CN101875683B - Small molecule peptide-based cholesteric organic gel molecules and preparation method thereof - Google Patents
Small molecule peptide-based cholesteric organic gel molecules and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of super-molecular chemistry and particularly relates to small molecule peptide-based cholesteric organic gel molecules and a preparation method thereof. The cholesteric organic gel molecules can form gel in an organic solvent and the formed gel has thermal stability and water stability and can respond to ultrasound for realizing transformation of ultrasonically-induced gel into gel. The organic gel molecule comprises 1) an anhydride naphthalene part serving as a luminophor, 2) a middle small peptide serving as a functional group for forming intermolecular hydrogen bonds and 3) a sterides part which has biocompatibility and serves as a gelation factor and a hydrophobic group. The molecule can form high-quality gel which has rich micro-nanoscale macro morphologies, such as nuclear shells, solid balls, defect balls, nanofiber, micro-fiber and the like, and has regular shape and high repeatability in nearly ten organic solvents including acetonitrile, ethanol, benzene, toluene, acetone and the like through a sol-gel process. The organic fluorescent gel has a certain application value in the aspects of nano material preparation, medicinal carrier transportation, biological marking and the like.
Description
Technical field
The invention belongs to the supramolecular chemistry technical field; Be specifically related to a kind of cholesteric organic gel molecule based on small-molecular peptides and preparation method thereof; This cholesteric organic gel molecule can form gel in organic solvent; And the gel that forms has thermostability and water stability, and can respond to ultrasonic.
Background technology
Organogel (Organogel) be through the supramolecule reactive force between the gel factor for example hydrogen bond, static, hydrophobic interaction etc. formed unique network-like structure, thereby can limit flowing of solvent.This organogel can be made response to environmental stimulus factors such as acid, alkali, light, sound, so organogel passes at material with memory, biomarker and medicine and carries and aspect such as release has wide application prospect.In addition, organogel generally all has more regular micro nano structure, can design nano-scale device and novel material provides molecular model and theoretical foundation for us.Therefore, the Low Molecular-Weight Gel with environmental stimulus responsiveness of design synthesizing new causes the extensive concern of researcher.
Present gel all is that the method through sol-gel prepares, and the gel that this method makes is sol-gel transition temperature lower (boiling point of＜solvent) often, does not have higher thermostability, and this shortcoming can limit the further application of these gels.The present invention has developed a kind of method that makes new type gel without solution state, and it is ultrasonic that this method is carried out through the organogel that traditional sol-gel method is made, and obtained a kind of novel more excellent gel of performance.This method is compared with sol-gel method, and the time is short, and mild condition does not need heating, can make under the normal temperature, and the gained gel has the characteristics of high thermal stability and water stability.
Summary of the invention
The object of the present invention is to provide a kind of novel have high thermal stability and water stability organogel and preparation method thereof.
The present invention provides the organogel compound of two types of cholesterics.The constitutional features of this compounds is to be parent with the courage steroid, and the naphthalene acid anhydride is a chromophoric group, and little peptide promotes gel formation as the fractal one-tenth intermolecular ydrogen bonding of middle interconnecting piece.Its structural formula is:
General molecular formula is: [6-O (CH
2)
4N-C
12NO
2-R-(NHCO)-(CH
2)
n-NHCOO-(C
27H
43)];
In the formula: R=-CHCH
3-CONH-(CH
2)
m-or-(CH
2)
m-(NHCO)-CHCH
3-, n wherein, m is 1 to 6 natural number.
Among the present invention; The preparation method of above-claimed cpd is following: will contain naphthalene acid anhydride and the amino acid of morpholine functional group or amino acid or the amino derivative that diamine compound reflux in water or ethanol obtains the naphthalene acid anhydride earlier; Further react the acquisition target compound with the courage steroid that is connected little peptide and amido again, compound method is simple.Acid amides in the molecule be easy to aggregate in molecule form hydrogen bond; Wherein the naphthalene acid anhydride is good luminophor, can realize the photoinduction response under solution or the gel state; The carbochain that connects acid amides or the middle different lengths of naphthalene acid anhydride and courage steroid has not only been controlled the sensitivity that gel stimulates to external world but also has been strengthened the interaction of this compound in organic solvent.In addition, this compounds can form difform nanometer micrometer structure in organic solvent.
Specifically describe technique effect of the present invention from several aspects below.
1. the gellifying property of gelatinous cpd (the gel factor).
This compounds can form good gel in nearly 10 kinds of organic solvents.The gelatinous cpd that relates among the present invention can have two kinds of methods that form gel: 1) the gelatinous cpd solution of finite concentration (this sentences 25 mg/ml is example) forms gel under the room temperature under the UW effect.2) gelatinous cpd of finite concentration (25 mg/ml) is heated to dissolved state (120 ℃) in organic solvent, forms gel after being cooled to room temperature.According to experiment test, this compounds is in the listed most of solvent of table 1, all can become glue under the situation of 15～30 mg/ml in concentration.These two kinds of gels all are the thermodynamics reversible, become flowable colloidal sol after the heating.After the colloidal sol that is wherein obtained by method 1 cools off still is colloidal sol, the ultrasonic gel that becomes; And cool off the directly reversible gel that becomes of back by the colloidal sol that method 2 obtains.Concrete gellifying property is seen table 1.
Table 1: the performance of gel
[a]
| Solvent | Compd A | Compd B |
| Ethanol acetone ETHYLE ACETATE YLENE octanol acetonitrile butanols amylalcohol Virahol methyl alcohol-benzene methylene dichloride hexanaphthene THF chloroform | Clear gel clear gel clear gel clear gel solution precipitation clear gel clear gel clear gel clear gel clear gel solution precipitation solution solution | The opaque gel clear gel of clear gel clear gel clear gel clear gel solution clear gel clear gel clear gel clear gel solution precipitation solution solution |
A: compd A: R=-CHCH
3-CONH-(CH
2)
m-, m=6, n=2; Compd B :-(CH
2)
m-(NHCO)-CHCH
3-, m=6, n=2; A or B are heated to dissolving in solvent, half a hour is waited in cooling then, promptly forms gel (25mg/mL).
2. compound (R=-CHCH
3-CONH-(CH
2)
m-, m=6 is n=2) in the fluorescence behavior of solution state and gel state.
Compound is at acetonitrile (10
-4M) maximum emission peak is at 551nm in, and the maximum emission peak of the deposition that in acetonitrile, forms (25mg/mL) is at 541nm, and the gel maximum emission peak that its ultrasonic back forms with respect to solution state, has shown bigger blue shift at 531nm.
3. compd A (R=-CHCH
3-CONH-(CH
2)
m-, m=6, n=2) and B (R=-(CH
2)
m-(NHCO)-CHCH
3-, m=6, n=2) sem photograph of gel.
The deposition of A compound in acetonitrile is a kind of irregular vesica, under less than the condition of 70 degree, can form opaque gel after ultrasonic, and the gel structure after ultrasonic is a kind of 3D fiber of height spiral of densification under SEM, has very high thermostability.The A compound can form stable clear gel at non-polar solvent toluene.The nano level fiber accumulations that obtains through sol-gel process has become a kind of bundle of shape structure, and this structure in ultrasonic back can be woven into hexagonal structure.
B has formed a kind of nucleocapsid structure of uniqueness in acetonitrile, be a kind of structure of twisting the fibers encapsulation micron ball of spiral, and this gel has the thermostability of height.Can discharge ball after this structure process is ultrasonic, and further be self-assembled into the fiber of height spiral as nuclear.The B compound can form very stable clear gel in non-polar solvent toluene, be a kind of very long fiber of width about 100nm.This fiber can be cut into the fiber of width at 20-40nm after ultrasonic.The ESEM of gelatinous cpd has explained that gel molecular takes the accumulation mode of two-dimensional layer in the process that forms gel.
4. the thermostability of gel and water stability test
In acetonitrile gel and ultrasonic after equal＞100 degree of sol-gel transition temperature of the gel that obtains, this temperature is much larger than the boiling point of acetonitrile, these gels have higher thermostability thus; When after adding entry on the gel interface, its interface kept at least 2 weeks and can not destroy, and explained that the gel that in acetonitrile, forms has very high water stability.
Description of drawings
Fig. 1: gelatinous cpd (R=-CHCH
3-CONH-(CH
2)
m-, m=6, n=2) solution state in acetonitrile (10
-4M) and the fluorescence spectrum of gel state (25mg/L).
Fig. 2: compound (R=-(CH
2)
m-(NHCO)-CHCH
3-, m=6, n=2) sem photograph of formation gel in acetonitrile.
Fig. 3: compound (R=-(CH
2)
m-(NHCO)-CHCH
3-, m=6, n=2) transmission electron microscope picture of formation gel in acetonitrile.
Fig. 4: compound (R=-(CH
2)
m-(NHCO)-CHCH
3-, m=6, the sem photograph of the new gel that obtains after the gel that n=2) in acetonitrile, forms is ultrasonic.
Embodiment
Further specify the preparation method of gelatinous cpd below.Following all raw materials can be self-controls or commercially available.
Embodiment 1
Gel factors A (R=-CHCH
3-CONH-(CH
2)
m-, m=6, synthetic and preparing gel n=2).
N-(R)-2-propionic acid-4-morpholinyl-1, the preparation of 8-naphthalene acid anhydride (2):
(1) the L-L-Ala (251.2mg, 2.82mmol) and NaOH (113mg, ethanolic soln 2.83mmol) stirred 20 minutes down at 40 ℃, added 4-morpholine-1 then, the 8-naphthalimide (800mg, 2.82mmol), N
2Reflux is 24 hours under the protection, and reaction product concentrates and removes ethanol, transfers to pH=6-7 with Hydrogen chloride, and crude product is purified through column chromatography and obtained pure article, productive rate (469mg, 47%).Fusing point: 148-150 ℃.
1H?NMR(400MHz，CDCl
3)：δ1.68-1.69(d，3H，J＝7.2Hz)，3.26-3.28(t，4H，J＝4.4Hz)，4.01-4.04(t，4H，J＝4.4Hz)，5.78-5.83(m，1H)，7.23-7.25(d，1H，J＝8Hz)，7.69-7.73(t，1H，J＝8Hz)，8.43-8.45(d，1H，J＝8Hz)，8.53-8.55(d，1H，J＝8Hz)，8.58-8.60(d，1H，J＝6.4Hz).
13C(100MHz，CDCl
3)：δ14.59，48.76，53.45，66.92，115.07，116.80，123.01，125.92，126.15，130.07，130.46，131.66，133.04，155.92，163.17，163.67，175.28；MS(ESI)calcd?for?C
19H
18N
2O
5：354.12；Found：354.9.
(2) preparation of N-alanine formicester-courage steroid (3):
The hydrochloride of 3-alanine formicester (822mg, 5.91mmol), the dichloromethane solution of 10mL triethylamine stirs half a hour; (2.6g 5.91mmol), continues stirred overnight to add courage steroid acyl chlorides then; Product is purified through column chromatography and is obtained pure article (1.36g, productive rate 45%).Fusing point: 106-108 ℃.
1H?NMR(400MHz，CDCl
3)：δ0.68(s，3H)，0.85-0.86(d，J＝1.6Hz，3H)，0.87-0.88(d，J＝1.6Hz，3H)，0.91-0.92(d，J＝6.4Hz，3H)，0.92-1.61(m，23H)，1.78-2.0(m，5H)，2.23-2.4(m，2H)，2.5-2.6(t，J＝11.6Hz，2H)，3.42-3.46(m，J＝6Hz，2H)，3.70(s，3H)，4.46-4.50(m，1H)，5.0(s，1H)，5.36-5.38(t，J＝2.4Hz，1H).
13C(100MHz，CDCl
3)：δ11.87，18.73，19.33，21.06，22.57，22.82，23.85，24.30，28.02，28.16，28.24，31.90，31.92，34.37，35.81，36.20，36.37，36.58，37.00，38.55，39.54，39.76，42.33，50.04，51.78，56.16，56.72，74.45，122.50，139.85，156.03，172.85；MALDI-TOF-MS?calcd?for?C
32H
53NO
4：515.4.Found：538.4[M+Na
+].
(3) 4 preparation:
(400mg 0.80mmol) is dissolved in 2mL CH will to go up step product 3
2Cl
2With 10mL CH
3Among the OH, dropwise join then hexanediamine (818mg, in methanol solution 7.05mmol), stirring at room 7 days, product concentrates, through column chromatography obtain pure article (230mg, yield:40%).Fusing point: 216-218 ℃.
1H?NMR(CDCl
3)：δ0.67(s，3H)，0.85-0.86(d，J＝1.6Hz，3H)，0.87(d，J＝1.2Hz，3H)，0.90-0.92(d，J＝6.4Hz，3H)，0.95-2.02(m，39H)，2.22-2.41(m，4H)，3.23-3.27(q，2H)，3.42-3.47(q，2H)，4.44-4.49(m，1H)，5.35-5.39(m，1H).
13C(CDCl
3)：δ11.88，18.73，19.36，21.06，22.59，22.85，23.87，24.30，25.73，28.03，28.18，28.25，29.28，29.72，31.88，31.92，35.82，36.20，36.28，36.58，37.00，38.60，38.85，39.53，39.75，42.33，50.02，56.16，56.71，74.41，122.50，139.87，156.43，171.40.
(4) preparation of title product A:
To go up one the step product 4 (391mg, 0.67mmol), N-(R)-2-propionic acid-4-morpholinyl-1; The 8-naphthalimide (391mg, 0.67mmol), DCC (274mg; 2mmol), and HOBt (134mg, dichloromethane solution 2mmol) stirred 24 hours; Product concentrates, through column chromatography obtain pure article (313mg, Yield:50%).Fusing point: 185-187 ℃.
1H?NMR(CDCl
3)：δ0.68(s，3H)，0.86-0.87(d，3H，J＝1.6Hz)，0.88(d，3H，J＝1.6Hz)，0.91-0.93(d，3H，J＝6.4Hz)，0.99-2.34(m，42H)，3.18-3.22(m，2H)，3.28-3.30(t，4H，J＝4.4Hz)，3.31-3.37(m，4H)，4.02-4.04(t，4H，J＝4.8Hz)，4.41-4.49(m，1H)，5.35-5.36(m，1H)，5.71-5.76(m，1H)，5.94(s，1H)，6.30-6.33(m，1H)，7.24-7.26(d，1H，J＝8.4Hz)，7.70-7.74(t，1H，J＝8Hz)，8.44-8.46(d，1H，J＝8.4Hz)，8.52-8.54(d，1H，J＝8Hz)，8.57-8.59(d，1H，J＝7.2Hz).
13C(CDCl
3)：δ11.87，14.57，18.45，18.73，19.34，21.05，22.58，22.83，23.85，24.30，25.16，25.38，28.02，28.17，28.24，29.05，29.36，29.71，31.88，31.92，35.81，35.87，36.20，36.57，37.00，37.05，38.44，38.59，38.84，39.53，39.76，42.33，50.03，50.18，53.44，56.16，56.71，66.95，74.25，115.03，116.86，125.92，126.09，130.04，130.47，131.53，132.95，139.91，156.00，163.62，164.11，170.24，171.39.MALDI-TOF-MS?calcd?for?C
56H
81N
5O
7：935.61.Found：958.7(M+Na
+).Anal.Calcd?for：C
56H
81N
5O
7·2Me
2CO：C?70.55％，H?9.17％，N，6.64％；Found：C?70.57％，H?9.03％，N，6.83％.
Embodiment 2
Gel factor B (R=-(CH
2)
m-(NHCO)-CHCH
3-, m=6, synthetic and preparing gel n=2)
(1) preparation of N-alanine courage steroid (5):
(1g, 2mmol), ((2.5g 60mmol) puts into the mixed solvent of 25mL water and 2mL THF, stirring at room 48 hours to hydronium(ion) oxidation lithium to the 3-alanine.Product concentrates, and transfers pH=2-3 with hydrochloric acid, obtain white solid (0.6g, yield:62%).Fusing point: 112-114 ℃.
1H?NMR(CDCl
3)：δ0.68(s，3H)，0.85-0.86(d，J＝2Hz，3H)，0.87-0.88(d，3H，J＝4.6Hz)，0.91-0.92(d，J＝9.6Hz，3H)，0.95-1.61(m，24H)，1.81-2.02(m，5H)，2.20-2.61(m，4H)，3.45-3.46(m，2H)，4.80-4.53(m，1H)，5.37-5.38(m，1H).
13C(CDCl
3)：δ8.68，11.87，18.73，19.34，21.05，22.57，22.83，23.84，24.30，28.03，28.20，31.90，34.36，35.81，36.20，36.57，37.00，38.55，39.53，39.75，42.33，45.89，50.03，51.80，56.15，56.71，74.46，122.51，139.84，156.04，172.89.MALDI-TOF-MS?calcd?for?C
31H
51NO
4：501.38.Found：522.7(M+Na
+).
(2) N-((R)-2-propionyloxy-formamyl-hexyl)-carboxylamine-tertiary butyl-4-morpholinyl-1, the preparation of 8-naphthalene acid anhydride (7): N-(the amino hexyl of 6-)-4-morpholinyl-1,8-naphthalene acid anhydride (500mg, 1.31mmol); The Boc-L-L-Ala (248mg, 1.31mmol), DCC (538.4mg; 3.93mol), HOBt (265.3mg, dichloromethane solution stirring at room 3.93mmol) 24 hours; Product is through concentrating, column chromatography to pure article (521mg, yield:72%).Fusing point: 134-136 ℃.
1H?NMR(CDCl
3)：δ1.36-1.37(d，3H)，1.40-1.42(m，2H)，1.44(s，9H)，1.49-1.54(m，2H)，1.72-1.78(m，4H)，3.10-3.11(m，2H)，3.26-3.29(t，4H，J＝4.4Hz)，4.02-4.04(t，4H，J＝4.4Hz)，4.15-4.18(t，2H，J＝7.6Hz)，5.08-5.12(m，1H)，7.24-7.26(d，1H，J＝8Hz)，7.69-7.73(q，1H)，8.43-8.45(d，1H，J＝8.4Hz)，8.53-8.55(d，1H，J＝8Hz)，8.59-8.60(d，1H，J＝7.2Hz).
13C(CDCl
3)：δ18.55，26.19，26.40，27.81，28.35，29.20，39.25，39.92，53.47，66.98，115.02，117.21，123.34，125.89，126.16，129.89，130.07，131.22，132.57，155.61，164.03，164.48，172.58.MS(ESI)calcd?for?C
19H
18N
2O
5：354.12；Found：354.9.
(3) preparation of title product B
(TFA 4.3mL) joins one and goes on foot product 7 (300mg, 0, CH 65mmol) trifluoroacetic acid
2Cl
2(5mL) in the solution, stirred overnight at room temperature.Product after concentrating adds 20mL exsiccant methylene dichloride and transfers to pH=7-8 with triethylamine; Add then DCC (267.2mg, 1.95mmol), HOBt (131.6mg; 1.95mmol) and N-alanine courage steroid; Reaction solution continues to stir 24 hours, and reaction product is through concentrating, and column chromatography obtains yellow pure article.Fusing point: 158-160 ℃.
1H?NMR(CDCl
3)：δ0.77(s，3H)，0.96(d，3H，J＝1.6Hz)，0.97-0.98(d，J＝1.6Hz)，1.04-2.15(m，42H)，2.31-2.46(m，2H)，2.55-2.57(t，2H，J＝5.6Hz)，3.30-3.32(m，2H)，3.37-3.39(t，4H，J＝4.4Hz)，3.55-3.60(m，2H)，4.12-4.14(t，4H，J＝4.4Hz)，4.25-4.29(t，2H，J＝7.6Hz)，4.54-4.61(m，1H)，5.45-5.46(m，1H)，6.44(s，1H)，6.53-6.55(m，1H)，7.34-7.36(d，2H，J＝8Hz)，7.80-7.84(t，1H，J＝7.6Hz)，8.53-8.55(d，1H，J＝8.4Hz)，8.63-8.65(1H，J＝8Hz)，8.69-8.70(d，1H，J＝7.2Hz)；
13C(CDCl
3)：δ11.86，18.55，18.72，19.32，21.04，22.57，22.82，23.85，24.28，26.10，26.31，27.79，28.01，28.16，28.23，29.04，31.87，31.89，35.80，36.20，36.55，37.00，38.56，39.31，39.53，39.74，39.91，42.31，48.89，50.01，53.47，56.16，56.69，67.00，74.41，115.01，117.12，122.48，123.30，125.89，126.15，129.89，130.13，131.24，132.61，139.81，155.70，156.31，164.06，164.51，172.14.MALDI-TOF-MS?calcd?for?C
56H
81N
5O
7：935.61，Found：958.8(M+Na
+).
Claims (4)
1. cholesteric organic gel molecule based on small-molecular peptides, it is characterized in that: the naphthalene acid anhydride is chromophoric group and aroma system, and the courage steroid is a hydrophobic grouping, and little peptide is as both intermediary linkers, and its concrete structure is following:
In the formula: R=-CHCH
3-CONH-(CH
2)
m-or-(CH
2)
m-(NHCO)-CHCH
3-, m=6, n=2.
2. the preparation method of the cholesteric organic gel molecule based on small-molecular peptides as claimed in claim 1; It is characterized in that to contain earlier naphthalene acid anhydride and the amino acid of morpholine functional group or amino acid or the amino derivative that diamine compound reflux in water or ethanol obtains the naphthalene acid anhydride, further react the acquisition target compound with the courage steroid that is connected little peptide and amido again.
3. the application of cholesteric organic gel molecule in the preparation organogel based on small-molecular peptides as claimed in claim 1 is characterized in that:
Said gel molecular can
(1) in organic solvent, is heated to dissolved state, forms gel after being cooled to room temperature;
Again can
(2) be dissolved under the situation of organic solvent through ultrasonic in room temperature, form gel;
And
(3) under the situation that state (1) is accomplished, the gel that has formed is carried out ultrasonicly, form new gel;
Said organic solvent is: methyl alcohol, ethanol, butanols, amylalcohol, Virahol, acetone, ETHYLE ACETATE, YLENE and benzene.
4. the application of courage steroid class organogel molecule according to claim 3 in the preparation gel, the gel strength that it is characterized in that said organogel molecule is 15～30 mg/ml.
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| CN101016325A (en) * | 2007-03-08 | 2007-08-15 | 复旦大学 | Cholesteric organogel compounds and preparing method theroef |
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