New Applications of Immobilized Metal Ion Affinity Chromatography in Chemical Biology

Codd, Rachel; Gu, Jiesi; Ejje, Najwa; Lifa, Tulip

doi:10.1002/9781118682975.ch1

Cited by 5 publications

(7 citation statements)

References 155 publications

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“…Although trans-metallation had not previously been observed in this study, this phenomenon was specifically examined for 9 , as a representative of 8–10 , given the high affinity between Fe(III) and hydroxamic acid compounds. , These experiments measured Fe(III)–hydroxamic acid complex formation using visible spectrophotometry and showed that while the trihydroxamic acid desferrioxamine B was effective in extracting the Fe(III) from the immobilized Fe(III)–IDA matrix, the monohydroxamic acid 9 was not (Figure S1). This is consistent with previous studies. , The most plausible explanation for the low AR values for 8–10 is the precipitation of the compounds on the Fe(III)-IMAC resin bed, which was supported by the irregular visual appearance of the resin bed (Figure S2).…”

Section: Resultssupporting

confidence: 92%

“…This is consistent with previous studies. 9,12 The most plausible explanation for the low AR values for 8−10 is the precipitation of the compounds on the Fe(III)-IMAC resin bed, which was supported by the irregular visual appearance of the resin bed (Figure S2). Sulfasalazine (13), which contains a 2-hydroxybenzoic acid binding motif, showed reversible binding behavior for variable amounts of the compound on all five IMAC resin beds (scenarios: Figures 3a,c and 5b).…”

Section: ■ Results and Discussionmentioning

confidence: 90%

“…X-ray crystal structures have been solved for complexes between ACE1 and 1−3, or omapatrilat (4) with data available for zofenopril (5) bound to Zn(II)-leucyl aminopeptidase (LAP) (Table 1). The Zn(II) coordination mode of the benzamide-based HDAC inhibitors entinostat (6) and tacedinaline (7) can be inferred from the structural analogue N-(4-amino-[1,1′-biphenyl]-3-yl)benzamide (ABPB, 18) bound to HDAC2, with hydroxamic acid-based inhibitors panobinostat (8), vorinostat (9), and belinostat (10) shown to be predominantly bidentate chelators to the HDAC Zn(II)active site. Coordination of the 5-LO inhibitors 4-aminosalicylic acid (11), zileuton (12), sulfasalazine (13), meclofenamic acid (14), and licofelone (15) could be inferred from the X-ray data of the complex between protocatechuic acid (PCA, 19) and 5-LO.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Six compounds (8−10, 13, 16, and 17) were retained on three or more of the IMAC resin beds. Close-toquantitative amounts of the hydroxamic acid HDAC inhibitors panobinostat (8), vorinostat (9), and belinostat (10) adsorbed on the Ni(II) or Zn(II)-IMAC resin beds were reversibly bound, with PR values averaged across 8−10 for the Ni(II) or Zn(II) systems of 1.02 or 1.03, respectively (Figure 5c). The potency of 8−10 as HDAC inhibitors (EC 50 values 3−68 nM against HDAC1) 62 supports the property of effective binding to the Zn(II)-IMAC resin bed.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Immobilized metal affinity chromatography (IMAC) is a separation technique that relies on the fundamentals of coordination chemistry to retain metal-binding compounds . IMAC is used widely to purify recombinant proteins, and has been used more recently to isolate clinical or preclinical LMW nonproteinaceous bacterial secondary metabolites with inherent or functional metal-binding capacity, including desferrioxamine B, trichostatin A, bleomycin, or doxorubicin, from the culture supernatant of the cognate Streptomyces species. − IMAC is easy to use and is aqueous compatible, which is attractive with respect to potential for automation and integration into high-throughput platforms, and to reduce the use of organic solvents in processing complex mixtures.…”

Section: Introductionmentioning

confidence: 99%

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Immobilized Metal Affinity Chromatography as a Drug Discovery Platform for Metalloenzyme Inhibitors

2020

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Immobilized metal-ion affinity chromatography (IMAC) used to purify recombinant proteins features a resin-bound 1:1 Ni(II)–iminodiacetic acid (IDA) complex. This hemi-saturated Ni(II)–IDA system containing exchangeable sites at the metal ion is re-cast as a surrogate of a coordinatively-unsaturated metalloenzyme active site, with utility for selecting compounds with metal-binding groups from mixtures as potential metalloenzyme inhibitors. Exchanging Ni(II) for other metal ions could broaden the scope of metalloenzyme target. This work examined the performance of Cu(II)-, Fe(III)-, Ga(III)-, Ni(II)-, or Zn(II)-IMAC resins to reversibly bind experimental or clinical metalloenzyme inhibitors of Zn(II)-ACE1, Zn(II)-HDAC, Fe(II)/(III)-5-LO or Cu(II)-tyrosinase from a curated mixture (1–17). Each IMAC system gave a distinct selection profile. The Zn(II)-IMAC system selectively bound the thiol-containing Zn(II)-ACE1 inhibitors captopril and omapatrilat, and the Fe(III)-IMAC system selectively bound the Fe(II)/(III)-5-LO inhibitor licofelone, demonstrating a remarkable IMAC-metalloenzyme metal ion match. IMAC provides a simple, water-compatible platform, which could accelerate metalloenzyme inhibitor discovery.

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Section: Resultssupporting

confidence: 92%

Section: ■ Results and Discussionmentioning

confidence: 90%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Immobilized Metal Affinity Chromatography as a Drug Discovery Platform for Metalloenzyme Inhibitors

2020

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Harnessing the Coordination Chemistry of 1,4,7‐Triazacyclononane for Biomimicry and Radiopharmaceutical Applications

et al. 2018

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1,4,7‐Triazacyclononane (TACN)‐based mono‐ and poly‐nuclear metal complexes have found extensive use as biological mimics for understanding the structural and operational aspects of complex natural systems. Their coordination flexibility has also provided researchers access to a vast library of radiometal‐binding motifs that display excellent thermodynamic stability and kinetic inertness upon metal complexation. Synthetic modification of the TACN backbone has yielded ligands that can form metal complexes with coordination geometries well suited for these applications. In particular, Leone Spiccia's research has played a significant role in accelerating the progress in these two fields. With a focus on his contributions to the topics of biomimicry and radiopharmaceuticals, this Minireview uses relevant examples to put in perspective the utility of macrocyclic coordination chemistry for biological inorganic chemistry applications.

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Affinity purification of metalloprotease from marine bacterium using immobilized metal affinity chromatography

Wang

Juan

et al. 2016

J of Separation Science

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In this study, an efficient affinity purification protocol for an alkaline metalloprotease from marine bacterium was developed using immobilized metal affinity chromatography. After screening and optimization of the affinity ligands and spacer arm lengths, Cu-iminmodiacetic acid was chosen as the optimal affinity ligand, which was coupled to Sepharose 6B via a 14-atom spacer arm. The absorption analysis of this medium revealed a desorption constant Kd of 21.5 μg/mL and a theoretical maximum absorption Qmax of 24.9 mg/g. Thanks to this affinity medium, the enzyme could be purified by only one affinity purification step with a purity of approximately 95% pure when analyzed by high-performance liquid chromatography and reducing sodium dodecyl sulfate polyacrylamide gel electrophoresis. The recovery of the protease activity reached 74.6%, which is much higher than the value obtained by traditional protocols (8.9%). These results contribute to the industrial purifications and contribute a significant reference for the purification of other metalloproteases.

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New Applications of Immobilized Metal Ion Affinity Chromatography in Chemical Biology

Cited by 5 publications

References 155 publications

Immobilized Metal Affinity Chromatography as a Drug Discovery Platform for Metalloenzyme Inhibitors

Immobilized Metal Affinity Chromatography as a Drug Discovery Platform for Metalloenzyme Inhibitors

Harnessing the Coordination Chemistry of 1,4,7‐Triazacyclononane for Biomimicry and Radiopharmaceutical Applications

Affinity purification of metalloprotease from marine bacterium using immobilized metal affinity chromatography

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