Luminescent Metalloreceptor with a Neutral Bis(Acylaminoimidazoline) Binding Site:  Optical Sensing of Anionic and Neural Phosphodiesters

Watanabe, Shigeru; Onogawa, Osamu; Komatsu, Yuka; Yoshida, Katsuhira

doi:10.1021/ja973263a

Cited by 125 publications

(53 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…For example, Watanabe et al reported a phosphoester sensor based on the ruthenium complex by attaching amide groups at 4,4Ј positions in the ligand to bind with the target molecule. 25 Beer et al also reported a calixarene attached ruthenium complex for an anion sensor. 26 They further reported that the absorption spectra of ruthenium(II) tris(5,5Ј-diamide-2,2Ј-bipyridine) were changed by binding with anions.…”

Section: Molecular Design Of Functional Peptides Utilizing 5-amino-2mentioning

confidence: 99%

Molecular design of functional peptides by utilizing unnatural amino acids: Toward artificial and photofunctional protein

2004

View full text Add to dashboard Cite

Unnatural amino acids are effective as building blocks to design functional peptides from the following two points: (1) utilization of rigid unnatural amino acids for the incorporated peptides to control the conformation to appear the function, and (2) incorporation of functional and unnatural amino acids into peptides resulting in appearance of the inherent functions. As a combined strategy, molecular design of artificial metalloproteins utilizing 5'-amino-2,2'-bipyridine-5-carboxilic acid (H-5Bpy-OH) as an unnatural amino acid is proposed. The peptide containing three residues of the unnatural amino acid would fold through coordination to a metal ion. In particular, ruthenium(II) ion would yield a ruthenium tris(bipyridine) derivative as the core complex of the artificial protein, which would appear the similar photochemical functions as that of ruthenium(II) tris(bipyridine) complex. The central complex could form two isomers, fac and mer. For selective synthesis of the mer complex, which is expected as the core complex in the artificial protein, dicyclohexylamide as a bulky group is introduced at the C-terminal of the unnatural amino acid to destabilize the fac complex due to steric hindrance. Furthermore, in order to know the photochemical properties and function of the protein mimics, ruthenium(II) tris(2,2'-bipyridine) complexes bearing amide groups at 5,5' positions have been synthesized as the model complexes. As a result, the direction of amide groups (RNHCO-or RCONH-) in ruthenium complexes is found to significantly affect the emission efficiency: the former reduces the quantum yield and the latter enhances it, respectively. The ruthenium(II) tris(5,5'-diamide-2,2'-bipyridine) complexes are also found to strongly bind with various anions [e.g., halogen ions (Cl-, Br-) and acetate anion] in acetonitrile and to detect these anions through the emission spectral changes under air. The molecular design of artificial protein is expected to develop new fields among peptide, organic, inorganic, and physical chemistry.

show abstract

Section: Molecular Design Of Functional Peptides Utilizing 5-amino-2mentioning

confidence: 99%

Molecular design of functional peptides by utilizing unnatural amino acids: Toward artificial and photofunctional protein

2004

View full text Add to dashboard Cite

show abstract

“…Two possible mechanisms may interpret the fluorescent enhancement: (1) inhibition of photoinduced electronic transfer (PET) and (2) the guest binding-induced rigidity of the host molecule. [37][38][39] Without the addition of AcO -, the hydrogen atoms of free compound 1 could form an intramolecular hydrogen bond with the nitrogen atom of Shiff base. The above structure may lead to a photoinduced electron transfer and the fluorescence was weak.…”

Section: Fluorescence Responsementioning

confidence: 99%

Theoretical and experimental study of organic nano-material for acetate anion based on 1, 10-phenanthroline

Shang

Fan²,

Fu³

et al. 2015

ACSi

View full text Add to dashboard Cite

New phenanthroline derivatives containing phenol groups have been synthesized and optimized. The nano-material involved bromine substituent was also developed which in the ortho-position of benzene ring. Their binding properties were evaluated for various biological anions (F -, Cl -, Br -, I -, AcO -and H 2 PO 4 -) by theoretical investigation, UV-vis, fluorescence, 1 H NMR titration experiments. These compounds all showed strong binding ability for AcO -without the interference of other anions tested. The anion binding ability could be regularized by electron push-pull properties of the ortho-or para-substituent on benzene. Theoretical investigation analysis revealed the effect of intramolecular hydrogen bond existed between -OH and other atoms in the structure of these compounds.

show abstract

“…Although the complexes were too weak to estimate the K a values, an 80% increase in luminescence enhancement was recorded from 1:1 and 1:2 binding geometries. In a related example, Yoshida et al appended a neutral bis(acylaminoimidazoline) onto a similar ruthenium (bpy) 3 complex and found that a high selectivity for both anionic and neutral receptors (Fig 13.22b) [44].…”

Section: Transition-metal Complexes Ru(bpy) 3 2+mentioning

confidence: 99%

New Fluorophore Design

Heagy

2011

Chemosensors

View full text Add to dashboard Cite

Luminescent Metalloreceptor with a Neutral Bis(Acylaminoimidazoline) Binding Site: Optical Sensing of Anionic and Neural Phosphodiesters

Cited by 125 publications

References 11 publications

Molecular design of functional peptides by utilizing unnatural amino acids: Toward artificial and photofunctional protein

Molecular design of functional peptides by utilizing unnatural amino acids: Toward artificial and photofunctional protein

Theoretical and experimental study of organic nano-material for acetate anion based on 1, 10-phenanthroline

New Fluorophore Design

Contact Info

Product

Resources

About