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Optical information gene material and its application in gene chip technology

A gene chip and optical information technology, which is applied in the directions of azine dyes, organic dyes, naphthalene dicarboxamide dyes/phthalimide dyes, etc., can solve the problems such as reports on light-modified gene chips that have not yet been seen, and achieve convenient and rapid detection. Disturbance-reducing, mild-condition effects

Inactive Publication Date: 2004-03-17
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there has been no report of this type of light-modified gene chip so far.

Method used

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  • Optical information gene material and its application in gene chip technology
  • Optical information gene material and its application in gene chip technology
  • Optical information gene material and its application in gene chip technology

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of fluorescent material 6-carboethyl-9-N-methyl N-carboxyethyl-benzo[a]phenoxazinone R-P:

[0023]

[0024] 10.4g (42.5mmol) of 4-nitroso-N-methyl-N-carboxyethylaniline hydrochloride and 8.0g (34.5mmol) of ethyl 1,3-dihydroxy-2-naphthoate in a dry Heated to reflux in hexanonitrile for 6 hours, cooled and concentrated to obtain 6.5 g of brown-red compound, m.p.232°C. Elemental Analysis: Found: C65.69, H4.75, N6.69.Calcd.For C 23 h 20 N 2 o 6 : C65.71, H4.79, N6.66.

[0025] Synthesis of carboxyl N-succinimide ester R-P-NHS of R-P:

[0026]

[0027] 0.42g (1mmol) R-P was dissolved in 10ml dry DMF, 0.15g (1.25mmol) N-hydroxysuccinimide (NHS), 0.26g (1.25mmol) DCC (dicyclohexylcarbodiimide) was added, Stir at room temperature for 24 hours, filter off the white solid, evaporate DMF under reduced pressure, dissolve the residue in ethyl acetate, wash with saturated NaHCO 3 After washing with aqueous solution and water, the organic layer was dried with an...

Embodiment 2

[0031] Synthetic photochromic material SPNHS:

[0032]

[0033] Dissolve 0.38g (1mmol) of 1-carboxyethyl-3,3'-dimethyl-6-nitrospiroindoline-2,2'[2H-1]benzopyran (SPCOOH) in 10ml DMF , add 0.15g NHS (1.25mmol) and 0.26g DCC (1.25mmol), stir at room temperature for 24h., filter off the solid, evaporate the solvent, add ethyl acetate, and use saturated NaHCO 3 Aqueous washing, anhydrous Na 2 SO 4 Dry, add petroleum ether and recrystallize to obtain 0.4 g of light yellow crystals, m.p.140°C. Elemental Analysis: Found: C62.82, H4.85, N8.73.Calcd.For C 25 h 23 N 3 o 7 : C62.89, H4.86, N8.80. The ethanol solution is light yellow, and turns blue-purple after light or ultraviolet light; UV(λ max , solid reflection) before illumination: 260nm, 320nm; after illumination: 260nm, 320nm, 580nm.

[0034] Synthetic photochromic genetic material:

[0035] Dissolve the specific sequence gene fragment with amino group at the 5' end in NaHCO containing 1M3 (PH=9.0) aqueous solution, ...

Embodiment 3

[0037] Synthetic photochromic material SPNCS:

[0038]

[0039] Mix 0.44g (2mmol) 1,3,3'-trimethyl-2-methylene-5-isothiocyanatoindoline with 0.34g (2mmol) 5-nitrosalicylaldehyde in 15ml without Heated under reflux in water and ethanol for 3 hours, filtered off the solid, and the filtrate was separated by column chromatography and recrystallized from acetone-petroleum ether to obtain 0.60 g of light yellow crystal product, m.p.165°C. Elemental Analysis: Found: C63.35, H4.55, N11.01.Calcd.For C 20 h 17 N 3 o 3 S: C63.31, H4.52, N11.07. The ethanol solution is light yellow, and turns purple after light or ultraviolet light; UV(λ max , solid reflection) before illumination: 260nm, 325nm; after illumination: 260nm, 325nm, 575nm.

[0040] Synthetic photochromic genetic material:

[0041] Dissolve the specific sequence gene fragment with amino group at the 5' end in NaHCO containing 1M 3 (PH=9.0) aqueous solution, add DMF solution in which excess photochromic compound SPNH...

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PUM

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Abstract

The novel optical information gene material of the present invention is compound with the composition of [B]-[L]-[G], [P]-[L]-[G], or [F]-[L1]-[G]-[L2]-[Q], where [B] and [F] are fluorescent optical information function group, [P] is photochromic optical information functional group, [G] is gene, [Q] is optical quenching group, and [L], [L1] and [L2] are connecting arm for the gene and the optical information group. The optical information gene material of the present invention may be used in the preparation of gene chip probe, and its application can simplify the detection process of chip, shorten detection time, and raise the specificity and accuracy of chip detection.

Description

technical field [0001] The invention relates to a novel optical information gene material and its application in gene chip technology. Background technique [0002] At present, there are many methods for gene marker detection, such as photobiotin, digoxin, fluorescent compounds, etc. Among them, fluorescent compounds are more and more widely used due to their low cost, convenient detection, and sensitivity. The more commonly used fluorescent dyes on the market, such as fluorescein, etc., have fluorescence emission wavelengths in the range of 450-600nm, but because many biological substances such as cells have fluorescent backgrounds in this range, people are looking for near emission wavelengths greater than 600nm. Infrared fluorescent dyes can effectively reduce fluorescent background interference in this range, thereby improving accuracy and sensitivity. At present, the fluorescent dyes used in this range on the market are mainly cyanines, but...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D279/36C07D405/12C07D491/107C07H21/04C12Q1/68
CPCC09B19/00C09B57/08
Inventor 孟继本张鹏高宇邹武新季奇王永梅
Owner NANKAI UNIV
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