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Markova L.I.,Ukrainian Academy of Sciences | Fedyunyayeva I.A.,Ukrainian Academy of Sciences | Povrozin Y.A.,Ukrainian Academy of Sciences | Semenova O.M.,Ukrainian Academy of Sciences | And 4 more authors.
Dyes and Pigments | Year: 2013

A series of mono-reactive, water-soluble, indodicarbocyanine dyes based on 2,3-dimethyl-3-(4-sulfobutyl)-3H-indole-5-sulfonic acid was synthesized. These dyes contain two aromatic sulfo groups and in addition to (up to 3) sulfoalkyl groups in the indolenine end groups. The impact of the number and position of sulfobutyl groups on the spectral properties and photostabilities of the dyes free in solutions and after binding to an antibody (IgG) was investigated. These dyes have absorption maxima between 649 and 653 nm, molar absorptivities between 240,000 and 256,000 M-1 cm-1, emission maxima from 668 to 672 nm, and fluorescence quantum yields between 28 and 32% in free form and up to 43% when bound to IgG. Independent of the number of sulfo groups, these dyes exhibit no aggregation in water at concentrations up to 5 × 10-5 M. The number of sulfoalkyl groups was found to directly correlate with the fluorescence quantum yields and photostabilities of the IgG conjugated dyes. © 2012 Elsevier Ltd. All rights reserved.


Markova L.I.,Ukrainian Academy of Sciences | Terpetschnig E.A.,SETA BioMedicals LLC | Patsenker L.D.,Ukrainian Academy of Sciences | Patsenker L.D.,SETA BioMedicals LLC
Dyes and Pigments | Year: 2013

Abstract Unlike cyanine dyes, which are widely used as fluorescent probes and labels for biomedical applications squaraine dyes are less investigated. A series of monoreactive, water-soluble, squaraine dyes with two aromatic sulfo groups and up to 3 sulfobutyl groups was synthesized and the spectral properties of these dyes were compared to dicarbocyanines of identical structure. Compared to the cyanines in aqueous solutions the squaraine dyes absorb and emit at shorter wavelengths (630-636 nm/639-645 nm vs. 647-653 nm/665-672 nm), have higher molar absorptivities (284,000-333,000 M-1 cm-1vs. 242,000-260,000 M-1 cm-1), lower fluorescence quantum yields (4.3-9.4% vs. 27-32%) and lower fluorescence lifetimes (0.2-0.3 ns vs. 1.0-1.2 ns) but the quantum yields and lifetimes substantially increase when bound to proteins (Bovine Serum Albumin (BSA) or antibodies, immunoglobulin G (IgG)). Squaraines with two aromatic sulfo groups show no aggregation tendency up to concentrations of 2 × 10-4 M while the corresponding cyanine dye is free of aggregation up to 5 × 10-4 M. The increase in the number of sulfobutyl groups bears a strong influence on the aggregation tendency of both dye classes upon covalent labeling to BSA and IgG resulting in increased quantum yields and lifetimes of the protein conjugates. Compared to cyanines, squaraine dyes exhibit higher photostabilities and much higher sensitivity of the quantum yields and fluorescence lifetimes toward the microenvironment and are therefore better suited as fluorescence sensors. © 2013 Elsevier Ltd. All rights reserved.


Fedyunyayeva I.A.,Ukrainian Academy of Sciences | Klochko O.P.,Ukrainian Academy of Sciences | Semenova L.M.,Ukrainian Academy of Sciences | Khabuseva S.U.,Ukrainian Academy of Sciences | And 6 more authors.
Dyes and Pigments | Year: 2011

Novel bis-styryl dyes based on a quaternized centrosymmetrical benzodipyrrolenine moiety were synthesized by reaction of a quaternized benzodipyrrolenine with two equivalents of 4-dimethylaminobenzaldehyde, 4-dimethylaminocinnamoic aldehyde or 4-(3,5-diphenyl-4,5-dihydro-1H-1-pyrazolyl) benzaldehyde. The molecular structures and spectral properties of these dyes were investigated using PM3 and PPP CI quantum chemical simulations and compared with biscyanines and parent "monomeric" styryl dyes. Conjugation of two uniform "monomeric" styryl chromophores to form a bis-chromophoric system was found to cause a pronounced red-shift (∼100 nm) of the absorption and emission maxima, an increase of the extinction coefficients but also a conformational rigidization of the molecules. This results in better vibrationally resolved absorption and emission bands and, in general, in increased quantum yields. Bis-styryl dyes absorb and emit in the red and near-IR spectral region (643-812 nm). They have high extinction coefficients (≤133,000 M-1 cm-1), large Stokes' shifts (up to 55 nm in chloroform and 90 nm in methanol), and quantum yields in chloroform ≤10%, whereas polar solvents decrease quantum yields. Despite their symmetrical structures these bis-styryl dyes exhibit spectral properties in solvents of different polarity that are more resemble those of unsymmetrical "monomeric" styryls. © 2011 Elsevier Ltd. All rights reserved.


Klochko O.P.,Ukrainian Academy of Sciences | Fedyunyayeva I.A.,Ukrainian Academy of Sciences | Khabuseva S.U.,Ukrainian Academy of Sciences | Semenova O.M.,Ukrainian Academy of Sciences | And 3 more authors.
Dyes and Pigments | Year: 2010

A novel method of synthesizing long-wavelength absorbing and emitting bis-trimethine dyes that consists of condensing benzodipyrrolenine dialdehyde with quaternized heterocyclic CH-acidic compounds was used to prepare a series of biscyanines. The new method is more convenient than its conventional counterepart, which relies upon condensation of a quaternized benzodipyrrolenine with Fisher's aldehyde, for the synthesis of a symmetrically substituted dyes that contain various heterocyclic end-groups. Investigations of the spectral and luminescent properties of the dyes in solution revealed that the absorption (596-717 nm) and emission (629-773 nm) maxima of the biscyanines were red-shifted by ∼100 nm compared to the parent "monomeric" cyanine that contained only one chromophoric polymethine system. The prepared dyes have high extinction coefficients (≤251,000 M-1 cm-1) and quantum yield (≤28%). Substitution of both terminal benzoxazole moieties with indolenine, benzothiazole, 2- and 4-quinoline imparted a red-shift in the absorption and emission maxima but lowered quantum yield. © 2009 Elsevier Ltd.


Trusova V.M.,Kharkiv National Medical University | Gorbenko G.P.,Kharkiv National Medical University | Sarkar P.,University of North Texas Health Science Center | Luchowski R.,University of North Texas Health Science Center | And 10 more authors.
Journal of Physical Chemistry B | Year: 2010

Intermolecular time-resolved and single-molecule Förster resonance energy transfer (FRET) have been applied to detect quantitatively the aggregation of polycationic protein lysozyme (Lz) in the presence of lipid vesicles composed of phosphatidylcholine (PC) and its mixture with 5, 10, 20, or 40 mol % of phosphatidylglycerol (PG) (PG5, PG10, PG20, or PG40, respectively). Upon binding to PC, PG5, or PG10 model membranes, Lz was found to retain its native monomeric conformation, while increasing content of anionic lipid up to 20 or 40 mol % resulted in the formation of Lz aggregates. The structural parameters of protein self-association (the degree of oligomerization, the distance between the monomers in protein assembly, and the fraction of donors present in oligomers) have been derived. The crucial role of the factors such as lateral density of the adsorbed protein and electrostatic and hydrophobic Lz-lipid interactions in controlling the protein self-association behavior has been proposed. © 2010 American Chemical Society.


Patent
Seta Biomedicals Llc | Date: 2013-10-07

Dyes and photoluminescent compounds based on polymethine dyes that contain at least one alkyl-phosphonate or substituted alkyl-phosphonate group, including the synthetic precursors, methods of synthesis, and applications thereof. Certain embodiments include heterocyclic ring systems and polymethine linkages selected such that the resulting polymethine dye is a cyanine dye, a merocyanine dye or a styryl dye.


Patent
SETA BioMedicals LLC | Date: 2015-05-18

Methods of performing assays with long lifetime compounds are disclosed. The long lifetime compounds have a lifetime of 4 ns or longer and relate to the structure: Linked reactive groups or conjugated substances may generally be located at R^(a), R^(b), or R^(c). Adjacent substituents R^(a )and R^(b )may form a substituted, 5- or 6-membered heterocyclic group with one ring nitrogen. R^(e )and R^(f )may both be H, R^(e )may be a sulfo group, or adjacent substituents R^(e )and R^(f )may form a cyclic ring structure. The long lifetime compounds contain at least one sulfo group and at least one ionic group, reactive group, or conjugated substance.


Patent
SETA BioMedicals LLC | Date: 2015-09-25

Disclosed viscosity-sensitive reporter compounds and methods allow tracing the changes in viscosity in a biological sample/environment (e.g., in medical, biochemical, biological, and/or pharmaceutical applications). Compounds and methods of the present disclosure can be used to identify the localization and the rheological state of hydrogels, their degradation products and other biostructural materials, including surgical implants, as well as the effectiveness of drug delivery by hydrogel carriers.


Patent
Seta Biomedicals Llc | Date: 2012-08-14

Dendronic reporters are described which incorporate a high density of luminescent or non-luminescent dyes at periphery sites and a focal point group that is reactive, ionic or a conjugated substance. Such dendronic reporters are capable of sensing analytes, or are otherwise useful in luminescent assays. Additionally, methods of synthesis are described.

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