Disodium Fluorescein Octahydrate

Yamaguchi, Kentaro; Tamura, Z.; Maeda, Masunobu

doi:10.1107/s0108270196010487

Cited by 18 publications

(12 citation statements)

References 1 publication

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“…We conducted several sessions of manual model building with QUANTA14 and alternating refinement cycles with REFMAC510 using data from 63.3 Å to 2.0 Å resolution. As soon as electron density at the binding site became visible, we positioned one molecule of fluorescein15 for each FluA monomer in the asymmetric unit, using the set of bond lengths and angles as supplied with the CCP4 program package. During the refinement, “loose” noncrystallographic restraints between the pair of polypeptide chains and their fluorescein ligands were applied for all residues not involved in packing interactions (i.e., 1–32, 41–48, 54–62, 67–118, 121–132, 143–151).…”

Section: Methodsmentioning

confidence: 99%

Crystallographic analysis of an “anticalin” with tailored specificity for fluorescein reveals high structural plasticity of the lipocalin loop region

2003

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The artificial lipocalin FluA with novel specificity toward fluorescein was derived via combinatorial engineering from the bilin-binding protein, BBP by exchange of 16 amino acids in the ligand pocket. Here, we describe the crystal structure of FluA at 2.0 A resolution in the space group P2(1) with two protein-ligand complexes in the asymmetric unit. In both molecules, the characteristic beta-barrel architecture with the attached alpha-helix is well preserved. In contrast, the four loops at one end of the beta-barrel that form the entrance to the binding site exhibit large conformational deviations from the wild-type protein, which can be attributed to the sidechain replacements. Specificity for the new ligand is furnished by hydrophobic packing, charged sidechain environment, and hydrogen bonds with its hydroxyl groups. Unexpectedly, fluorescein is bound in a much deeper cavity than biliverdin IX(gamma) in the natural lipocalin. Triggered by the substituted residues, unmutated sidechains at the bottom of the binding site adopt conformations that are quite different from those observed in the BBP, illustrating that not only the loop region but also the hydrophobic interior of the beta-barrel can be reshaped for molecular recognition. Particularly, Trp 129 participates in a tight stacking interaction with the xanthenolone moiety, which may explain the ultrafast electron transfer that occurs on light excitation of the bound fluorescein. These structural findings support our concept of using lipocalins as a scaffold for the engineering of so-called "anticalins" directed against prescribed targets as an alternative to recombinant antibody fragments.

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Section: Methodsmentioning

confidence: 99%

Crystallographic analysis of an “anticalin” with tailored specificity for fluorescein reveals high structural plasticity of the lipocalin loop region

2003

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“…The use of the uncharged free acid did not improve sorption uptake when ethanol was used as the loading solvent; however, when acetone was used instead of ethanol uptake increased to 17 % ( Figure 4). The singlecrystal data for disodium fluorescein octahydrate [11] was loaded into the molecular graphics program Cameron [12] to determine the dimensions of the molecule. These were found to be 10.40 ä in length, 8.00 ä in height, and 7.00 ä at the widest point.…”

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confidence: 99%

Comparison of Micro‐ and Mesoporous Inorganic Materials in the Uptake and Release of the Drug Model Fluorescein and Its Analogues

Fisher

Huddersman

Taylor

2003

Chemistry A European J

112

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The uptake of the three species of the drug model fluorescein (fluorescein sodium salt (FNa), fluorescein free acid (F), and fluorescein diacetate (FDA)) by zeolite NaX and the mesoporous zeotype MCM-41 was investigated as well as their release rates into solutions at pH 7 and pH 4.5. UV/Vis analysis was carried out at a wavelength of 490 nm. Uptakes of the sodium salt of 9 % for zeolite X and 14 % for MCM suggest little penetration of the pores. The use of ethanol as the loading solvent for F resulted in little uptake for both zeolitic materials due to the successful competition of the ethanol for binding sites. Use of acetone (weaker proton acceptor) as loading solvent significantly improved the uptake of F to 17 % and 12 % for zeolite X and MCM, respectively, whilst the uptake of FDA in acetone increased still further to 22 % and 17 % for zeolite X and MCM, respectively. Generally there was a large initial release of the fluorescein analogues from the surface of the zeolites with very little further increase over time. The prescence of an esterase enzyme in the release medium of FDA tripled the release from MCM to 15 % but left the release from zeolite X unaffected at 6 %. The results obtained show that uptake of fluorescein and its analogues is dependent on the loading solvent used, the amount released is influenced by not only the solvent but the pH and the presence of enzymes in the release medium.

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“…In fact, there are only small differences observed in the absorbance among fluorescein derivatives. And their dihedral angle between benzoic acid moiety and fluorogenic xanthene ring is almost 90 , as found by X-ray analysis [59]. Both observations suggested that benzoic acid and xanthenes moieties in fluorescein are orthogonal to each other and there is no ground-state interaction between them.…”

Section: Xanthene-based Targeted Approachmentioning

confidence: 57%

Discovery of New Fluorescent Dyes: Targeted Synthesis or Combinatorial Approach?

Kim

Park

2010

Springer Series on Fluorescence

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Because of their advantageous properties, fluorescent organic molecules have been used extensively in various applications. Despite the high demand for fluorophores, there are only a limited number of fluorescent organic core skeletons with sufficient flexibility in their synthetic strategies. The rational design of fluorescent probes having desirable photophysical properties is still far from being achieved because of the complexity of underlying photophysical phenomena of fluorescent small molecules. To study and improve the photophysical properties of fluorescent core skeletons, many efforts have been pursued. Traditionally, targeted approach had been used to rationally study the photophysical properties of known fluorescent core skeleton. On the other hand, recent studies showed that combinatorial approach can act as a powerful tool to discover or develop novel fluorescent probes. Through a comparison between targeted synthesis and combinatorial approach in the study of fluorescent organic compounds, we can conclude that the targeted synthesis with rational design and systematic modification using combinatorial approach are complementary to each other for the discovery of novel, small molecules with desired photophysical properties.

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Disodium Fluorescein Octahydrate

Cited by 18 publications

References 1 publication

Crystallographic analysis of an “anticalin” with tailored specificity for fluorescein reveals high structural plasticity of the lipocalin loop region

Crystallographic analysis of an “anticalin” with tailored specificity for fluorescein reveals high structural plasticity of the lipocalin loop region

Comparison of Micro‐ and Mesoporous Inorganic Materials in the Uptake and Release of the Drug Model Fluorescein and Its Analogues

Discovery of New Fluorescent Dyes: Targeted Synthesis or Combinatorial Approach?

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