Selective chromo-fluorogenic detection of DFP (a Sarin and Soman mimic) and DCNP (a Tabun mimic) with a unique probe based on a boron dipyrromethene (BODIPY) dye

被引:38
作者
Barba-Bon, Andrea [1 ,2 ]
Costero, Ana M. [1 ,2 ]
Gil, Salvador [1 ,2 ]
Martinez-Manez, Ramon [1 ,3 ,4 ]
Sancenon, Felix [1 ,3 ,4 ]
机构
[1] Unidad Mixta Univ Valencia Univ Politecn Valencia, Ctr Reconocimiento Mol & Desarrollo Tecnol IDM, Valencia, Spain
[2] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain
[3] Univ Politecn Valencia, Dept Quim, Valencia 46022, Spain
[4] CIBER BBN, Valencia, Spain
关键词
NERVE AGENTS; ORGANOPHOSPHATE PESTICIDES; RHODAMINE-B; ACETYLCHOLINESTERASE; FLUORESCENT; NANOTUBES; SENSORS; SURFACE;
D O I
10.1039/c4ob01299b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel colorimetric probe (P4) for the selective differential detection of DFP (a Sarin and Soman mimic) and DCNP (a Tabun mimic) was prepared. Probe P4 contains three reactive sites; i.e. (i) a nucleophilic phenol group able to undergo phosphorylation with nerve gases, (ii) a carbonyl group as a reactive site for cyanide; and (iii) a triisopropylsilyl (TIPS) protecting group that is known to react with fluoride. The reaction of P4 with DCNP in acetonitrile resulted in both the phosphorylation of the phenoxy group and the release of cyanide, which was able to react with the carbonyl group of P4 to produce a colour modulation from pink to orange. In contrast, phosphorylation of P4 with DFP in acetonitrile released fluoride that hydrolysed the TIPS group in P4 to yield a colour change from pink to blue. Probe P4 was able to discriminate between DFP and DCNP with remarkable sensitivity; limits of detection of 0.36 and 0.40 ppm for DCNP and DFP, respectively, were calculated. Besides, no interference from other organophosphorous derivatives or with presence of acid was observed. The sensing behaviour of P4 was also retained when incorporated into silica gel plates or onto polyethylene oxide membranes, which allowed the development of simple test strips for the colorimetric detection of DCNP and DFP in the vapour phase. P4 is the first probe capable of colorimetrically differentiating between a Tabun mimic (DCNP) and a Sarin and Soman mimic (DFP).
引用
收藏
页码:8745 / 8751
页数:7
相关论文
共 57 条
[31]   3,5-Diformyl-borondipyrromethene for selective detection of cyanide anion [J].
Madhu, Sheri ;
Basu, Santanu Kumar ;
Jadhav, Sameer ;
Ravikanth, Mangalampalli .
ANALYST, 2013, 138 (01) :299-306
[32]  
Nagale S., 2006, J AM CHEM SOC, V128, P5041
[33]   Chromogenic detection of Sarin by discolouring decomplexation of a metal coordination complex [J].
Ordronneau, Lucie ;
Carella, Alexandre ;
Pohanka, Miroslav ;
Simonato, Jean-Pierre .
CHEMICAL COMMUNICATIONS, 2013, 49 (79) :8946-8948
[34]   A selective fluorescent sensor for imaging Cd2+ in living cells [J].
Peng, Xiaojun ;
Du, Jianjun ;
Fan, Jiangli ;
Wang, Jingyun ;
Wu, Yunkou ;
Zhao, Jianzhang ;
Sun, Shiguo ;
Xu, Tao .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) :1500-+
[35]   Photophysical properties of an on/off fluorescent pH indicator excitable with visible light based on a borondipyrromethene-linked phenol [J].
Qin, Wenwu ;
Baruah, Mukulesh ;
De Borggraeve, Wim M. ;
Boens, Noel .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2006, 183 (1-2) :190-197
[36]   Chromogenic and fluorogenic reagents for chemical warfare nerve agents' detection [J].
Royo, Santiago ;
Martinez-Manez, Ramon ;
Sancenon, Felix ;
Costero, Ana M. ;
Parra, Margarita ;
Gil, Salvador .
CHEMICAL COMMUNICATIONS, 2007, (46) :4839-4847
[37]   Chromogenic, Specific Detection of the Nerve-Agent Mimic DCNP (a Tabun Mimic) [J].
Royo, Santiago ;
Costero, Ana M. ;
Parra, Margarita ;
Gil, Salvador ;
Martinez-Manez, Ramon ;
Sancenon, Felix .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) :6931-6934
[38]   Biomaterials for mediation of chemical and biological warfare agents [J].
Russell, AJ ;
Berberich, JA ;
Drevon, GE ;
Koepsel, RR .
ANNUAL REVIEW OF BIOMEDICAL ENGINEERING, 2003, 5 :1-27
[39]   Detection of V-type nerve agent degradation products at electrodes modified by PPy/PQQ using CaCl2 as supporting electrolyte [J].
Shulga, Olga V. ;
Palmer, Christopher .
ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2006, 385 (06) :1116-1123
[40]  
Silver A., 1974, THE BIOLOGY OF CHOLI, P449