Dirhodium(II,II) complexes: Molecular characteristics that affect in vitro activity

Alfredo M. Angeles-Boza; Helen T. Chifotides; J. Dafhne Aguirre; Abdellatif Chouai; Patty K.L. Fu; Kim R. Dunbar; Claudia Turro

doi:10.1021/jm060592h

Dirhodium(II,II) complexes: Molecular characteristics that affect in vitro activity

Alfredo M. Angeles-Boza, Helen T. Chifotides, J. Dafhne Aguirre, Abdellatif Chouai, Patty K.L. Fu, Kim R. Dunbar, Claudia Turro

Research output: Contribution to journal › Article › peer-review

111 Scopus citations

Abstract

In the series Rh₂(O₂CR)₄ (R = CH ₃, 1; R = CF₃, 2), [Rh₂(O₂CR) ₂(phen)₂]²⁺ (R = CH₃, 3; R = CF ₃, 4), and [Rh₂(O₂CR)₂(dppz) ₂]²⁺ (R = CH₃, 5; R = CF₃, 6), 2, 4, and 6 are twice as cytotoxic as 1, 3, and 5, respectively. The substitution reactions of 2 with 9-ethylguanine at various temperatures take place at faster rates than those of 1, and the activation energy E_a(1) = 69 ± 4 kJ/mol is twice E_a(2) = 35 ± 2 kJ/mol. The higher cytotoxicities of [Rh₂(μ-O₂CCH₃) ₂(η¹-O₂CCH₃)L(MeOH)] ⁺ (L = dppz, 7; L = dppn, 8) relative to [Rh₂(μ-O ₂CCH₃)₂(bpy)L]²⁺ (L = dppz, 10; L = dppn, 11) are attributed to the labile equatorial groups in 7 and 8 not present in 10 and 11. The toxicities of complexes 1-8 are not related to their charge or the ease by which they transverse the cellular membrane but to the lability of the ligands on the dirhodium core.

Original language	English (US)
Pages (from-to)	6841-6847
Number of pages	7
Journal	Journal of Medicinal Chemistry
Volume	49
Issue number	23
DOIs	https://doi.org/10.1021/jm060592h
State	Published - Nov 16 2006
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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@article{941706a3a4f54e27bd933e74fb70c36e,

title = "Dirhodium(II,II) complexes: Molecular characteristics that affect in vitro activity",

abstract = "In the series Rh2(O2CR)4 (R = CH 3, 1; R = CF3, 2), [Rh2(O2CR) 2(phen)2]2+ (R = CH3, 3; R = CF 3, 4), and [Rh2(O2CR)2(dppz) 2]2+ (R = CH3, 5; R = CF3, 6), 2, 4, and 6 are twice as cytotoxic as 1, 3, and 5, respectively. The substitution reactions of 2 with 9-ethylguanine at various temperatures take place at faster rates than those of 1, and the activation energy Ea(1) = 69 ± 4 kJ/mol is twice Ea(2) = 35 ± 2 kJ/mol. The higher cytotoxicities of [Rh2(μ-O2CCH3) 2(η1-O2CCH3)L(MeOH)] + (L = dppz, 7; L = dppn, 8) relative to [Rh2(μ-O 2CCH3)2(bpy)L]2+ (L = dppz, 10; L = dppn, 11) are attributed to the labile equatorial groups in 7 and 8 not present in 10 and 11. The toxicities of complexes 1-8 are not related to their charge or the ease by which they transverse the cellular membrane but to the lability of the ligands on the dirhodium core.",

author = "Angeles-Boza, {Alfredo M.} and Chifotides, {Helen T.} and Aguirre, {J. Dafhne} and Abdellatif Chouai and Fu, {Patty K.L.} and Dunbar, {Kim R.} and Claudia Turro",

year = "2006",

month = nov,

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doi = "10.1021/jm060592h",

language = "English (US)",

volume = "49",

pages = "6841--6847",

journal = "Journal of Medicinal Chemistry",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Dirhodium(II,II) complexes

T2 - Molecular characteristics that affect in vitro activity

AU - Angeles-Boza, Alfredo M.

AU - Chifotides, Helen T.

AU - Aguirre, J. Dafhne

AU - Chouai, Abdellatif

AU - Fu, Patty K.L.

AU - Dunbar, Kim R.

AU - Turro, Claudia

PY - 2006/11/16

Y1 - 2006/11/16

N2 - In the series Rh2(O2CR)4 (R = CH 3, 1; R = CF3, 2), [Rh2(O2CR) 2(phen)2]2+ (R = CH3, 3; R = CF 3, 4), and [Rh2(O2CR)2(dppz) 2]2+ (R = CH3, 5; R = CF3, 6), 2, 4, and 6 are twice as cytotoxic as 1, 3, and 5, respectively. The substitution reactions of 2 with 9-ethylguanine at various temperatures take place at faster rates than those of 1, and the activation energy Ea(1) = 69 ± 4 kJ/mol is twice Ea(2) = 35 ± 2 kJ/mol. The higher cytotoxicities of [Rh2(μ-O2CCH3) 2(η1-O2CCH3)L(MeOH)] + (L = dppz, 7; L = dppn, 8) relative to [Rh2(μ-O 2CCH3)2(bpy)L]2+ (L = dppz, 10; L = dppn, 11) are attributed to the labile equatorial groups in 7 and 8 not present in 10 and 11. The toxicities of complexes 1-8 are not related to their charge or the ease by which they transverse the cellular membrane but to the lability of the ligands on the dirhodium core.

AB - In the series Rh2(O2CR)4 (R = CH 3, 1; R = CF3, 2), [Rh2(O2CR) 2(phen)2]2+ (R = CH3, 3; R = CF 3, 4), and [Rh2(O2CR)2(dppz) 2]2+ (R = CH3, 5; R = CF3, 6), 2, 4, and 6 are twice as cytotoxic as 1, 3, and 5, respectively. The substitution reactions of 2 with 9-ethylguanine at various temperatures take place at faster rates than those of 1, and the activation energy Ea(1) = 69 ± 4 kJ/mol is twice Ea(2) = 35 ± 2 kJ/mol. The higher cytotoxicities of [Rh2(μ-O2CCH3) 2(η1-O2CCH3)L(MeOH)] + (L = dppz, 7; L = dppn, 8) relative to [Rh2(μ-O 2CCH3)2(bpy)L]2+ (L = dppz, 10; L = dppn, 11) are attributed to the labile equatorial groups in 7 and 8 not present in 10 and 11. The toxicities of complexes 1-8 are not related to their charge or the ease by which they transverse the cellular membrane but to the lability of the ligands on the dirhodium core.

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Dirhodium(II,II) complexes: Molecular characteristics that affect in vitro activity

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