EXPLOSIVES DETECTION MARKERS

• US 20110003396A1
• Filed: 05/15/2007
• Published: 01/06/2011
• Est. Priority Date: 05/15/2006
• Status: Active Grant

• Current Assignee: Syddansk Universitet
• Original Assignee: Syddansk Universitet
• Inventors: Jeppesen, Jan O., Nielsen, Kent A.
• Granted Patent: US 8,378,093 B2
• Time in Patent Office: Days
• US Class Current: 436/110
• CPC Class Codes: C07D 495/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C07D 519/00 Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
• CPC Class Codes: Y10T 436/173076 Nitrite or nitrate

Abstract

The present invention relates to a porphyrinogen based sensor having selective binding affinity for an explosive chemical. Upon binding of the target molecule, the porphyrinogen derivative undergoes a detectable adsorption and emission of electromagnetic radiation.

Claims

1. Compound of the general formula 2

2. Compound of claim 1 wherein R¹-R⁸ is independently selected from the group consisting of

i) SR^A in which R^A represents an alkyl chain from C1 to C20 or a —

CH₂CH₂—

O—

(CH₂CH₂O)_n group in which n=0-5;

ii) COOR^B in which R^B represents an alkyl chain from C1 to C20 or a —

CH₂CH₂—

O—

(CH₂CH₂O)_n group in which n=0-5;

iii) CH₂Ar, in which Ar represents an aryl group; and

iv) CH₂XR^C in which X represents and O, S, or N atom and R^C represents an alkyl chain from C1 to C20 or a —

CH₂CH₂—

O—

(CH₂CH₂O)_n group in which n=0-5;

with the proviso that protection is excluded for the compound, wherein R¹-R⁸ is exclusively —

S—

CH2-CH2-CH3 and R⁹-R¹⁶ is exclusively methyl.

3. Compound of claim 1 selected from:

4. A kit for the detection of explosives comprising:

(i) a porphyrinogen derivative according to formula 2 of claim 1 which undergoes a detectable change in absorption and/or emission of electromagnetic radiation when TNT, TNB, or TNP binds thereto

(ii) means for detecting any change in absorption and/or emission of electromagnetic radiation by the porphyrinogen derivative, said detected change being indicative of the presence of explosive in, on, or in association with said environment.

5. A kit according to claim 4, wherein the porphyrinogen derivative has the following formula

6. A fiber optic sensor device for detecting the presence of a nitro-group containing explosive, the sensor comprising:

i) at least one optical fiber means having a proximal end and a distal end for transmitting light energy, the proximal end being disposed within a probe housing;

the porphyrinogen derivative of claim 1 disposed on the distal end of the optical fiber means, wherein the porphyrinogen derivative is capable of chemically binding with said nitro-group containing explosive;

ii) light source means for generating excitation energy, said light source means being operatively associated with said optical fiber means such that said excitation light passes through said optical fiber means; and

iii) detection means operatively associated with said optical fiber means, for detecting an emission signal generated by the porphyrinogen derivative.

7. The sensor of claim 6, wherein the nitro-group containing explosive is selected from the group consisting of TNT, TNB, and TNP.

8. The device of claim 7, wherein the light source means is selected from the group consisting of an argon laser, blue laser, tunable laser, and light emitting diode.

9. The device of claim 8 wherein the detection means is selected from the group consisting of a spectrophotometer, spectrometer, photomultiplier tube, monochromator equipped with a CCD camera, filters, and the naked eye.

10. A method for detecting the presence of a target molecule comprising an explosive chemical comprising the steps of:

i) providing a fiber optic sensor device comprising;

A) at least one optical fiber means having a proximal end and a distal end for transmitting light energy, the proximal end being disposed within a probe housing;

the porphyrinogen derivative of claim 1 disposed on the distal end of the optical fiber means, wherein the porphyrinogen is capable of chemically binding with said target molecule;

B) light source means for generating excitation energy, said light source means being operatively associated with said optical fiber means such that said excitation light passes through said optical fiber means; and

C) detection means operatively associated with said optical fiber means, for detecting an emission signal generated by the porphyrinogen derivative;

ii) exposing the porphyrinogen derivative to an environment containing the explosive such that the explosive come in contact with the porphyrinogen, and

iii) detecting any change in absorption and/or emission of electromagnetic radiation by the porphyrinogen derivative, said detected change being indicative of the presence of the explosive in, on or in association with said environment.

11. The method of claim 10, wherein the explosive chemical is selected from the group consisting of TNT and TNB.

12. The method of claim 11, wherein the light source means is selected from the group consisting of an argon laser, blue laser, tunable laser, and light emitting diode.

13. The method of claim 12, wherein the detection means is selected from the group consisting of a spectrophotometer, spectrometer, photomultiplier tube, monochromator equipped with a CCD camera, quartz crystal microbalance (QCM), filters, and the naked eye.

14. Use of the porphyrinogen derivative of claim 1 for the detection of an explosive chemical, wherein the derivative changes colour from yellow to green upon interaction with the explosive chemical.