NL2032012B1 - Rhodamine - based near - infrared fluorescent probe as well as preparation method and application thereof - Google Patents
Rhodamine - based near - infrared fluorescent probe as well as preparation method and application thereof Download PDFInfo
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Abstract
Disclosed is a rhodamine-based near-infrared fluorescent probe as well as a preparation method and application thereof. The probe is formed by taking a near-infrared emission rhodamine derivative as a fluorophore and taking nitro as a quencher of the fluorophore and a receptor unit of nitroreductase through covalent bonding. Fluorescence quenching of the fluorophore is caused due to high electron withdrawing ability of the nitro in the probe structure. When the probe enters hypoxic cells, under the effect of the highly expressed nitroreductase in a hypoxic internal environment, the nitro in the probe structure is reduced into amino, and the fluorophore recovers fluorescence and emits near-infrared fluorescence of 740 nm, thereby realizing fluorescence detection of the nitroreductase and further realizing fluorescence imaging of tumours and colonitis. The probe shows high sensitivity and high specificity in application, and has wide application prospects in the fields of cell hypoxia analysis and tumour and colonitis imaging.
Description
RHODAMINE - BASED NEAR - INFRARED FLUORESCENT PROBE AS WELL AS
PREPARATION METHOD AND APPLICATION THEREOF
The present invention relates to the field of organic small molecule probes, and particularly relates to a rhodamine-based near-infrared fluorescent probe as well as a preparation method and application thereof.
The number of global cancer deaths accounts for almost one in six of the total death toll.
Cancer is becoming an important factor that threatens human health. How to discover the cancer early and sketch the boundary of tumour tissues in clinical medicine is always a tough problem.
Therefore, researching and developing a method for accurately recognizing and locating tumours has important significance.
Ulcerative colitis shows usual symptoms such as stomach - ache, diarrheal, inappetence, fever and weight loss, and is one of the most important factors of causing colon cancer. Only advanced colitis can be diagnosed in an existing detection technique, and early diagnosis does not work as expected, which inevitably hinders timely intervention treatment. As a chronic inflammatory bowel disease, the ulcerative colitis has been proved to be related to hypoxia intensity of a colonic microenvironment.
When an oxygen concentration in tissues is insufficient, i.e., “hypoxia”, overexpression of nitrate reductase (NTR) may be caused in solid tumours and at colonitis location. Therefore, the
NTR is regarded as an important biomarker of judging early diagnosis of the ulcerative colitis.
NTR enzyme activity may reflect severity of the condition.
Therefore, developing a method that can be used for NTR analysis imaging has important significance on recognition of tumours and early diagnosis of the colonitis.
The NTR is a reducing enzyme and can reduce aromatic nitro. In the current technical method for detecting the NTR, fluorescence imaging receives much attention because of the advantages of simplicity in operation, high sensitivity and quick response. However, up to now, due to low tissue penetrability and short emission wavelength, the reported probe is easily subjected to background fluorescence interference and thus is greatly limited in biological applications thereof. Therefore, developing a near-infrared nitroreductase probe to monitor nitroreductase at tumour and colonitis location in real time has important significance in clinical test.
With respect to the above problems, the present invention provides a rhodamine-based near- infrared fluorescent probe. The probe is formed by taking a near-infrared emission rhodamine derivative as a fluorophore and taking nitro as a quencher of the fluorophore and a receptor unit of nitroreductase through covalent bonding. Fluorescence quenching of the fluorophore is caused due to high electron withdrawing ability of the nitro in the probe structure. When the probe enters hypoxic cells, under the effect of the highly expressed nitroreductase in a hypoxic internal environment, the nitro in the probe structure is reduced into amino, and the fluorophore recovers fluorescence and emits near-infrared fluorescence of 740 nm, thereby realizing fluorescence detection of the nitroreductase and further realizing fluorescence imaging of tumours and colonitis. The probe shows high sensitivity and high specificity in application, and has wide application prospects in the fields of cell hypoxia analysis and tumour and colonitis imaging.
To achieve the above purpose, technical solutions are as follows :
A structural formula IW-1 of the rhodamine-based near-infrared fluorescent probe is as follows :
LATA)
N
LU _ + “~N #
A preparation method of the above fluorescent probe IW-1 is as follows : cooH © (J COOH
Ci O = GCC — | +e @ OH oN 0 1 2 3
NO,
N_ 35 i Br oJ on oO —t OID sp LC — . . 0 N oO acetic anhydride @ ~ DMF ,K,CO,,6h q ~ + + ne + 5 wa
(1) enabling a compound 1 {2-(4 - diethylamino -2-hydroxybenzoyl)benzoic acid) to react with a compound 2 (cyclohexanone) under concentrated sulfuric acid catalysis to produce a compound 3; (2) enabling the compound 3 to react with a compound 4 (Fischer aldehyde) in an acetic anhydride solution to produce a compound 5; (3) adding K:CO: into the compound 5 while stirring; then adding a compound 8 (p-nitrobenzyl bromide) into the mixture; and stirring the product to obtain the probe IW-1.
Preferably, in the step (1), a molar ratio of the concentrated sulfuric acid to the compound 1 to the compound 2 is (30 - 100) : 1: (2.0 - 5.0); reaction temperature is 60 - 100°C; and reaction time is 4 - 8 hours.
Preferably, in the step (2), a molar ratio of the acetic anhydride to the compound 3 to the compound 4 is (50 - 100) : 1: (1 - 2); reaction temperature is 40 - 60°C; and reaction time is 4 - 8 hours.
Preferably, in the step (3), a molar ratio of the K2CO: to the compound 5 to the compound 6 is (8-2):1: (1-2); reaction temperature is (-10)°C - 20°C; and reaction time is 4 - 8 hours.
The present invention further discloses an application of the above rhodamine-based near- infrared fluorescent probe or the rhodamine-based near-infrared fluorescent probe prepared by the above preparation method in preparation of a nitroreductase detection reagent.
The present invention further discloses an application of the above rhodamine-based near- infrared fluorescent probe or the rhodamine-based near-infrared fluorescent probe prepared by the above preparation method in preparation of a nitroreductase fluorescent imaging reagent in
Hela cells.
The present invention further discloses an application of the above rhodamine-based near- infrared fluorescent probe or the rhodamine-based near-infrared fluorescent probe prepared by the above preparation method in preparation of a diagnostic reagent of tumours and colonitis.
A recognition mechanism of the probe is as follows : 1 =700 nm , Ê
CL LI CL. c 2 = NTR of CL, mY CL fe # ON” ® ben =740 nm I
According to the fluorescent probe IW-1 prepared in the present invention, in absence of the nitroreductase, own background fluorescence of the probe is negligible due to a quenching effect of the nitro, while in a reaction with the nitroreductase, the nitro is specifically reduced into amino,
and the probe emits near-infrared fluorescence at 740 nm, thereby recognizing the nitroreductase. Cell experiments discover that, the probe may evaluate hypoxia intensity of the
Hela cells by detecting expression of the nitroreductase.
To clearly describe technical solutions in embodiments of the present invention or in the prior art, drawings that need to be used in descriptions of the embodiments or the prior art will be briefly introduced below. Apparently, drawings in descriptions below are merely the embodiments of the present invention. Other drawings may be obtained by those ordinary skilled in the art without making any creative labour according to the provided drawings.
Fig. 1 is a *H NMR spectrum of a probe IW-1.
Fig. 2 is a *C NMR spectrum of a probe IW-1.
Fig. 3 is an HR - MS spectrum of a probe IW-1.
Fig. 4 is an HR - MS spectrum of a response mechanism of a probe IW-1.
Fig. 5 shows an ultraviolet absorption spectrum and a fluorescence emission spectrum of a probe IW-1, wherein Fig. 5A is an ultraviolet absorption spectrum of the probe before (curve a) and after (curve b) addition of nitroreductase; and Fig. 5B is a fluorescence emission spectrum of the probe before (curve a) and after (curve b) addition of the nitroreductase.
Fig. 6 is a fluorescence emission spectrum of a probe IW-1 at different nitroreductase concentrations, wherein Fig. 6A shows gradually increasing fluorescence intensity of the probe at 740 nm; and Fig. 6B shows a good linear relationship between the fluorescence intensity of the probe at 740 nm and the concentrations of the nitroreductase.
Fig. 7 is a selective schematic diagram of a probe IW-1, wherein the vertical coordinate is fluorescence intensity of the probe IW-1 at 740 nm; and substances at the horizontal coordinate are in order from the left to right as follows : (1) NADH (500 pM) + NTR (10ug/ml), (2) blank, (3)
NADH (500 pM), (4) cysteine (50 uM), (5) glutathione (50 pM), (6) alanine (50 uM), (7) homoserine (50 uM), (8) glutamic acid (50 uM), (9) arginine (50 uM), (10) serine (50 uM), (11) histidine (50
HM), (12) H2O2 (10 uM), (13) NaNO: (50 pM), (14) NaNO: (50 pM), (15) NazS (50 uM), (16)
Na2SO: (50 uM), (17) NaCIO (10 uM), (18) Ag* (50 uM), (19) AI®* (50 uM), (20) Ca?* (50 uM), (21)
Fe? (50 uM), (22) K* (50 HM), (23) Mg?" (50 uM), (24) Na’ (50 uM), (25) Zn?* (50 uM), (26) CI: (50 HM), (27) COz2- (50 uM), (28) SO? (50 uM).
Fig. 8 is a fluorescence emission spectrum of a probe IW-1 in different pH environments (Fig. 8A) and at different temperatures (Fig. 8B).
Fig. 9 is a cytotoxicity map of a probe IW-1.
Fig. 10 shows fluorescence imaging (Fig. 10A) and fluorescence intensity statistics (Fig. 10B) of a probe IW-1 in HeLa cells in an environment of different oxygen content.
Fig. 11 shows an application of a probe IW-1 in mouse tumour imaging, wherein Fig. 11A shows fluorescent brightness of a mouse tumour location and a normal position in different time periods; and Fig. 11B shows a statistical chart of fluorescence intensity.
Fig. 12 shows an application of a probe IW-1 in imaging of mice with colonitis, wherein Fig. 5 12A shows fluorescence imaging of colon parts of mice with drug - induced colonitis and normal mouse colon parts; and Fig. 12B shows a statistical chart of fluorescence intensity.
Technical solutions in embodiments of the present invention will be clearly and fully described below. Apparently, the described embodiments are merely part of embodiments in the present invention, rather than all of embodiments. Based on the embodiments in the present invention, all other embodiments obtained by those ordinary skilled in the art without making creative labour shall belong to the protection scope of the present invention.
Embodiment 1: Specific synthesis method of near-infrared fluorescent probe
DQ ‚ ® cre "> 67 7) /) 0.98 g of cyclohexenone 2 (10 mmol) was dissolved into 20 ml of cold concentrated sulfuric acid and continuously stirred; then 3.13 g of (2-{4 - diethylamino -2-hydroxybenzoyl)benzoic acid) 1 (10 mmol) was added into the mixture; the (2-(4 - diethylamino -2-hydroxybenzoyl)benzoic acid) reacted with the mixture at 90°C for 4 hours; later, the mixture was poured into 300 g of ice block; then 5 ml of perchloric acid was dropped into the mixture and continuously stirred; after standing for 1 h, the solution was filtered; a precipitate was collected; and the product was subjected to freeze drying to obtain a compound 3 (dark red solid, 2.71 g, yield of 72.1%). sr OO i (> NO! COOH ~ COX)
N 4 —
O0 To 0 ; ; NS
LON acetic anhydride J
J + “~N ’
Ry
1.88 g of the compound 3 and 1.005 g of Fischer aldehyde 4 were dissolved into 30 ml of acetic anhydride; the compound 3 reacted with the Fischer aldehyde 4 at 50°C for 8 hours; the solution was extracted with dichloromethane after the reaction; the extract was dried and subjected to rotary evaporation; and the product was subjected to column chromatography purification to obtain a compound 5 (green solid, 1.470 g, 52.6%).
NO
(> Br DQ ET
COOH © ~~ o
CU ZA) o — L o 7) > 8h x ts _ + 5 ® 9 3.0 mmol of KsCO:3 and 1 mmol of compound 5 were added into 20 ml of DMF while stirring at 0°C; then 1.0 mmol of p-nitrobenzyl bromide 6 was added into the above mixture and stirred for 6 hours; and then the product was subjected to column chromatography purification to obtain a probe IW-1 (dark green solid, 0.163 g, 41.4%). 'H NMR (400 MHz, DMSO - ds) 5 8.41 (d, J = 13.7
Hz), 8.20 (d, J = 7.0 Hz), 8.03 (d, J = 8.7 Hz), 7.85 {t, J = 7.5 Hz), 7.74 (dd, J = 15.1, 7.4 Hz), 7.57 — 7.43 (m), 7.37 - 7.29 (m), 6.77 (dd, J = 9.2, 2.3 Hz), 6.55 (d, J = 9.1 Hz), 8.49 (d, J = 2.2 Hz), 6.24 (d, J = 13.5 Hz), 5.29 — 5.08 (m), 3.76, 3.52 (q, J = 8.9 Hz), 2.27 — 2.06 (m), 1.80, 1.72, 1.63 (d, J = 29.1 Hz), 1.24, 1.18 (d, J = 7.0 Hz). *C NMR (100 MHz, DMSO - ds) ò 174.82, 165.73, 161.64, 155.10, 151.65, 149.43, 147.53, 143.17, 142.79, 142.17, 141.53, 135.34, 133.96, 131.33, 130.30 — 129.66 (m), 129.18 (d, J = 24.8 Hz), 127.93, 125.96, 123.72, 122.97, 120.56, 114.70, 112.69, 112.26 (d, J = 22.5 Hz), 101.34, 95.82, 66.19, 60.22, 55.37, 49.70, 44.74, 32.18, 28.24, 27.90, 12.71. CaaHs4N3Os [M]* : m/z : 694.3276; found : 694.3287.
Embodiment 2: Responsiveness of probe IW-1 on nitroreductase
After nitroreductase (10pg/ml) and NADH (500 pM) were added into a PBS solution of a probe IW-1 having a concentration of 10 uM, absorption strength of the probe was increased.
Before the nitroreductase was added, the probe IW-1 hardly emitted fluorescence, while after the nitroreductase (10ug/ml) and NADH (500 uM) were added, the probe emitted strong fluorescence at 740 nm. Experimental results showed that, the probe may have high - sensitivity response on the nitroreductase, as shown in Fig. 5.
In the PBS solution of the probe IW-1 having the concentration of 10 uM, with the increase of the concentration of the added nitroreductase (0 - 10 pg/ml), fluorescence intensity of the probe at 740 nm was gradually increased, as shown in Fig. 6A. A good linear relationship was formed between the fluorescence intensity of the probe at 740 nm and the concentration of the nitroreductase, as shown in Fig. 6B.
Embodiment 3: Selectivity of probe IW-1
Common metal ions, reactive oxygen, amino acids and other substances were added into a
PBS solution of a probe IW-1 having a concentration of 10 uM to investigate selectivity of the probe on nitroreductase. As shown in Fig. 7, after the above substances were added, fluorescence of the probe at 740 nm was hardly enhanced, which indicated that the probe had high selectivity on the nitroreductase. In Fig. 7, the vertical coordinate was fluorescence intensity of the probe IW-1 at 740 nm; and substances at the horizontal coordinate were in order as follows : (1) NADH (500 pM) + NTR (10 pg/ml), (2) blank, (3) NADH (500 uM), (4) cysteine (50 uM), (5) glutathione (50 pM), (8) alanine (50 uM), (7) homoserine (50 pM), (8) glutamic acid (50 uM), (9) arginine (50 HM), (10) serine (50 pM), (11) histidine (50 pM), (12) H20: (10 uM), (13) NaNO; (50
MM), (14) NaNO: (50 HM), (15) NazS (50 uM), (16) Na2SO:3 (50 uM), (17) NaCIO (10 pM), (18) Ag* (50 uM), (19) AI*% (50 uM), (20) Ca?* (50 uM), (21) Fe?" (50 uM), (22) K* (50 uM), (23) Mg?* (50
HM), (24) Na* (50 pM), (25) Zn?* (50 uM), (26) CI: (50 uM), (27) CO32° (50 uM), (28) SO? (50
MM).
The PBS solution of different pH gradients was respectively prepared into a probe IW-1 solution having a concentration of 10 uM for testing spectral changes. As shown in Fig. 8A, curve a was a fluorescence spectrum of the probe when the nitroreductase was added; and curve b was a fluorescence spectrum of the probe when the nitroreductase was not added. The PBS solution of the probe IW-1 having the concentration of 10 uM was respectively placed in a shaker at different temperatures for testing interference results of the temperatures on the probe IW-1.
Fig. 8B respectively showed the fluorescence emission spectrum of the probe before (b) and after (a) addition of the nitroreductase. Test results showed that, the probe IW-1 had good responsiveness on the nitroreductase under physiological conditions (pH of 7.4, 37°C), and was applicable to analysis and detection of the nitroreductase in biological samples.
Embodiment 4: Hela cell imaging experiment of probe IW-1
By investigating cytotoxicity of the probe in a concentration range of 0 - 30 uM, it is discovered that the probe IW-1 has low cytotoxicity on the Hela cells, as shown in Fig. 9.
When the Hela cells were incubated with the probe IW-1 having a concentration of 1 uM, the probe had different fluorescence intensity in an environment of different oxygen content. The lower the oxygen content in the environment is, the higher the fluorescence intensity of the probe in the cells is. Fig. 10A shows confocal imaging of the probe in the Hela cells under different oxygen content conditions; and Fig. 10B shows statistic of the fluorescence intensity of the HeLa cells. Experimental results show that, the probe may be used for imaging analysis of cell hypoxia intensity.
Embodiment 5: Application of probe IW-1 in mouse tumour imaging 50 ul of a probe IW-1 having a concentration of 10 uM was injected into a HeLa tumour of a mouse with tumour; and the tumour was photographed by a small animal living imager. It was discovered that, the tumour area was obviously brightened within 5 minutes; with time extension after injection, the brightness in the tumour area was enhanced; maximum brightness was achieved within 30 minutes, while fluorescence intensity at a normal body part of the mouse was far lower than that of the tumour part, which indicated that the probe IW-1 may be applied to imaging analysis of the mouse tumour, as shown in Fig. 11. Fig. 11A shows fluorescent brightness of the mouse tumour location and a normal position in different time periods; and Fig. 11B shows a statistical chart of the fluorescence intensity.
Embodiment 6: Application of probe IW-1 in imaging of mouse with colonitis 50 pl of a probe IW-1 having a concentration of 100 uM was injected into abdomen of a mouse with colonitis; and the abdomen was photographed by a small animal living imager. It was discovered that, the colon area was obviously brightened within 5 minutes; with time extension after injection, the brightness in the colon area was enhanced; maximum brightness was achieved within 45 minutes, while fluorescence intensity at a colon part of the mouse in a control group was extremely low, which indicated that the probe IW-1 may be applied to imaging analysis of the mouse with colonitis, as shown in Fig. 12. Fig. 12A shows fluorescent brightness of colon parts of mice and normal mouse colon parts in different time periods; and Fig. 12B shows a statistical chart of fluorescence intensity.
Each embodiment in the description is described in a progressive way. The difference of each embodiment from each other is the focus of explanation. The same and similar parts among all of the embodiments can be referred to each other. For a device disclosed by the embodiments, because the device corresponds to a method disclosed by the embodiments, the device is simply described. Refer to the description of the method part for the related part.
The above description of the disclosed embodiments enables those skilled in the art to realize or use the present invention. Many modifications to these embodiments will be apparent to those skilled in the art. The general principle defined herein can be realized in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention will not be limited to these embodiments shown herein, but will conform to the widest scope consistent with the principle and novel features disclosed herein.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749153A (en) * | 2016-12-19 | 2017-05-31 | 华东理工大学 | The specificity fluorescent probe of nitroreductase and its preparation and the application for cancer target fluorescence imaging and monitoring tumor hypoxia degree |
| CN109627236A (en) * | 2018-12-13 | 2019-04-16 | 华南师范大学 | Optoacoustic probe and the preparation method and application thereof for In vivo detection nitroreductase |
| CN110483682A (en) * | 2019-08-28 | 2019-11-22 | 济南大学 | Detect the high molecular fluorescent probe and the preparation method and application thereof of viscosity |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749153A (en) * | 2016-12-19 | 2017-05-31 | 华东理工大学 | The specificity fluorescent probe of nitroreductase and its preparation and the application for cancer target fluorescence imaging and monitoring tumor hypoxia degree |
| CN109627236A (en) * | 2018-12-13 | 2019-04-16 | 华南师范大学 | Optoacoustic probe and the preparation method and application thereof for In vivo detection nitroreductase |
| CN110483682A (en) * | 2019-08-28 | 2019-11-22 | 济南大学 | Detect the high molecular fluorescent probe and the preparation method and application thereof of viscosity |
Non-Patent Citations (1)
| Title |
|---|
| FAN XIAOPENG ET AL: "Activatable photoacoustic/fluorescent dual-modal probe for monitoring of drug-induced liver hypoxia in vivo", CHEMICAL COMMUNICATIONS, vol. 57, no. 69, 26 August 2021 (2021-08-26), UK, pages 8644 - 8647, XP093013030, ISSN: 1359-7345, DOI: 10.1039/D1CC02999A * |
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