A thermodynamic and crystallographic study of complexes of the highly preorganized ligand 8-hydroxyquinoline-2-carboxylic acid

McDonald, F. Crisp; Applefield, Rachel C.; Halkides, Christopher J.; Reibenspies, Joseph H.; Hancock, Robert D.

doi:10.1016/j.ica.2007.10.004

Cited by 18 publications

(8 citation statements)

References 26 publications

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“…The Cd 2+ ion is coordinated with two nitrogen atoms (N5, N6) from a chelating 2, 2′‐bipy ligand, two oxygen atoms (O1, O4) and two nitrogen atoms (N1, N3) from two bidentate NQ ligands to form a distorted trigonal prism, in which O4, N1, N5 and O1, N3, N6 occupy the vertices of the prism, the metal ion lies in the center (Figure 5). The Cd–N distances are in the range of 2.329(3)–2.361(3) Å and the Cd–O distances are in the range of 2.292(2)–2.329(2) Å, which are close to the literature values 38,39. The dihedral angle between two pyridine rings in the same 2, 2′‐bipy is 15.77°.…”

Section: Resultssupporting

confidence: 88%

Solvothermal Syntheses, Crystal Structures, and Luminescent Properties of Two Transition Metal Complexes with 5‐Nitro‐8‐hydroxyquinoline and N‐Containing Auxiliary Ligands

Qü

Yao

et al. 2012

Zeitschrift anorg allge chemie

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Two complexes, Zn 4 (C 9 H 5 N 2 O 3 ) 8 (4,4Ј-bipy) 2 (1) and [Cd(C 9 H 5 N 2 O 3 ) 2 (2,2Ј-bipy)]·2H 2 O (2) were synthesized by solvothermal reactions of transition metal nitrates with 5-nitro-quinoline-8-yl acetate (NQA) under intervention of auxiliary ligands, and characterized by elemental analysis, IR spectroscopy, TGA, and single-crystal X-ray diffraction. In complex 1, every 4,4Ј-bipy adopts a mono-

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Section: Resultssupporting

confidence: 88%

Solvothermal Syntheses, Crystal Structures, and Luminescent Properties of Two Transition Metal Complexes with 5‐Nitro‐8‐hydroxyquinoline and N‐Containing Auxiliary Ligands

Qü

Yao

et al. 2012

Zeitschrift anorg allge chemie

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“…The binding stoichiometry of HCA and free zinc (II) in solution determined by ITC matches current X-ray crystallography data for the structure of HCA bound to free zinc (II), which also showed HCA and zinc (II) interacting in a ratio of 2:1. 55 Intriguingly, the data from the enzymatic assay showed that HCA's inhibitory effects against MtFBA are not reduced in the presence of a 2-fold excess of ZnCl 2 . Therefore, to assess the thermodynamic factors that may favor HCA's interaction with MtFBA versus free zinc (II), HCA was first combined with a 3-fold excess of ZnCl 2 required for the formation of the HCA–free zinc (II) complex and then titrated into MtFBA.…”

Section: Resultsmentioning

confidence: 97%

A Noncompetitive Inhibitor forMycobacterium tuberculosis’s Class IIa Fructose 1,6-Bisphosphate Aldolase

et al. 2013

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Class II fructose 1,6-bisphosphate aldolase (FBA) is an enzyme critical for bacterial, fungal, and protozoan glycolysis/gluconeogenesis. Importantly, humans lack this type of aldolase, having instead a class I FBA that is structurally and mechanistically distinct from class II FBAs. As such, class II FBA is considered a putative pharmacological target for the development of novel antibiotics against pathogenic bacteria such as Mycobacterium tuberculosis, the causative agent for tuberculosis (TB). To date, several competitive class II FBA substrate mimic-styled inhibitors have been developed; however, they lack either specificity, potency, or properties that limit their potential as possible therapeutics. Recently, through the use of enzymatic and structure-based assisted screening, we identified 8-hydroxyquinoline carboxylic acid (HCA) that has an IC50 of 10 ± 1 μM for the class II FBA present in M. tuberculosis (MtFBA). As opposed to previous inhibitors, HCA behaves in a noncompetitive manner, shows no inhibitory properties toward human and rabbit class I FBAs, and possesses anti-TB properties. Furthermore, we were able to determine the crystal structure of HCA bound to MtFBA to 2.1 Å. HCA also demonstrates inhibitory effects for other class II FBAs, including pathogenic bacteria such as methicillin-resistant Staphylococcus aureus. With its broad-spectrum potential, unique inhibitory characteristics, and flexibility of functionalization, the HCA scaffold likely represents an important advancement in the development of class II FBA inhibitors that can serve as viable preclinical candidates.

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“…The copper(II) and zinc(II) complexes of 4 have been also characterized and the coordination of metal ion by N, phenolate O, and COO − groups has been reported 42. 43…”

Section: Resultsmentioning

confidence: 99%

“…The copper(II) and zinc(II) complexes of 4 have been also characterized and the coordination of metal ion by N, phenolate O, and COO À groups has been reported. [42,43] From the data reported in Table 1, it is interesting to note that the presence of the CyD does not decrease the affinity of 8-OHQ moiety for the metal ion. In these ligands, in addition to donor atoms of quinoline moiety, other potential donor atoms can be identified.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

New Cyclodextrin‐Bearing 8‐Hydroxyquinoline Ligands as Multifunctional Molecules

Oliveri

Puglisi

Viale

et al. 2013

Chemistry A European J

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Recent investigations have rekindled interest in 8-hydroxyquinolines as therapeutic agents for cancer, Alzheimer's disease, and other neurodegenerative disorders. Three new β-cyclodextrin conjugates of 8-hydroxyquinolines and their copper(II) and zinc(II) complexes have been synthesized and characterized spectroscopically. In addition to improving aqueous solubility, due to the presence of the cyclodextrin moiety, the hybrid systems have interesting characteristics including antioxidant activity, and their copper(II) complexes are efficient superoxide dismutase (SOD) mimics. The ligands and their copper(II) complexes show low cytotoxicity, attributed to the presence of the cyclodextrin moiety. These compounds have potential as therapeutic agents in diseases related both to metal dyshomeostasis and oxidative stress.

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A thermodynamic and crystallographic study of complexes of the highly preorganized ligand 8-hydroxyquinoline-2-carboxylic acid

Cited by 18 publications

References 26 publications

Solvothermal Syntheses, Crystal Structures, and Luminescent Properties of Two Transition Metal Complexes with 5‐Nitro‐8‐hydroxyquinoline and N‐Containing Auxiliary Ligands

Solvothermal Syntheses, Crystal Structures, and Luminescent Properties of Two Transition Metal Complexes with 5‐Nitro‐8‐hydroxyquinoline and N‐Containing Auxiliary Ligands

A Noncompetitive Inhibitor forMycobacterium tuberculosis’s Class IIa Fructose 1,6-Bisphosphate Aldolase

New Cyclodextrin‐Bearing 8‐Hydroxyquinoline Ligands as Multifunctional Molecules

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