A fluorescein-containing, small-molecule, water-soluble receptor for cytosine free bases

Jiang, Yu; Patel, Puneet; Klein, Suzane M.

doi:10.1016/j.bmc.2010.08.013

Cited by 6 publications

(2 citation statements)

References 50 publications

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“…The synthesis and investigations of small fluorescent heterocyclic molecules is a subject of growing interest in the development of specific functional materials for application in a broad variety of scientific and technological areas, including organic electronics [ 1 , 2 ], fluorescence bioimaging [ 3 , 4 ], sensing [ 5 , 6 ], non-linear optics [ 7 , 8 ], tissue engineering [ 9 ], etc. Among known fluorescent heterocyclic compounds the pyrrolo[3,4-c]pyridine derivatives are promising candidates for fluorescent materials, exhibiting emission maxima in the blue–green spectral range [ 10 ], good potential for sensing [ 11 ], and probing physiological activities [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

Nature of Linear Spectral Properties and Fast Electronic Relaxations in Green Fluorescent Pyrrolo[3,4-c]Pyridine Derivative

Башмакова

Dmytruk

Świergosz

et al. 2021

IJMS

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The electronic nature of 4-hydroxy-1H-pyrrolo[3,4-c]pyridine-1,3,6(2H,5H)-trione (HPPT) was comprehensively investigated in liquid media at room temperature using steady-state and time-resolved femtosecond transient absorption spectroscopic techniques. The analysis of the linear photophysical and photochemical parameters of HPPT, including steady-state absorption, fluorescence and excitation anisotropy spectra, along with the lifetimes of fluorescence emission and photodecomposition quantum yields, revealed the nature of its large Stokes shift, specific changes in the permanent dipole moments under electronic excitation, weak dipole transitions with partially anisotropic character, and high photostability. Transient absorption spectra of HPPT were obtained with femtosecond resolution and no characteristic solvate relaxation processes in protic (methanol) solvent were revealed. Efficient light amplification (gain) was observed in the fluorescence spectral range of HPPT, but no super-luminescence and lasing phenomena were detected. The electronic structure of HPPT was also analyzed with quantum-chemical calculations using a DFT/B3LYP method and good agreement with experimental data was shown. The development and investigation of new pyrrolo[3,4-c]pyridine derivatives are important due to their promising fluorescent properties and potential for use in physiological applications.

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Section: Introductionmentioning

confidence: 99%

Nature of Linear Spectral Properties and Fast Electronic Relaxations in Green Fluorescent Pyrrolo[3,4-c]Pyridine Derivative

Башмакова

Dmytruk

Świergosz

et al. 2021

IJMS

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“…Much recent research has focused upon linear arrays employing four [12,13,[25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42] or more [43][44][45][46][47] hydrogen bonds because of the enhanced strength of association that may be achieved. However, recent interest in triply hydrogen-bonded systems [15,[21][22][23][48][49][50][51][52] has illustrated that useful affinity can be achieved for assembly of dynamic architectures. [53][54][55][56] Within this family of hydrogen-bond receptors two classes emerge: I) rigid (poly)cyclic aromatic systems with pendant exocyclic hydrogen-bond donor/acceptor functionality [3,4] and II) systems in which individual donors (D) and acceptors (A) are separated from one another.…”

Section: Introductionmentioning

confidence: 99%

Conformer‐Independent Ureidoimidazole Motifs—Tools to Probe Conformational and Tautomeric Effects on the Molecular Recognition of Triply Hydrogen‐Bonded Heterodimers

Pellizzaro

McGhee

Renton

et al. 2011

Chemistry A European J

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Linear arrays of hydrogen bonds are useful for the reversible assembly of "stimuli-responsive" supramolecular materials. There is thus an ongoing requirement for easy-to-synthesise motifs that are capable of presenting hydrogen-bonding functionality in a predictable manner, such that high-affinity and high-fidelity recognition occurs. The design of linear arrays is made challenging as a consequence of their ability to adopt multiple conformational and tautomeric configurations; with each additional hydrogen-bonding heteroatom added to an array, the available tautomeric and conformational space increases and it can be difficult to anticipate where unproductive conformers/tautomers will arise. This paper describes a detailed study on the complementary ureidoimidazole donor-donor-acceptor (DDA) array (1) and amidoisocytosine donor-acceptor-acceptor (DAA) array (2). A specific feature of 1 is that two degenerate, intramolecular hydrogen-bonded conformations are postulated, both of which present a DDA array that is complementary to appropriate DAA partners. 1D and 2D (1)H NMR spectroscopy, isothermal titration calorimetry, and ab initio structure calculations confirm 1 interacts with 2 (K(a) ≈ 33,000 M(-1) in CDCl(3)) in a conformer-independent fashion driven by enthalpy. Comparison of the binding behaviour of 1 with hexylamidocytosine (4) and amidonaphthyridine (5) provides insight on the role that intramolecular hydrogen-bonding plays in mediating affinity towards DAA partners.

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A specific molecular beacon probe for the detection of human prostate cancer cells

Jiang

McGoldrick

Yin

et al. 2012

Bioorganic & Medicinal Chemistry Letters

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A fluorescein-containing, small-molecule, water-soluble receptor for cytosine free bases

Cited by 6 publications

References 50 publications

Nature of Linear Spectral Properties and Fast Electronic Relaxations in Green Fluorescent Pyrrolo[3,4-c]Pyridine Derivative

Nature of Linear Spectral Properties and Fast Electronic Relaxations in Green Fluorescent Pyrrolo[3,4-c]Pyridine Derivative

Conformer‐Independent Ureidoimidazole Motifs—Tools to Probe Conformational and Tautomeric Effects on the Molecular Recognition of Triply Hydrogen‐Bonded Heterodimers

A specific molecular beacon probe for the detection of human prostate cancer cells

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