3-Hydroxychromone dyes exhibiting excited-state intramolecular proton transfer in water with efficient two-band fluorescence

被引：83

作者：

Klymchenko, AS ^{[1
]}

Demchenko, AP

机构：

[1] Univ Strasbourg 1, Fac Pharm, CNRS,UMR 7034, Lab Pharmacol & Physicochim, F-67401 Illkirch Graffenstaden, France

[2] TUBITAK Res Inst Genet Engn & Biotechnol, TR-41470 Gebze, Turkey

[3] AV Palladin Biochem Inst, UA-01030 Kiev, Ukraine

来源：

NEW JOURNAL OF CHEMISTRY | 2004年 / 28卷 / 06期

关键词：

D O I：

10.1039/b316149h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We demonstrate that newly synthesised 7-acetamido-3-hydroxychromones, as well as their parent 3-hydroxychromone (3HC) analogues, exhibit excited-state intramolecular proton transfer reaction in polar protic media including water, resulting in well-resolved two-band fluorescence. Among all 3HCs reported so far, the new compounds show the highest quantum yields ever reported in water (4-13%), while maintaining the sensitive ratiometric response to solvent polarity. This makes them very promising precursors for the development of two-band fluorescent labels and probes, operating in water and other protic media.

引用

页码：687 / 692

页数：6

共 41 条

[1]

Algar J., 1934, Proc. R. Ir. Acad, V42B, P1

[2] EXCITED-STATE PROTON-TRANSFER REACTIONS .1. FUNDAMENTALS AND INTERMOLECULAR REACTIONS [J].

ARNAUT, LG ;

FORMOSINHO, SJ .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1993, 75 (01) :1-20

[3] Flavonols - new fluorescent membrane probes for studying the interdigitation of lipid bilayers [J].

Bondar, OP ;

Pivovarenko, VG ;

Rowe, ES .

BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES, 1998, 1369 (01) :119-130

[4] REVERSAL OF EXCITATION BEHAVIOR OF PROTON-TRANSFER VS CHARGE-TRANSFER BY DIELECTRIC PERTURBATION OF ELECTRONIC MANIFOLDS [J].

CHOU, PT ;

MARTINEZ, ML ;

CLEMENTS, JH .

JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (11) :2618-2622

[5] PROTEIN FLUORESCENCE, DYNAMICS AND FUNCTION - EXPLORATION OF ANALOGY BETWEEN ELECTRONICALLY EXCITED AND BIOCATALYTIC TRANSITION-STATES [J].

DEMCHENKO, AP .

BIOCHIMICA ET BIOPHYSICA ACTA-PROTEIN STRUCTURE AND MOLECULAR ENZYMOLOGY, 1994, 1209 (02) :149-164

[6] Excited-state intramolecular proton transfer (ESIPT) and charge transfer (CT) fluorescence probe for model membranes [J].

Dennison, SM ;

Guharay, J ;

Sengupta, PK .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1999, 55 (05) :1127-1132

[7] SYNTHESIS AND CHARACTERIZATION OF WAVELENGTH-SHIFTING MONOMERS AND POLYMERS BASED ON 3-HYDROXYFLAVONE [J].

DHARIA, JR ;

JOHNSON, KF ;

SCHLENOFF, JB .

MACROMOLECULES, 1994, 27 (18) :5167-5172

[8] Neutral fluorescence probe with strong ratiometric response to surface charge of phospholipid membranes [J].

Duportail, G ;

Klymchenko, A ;

Mely, Y ;

Demchenko, A .

FEBS LETTERS, 2001, 508 (02) :196-200

[9] CYANINE DYE LABELING REAGENTS FOR SULFHYDRYL-GROUPS [J].

ERNST, LA ;

GUPTA, RK ;

MUJUMDAR, RB ;

WAGGONER, AS .

CYTOMETRY, 1989, 10 (01) :3-10

[10] PH EFFECTS ON FLUORESCENCE OF UMBELLIFERONE [J].

FINK, DW ;

KOEHLER, WR .

ANALYTICAL CHEMISTRY, 1970, 42 (09) :990-&

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