Glycosylated boron dipyrromethene fluorophore derivatives as well as preparation and application thereof

A technology of fluorobodipyrrole and its derivatives, which is applied in the field of glycosylated fluorobodipyrrole anti-tumor photosensitive drugs and its preparation, and can solve skin phototoxicity, weak tissue penetration ability, and uncertain composition of photosensitizers And other problems, to achieve the effect of not easy skin phototoxicity, strong tissue penetration ability, and low cost

Inactive Publication Date: 2014-04-30
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Porphyrin, chlorophyll, hypocrellin, etc. are traditional photosensitizers. The composition of these photosensitizers is uncertain, the maximum absorption wavelength is near the short wavelength, and the tissue penetration ability is weak. Photodynamic therapy is likely to cause skin phototoxicity. Not an ideal photosensitizer

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 1) the compound (100 mg, 0.09 mmol), (R is Ac, n is 1) (110 mg, 0.26 mmol), CuSO 4 ·5H 2 O (15 mg, 0.06 mmol) and sodium ascorbate (24 mg, 0.12 mmol) were dissolved in 7 ml CHCl 3 , ethanol and water (volume ratio 12:1:1), vigorously stirred at room temperature for 24 hours. CH 2 Cl 2 and water extraction, the organic layer with Na 2 SO 4 After drying, spin dry under reduced pressure. in CH 2 Cl 2 / methanol (20:1 v / v) is the eluent, purified by silica gel column chromatography to obtain the compound: (R is Ac, n is 1) (71 mg, 53%). H NMR spectrum[ 1 H NMR (400 MHz, CDCl 3 )]: δ = 8.13 (d, J = 16.8 Hz, 2 H, CH=CH), 7.78 (s, 1 H, triazole-H), 7.60 (d, J = 8.8 Hz, 4 H, ArH), 7.58 (d, J = 17.6 Hz, 2 H, CH=CH), 7.20 (d, J = 8.8 Hz, 2 H, ArH), 7.15 (d, J = 8.8 Hz, 2 H, ArH), 6.96 (d, J = 8.8 Hz, 4 H, ArH), 5.25 (s, 2 H, OCH 2 ), 5.23-5.16 (m, 1 H, H4), 5.12-5.06 (m, 1 H, H3), 5.03 (dd, J 1 = 9.6Hz, J 2 = 8.0 Hz, 1 H, H2), 4.67 (dt,1 H, J ...

Embodiment 2

[0042] compound (200 mg, 0.18 mmol), (R is H, n is 1) (100 mg, 0.40 mmol), CuSO 4 ·5H 2 O (15 mg, 0.06 mmol) and sodium ascorbate (24 mg, 0.12 mmol) were dissolved in 7 ml CHCl 3 ﹑In a mixture of ethanol and water (volume ratio 12:1:1), stir vigorously at room temperature for 24 h. The reaction mixture was CH 2 Cl 2 and water extraction. Na for organic layer 2 SO 4 After drying, spin dry under reduced pressure. in CH 2 Cl 2 / methanol (10:1, v / v) is eluent, and silica gel column chromatography obtains product: (R is H, n is 1) (126 mg, 51%). H NMR spectrum[ 1 H NMR (400 MHz, DMSO-d 6 )]: δ = 8.37 (s, 1 H, triazole-H), 8.07 (d, J = 16.4 Hz, 2 H, CH=CH), 7.58 (d, J = 8.8 Hz, 4 H, ArH), 7.44 (d, J = 16.8 Hz, 2 H, CH=CH), 7.37 (d, J = 8.0 Hz, 2 H, ArH), 7.27 (d, J = 8.8 Hz, 2 H, ArH), 7.07 (d, J = 8.4 Hz, 4 H, ArH), 5.22 (s, 2 H, OCH 2 ), 5.13 (d, J = 4.8 Hz, 1 H, OH), 4.98 (d, J = 4.4 Hz, 1 H, OH), 4.94 (d, J = 4.8 Hz, 1 H, OH), 4.63 (t, ...

Embodiment 3

[0044] compound (100 mg, 0.09 mmol), (R is Ac, n is 2) (110 mg, 0.24 mmol), CuSO 4 ·5H 2 O (15 mg, 0.06 mmol) and sodium ascorbate (24 mg, 0.12 mmol) were dissolved in 7 ml CHCl 3 , ethanol and water (volume ratio 12:1:1), vigorously stirred at room temperature for 24 hours. CH 2 Cl 2 and water extraction, the organic layer was washed with Na 2 SO 4 After drying, spin dry under reduced pressure. in CH 2 Cl 2 / methanol (20:1 v / v) is the eluent, purified by silica gel column chromatography to obtain the compound (R is Ac, n is 2) (74 mg, 53%). H NMR spectrum[ 1 H NMR (400 MHz, CDCl 3 )]: δ = 8.12 (d, J = 16.4 Hz, 2 H, CH=CH), 7.89 (s, 1 H, triazole-H), 7.60 (d, J = 8.4 Hz, 4 H, ArH), 7.57 (d, J = 16.8 Hz, 2 H, CH=CH), 7.20 (d, J = 8.8 Hz, 2 H, ArH), 7.16 (d, J = 8.8 Hz, 2 H, ArH), 6.97 (d, J = 8.4 Hz, 4 H, ArH), 5.26 (s, 2 H, OCH 2 ), 5.20 (t, J= 9.6 Hz, 1 H, H4), 5.08 (t, J = 9.2 Hz, 1 H, H3), 4.99 (dd, J 1 = 9.2 Hz, J 2 = 8.0 Hz, 1 H,...

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Abstract

The invention discloses glycosylated boron dipyrromethene fluorophore derivatives as well as a preparation method and application of the glycosylated boron dipyrromethene fluorophore derivatives. The method comprises the following steps: by taking glucose and glucosides thereof as action targets, connecting covalent bonds of the action targets to boron dipyrromethene fluorophore derivatives for photodynamics therapy, so that a third generation photosensitizer against cancer which can be used for targeted therapy is obtained. The dipyrromethene fluorophore derivatives containing glucose and glucosides are taken as study researches, activity study of in-vitro breast cancer-resistant cells MBA-MD-231 is expanded, a prodrug suitable for molecular targeted therapy is screened, and a foundation is laid for applying the glycosylated boron dipyrromethene fluorophore derivatives to targeted therapy of cancers. Moreover, the compound synthesis method is simple, readily available in raw materials, low in cost, few in side reactions, high in yield and simple in purification, and industrial production is promoted.

Description

technical field [0001] The invention belongs to the field of design and synthesis of anticancer drugs, and in particular relates to a kind of glycosylated fluorobodipyrrole antitumor photosensitive drug and its preparation method and application. Background technique [0002] Tumor is one of the diseases with the highest mortality rate in the world. Photodynamic therapy (PDT) is a new type of medical technology, which has shown unique advantages in the treatment of tumor and non-tumor diseases, and has attracted extensive attention from researchers. . The photosensitizer is a key factor affecting the effect of photodynamic therapy, which can be selectively enriched in tumor tissue, reduce damage to surrounding normal tissues, and produce ideal biological effects. Porphyrin, chlorophyll, hypocrellin, etc. are traditional photosensitizers. The composition of these photosensitizers is uncertain, the maximum absorption wavelength is near the short wavelength, and the tissue pen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07H1/00A61K41/00A61P35/00
Inventor 刘见永刘晓琼叶发荣卢源薛金萍
Owner FUZHOU UNIV
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