-ethanol solvate

par Ng, Waikuen;Hook, James;Gielen, Marcel
Référence Applied organometallic chemistry, 14, 1, page (1-7)
Publication Publié, 2000-01

Article révisé par les pairs

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Résumé :

The 119Sn cross polarization-magic angle spinning NMR spectrum of bis[1,3-bis(3-oxapentamethylenecarbamoylthioacetato)-1,1,3,3-tetrabutyl-1,3-distannoxane], {[(C4H9)2SnO2CCH2SC(O)N(CH2CH2)2O]2O}2, which consists of two resonances of similar chemical shifts and symmetry (δiso = −152, −202 ppm; asymmetry, κ = 0.38), implies the existence of two five-coordinate tin sites in the centrosymmetric dimer. The assignment has been corroborated by X-ray diffraction analysis on the compound that has been crystallized from ethanol; the crystal structure shows two tin atoms in cis-C2SnO3 trigonal-bipyramidal coordination [C-Sn-C = 131.5(1), 131.3(2) °]. The analysis also reveals the presence of two lattice ethanol molecules that are hydrogen-bonded to the dimer [OO = 2.779(5) Å]. When exposed to air, the distannoxane loses ethanol. The unsolvated distannoxane is more active than cis-platin when screened against MCF-7 (mammary cancer), EVSA-T (mammary cancer), WiDr (colon cancer), IGROV (ovarian cancer), M19 MEL (melanoma), A498 (renal cancer) and H226 (lung cancer) cell lines. Copyright © 2000 John Wiley & Sons, Ltd.