Ionization constants of arylhydrazonoisoxazolone fungicides and related compounds

Lehtonen, K; Summers, L. A.

doi:10.1071/ch9701699

Cited by 7 publications

(4 citation statements)

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“…The ligands pyrazino[2,3-f][1,10]phenanthroline (dpq), 21 dipyrido[3,2-a:2′,3′-c]phenazine (dppz), 22 benzodipyrido[3,2-a:2′,3′c]phenazine (dppn), 23 and 4,7-dihydrodibenzo[de,gh][1,10]phenanthroline (dap) 24 were synthesized according to reported procedures. [21][22][23][24] The dirhodium complex Rh 2 (µ-O 2 CCH 3 ) 4 was prepared according to published literature procedures. 25 The following monosubstituted dirhodium complexes were all prepared according to previously described procedures: Instrumentation.…”

Section: Methodsmentioning

confidence: 99%

“…The ligands pyrazino[2,3- f ][1,10]phenanthroline (dpq), dipyrido[3,2- a :2′,3′- c ]phenazine (dppz), benzodipyrido[3,2- a :2′,3′- c ]phenazine (dppn), and 4,7-dihydrodibenzo[ de , gh ][1,10]phenanthroline (dap) were synthesized according to reported procedures. − The dirhodium complex Rh 2 (μ-O 2 CCH 3 ) 4 was prepared according to published literature procedures . The following monosubstituted dirhodium complexes were all prepared according to previously described procedures: cis -[Rh 2 (μ-O 2 CCH 3 ) 2 (η 1 -O 2 CCH 3 )(bpy)(CH 3 OH)](O 2 CCH 3 ) ( 1 ), cis -[Rh 2 (μ-O 2 CCH 3 ) 2 (η 1 -O 2 CCH 3 )(phen)(CH 3 OH)](O 2 CCH 3 ) ( 2 ), cis -[Rh 2 (μ-O 2 CCH 3 ) 2 (η 1 -O 2 CCH 3 )(dppz)(CH 3 OH)](O 2 CCH 3 ) ( 4 ), , cis -[Rh 2 (μ-O 2 CCH 3 ) 2 (η 1 -O 2 CCH 3 )(dppn)(CH 3 OH)](O 2 CCH 3 ) ( 5 ), and cis -[Rh 2 (μ-O 2 CCH 3 ) 2 (η 1 -O 2 CCH 3 )(dap)(CH 3 OH)](O 2 CCH 3 ) ( 6 ) …”

Section: Methodsmentioning

confidence: 99%

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Live Cell Cytotoxicity Studies: Documentation of the Interactions of Antitumor Active Dirhodium Compounds with Nuclear DNA

et al. 2009

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The promising antitumor activity of dirhodium complexes has been known for over 30 years. There remains, however, a general lack of understanding of their activity in cellulo. In this study, we report the DNA interactions and activity in living cells of six monosubstituted dirhodium(II,II) complexes of general formula [Rh(2)(mu-O(2)CCH(3))(2)(eta(1)-O(2)CCH(3))(L)(CH(3)OH)](+), where L = bpy (2,2'-bipyridine) (1), phen (1,10-phenanthroline) (2), dpq (dipyrido[3,2-f:2',3'-h]quinoxaline) (3), dppz (dipyrido[3,2-a:2',3'-c]phenazine) (4), dppn (benzo[i]dipyrido[3,2-a:2',3'-c]phenazine) (5), and dap (4,7-dihydrodibenzo[de,gh][1,10]phenanthroline) (6). DNA interactions were investigated by UV/visible spectroscopy, relative viscosity measurements, and electrophoretic mobility shift assay. These measurements indicate that compound 5 exhibits the strongest interaction with DNA. Compound 5 also causes the most damage to DNA after cellular internalization, as evaluated by the alkaline comet assay. Compound 5, however, is not the most effective at inhibiting cell viability of the human cancer cells HeLa and COLO-316. The greater hydrophobicity of 5 as compared to that of 4, which is the most effective compound in the series, hinders its ability to reach its cellular target(s). Data from modulation studies of glutathione using N-acetylcysteine and L-buthionine-sulfoximine indicate that changes in glutathione levels do not affect the activity of these particular dirhodium complexes. These results suggest that glutathione is not the only agent involved in the deactivation of these dirhodium complexes.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Live Cell Cytotoxicity Studies: Documentation of the Interactions of Antitumor Active Dirhodium Compounds with Nuclear DNA

et al. 2009

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“…The ligands pyrazino[2,3-f ][1,10]phenanthroline (dpq), 54 dipyrido[3,2-a:2¢,3¢-c]phenazine (dppz) 55 and benzodipyrido-[3,2-a:2¢,3¢-c]phenazine (dppn), 56 were synthesized according to reported procedures. 54,55, 57 The dirhodium complexes Rh 2 (m- 5) 33 were synthesized according to published literature procedures.…”

Section: Experimental Materialsmentioning

confidence: 99%

Anticancer activity of heteroleptic diimine complexes of dirhodium: A study of intercalating properties, hydrophobicity and in cellulo activity

et al. 2009

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The series of complexes cis-[Rh(2)(mu-O(2)CCH(3))(2)(dppn)(L)](2+), where dppn = benzo[i]dipyrido[3,2-a:2',3'-c] phenazine, and L = bpy (2,2'-bipyridine) (1), phen (1,10-phenanthroline) (2), dpq (dipyrido[3,2-f:2',3'-h]quinoxaline) (3), dppz (dipyrido[3,2-a:2',3'-c]phenazine) (4), and dppn (5) were synthesized and their effect on the human cancer cells HeLa and COLO-316 was monitored. Complexes 1 and 2 interact with DNA through intercalation, whereas compounds 3-5 bind only electrostatically. It was found that the dirhodium complex 4 is the most effective compound at inhibiting cell viability of the human cancer cells HeLa and COLO-316. A general conclusion is that the hydrophobicity of the compounds correlates with their in cellulo activity in both cell lines. The ability of the compounds to reach nuclear DNA and form adducts was explored using the comet assay. The results indicate that compounds 1-5 either do not form adducts with DNA that are detrimental to the cell or that they are successfully repaired by the cellular machinery. The results of an annexin V assay indicate that compounds 1-4 trigger apoptosis, whereas compound 5 clearly does not. These findings are significant because they support the contention that dirhodium complexes can be tuned to direct their effect to cellular targets other than nuclear DNA.

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“…[Rh 2 (OCCH 3 NH) 2 (CH 3 CN) 6 ](BF 4 ) 2 was prepared according to the published method 26. Following the known procedure, dipyrido[3,2‐a:2′,3′‐c]phenazine was prepared from the condensation reaction using stoichiometric amounts of o ‐phenylenediamine (Aldrich) and 1,10‐phenanthroline‐5,6‐dione (Aldrich) 36. D 2 O (99.9 % D) was purchased from Aldrich and used for NMR experiments.…”

Section: Methodsmentioning

confidence: 99%

Mg_4.85Rh₆Si₁₃, a Magnesium Rhodium Silicide with Silicon Clusters Si₄ and Si₁₈

Kessens

Schnelle

Jung

2014

Zeitschrift anorg allge chemie

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Ionization constants of arylhydrazonoisoxazolone fungicides and related compounds

Cited by 7 publications

References 0 publications

Live Cell Cytotoxicity Studies: Documentation of the Interactions of Antitumor Active Dirhodium Compounds with Nuclear DNA

Live Cell Cytotoxicity Studies: Documentation of the Interactions of Antitumor Active Dirhodium Compounds with Nuclear DNA

Anticancer activity of heteroleptic diimine complexes of dirhodium: A study of intercalating properties, hydrophobicity and in cellulo activity

Mg_4.85Rh₆Si₁₃, a Magnesium Rhodium Silicide with Silicon Clusters Si₄ and Si₁₈

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Ionization constants of arylhydrazonoisoxazolone fungicides and related compounds

Cited by 7 publications

References 0 publications

Live Cell Cytotoxicity Studies: Documentation of the Interactions of Antitumor Active Dirhodium Compounds with Nuclear DNA

Live Cell Cytotoxicity Studies: Documentation of the Interactions of Antitumor Active Dirhodium Compounds with Nuclear DNA

Anticancer activity of heteroleptic diimine complexes of dirhodium: A study of intercalating properties, hydrophobicity and in cellulo activity

Mg4.85Rh6Si13, a Magnesium Rhodium Silicide with Silicon Clusters Si4 and Si18

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Mg_4.85Rh₆Si₁₃, a Magnesium Rhodium Silicide with Silicon Clusters Si₄ and Si₁₈