CN109836429B - Calix [ n ] carbazole derivative and application thereof as T cross DNA fluorescent molecular probe - Google Patents
Calix [ n ] carbazole derivative and application thereof as T cross DNA fluorescent molecular probe Download PDFInfo
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Abstract
The invention belongs to the technical field of medicine, and relates to a preparation cup [ n]Carbazole derivatives and application thereof as T cross DNA fluorescent molecular probes. The cup [ n ] of the invention]The carbazole derivative has the chemical structural general formula shown in the specification. The calixazole derivative (1) can interact with nucleic acids with different structures under physiological conditions, specifically recognize T cross DNA and stabilize the T cross DNA. (2) The fluorescence selectivity exhibited by the mutual combination of the two has application value in early diagnosis and prevention of T cross DNA related diseases.
Description
Technical Field
The invention belongs to the technical field of medicines, and relates to a calix [ n ] carbazole derivative and application thereof as a T cross DNA fluorescent molecular probe.
Background
Limited by structural factors such as size and the like, the matching degree of the calixarene of the traditional phenol skeleton and ions and biological macromolecules with larger volume is not high. In view of the important significance of macrocyclic host molecules in supramolecular chemistry, the creation of novel macrocyclic compounds has gained increasing attention. The novel macrocyclic host molecule is constructed and applied to the fields of ion detection, environmental detection, drug delivery, early diagnosis and treatment of diseases and the like, and has important significance.
During replication and transcription, DNA may melt locally, resulting in a variant. This variation results in the formation of an unusual DNA structure called a supercoil (e.g.branched DNA linkers, triplex and quadruplex DNA, etc.). The structure of this supercoiled form hinders the normal transport of DNA. In recent years, quadruplex DNA has attracted sufficient attention from chemists and biologists, but studies on branched DNA linkers (T cross DNA, Three Way Junction, TWJ) have not been deep enough. In DNA, TWJ is produced during the recombination and replication of phage followed by a strand. Further, the structure of TWJ can be observed in the adenovirus inverted terminal repeats. It is involved in the replication of viral DNA and in binding the viral DNA to the host genome. Based on this binding characteristic, viruses can be developed as gene therapy vectors. The structure of T cross DNA is stabilized by an external drug, which may prevent the normal enzyme reaction process of DNA, thereby causing instability of genome and achieving the purpose of inhibiting DNA replication.
The significant difference of the calicarbazoles derivatives before and after the calicarbazoles derivatives are combined with T cross DNA improves the detection sensitivity, and the fluorescent probe dye has fast labeling speed, physiological pH condition and small influence on the function activity of biological molecules.
Disclosure of Invention
The invention aims to improve the structure of calix [ n ] carbazole derivatives, optimize the preparation method thereof and improve the response sensitivity thereof. The invention does not change the parent structure of the calixazole, introduces different substituents on N atoms at 2,7 and 9 positions of the carbazole, prepares a series of derivative structures, increases the binding capacity of the probe and T cross DNA, and has the limit concentration of the detected nucleic acid of 275 nM. The dicarbazole derivative can be used as a high-sensitivity probe for quantitatively detecting T cross DNA.
The calix [ n ] carbazole derivative has a chemical structural general formula as follows:
R2＝-H,C1～C4alkyl or alkoxy of, halogen
Further, the calix [ n ] carbazole derivative according to the present invention is selected from:
the invention also provides a preparation method of the calix [ n ] carbazole derivative, which comprises the following steps:
(1) in a solvent such as Tetrahydrofuran (THF), N, N-Dimethylformamide (DMF) or N, N-dimethyl sulfoxide (DMSO), etc1Adding 5-30 times (mol ratio) of N, N-dimethylethylenediamine to an ester group-containing compound, and heating at 25-90 ℃ for 5-24 hours to prepare R1Compounds containing alkylamino side chains;
(2) adding solvents such as tetrahydrofuran, N, N-dimethylformamide and N, N-dimethyl sulfoxide to dissolve the compound, adding 3-10 times of methyl iodide, and heating at 25-60 ℃ for 3-10 hours to prepare R1Compounds containing quaternary ammonium salt side chains.
The calix [ n ] carbazole derivative can be used for detecting nucleic acid, and comprises the following steps:
(1) ultraviolet detection
Gradually adding DNA solution into buffer solution dissolved in compound to obtain ultraviolet absorption value of 260nm-450 nm.
(2) Fluorescence detection
Setting the spectrum range to 310nm-600nm and the excitation wavelength to300nm, and gradually adding the DNA solution into the buffer solution dissolved in the compound to obtain a spectrum of fluorescence absorption of the DNA solution. Plotting the concentration of DNA as abscissa and fluorescence intensity F as ordinate, selecting 389nm to fit with 1:1 model in fluorescence enhancement range with binding energy of 1 × 102～1×105M-1In the meantime.
The invention has the advantages that: t cross DNA has important research value as a new drug target, but the reports of the ligand of the T cross DNA are rare at present, and particularly the report of the ligand with selective fluorescent response to the T cross DNA is not reported. The development of selective fluorescent ligands for T-cross DNA is of academic and commercial value. The calixazole derivative can interact with nucleic acids with different structures under physiological conditions, specifically recognize T cross DNA and stabilize the T cross DNA. (2) The fluorescence selectivity exhibited by the mutual combination of the two has application value in early diagnosis and prevention of T cross DNA related diseases.
Drawings
FIG. 1 shows a 2, 7-dimethoxycup [3 ]]Ultraviolet full spectrum of carbazole quaternary ammonium salt (compound 3): the concentration of the compound was 10. mu.M, [ C ]DNA/CCompound (I)]0.2 equivalent of T-cross DNA (TWJ) is added from 0, the color is slightly reduced by ultraviolet, and obvious color increase appears when the T-cross DNA is continuously added.
FIG. 2 is a graph of empirical formula for the 329nm hyperchromic region in FIG. 1: linear intervals of both ends intersect at [ C ]DNA/CCompound (I)]1.
FIG. 3 is a 2, 7-dimethoxy-cup [3 ]]Fluorescence full spectrum of carbazole quaternary ammonium salt (compound 3): the compound concentration was 3. mu.M, T-cross DNA, [ C ] was gradually addedDNA/CCompound (I)]0.1 and 0.3 equivalents of fluorescence were quenched starting at 0, after 0.3 equivalents, the fluorescence gradually increased at 389nm, saturating in intensity when T-cross DNA was added to 6.0 equivalents.
FIG. 4 is a curve fitted to the fluorescence enhancement range at 389nm in FIG. 3: using a 1:1 model fit, a binding energy of 4.33X 10 was obtained4M-1。
FIG. 5 is a 2, 7-dimethoxycup [3 ]]Fluorescence full spectrum of carbazole quaternary ammonium salt (compound 3): the concentration of the compound was 4. mu.M, and gradually addedInto double helix DNA (ds-DNA) [ CDNA/CCompound (I)]0.1-8.0 equivalents of fluorescence are quenched.
FIG. 6 is a 2, 7-dimethoxycup [3 ]]Fluorescence full spectrum of carbazole quaternary ammonium salt (compound 3): the concentration of the compound was 4. mu.M, and G-quadruplex DNA (G4-DNA) [ C ] was gradually addedDNA/CCompound (I)]0.1-8.0 equivalents of fluorescence are quenched.
FIG. 7 is a 2, 7-dimethoxycup [3 ]]Ultraviolet full spectrum of carbazole quaternary ammonium salt (compound 3): the concentration of the compound was 10. mu.M, [ C ]DNA/CCompound (I)]The double helix DNA (ds-DNA) was added from 0, the UV intensity increased before 0.4 equivalents and gradually decreased from 0.4 to 6.0 equivalents.
FIG. 8 shows a 2, 7-dimethoxycup [3 ]]Ultraviolet full spectrum of carbazole quaternary ammonium salt (compound 3): the concentration of the compound was 10. mu.M, [ C ]DNA/CCompound (I)]G-quadruplex DNA (G4-DNA) was added from 0, and no significant change in UV was observed.
Fig. 9 is a high resolution mass spectrum of compound 3.
FIG. 10 is a high resolution mass spectrum of Compound 6.
Detailed Description
Example 1
Synthesis of Compound 3
20mg (0.018mmol) of dried compound 1, 0.5mL of N, N-dimethylethylenediamine and 0.2mL of THF are weighed out and dissolved by ultrasonic oscillation, and stirred at 60 ℃ for 24h, during which white precipitate gradually precipitates out. After cooling to room temperature, the mixture was poured into ether, and the precipitate was collected by centrifugation to give a solid, which was washed with methanol 3 times and dried to give compound 2, 11.7mg, with a yield of 70.5%.
After drying, 10mg (0.011mmol) of Compound 2 was weighed out, dissolved in 0.3mL of DMF, and then 0.1mL of methyl iodide was added thereto, and the mixture was stirred at 50 ℃ for 12 hours under a closed condition. Precipitating to give yellowish precipitate, cooling to room temperature, adding into diethyl ether, centrifuging, collecting precipitate, washing the obtained solid with methanol for 3 times, and drying to obtain compound 3,10.0mg, with yield of 72.1%.
1H-NMR(600MHz,DMSO-d6):δ8.31(t,J＝5.8Hz,3H),7.53(s,6H),7.02(s,6H),5.02(s,6H),4.06(s,6H),3.86(s,18H),3.53(q,J＝6.0Hz,6H),3.36(q,J＝6.0Hz,6H),3.05(s,27H).13C-NMR(151MHz,DMSO-d6):δ168.97,155.91,140.62,121.96,120.45,115.84,,92.57,63.77,56.32,52.94,46.22,34.78,33.71.HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for 382.2125,found382.2143
Example 2
Synthesis of target Compound 4
1H-NMR(600MHz,DMSO-d6):δ8.37(s,6H),8.18(t,J＝5.6Hz,3H),7.41(d,J＝8.2Hz,6H),7.31(d,J＝8.2Hz,6H),4.92(s,6H),4.21(s,6H),3.40(t,J＝6.0Hz,6H),3.26(t,J＝6.0Hz,6H),2.96(s,27H,).13C-NMR(151MHz,DMSO-d6):δ168.71,139.77,134.23,126.71,123.26,120.11,109.19,63.76,52.85,46.07,41.99,33.56.HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for322.1914,found 322.1947.
Example 3
1H-NMR(600MHz,DMSO-d6):δ8.35(s,6H),8.17(t,3H),7.40(d,6H),7.31(d,6H),4.89(s,6H),4.21(s,6H),3.37(m,6H),3.25(q,6H),2.87(s,27H),1.83(m,6H).HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for 336.2070,found 336.2097.
Example 4
1H-NMR(600MHz,DMSO-d6):δ8.32(s,6H),8.18(t,3H),7.40(d,6H),7.32(d,6H),4.88(s,6H),4.20(s,6H),3.34(m,6H),3.27(q,6H),2.83(s,27H),1.75(m,6H),1.58(m,6H).HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for 350.2227,found 350.2253.
Example 5
1H-NMR(600MHz,DMSO-d6)δ8.27(t,3H),7.56(s,6H),7.07(s,6H),4.99(s,6H),4.07(s,6H),3.88(s,18H),3.23(m,6H),3.17(q,6H),2.96(s,27H),1.83(m,6H).13C NMR(150MHz,DMSO-d6)δ168.3,155.9,140.6,121.9,120.4,115.8,92.7,63.8,56.4,52.6,46.3,36.1,27.4,23.2.HRMS(ESI/TOF-Q)Calcd.For[M-3I]3+:396.2282；found:396.2282.
Example 6
1H-NMR(600MHz,DMSO-d6)δ8.30(t,3H),7.55(s,6H),7.09(s,6H),5.02(s,6H),4.06(s,6H),3.87(s,18H),3.22(q,6H),3.05(t,6H),2.97(s,27H),1.65-1.52(m,12H).13C NMR(150MHz,DMSO-d6)δ168.8,155.9,140.6,121.8,120.4,115.8,92.5,63.9,56.2,46.3,35.8,33.8,32.6,27.3,23.8.HRMS(ESI/TOF-Q)Calcd.For[M-3I]3+:410.2438；found:410.2476
Example 7
1H-NMR(600MHz,DMSO-d6)δ8.19(s,4H),7.07(s,8H),7.00(s,8H),5.10(s,8H),3.89(s,8H),3.81(s,24H),3.52(s,8H),3.38(s,8H),3.06(s,36H).13C NMR(150MHz,DMSO-d6)δ169.0,156.0,140.5,121.0,119.7,115.7,92.3,63.8,56.1,52.9,46.3,33.8,30.2.HRMS(ESI/TOF-Q)Calcd.For[M-4I]4+:382.2125；found:382.2137.
Example 8
1H-NMR(600MHz,DMSO-d6)δ8.21(t,4H),7.14(s,8H),7.03(s,8H),5.12(s,8H),3.90(s,8H),3.83(s,24H),3.28(s,8H),3.19(s,8H),3.00(s,36H),1.85(s,8H).13C NMR(150MHz,DMSO-d6)δ168.3,156.0,140.6,120.8,119.8,115.7,92.4,63.8,56.2,52.6,46.4,36.1,30.5,23.2.HRMS(ESI/TOF-Q)Calcd.For[M-4I]4+:396.2282；found:396.2304.
Example 9
1H-NMR(600MHz,DMSO-d6)δ8.21(t,J＝6.0Hz,4H),7.13(s,8H),7.03(s,8H),5.11(s,8H),3.90(s,8H),3.83(s,24H),3.23(m,8H),3.16(q,J＝6.0Hz,J＝6.0Hz,8H),2.93(s,36H),1.64(m,8H),1.45(m,8H).13C NMR(150MHz,DMSO-d6)δ168.1,156.0,140.6,120.7,119.7,115.6,92.3,65.2,56.2,52.5,38.2,34.8,26.4,19.9.HRMS(ESI/TOF-Q)Calcd.For[M-3I]3+:589.6279；found:589.6298.For[M-4H]4+:410.4947；found:410.4989
Example 10
1H-NMR(600MHz,DMSO-d6),δ(ppm):8.43(s,1H),8.02(s,6H),7.38(s,6H),5.12(s,6H),4.32(s,6H),3.21(q,6H),3.06(s,27H),2.73(s,6H).HRMS(ESI/TOF-Q)Calcd.For[M-3I]3+480.0104,found 480.0149
Example 11
1H-NMR(600MHz,DMSO-d6),δ(ppm):8.41(s,1H),8.00(s,6H),7.36(s,6H),5.10(s,6H),4.36(s,6H),3.27(q,6H),3.13(t,6H),3.22(s,27H),1.94(s,6H).HRMS(ESI/TOF-Q)Calcd.For[M-3I]3+494.0260,found 494.0293
Example 12
1H-NMR(600MHz,DMSO-d6),δ(ppm):8.40(s,1H),8.01(s,6H),7.36(s,6H),5.14(s,6H),4.36(s,6H),3.21(m,6H),3.12(q,6H),3.16(s,27H),1.70(m,6H),1.54(m,6H).HRMS(ESI/TOF-Q)Calcd.For[M-3I]3+508.0417found 508.0433
Example 13
1H-NMR(600MHz,DMSO-d6):δ8.30(s,6H),7.32(d,6H),7.27(d,6H),4.62(s,6H),4.20(s,6H),3.63(s,6H),3.22(t,6H),3.16(t,6H),2.85(s,27H).HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for 308.2121,found 308.2156.
Example 14
1H-NMR(600MHz,DMSO-d6):δ8.30(s,6H),7.32(d,6H),7.27(d,6H),4.62(s,6H),4.18(s,6H),3.63(s,6H),3.19(m,6H),3.12(q,6H),2.83(s,27H),1.75(m,6H).HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for 322.2278,found 322.2305.
Example 15
1H-NMR(600MHz,DMSO-d6):δ8.29(s,6H),7.30(d,6H),7.28(d,6H),4.60(t,6H),4.18(s,6H),3.62(t,6H),3.15(m,6H),3.11(q,6H),2.79(s,27H),1.62(m,6H),1.53(m,6H).HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for 336.2434,found 336.2477.
Example 16
1H-NMR(600MHz,DMSO-d6)δ8.27(m,3H),7.50(s,6H),7.01(s,6H),4.65(t,6H),4.02(s,6H),3.84(s,18H),3.66(t,6H),3.43(q,6H),3.30(t,6H),2.98(s,27H).HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for 368.2333,found 368.2362.
Example 17
1H-NMR(600MHz,DMSO-d6)7.48(s,6H),7.00(s,6H),4.65(t,6H),4.02(s,6H),3.84(s,18H),3.64(t,6H),3.10(m,6H),3.04(q,6H),2.86(s,27H),1.78(m,6H).HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for 382.2489,found 382.2517.
Example 18
1H-NMR(600MHz,DMSO-d6)δ7.46(s,6H),7.00(s,6H),4.64(t,6H),4.02(s,6H),3.85(s,18H),3.62(t,6H),3.02(q,6H),2.87(t,6H),2.83(s,27H),1.61-1.48(m,12H).HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for 396.2646,found 396.2671
Example 19
1H-NMR(600MHz,DMSO-d6)δ7.02(s,8H),6.97(s,8H),4.72(t,8H),3.86(s,8H),3.78(s,24H),3.68(t,8H),3.43(q,8H),3.30(t,8H),2.98(s,36H).HRMS(ESI/TOF-Q):m/z[M-4I]4+calcd.for 368.2333,found 368.2347.
Example 20
1H-NMR(600MHz,DMSO-d6)δ7.11(s,8H),7.00(s,8H),4.71(t,8H),3.86(s,8H),3.77(s,24H),3.68(t,8H),3.16(t,8H),3.08(m,8H),2.87(s,36H),1.71(m,8H).HRMS(ESI/TOF-Q):m/z[M-4I]4+calcd.for 382.2489,found 382.2513
Example 21
1H-NMR(600MHz,DMSO-d6)δ.10(s,8H),7.00(s,8H),4.72(t,8H),3.86(s,8H),3.77(s,24H),3.67(t,8H),3.12(t,8H),3.04(m,8H),2.81(s,36H),1.58(m,8H),1.37(m,8H).HRMS(ESI/TOF-Q):m/z[M-4I]4+calcd.for 396.2646,found 396.2669
Example 22
1H-NMR(600MHz,DMSO-d6)δ7.98(s,6H),7.38(s,6H),4.71(t,6H),4.30(s,6H),3.67(t,6H),3.10(q,6H),2.93(s,27H),2.70(t,6H).HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for466.0311,found 466.0348
Example 23
1H-NMR(600MHz,DMSO-d6)δ7.98(s,6H),7.38(s,6H),4.70(t,6H),4.32(s,6H),3.65(t,6H),3.12(q,6H),3.06(t,6H),2.97(s,27H),1.91(t,6H).HRMS(ESI/TOF-Q):m/z[M-3I]3+calcd.for 480.0468,found 480.0482
Example 24
1H-NMR(600MHz,DMSO-d6)δ7.98(s,6H),7.32(s,6H),4.71(t,6H),4.30(s,6H),3.67(t,6H),3.12(m,6H),3.07(q,6H),2.84(s,27H),1.57(m,6H),1.39(m,6H).HRMS(ESI/TOF-Q)Calcd.For[M-3I]3+494.0624,found 494.0650
Example 25
Fluorescence detection
The spectrum was set at 310-600nm and the excitation wavelength was set at 300nm, 2000. mu.l of buffer solution (pH 7.25-7.35) was added to the cuvette, the compound was added to a final concentration of 3. mu.M, and T-cross DNA solution (FIG. 3) was gradually added to the buffer solution dissolved in the compound to obtain a spectrum of the fluorescence absorption.
The fluorescence of compounds 4,5,6,15,16,17 was determined to be quenched by DNA; the addition of DNA has little effect on the fluorescence of compounds 1,12,13,14,24,25, 26; the addition of DNA enhanced the fluorescence intensity of compounds 2,3,7,8,9,10,11,18,19,20,21,22,23, with the fluorescence enhancement of compound 3 being most pronounced.
With CDNAPlotting with fluorescence intensity F as ordinate and selecting 389nm as fluorescence enhancement range, fitting with 1:1 model with binding energy of 4.33 × 104M-1(FIG. 4). The detection limit for T-cross DNA was 275 nM.
Example 26
Fluorescence detection
Under the same detection conditions, the compound 3 is used for simply quenching the fluorescence of the double-helix DNA and the G-quadruplex DNA (see attached figures 4 and 5), and the phenomenon of fluorescence enhancement does not occur.
Claims (5)
1. Calix [ n ] carbazole derivatives of the general formula:
2. calix [ n ] carbazole derivatives as described below, selected from:
3. use of calix [ n ] carbazole derivatives as claimed in claim 1 or 2 as T-junction DNA fluorescent molecular probes.
4. Use of calix [ n ] carbazole derivatives according to claim 1 or 2 for the detection of nucleic acids.
5. The use of claim 3, wherein the fluorescent molecular probe has a minimum detectable concentration of 0.275 μ M.
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