Progress toward artificial metalloenzymes: New ligands for transition metal ions and neutral molecules

Kinneary, Joanne F.; Roy, Therese M.; Albert, Jeffrey S.; Yoon, Hyun-Ki; Wagler, Thomas R.; Shen, Lucy; Burrows, Cynthia J.

doi:10.1007/bf01060717

Cited by 22 publications

(13 citation statements)

References 24 publications

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“…Several groups have demonstrated the use of these complexes as potent enzyme mimics in a variety of biomolecule fragmentation and oxidation reactions 44. 48–51 Inspired by these studies, we investigated several bis(salicylidene)ethylenediamine (salen) and 1,4,8,11‐tetraazacyclotetradecane (cyclam) complexes of Cu II , Zn II , Ti IV , Cr III , Mn III , Fe II , Ru III , Co II , Rh III , and Ni II for their activity in corroding porous silicon layers. As well as the commercially available parent salen ligand, bishydroxysalen was also synthesized.…”

Section: Resultsmentioning

confidence: 99%

Catalyzed Oxidative Corrosion of Porous Silicon Used as an Optical Transducer for Ligand–Receptor Interactions

2008

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Biosensors fabricated on the nanoscale offer exciting new avenues in the quest for better understanding and characterization of biological systems. Porous silicon is an ideal nanostructured material for the construction of optical transducer matrices because it is easily functionalized with biomolecular probes and displays strong optical interferences. Here, we show that certain transition metal complexes, including nickel(II)cyclam, are able to induce corrosion in porous silicon films rapidly, generating a strong optical interferometric signal that originates from the porous layer. We subsequently exploit this effect to design a transducer for ligand-receptor recognition. With a nickel(II)cyclam derivative as a catalytic label, DNA- and avidin-binding events are detected by time-lapse interferometric reflectance spectroscopy in a fast, simple, and inexpensive fashion.

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Section: Resultsmentioning

confidence: 99%

Catalyzed Oxidative Corrosion of Porous Silicon Used as an Optical Transducer for Ligand–Receptor Interactions

2008

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“…Insight into how selectivity in binding carbohydrates by way of H-bonding can be obtained has been gained mainly in binding studies in CHCI, with macrocyclic hosts and pyranosides [23] [24]. Diastereo-and enantioselective recognition with a 'cholaphane' receptor, composed of two bridged cholic acids, was reported by Davis and coworkers [25].…”

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confidence: 99%

Molecular Clefts Derived from 9,9′‐spirobi[9H‐fluorene] for enantioselective complexation of pyranosides and dicarboxylic acids

Cuntze¹,

Owens²,

Alcázar³

et al. 1995

Helvetica Chimica Acta

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The molecular clefts (R)and (S)-3, incorporating 9,9-spirobi[9H-fluorene] as a spacer and two N-(5,7dimethyl-1 ,8-naphthyridin-2-yl)carboxamide (CONH(naphthy)) units as H-bonding sites were prepared via the bis(succinimid-N-yl esters) of (R)and (S)-9,9'-spirobi[9H-fluorene]-2,2-dicarboxylic acid (5). Derivative 6, with one CONH(naphthy) unit and one succinimid-N-yl ester residue allowed easy access to spirobifluorene clefts with two different H-bonding sites, as exemplified by the synthesis of 4. Binding studies with ( R )and ( S ) -3 and optically active dicarboxylic acids in CDCl, exhibited differences in free energy of the formed diastereoisomeric complexes (d(dCo)) between 0.5 and 1.6 kcal mol-I (T300 K). Similar enantioselectivities were observed with the spirobifluorene clefts (R)and (S)-1, bearing two N-(6-methylpyridin-2-yl)carboxamide (CONH(py)) H-bonding sites. The thermodynamic quantities AH" and AS" for the recognition processes with (R)and (S)-1 were determined by variable-temperature 'H-NMR titrations and compared to those with (R)and (S)-2, which have two CONH(py) moieties attached to the 6,6'-positions of a conformationally more flexible 1,l'-binaphthyl cleft. All association processes showed high enthalpic driving forces which are partially compensated by unfavorable changes in entropy. Pyranosides bind to the optically active clefts 1 and 3 in CDCI, with -AGO = 3.04.3 kcal mol-'. Diastereoisomeric selectivities up to 1.2 kcal mol-' and enantioselectivities up to 0.4 kcal mol-' were observed. Cleft 4 and N-(5,7-dimethyl-1,8-naphthyridin-2-yl)acetamide (25) complexed pyranosides 22-24 as effectively as 3 indicating that only one CONH(naphthy) site in 3 associates strongly with the sugar derivatives. Based on the X-ray crystal structure of 3, a computer model for the complex between ( S ) -3 and pyranoside 22 was constructed. Molecular-dynamics (MI)) simulations showed that differential geometrical constraints are at the origin of the high enantioselectivity in the complexation of dicarboxylic acid (S)-7 by (R)and (5')-1 and ( R )and (S)-3.

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“…Besides being used as a linker in synthesized drug molecules, 1,2,3‐triazole, obtained by the “click” reaction, was considered as the key binding site for biomolecular targets and spacers. It was known that bile acids possessed the inclusive complexation of N ‐nitrosamine and trans ‐azobenzene in their crystal lattice,20 and they also exhibited inclusion of methanol,21 carbohydrate,22 perylene without micelle formation, and DNA in the dimeric form 23. Meanwhile, such dimers always acted as artificial ionophores and potential receptors for neutral molecules or metal cations.…”

Section: Steroid Conjugates and Cuaac “Click” Chemistrymentioning

confidence: 99%

“…It was known that bile acids possessed the inclusive complexation of N-nitrosamine and trans-azobenzene in their crystal lattice, [20] and they also exhibited inclusion of methanol, [21] carbohydrate, [22] perylene without micelle formation, and DNA in the dimeric form. [23] Meanwhile, such dimers always acted as artificial ionophores and potential receptors for neutral molecules or metal cations.…”

Section: Introductionmentioning

confidence: 99%

“…[23] Meanwhile, such dimers always acted as artificial ionophores and potential receptors for neutral molecules or metal cations. Based on the advantages above, bile acid dimers, trimers, and tetramers (19)(20)(21)(22)(23)(24)(25)(26) linked with a 1,4-disubsituted 1,2,3-triazole moiety were prepared by Pore s group (Figure 3). [24] Their micellar properties were studied using the hydrophilic dye cresol red (CR) and it was found that all these molecules showed reverse micellar characteristics in nonpolar solvent, [25] and cholic acid-based molecules were able to encapsulate greater amounts of hydrophilic dye than deoxycholic acid-based molecules, which had a direct relationship with the numbers of hydroxy groups.…”

Section: Introductionmentioning

confidence: 99%

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Steroid/Triterpenoid Functional Molecules based on “Click Chemistry”

2011

Chemistry An Asian Journal

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On the occasion of the 10th anniversary of click chemistry FOCUS REVIEWSAbstract: This Focus Review highlights the design and synthesis of various functional molecules based on steroid/triterpenoid as building blocks through the coppercatalyzed azide-alkyne cycloaddition (CuAAC) "click" reaction, as well as their applications in bioactivity, recognition, and assembly. This method shows great promise to allow us to develop novel molecules with characteristic functions using the CuAAC "click" reaction.

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Progress toward artificial metalloenzymes: New ligands for transition metal ions and neutral molecules

Cited by 22 publications

References 24 publications

Catalyzed Oxidative Corrosion of Porous Silicon Used as an Optical Transducer for Ligand–Receptor Interactions

Catalyzed Oxidative Corrosion of Porous Silicon Used as an Optical Transducer for Ligand–Receptor Interactions

Molecular Clefts Derived from 9,9′‐spirobi[9H‐fluorene] for enantioselective complexation of pyranosides and dicarboxylic acids

Steroid/Triterpenoid Functional Molecules based on “Click Chemistry”

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