Synthesis and photophysical properties of novel succinimidyl benzazole derivatives, evaluated by Candida albicans ATCC 10231 fluorescent staining

被引：30

作者：

dos Santos, Rosane Catarina ^{[1
]}

da Silva Faleiro, Nalva Vivian ^{[1
]}

Campo, Leandra Franciscato ^{[1
]}

Scroferneker, Maria Lucia ^{[2
]}

Corbellini, Valeriano Antonio

Rodembusch, Fabiano Severo ^{[1
]}

Stefani, Valter ^{[1
]}

机构：

[1] Univ Fed Rio Grande do Sul, Inst Quim, BR-91501970 Porto Alegre, RS, Brazil

[2] Univ Fed Rio Grande do Sul, Inst Ciencias Basicas Saude, BR-90050170 Porto Alegre, RS, Brazil

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 23期

关键词：

Fluorescent probes; ESIPT; Succinimidyl dyes; Epifluorescence; Candida albicans; INTRAMOLECULAR PROTON-TRANSFER; CLINICAL SPECIMENS; FUNGAL ELEMENTS; IN-VIVO; VISUALIZATION; INFECTIONS; CALCOFLUOR; CELLS; YEAST;

D O I：

10.1016/j.tetlet.2011.04.026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New fluorescent succinimidyl benzazole derivatives were synthesised and successfully used to stain Candida albicans ATCC 10231 cells. The dyes were characterised by means of infrared, C-13 and H-1 NMR spectroscopies and elemental analysis. UV-Vis and steady-state fluorescence in solution were also applied to characterise their photophysical behaviour. The novel dyes were fluorescent in the yellow-green region by a phototautomerism in the excited state (ESIPT) with a large Stokes shift (9065-10962 cm(-1)). Dual fluorescence could also be observed depending on the solvent polarity. The present dyes were used as new probes by means of culture methodology or direct staining to study the micromorphology of Candida albicans. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：3048 / 3053

页数：6

共 35 条

[1]

Banerjee U, 2005, INDIAN J MED RES, V121, P395

[2] A fast and cost-effective methodology for Fonsecaea pedrosoi ATCC46428 staining using ESIPT fluorescent dyes [J].

Corbellini, Valeriano Antonio ;

Scroferneker, Maria Lucia ;

Carissimi, Mariana ;

Rodembusch, Fabiano Severo ;

Stefani, Valter .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 2010, 99 (03) :126-132

[3] Investigation of nonspecific effects of different dyes in the screening of labeled carbohydrates against immobilized proteins [J].

Dowlut, M ;

Hall, DG ;

Hindsgaul, O .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) :9809-9813

[4] Carboxy-fluorescein diacetate, succinimidyl ester labeled papillomavirus virus-like particles fluoresce after internalization and interact with heparan sulfate for binding and entry [J].

Drobni, P ;

Mistry, N ;

McMillan, N ;

Evander, M .

VIROLOGY, 2003, 310 (01) :163-172

[5] Assessment of FUN-1 vital dye staining: Yeast with a block in the vacuolar sorting pathway have impaired ability to form CIVS when stained with FUN-1 fluorescent dye [J].

Essary, Brandin D. ;

Marshall, Pamela A. .

JOURNAL OF MICROBIOLOGICAL METHODS, 2009, 78 (02) :208-212

[6] Yeasts species distribution in Neonatal Intensive Care Units in northeast Argentina [J].

Giusiano, GE ;

Mangiaterra, M ;

Rojas, F ;

Gómez, V .

MYCOSES, 2004, 47 (07) :300-303

[7] Comparison of two fluorescent whiteners, Calcofluor and Blankophor, for the detection of fungal elements in clinical specimens in the diagnostic laboratory [J].

Hamer, EC ;

Moore, CB ;

Denning, DW .

CLINICAL MICROBIOLOGY AND INFECTION, 2006, 12 (02) :181-184

[8] In situ visualisation of fungi in soil thin sections:: problems with crystallisation of the fluorochrome FB 28 (Calcofluor M2R) and improved staining by SCRI Renaissance 2200 [J].

Harris, K ;

Crabb, D ;

Young, IM ;

Weaver, H ;

Gilligan, CA ;

Otten, W ;

Ritz, K .

MYCOLOGICAL RESEARCH, 2002, 106 :293-297

[9] Adaptation of FUN-1 and Calcofluor white stains to assess the ability of viable and nonviable yeast to adhere to and be internalized by cultured mammalian cells [J].

Henry-Stanley, MJ ;

Garni, RM ;

Wells, CL .

JOURNAL OF MICROBIOLOGICAL METHODS, 2004, 59 (02) :289-292

[10] Synthesis and spectroscopic characterisation of 2-(2′-hydroxyphenyl)benzazole isothiocyanates as new fluorescent probes for proteins [J].

Holler, MG ;

Campo, LF ;

Brandelli, A ;

Stefani, V .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2002, 149 (1-3) :217-225

← 1 2 3 4 →