Arylstyrylimidazo[1,2-a]pyridine-based donor–acceptor acidochromic fluorophores: Synthesis, photophysical, thermal and biological properties

Aydıner, Burcu; Yalçın, Ergin; Ihmels, Heiko; Arslan, Leyla; Açık, Leyla; Seferoğlu, Zeynel

doi:10.1016/j.jphotochem.2015.05.030

Cited by 10 publications

(4 citation statements)

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“…Therefore, we sought to develop novel dye structures for use in biological systems by integrating imidazopyridine units into styryl-type dicationic structures. We prepared two dicationic styrylimidazo[1,2-a]pyridinium dyes, called 2a and 2b for this purpose (Scheme 1) (25,26). We assumed with compound 2b that the electronic effect on substituted phenyl ring with a metoxy group as an electron donor at the para position of phenyl ring might influence the binding properties of the compound to HSA, where there is an established donor-acceptor system by resonance compared with the unsubstituted phenyl ring in compound 2a.…”

Section: Introductionmentioning

confidence: 67%

“…They are of significant importance in the pharmaceutical industry, due to their interesting biological activities, which fall under a broad range of therapeutic classes. We prepared two dicationic styrylimidazo[1,2-a]pyridinium dyes, called 2a and 2b for this purpose (Scheme 1) (25,26). Therefore, we sought to develop novel dye structures for use in biological systems by integrating imidazopyridine units into styryl-type dicationic structures.…”

Section: Introductionmentioning

confidence: 99%

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Investigation of binding properties of dicationic styrylimidazo[1,2‐a]pyridinium dyes to human serum albumin by spectroscopic techniques

et al. 2016

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The binding interaction between two dicationic styrylimidazo[1,2-a]pyridinium dyes and human serum albumin (HSA) was investigated at physiological conditions using fluorescence, UV-vis absorption, and circular dichroism (CD) spectroscopies. Analysis of the fluorescence titration data at different temperatures suggested that the fluorescence quenching mechanism of HSA by these dyes was static. The calculated thermodynamic parameters (ΔG°, ΔH° and ΔS°) indicated that hydrogen bonding and van der Waals forces played a major role in the formation of the dye-HSA complex. Binding distances (r) between dyes and HSA were calculated according to Förster's non-radiative energy transfer theory. Studies of conformational changes of HSA using CD measurements indicate that the α-helical content of the protein decreased upon binding of the dyes. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 67%

Section: Introductionmentioning

confidence: 99%

Investigation of binding properties of dicationic styrylimidazo[1,2‐a]pyridinium dyes to human serum albumin by spectroscopic techniques

et al. 2016

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“…44 65.07 2g 63.17HURZOL 45 65.16RELQUW 46 64.98 2h 64.74KABMIM 47 66.21RUJNEQ. 48 64.61 2i 63.81MIXZOJ 49 65.44TIDVIN 50 66.07 2j 64.63MIXZUP 51 67.52TUZYEU 52 65.44 2k 65.36MONREO 53 66.12UTITEX 54 62.07 2l 67.34NAGGEH 55 65.27VEGKAU 56 64.34 2m 60.69NAGGEH01 57 64.84WUHKER 58 62.24 2n 62.87NOGRIM 59 65.44YEDHIY 60 63.06 2o 66.69NONFOM 61 64.30ZUNVOV 62 68.57AHOMIV 63 63.75NONFOM01 61 65.95ZUPCOE 62 66.04BEGTUE 64 62.92NUBVUD 65 63.87ZUSSAJ 66 63.31CAJTIQ 67 67.82NUBWAK 65 64.00…”

Section: Resultsmentioning

confidence: 99%

Crystal Correlation Of Heterocyclic Imidazo[1,2-a]pyridine Analogues and Their Anticholinesterase Potential Evaluation

Kwong

Kumar

Mah

et al. 2019

Sci Rep

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Imidazo[1,2-a]pyridine-based compounds are clinically important to the treatments of heart and circulatory failures, while many are under development for pharmaceutical uses. In this study, a series of imidazo[1,2-a]pyridine-based derivatives 2(a–o) were synthesized by reacting a-haloketones with 2-aminopyridines in a basic media at ambient temperature. Single crystal X-ray diffraction studies suggest that with low degree-of-freedom, the introduction of bulky adamantyl or electron-rich biphenyl moiety into the imidazopyridine derivatives will not affect its structural occupancy. Imidazo[1,2-a]pyridine-based derivatives with biphenyl side chain are potential AChE inhibitors. Compound 2h which bears a biphenyl side chain and methyl substituent at the position R4 of the imidazo[1,2-a]pyridine ring showed the strongest AChE inhibition with an IC50 value of 79 µM. However, imidazo[1,2-a]pyridine derivatives with phenyl side chain exhibit better BChE inhibition effect among the series. Compound 2j with 3,4-dichlorophenyl side chain and unsubstituted imidazo[1,2-a]pyridine ring appears to be the strongest BChE inhibitor with an IC50 value of 65 µM and good selectivity. The inhibitory effects of active compounds were further confirmed by computational molecular docking studies. The results unveiled that peripheral anionic sites of AChE and acyl pocket of BChE were the predominated binding sites for the subjected inhibitors.

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“…A few examples of D–π–A structures have been described by using the imidazo[1,2- a ]pyridine moiety. Tao, Tong et al and Thomas et al describe it as an electron-deficient unit, with a phenanthroimidazole group introduced at position 2, in the design of blue-emitting fluorophores for organic light-emitting diodes, as do Seferoğlu et al in their study of a series of arylstyrylimidazo[1,2- a ]pyridine compounds functionalized at position 7, whose absorption and emission are modulated by the protonation of the imidazo[1,2- a ]pyridine moiety . In contrast, Jadhav and Sekar utilized the imidazo[1,2- a ]pyridine moiety as an electron donor group, incorporating different electron acceptor groups, such as (3,5,5-trimethylcyclohex-2-enylidene)malononitrile ( DCI ), at position 3.…”

Section: Introductionmentioning

confidence: 99%

Imidazo[1,2-a]pyridine and Imidazo[1,5-a]pyridine: Electron Donor Groups in the Design of D–π–A Dyes

Valla,

Pitrat,

Mulatier

et al. 2024

J. Org. Chem.

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Arylstyrylimidazo[1,2-a]pyridine-based donor–acceptor acidochromic fluorophores: Synthesis, photophysical, thermal and biological properties

Cited by 10 publications

References 54 publications

Investigation of binding properties of dicationic styrylimidazo[1,2‐a]pyridinium dyes to human serum albumin by spectroscopic techniques

Investigation of binding properties of dicationic styrylimidazo[1,2‐a]pyridinium dyes to human serum albumin by spectroscopic techniques

Crystal Correlation Of Heterocyclic Imidazo[1,2-a]pyridine Analogues and Their Anticholinesterase Potential Evaluation

Imidazo[1,2-a]pyridine and Imidazo[1,5-a]pyridine: Electron Donor Groups in the Design of D–π–A Dyes

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