A diethylamino pyridine formyl Schiff base as selective recognition chemosensor for biological thiols

Yu, Xueying; Wang, Kang‐Nan; Cao, Duxia; Liu, Zhi Qiang; Guan, Ruifang; Wu, Qianqian; Xu, Yongxiao; Sun, Yongjian; Zhao, Xin

doi:10.1016/j.snb.2017.04.147

Cited by 25 publications

(8 citation statements)

References 39 publications

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“…As shown in Fig. S6, † 1 H NMR titration of Ni 2+ to compound DTEP shows that N atom in imide group plays a key role in the coordination, in combination with previous report, 34 it is reasonable to infer that N atoms in imide, amide and pyridine groups, and O atom in amide group coordinate to Ni 2+ with a 1 : 2 binding mode as depicted in Scheme 1. We also found that compound DTEP in the photostationary state could selectively respond to Cu 2+ and Ni 2+ with different absorption and color changes (Fig.…”

Section: Responses To Cu 2+ and Ni 2+supporting

confidence: 76%

A monomolecular platform with varying gated photochromism

Chen

Weng

et al. 2020

RSC Adv.

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Section: Responses To Cu 2+ and Ni 2+supporting

confidence: 76%

A monomolecular platform with varying gated photochromism

Chen

Weng

et al. 2020

RSC Adv.

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“…Teorik hesaplamalar; CS ChemBioDraw Ultra 16.0.1.4 for Microsoft Windows [26], Gaussian09 [27], and GaussView 5.0.9 [28], programları kullanılarak yapılmıştır. Intel(R) Core(TM) i7 X 990, 3…”

Section: Teorik Hesaplamalarunclassified

“…Nobel ödüllü kimyager Hugo Schiff tarafından ilk kez sentezlenen Schiff bazları; imin (-CH=N-) içeren, aldehit ve ketonların aminler ile nükleofilik katılma reaksiyonu ile oluşan kondenzasyon ürünü bileşiklerdir [1]. Schiff bazları ve kompleksleri kemosensör [2,3], katalitik [4], optik anahtar [5], solvatokromik [6,7], floresans materyal [6], boyar madde [8] olarak kullanımları, sıvı kristal özellikleri [9] ve diğer kullanımları [10][11][12] nedeniyle boyarmadde, ilaç ve plastik sanayi gibi birçok alanda yaygın olarak kullanılmaktadır. Schiff bazları yapılarında azometin grubu bulundurmaları nedeniyle [13][14] biyolojik aktivite çalışmalarında da çok kullanılmaktadır [12,[15][16][17].…”

Section: Introductionunclassified

2-Etoksi-6-[(E)-[(2-Hidroksifenil)imino]metil]fenol Türevi Schiff Bazlarının Sentezi ve Teorik Çalışmalar

Berber

Erdönmez

Uysal

2020

Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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2-hidroksifenil)imino]metil]fenol türevi Schiff bazları (4kloro-2-((3-etoksi-2-hidroksibenziliden)amino)fenol; 5S1 ve 2-((3-etoksi-2hidroksibenziliden)amino)-4-metilfenol); 5S2 bileşikleri sentezlenmiştir. Karekterizasyonu 1 H ve 13 C NMR, elemental analiz ve FT-IR Spektrometresi ile yapılmıştır. Bileşiklerin ve olası tautomer formlarının kararlı konformasyonları teorik hesaplamalarla belirlenmiştir. Tüm hesaplamalar; kararlı konformasyonlar kullanılarak ve vakumda B3LYP/6-311g(2d,p) yöntemiyle yapılmıştır. Hesaplamalarda bileşiklerin enerjileri, kararlı taotomer formları, H-bağları, Mulliken yükleri, dipol momentleri, Çözücüyle erişilebilen yüzey alanı (Solvent accessibility surface), Moleküler elektrostatik potansiyel değerleri (MEP) (Molecular electrostatic potentials values), HOMO, LUMO ve enerji bant aralığı enerjileri (HOMO, LUMO and band gap energies) hesaplamaları yapılmıştır. Deneysel ve teorik IR, 1 H ve 13 C NMR uyumu incelenmiştir.

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“…[1,7] We are not aware of fluorimetric studies describing the interaction of vanadium compounds with Cys, Hcy, and GSH. Merely, coordination complexes of Cu, Cd, and Hg have exclusively been explored with biothiols because of the strong affinity of the metals toward biothiols (Table S1) [8–22] . Recently, our group reported a series of water‐soluble Cu complexes, which showed a ‘turn‐on’ fluorescence response with homocysteine facilitated via reduction‐induced‐emission‐enhancement [22] .…”

Section: Introductionmentioning

confidence: 99%

Coumarin‐Ensembled Vanadium(V) Compounds and Their Affinity Studies Toward Biological Thiols Probed by Fluorescence Spectroscopy

Debnath

Navadiya

Ghosh

et al. 2022

Chemistry An Asian Journal

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Fluorescence spectroscopic studies of a pair of new oxido-vanadium(V) compounds with biological thiols, such as homocysteine (Hcy), cysteine (Cys), and glutathione (GSH), have been investigated in this article. Despite notable progress in vanadium-thiol chemistry, no attention has been paid to exploring vanadium-based optical probes to study their interaction with biothiols. For this purpose, two oxidovanadium(V) compounds, 1 and 2, have been prepared involving a tridentate ONO donor-based luminescent coumarin-derived ligand. Single crystal X-ray diffraction analysis, NMR ( 1 H, 13 C, and 51 V) spectroscopy, XPS, and DFT calculations have been used to establish their identities. The vanadium center in these compounds has a distorted octahedral environment. In compound 2, a methanol molecule is coordinated to the vanadium(V) center in the trans position of the terminal oxido moiety. The latter exerts a strong translabilizing influence on the coordinating methanol. Both 1 and 2 are weakly fluorescent. Photophysical investigations of the vanadium complexes in aqueous media at physiological pH (7.4) in the presence of various biothiols and amino acids showed significant fluorescence enhancement (83-fold) of the vanadium complexes, specifically with Hcy. The specific affinity of the complexes for Hcy remained unchanged even in the presence of other biothiols and amino acids. Kinetic investigation reveals pseudo-first order behavior of the compound with Hcy. Mechanistic studies have manifested that Hcy-induced reduction triggers the decomplexation of the vanadium compound, followed by hydrolysis and subsequent cyclization. Time-correlated single photon counting suggested that the radiative rate constant (k r ) of 1 and 2 in the presence of Hcy serves as the prime factor for the fluorescence enhancement of the medium. Compound 1 has been tested efficiently for Hcy measurement in blood plasma rendering it suitable for practical applications.

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A diethylamino pyridine formyl Schiff base as selective recognition chemosensor for biological thiols

Cited by 25 publications

References 39 publications

A monomolecular platform with varying gated photochromism

A monomolecular platform with varying gated photochromism

2-Etoksi-6-[(E)-[(2-Hidroksifenil)imino]metil]fenol Türevi Schiff Bazlarının Sentezi ve Teorik Çalışmalar

Coumarin‐Ensembled Vanadium(V) Compounds and Their Affinity Studies Toward Biological Thiols Probed by Fluorescence Spectroscopy

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