An unusual asymmetric pseudomacrocyclic free base ligand and nickel(II) chelate: X-ray crystallographic and DFT studies

Bhikraj, Sandipa; Munro, Orde Q.; Akerman, Matthew P.

doi:10.1016/j.poly.2016.12.026

Cited by 6 publications

(7 citation statements)

References 35 publications

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“…[4][5][6] Such ligands stabilize metal ions in a range of oxidation states. [7] Examples include structurally characterized Co II/III , [8][9][10][11] Rh I/III , [12][13][14][15] Ir III , [16,17] Ni II , [18][19][20] Pd II , [20][21][22] Pt II , [23][24][25] Cu II , [26][27][28][29] Ag I , [30] and Au III complexes. [31] While pyrrole compounds are key building blocks for organic pharmaceuticals, [32] for example, Tolmetin, [33] Sunitinib, [34] and Glimepiride, [35] studies over the last two decades suggest that pyrrole-imine metal chelates exhibit significant medicinal potential.…”

Section: Introductionmentioning

confidence: 99%

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Complexities of the Interaction of Ni^II, Pd^II and Pt^II Pyrrole‐Imine Chelates with Human Serum Albumin**

Sookai

Munro

2023

ChemistryEurope

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Human serum albumin (HSA) efficiently transports drugs in vivo: most are organic. Here, HSA binding affinity and site specificity are shown to depend on the identity of the d8 metal ion in NiII, PdII and PtII chelates of the bis(pyrrole‐imine) ligand H2PrPyrr. Fluorescence quenching data for native and probe‐bound HSA showed sites close to Trp‐214 (subdomain IIA) are targeted. The Stern‐Volmer constants, KSV, ranged from 104 M−1 to 105 M−1 while the affinity constants, Ka, ranged from ∼3.5×103 M−1 to ∼1×106 M−1 at 37 °C, following the order Pd(PrPyrr) > Pt(PrPyrr) > Ni(PrPyrr) > H2PrPyrr. Ligand uptake is enthalpically driven, hinging mainly on London dispersion forces. Induced CD spectra for the protein‐bound ligands could be simulated by hybrid QM:MM TD‐DFT methods, proving that the metal chelates neither decompose nor demetallate after uptake by HSA. Transport and delivery of the metal chelates by HSA in vivo could therefore be feasible.

show abstract

Section: Introductionmentioning

confidence: 99%

“…Such ligands stabilize metal ions in a range of oxidation states [7] . Examples include structurally characterized Co II/III , [8–11] Rh I/III , [12–15] Ir III , [16,17] Ni II , [18–20] Pd II , [20–22] Pt II , [23–25] Cu II , [26–29] Ag I , [30] and Au III complexes [31] …”

Section: Introductionmentioning

confidence: 99%

Complexities of the Interaction of Ni^II, Pd^II and Pt^II Pyrrole‐Imine Chelates with Human Serum Albumin**

Sookai

Munro

2023

ChemistryEurope

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“…[4][5][6] Such ligands stabilize metal ions in a range of oxidation states. [7] Examples include structurally characterized Co II/III , [8][9][10][11] Rh I/III , [12][13][14][15] Ir III , [16,17] Ni II , [18][19][20] Pd II , [20][21][22] Pt II , [23][24][25] Cu II , [26][27][28][29] Ag I , [30] and Au III complexes. [31] While pyrrole compounds are key building blocks for organic pharmaceuticals, [32] e.g., Tolmetin, [33] Sunitini, [34] and Glimepiri, [35] studies over the last two decades suggest that pyrrole-imine metal chelates exhibit significant medicinal potential.…”

Section: Introductionmentioning

confidence: 99%

Complexities of the interaction of Ni(II), Pd(II) and Pt(II) pyrrole-imine chelates with human serum albumin

Sookai

Munro

2023

Preprint

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Human serum albumin (HSA) efficiently transports drugs in vivo: most are organic. Here, HSA binding affinity and site specificity are shown to depend on the identity of the d8 metal ion in Ni(II), Pd(II) and Pt(II) chelates of the bis(pyrrole-imine) ligand H2PrPyrr. Fluorescence quenching data for native and probe-bound HSA showed sites close to Trp-214 (subdomain IIA) are targeted. The Stern-Volmer constants, KSV, ranged from 10^4 M^(-1) to 10^5 M^(-1) while the affinity constants, Ka, ranged from 3.5 x 10^3 M^(-1) to 1 x 10^6 M^(-1) at 37 degrees Centigrade, following the order Pd(PrPyrr) > Pt(PrPyrr) > Ni(PrPyrr) > H2PrPyrr. Ligand uptake is enthalpically driven, hinging mainly on London dispersion forces. Induced CD spectra for the protein-bound ligands could be simulated by hybrid QM:MM TD-DFT methods, proving that the metal chelates neither decompose nor demetallate after uptake by HSA. Transport and delivery of the metal chelates by HSA in vivo could therefore be feasible.

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“…3 Upon reaction with suitable metal ions, deprotonation of the pyrrole nitrogen occurs. Pyrrole-imine chelating agents are therefore strong σ-donor ligands with π-bonding character that dextrously stabilize metal ions in both low and high oxidation states, including Ni(II), [4][5][6] Pd(II), [6][7][8] Pt(II), [9][10][11] Cu(II), [12][13][14][15] Ag(I), 16 and Au(III). 17 Pt(II) complexes are among the most widely studied metal complexes in medicine.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic and computational study of the interaction of Pt(ii) pyrrole-imine chelates with human serum albumin

Sookai,

Munro

2023

Dalton Trans.

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An unusual asymmetric pseudomacrocyclic free base ligand and nickel(II) chelate: X-ray crystallographic and DFT studies

Cited by 6 publications

References 35 publications

Complexities of the Interaction of Ni^II, Pd^II and Pt^II Pyrrole‐Imine Chelates with Human Serum Albumin**

Complexities of the Interaction of Ni^II, Pd^II and Pt^II Pyrrole‐Imine Chelates with Human Serum Albumin**

Complexities of the interaction of Ni(II), Pd(II) and Pt(II) pyrrole-imine chelates with human serum albumin

Spectroscopic and computational study of the interaction of Pt(ii) pyrrole-imine chelates with human serum albumin

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An unusual asymmetric pseudomacrocyclic free base ligand and nickel(II) chelate: X-ray crystallographic and DFT studies

Cited by 6 publications

References 35 publications

Complexities of the Interaction of NiII, PdII and PtII Pyrrole‐Imine Chelates with Human Serum Albumin**

Complexities of the Interaction of NiII, PdII and PtII Pyrrole‐Imine Chelates with Human Serum Albumin**

Complexities of the interaction of Ni(II), Pd(II) and Pt(II) pyrrole-imine chelates with human serum albumin

Spectroscopic and computational study of the interaction of Pt(ii) pyrrole-imine chelates with human serum albumin

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Product

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Complexities of the Interaction of Ni^II, Pd^II and Pt^II Pyrrole‐Imine Chelates with Human Serum Albumin**

Complexities of the Interaction of Ni^II, Pd^II and Pt^II Pyrrole‐Imine Chelates with Human Serum Albumin**