Effects of 9,10-dihydroxy-4,4-dimethyl-5,8-dihydro-1(4H)-anthracenone derivatives on tumor cell respiration

Araya‐Maturana, Ramiro; Cardona, Wilson; Cassels, Bruce K.; Delgado‐Castro, Tomás; Ferreira, Jorge; Miranda, Dante; Pavani, Mario; Pessoa‐Mahana, Hernán; Soto‐Delgado, Jorge; Weiss-López, Boris

doi:10.1016/j.bmc.2006.02.011

Cited by 33 publications

(26 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[25,26] Also, isoquinoline quinone III has been used as a substrate in oxidative coupling reactions with amines to produce anti-tumour quinones. [27] The two goals of this work were: first, to contribute to the understanding of how water affects the reactivity and selectivity of quinones in C-N coupling reactions with amines, and second, to study a non-catalytic eco-friendly methodology, for the regioselective oxidative coupling reaction of amines with quinones.…”

Section: Introductionmentioning

confidence: 99%

On-Water Reactivity and Regioselectivity of Quinones in C–N Coupling with Amines: Experimental and Theoretical Study

et al. 2014

Self Cite

View full text Add to dashboard Cite

A study about the oxidative coupling of some representative carbo-and heterocyclic non-symmetrical quinones with aryland alkylamines, was carried out comparing dichloromethane and water as reaction mediums. We found that the on-water reactions gave better or, at worst, the same results as a conventional organic medium like dichloromethane. Descriptors derived from conceptual density functional theory and approaches of electrostatic nature, such as the molecular electrostatic potential, were used to explain the observed chemical reactivity and regioselectivity. Further, the on-water conditions were used to obtain 24 new aminoquinones with potential biological activity.

show abstract

Section: Introductionmentioning

confidence: 99%

On-Water Reactivity and Regioselectivity of Quinones in C–N Coupling with Amines: Experimental and Theoretical Study

et al. 2014

Self Cite

View full text Add to dashboard Cite

show abstract

“…The synthesis of deuterated Q1 and Q2 were performed following a previously reported methodology 12 , only replacing 1,3-butadiene by the fully deuterated reagent, which is commercially available (Aldrich). CsDS was prepared from the reaction between decanol and sulfuric acid, followed by neutralization with CsOH and crystallized three times before use.…”

Section: Synthesis Sample Preparation and Nmr Spectramentioning

confidence: 99%

“…9 In the past, significant work of our group has been devoted to the synthesis, mechanism of formation and biological evaluation of quinones and hydroquinones. [10][11][12] Biological activity of these products has been measured trough IC 50 values against tumor cell respiration of TA3 cell line and TA3-MTX-R multidrug resistant variety. 13 It is now accepted that mitochondria are involved in cell apoptosis.…”

Section: Introductionmentioning

confidence: 99%

“…They were selectively deuterated at positions 5, 6, 7 and 8 (see figure 1), and dissolved in anionic discotic nematic lyotropic liquid crystal (dnllc) solution. Despite their apparent structural similarity these two molecules show different anti-cancer activity: Q2 is two to three times more active than Q1 as a tumor cell respiration inhibitor (IC 50 Q1 = 0.22±0.02mM and IC 50 Q2 =0.08±0.01mM against TA3 cell line; IC 50 Q1 = 0.17±0.02mM and IC 50 Q2 = 0.07±0.01mM against the TA3-MTX-R variety) (12,13). In general, IC 50 for oxygen uptake inhibition are about an order of magnitude greater than IC 50 for cytotoxicity; however, it is a quick test for preliminary screening of possible anti-cancer activity.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Location, Orientation and Dynamics of Two Molecules With Mitochondrial Activity Dissolved in Anionic Lyomesophase: A ²h-NMR and Md Study

Bahamonde-Padilla¹,

Martínez-Cifuentes²,

Muñoz-Masson³

et al. 2012

J. Chil. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

ABSTRACT4,4-Dimethyl-5,8-dihydroanthracene-1,9,10(4H)-trione (Q1) and 9,10-Dihydroxy-4,4-dimethyl-5,8-dihydro-1(4H)-anthracenone (Q2), two molecules that inhibit cancer cell respiration, were selectively deuterated and dissolved in an anionic discotic nematic lyotropic liquid crystal (dnllc) solution. The solution provides a magnetic field oriented anisotropic medium, where the location, average orientation and dynamics of Q1 and Q2 were examined by measuring 2 H-NMR quadrupole splittings (Dn Q ) and 2 H longitudinal relaxation times (T 1 ). The NMR data shows that both molecules are strongly attached to the aggregate and, when dissolved, increase the alignment of the interface components with the magnetic field. However they present different average orientations. To assist with the interpretation of the experimental results, 300ns Molecular Dynamics (MD) trajectories of a bilayer model of the aggregate were calculated. The results show that both molecules spontaneously diffuse inside the bilayer, to locate in the limit between the hydrophobic core and the interface. The orientations of both molecules in the aggregate are determined by the formation of H-bonds with water.

show abstract

“…[5] In addition, we have demonstrated that compounds incorporating a carbonyl group at position ortho with regard to a phenol function inhibit tumor cell respiration. [6] Moreover, we have also reported a series of simple and angular chromones [7] and tricyclic hydroquinones, [8] possessing the mentioned structural feature, as inhibitors of oxygen uptake against the TA3 mouse carcinoma cell line and its multidrug-resistant variant TA3-MTX-R. The 9,10-dihydroxy-4,4-dimethyl-5,8-dihydro-1(4H)-anthracenone (1), [9,10] which proved to be the most active one in the series, also exhibited low micro molar dose-dependent growth inhibition of the human U937 cell line (human monocytic leukemia), [8] in addition to other interesting biological activities such as antifungal [11] and antioxidant.…”

Section: Introductionmentioning

confidence: 98%

NMR assignment in regioisomeric hydroquinones

Dobado

Gómez-Tamayo

Calvo‐Flores

et al. 2011

Magnetic Reson in Chemistry

Self Cite

View full text Add to dashboard Cite

A set of regioisomeric pairs of tricyclic hydroquinones, analogues of antitumor 9,10-dihydroxy-4,4-dimethyl-5,8-dihydroanthracen-1(4H)-one (1) and other derivatives, were synthesized and their regiochemistry and NMR spectra assigned by using (1)H-detected one-bond (C-H) HMQC and long-range C-H HMBC, in good agreement with theoretical O3LYP/Alhrichs-pVTZ calculations. The 5-hydroxymethyl derivatives (11, 15, 19) showed a (3)J(H, H) coupling constant of methylene protons evidencing the presence of a seven-membered intramolecular hydrogen bonded ring, not observed for the 8-hydroxymethyl isomers.

show abstract

Effects of 9,10-dihydroxy-4,4-dimethyl-5,8-dihydro-1(4H)-anthracenone derivatives on tumor cell respiration

Cited by 33 publications

References 35 publications

On-Water Reactivity and Regioselectivity of Quinones in C–N Coupling with Amines: Experimental and Theoretical Study

On-Water Reactivity and Regioselectivity of Quinones in C–N Coupling with Amines: Experimental and Theoretical Study

Location, Orientation and Dynamics of Two Molecules With Mitochondrial Activity Dissolved in Anionic Lyomesophase: A ²h-NMR and Md Study

NMR assignment in regioisomeric hydroquinones

Contact Info

Product

Resources

About