Complex daunomycin–butanol

Abstract

C 25H29NO 10" HC1. C4H 10 O, monoclinic, P2~, a = 17.389 (8), b = 5.557 (3), c = 16.405 (8) A and fl = 91.41 (8) °, Z = 2. The structure was solved by direct methods and refined to an R of 0.07 for 2611 unique diffractometer data. The conformation and the interactions present in the complex structure allow us to propose a model for intercalation with DNA.

Interaction of Uranyl Ions with Daunorubicin and Adriamycin

“…A typical NMR sample contained 10 m anthracycline in [D 4 ]methanol. 1 H and 13 C chemical shifts were referenced to the solvent peak at δ ϭ 3.31 (25°C).…”

“…The 1D FIDs were multiplied by an exponential window function (0.3 Hz line broadening added) and zero filing was performed prior to Fourier transformation. 1 H-Detected heteronuclear multiple-quantum coherence HMQC [35] and 1 H-detected heteronuclear multiple bond correlation HMBC [36] (optimized for long range couplings with a low-pass Jfilter to suppress one bond correlations) experiments were acquired at 800 MHz and at 25°C. Data sets with 2048 ϫ 512 complex points were acquired with a 9 KHz sweep width in the proton dimension and 40 KHz in the carbon dimension.…”

“…These antibiotics contain an anthraquinone chromophore and an amino glycoside sugar (Scheme 1). [1] Despite their severe cardiotoxicity and other side effects, they are both used clinically as Scheme 1. Structures of daunorubicin (R ϭ H) and adriamycin (R ϭ OH) based on the crystal structure of Dnr [1] the formation of complex I takes place with two drug molecules per UO 2 2+ ion.…”

“…[1] Despite their severe cardiotoxicity and other side effects, they are both used clinically as Scheme 1. Structures of daunorubicin (R ϭ H) and adriamycin (R ϭ OH) based on the crystal structure of Dnr [1] the formation of complex I takes place with two drug molecules per UO 2 2+ ion. At higher pH or R values, complex II forms, and probably has a polymeric structure with one uranyl ion bridging two drug chromophores through both the keto-phenolate sites.…”

Design of potential angiogenin inhibitors

“…First a molecular dynamics conformational search procedure was undertaken on the daunomycin molecule to generate an ensemble of low-energy structures. The crystal structure of daunomycin [17] was energy minimised, with charges calculated using the charge templates option within QUANTA. Daunomycin was then subjected to molecular dynamics for 1 ns at a simulated temperature of 1000 K, quenching every picosecond to give 1000 structures, which were then clustered according to an rms torsion angle deviation of 15 °.…”