CN109467517A - A kind of acylhydrazone molecular switch, preparation method and application - Google Patents
A kind of acylhydrazone molecular switch, preparation method and application Download PDFInfo
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- CN109467517A CN109467517A CN201811222654.3A CN201811222654A CN109467517A CN 109467517 A CN109467517 A CN 109467517A CN 201811222654 A CN201811222654 A CN 201811222654A CN 109467517 A CN109467517 A CN 109467517A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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Abstract
The present invention provides a kind of novel acylhydrazone molecular switch, its synthesis and for the method for the photic controlled release of drug.The molecular switch is condensed by 2- methoxyl group naphthaldehyde with benzoyl hydrazine.Due to the group that the adjacent both sides of acylhydrazone imine group have steric hindrance big, E- isomers is easy to be converted into Z- isomers under light illumination, so that the transformation efficiency of E-Z isomers is up to 99%, quantum yield is up to 89%.After being prepared into amphipathic molecule switch, self assembly nano vesicle can be generated in water, the E-Z isomers transformation of high conversion can also occur under light illumination for this vesica.Vesica, which can include, loads anticancer drug procarbazine, increases the solubility of drug in water by 225 times.Under light illumination, the procarbazine of inclusion can be released out of vesica.
Description
Technical field
The invention belongs to chemical fields, more particularly, to a kind of acylhydrazone molecular switch, preparation method and application.
Background technique
Photic molecular switch information storage, light impeller, photopharmacology, react long-range control, light-controlled electronic device, can
Controlling drug conveying and release etc. has huge potential use, attracts wide attention and studies, Nobel's chemistry in 2016
Prize is granted by the scientist that research molecule machine includes molecular switch.But common photic molecular switch, such as azo-based
The molecular switch of the derivatives such as benzene, double aromatic hydrocarbon ethylene and spiro-pyrans synthesizes non-although there is preferable light activated switch performance
Normal difficulty (Chem.Soc.Rev.2012,41,1809-1825；Chem.Soc.Rev.2013,43,148-184；
Chem.Rev.2014,114,12174-12277)。
The photic molecular switch of acylhydrazone class occurred recently, synthesis are easy, and have modifiability, and photo-isomerisable body changes performance
Excellent (J.Am.Chem.Soc.2017,139,9140-9143；Nature 2017,549,374–378).But this kind of acylhydrazone molecule
Switch is in Z- formula isomers, it is necessary to can form intramolecular hydrogen bond, otherwise its E-Z conversion ratio is very low, and quantum yield is also very low
(J.Am.Chem.Soc.2015,137,14982-14991).In addition, all acylhydrazone molecular switches its photic E-Z in aqueous solution
Conversion ratio is very low, does not see the report loaded for drug in aqueous solution with controlled release.
Summary of the invention
Aiming at the above defects or improvement requirements of the prior art, the present invention provides a kind of acylhydrazone molecular switches, its preparation
Method and application make the reduction of its E- isomer by the adjacent both sides of group introducing acylhydrazone imine group that steric hindrance is big,
It is easy to be converted into Z- isomers from E- isomers under light illumination, transformation efficiency is up to 99%, and quantum yield is up to 89%, thus solves
Certainly the acylhydrazone molecular switch of the prior art is only capable of just being able to achieve E- isomers turn by forming intramolecular hydrogen bond in Z- formula isomers
Z- isomers is turned to, and the very low technical problem of photic E-Z conversion ratio in aqueous solution.
The object of the present invention is to provide a kind of photic molecular switches of acylhydrazone class, not only have in organic solvent very high
E-Z conversion ratio also has very high conversion ratio in water, can be used for the loading of anticancer drug and control release in water.
It is a further object to provide the preparation methods of this acylhydrazone molecular switch.
To achieve the above object, according to one aspect of the present invention, it is logical to provide a kind of structure having as described in formula (I)
The compound of formula:
Wherein:
R1、R2And R3It is each independently H, alkyl or multicondensed ethylene glycol ether；
R4For alkyl；
R5For H, alkenyl, imido grpup or phenyl；
R6For alkyl, alkoxy or multicondensed ethylene glycol ether.
Preferably, the multicondensed ethylene glycol ether is expressed as-(OCH2CH2)nOH, wherein n is the integer of 3-30.
Other side according to the invention provides the preparation method of compound described in one kind, by 2- methoxyl group
Naphthaldehyde is condensed with benzoyl hydrazine.
Preferably, the preparation method specifically comprises the following steps: the ethanol solution and formula of formula (II) compound
(III) it after the ethanol solution mixing of compound, at 40-80 DEG C after heating stirring 1-10min, is separated by solid-liquid separation, to what is be collected into
Solid ethanol washing obtains formula (I) described compound；Wherein:
The proportion of formula (II) compound, formula (III) compound and ethyl alcohol are as follows: 0.2-2g:0.3-5g:10-50mL；
Formula (II) compound structure general formula is as follows:
Formula (III) compound structure general formula is as follows:
R1、R2And R3It is each independently H, alkyl or multicondensed ethylene glycol ether；
R4For alkyl；
R5For H, alkenyl, imido grpup or phenyl；
R6For alkyl, alkoxy or multicondensed ethylene glycol ether.
Other side according to the invention provides a kind of application of compound described in formula (I), the dress for drug
Load and controlled release.
Preferably, which is prepared into amphipathic molecule switch, self assembly can generates nanocapsule in water
Bubble is included using the vesica and loads drug；Under light illumination, which occurs the transformation of E-Z isomers, makes the drug of inclusion from vesica
Inside release.
Other side according to the invention provides a kind of photic molecular switch loaded for drug with controlled release, should
Molecular switch contains compound described in formula (I).
In general, through the invention it is contemplated above technical scheme is compared with the prior art, can obtain down and show
Beneficial effect:
The present invention drops its E- isomer by the way that the big group of steric hindrance is introduced the adjacent both sides of acylhydrazone imine group
It is low, even if Z- isomers cannot form the intramolecular hydrogen bond of stabilization, also it is easy to be converted into from E- isomers under light illumination
Z- isomers, transformation efficiency are up to 99%, and quantum yield is up to 89%.
The present invention is photic by the way that acylhydrazone class of the present invention is made with benzoyl hydrazine condensation reaction in 2- methoxyl group naphthaldehyde
Molecular switch, by selecting suitable substituent group, so that the molecular switch has amphipathic, and preparation method is simple.
The photic molecular switch of acylhydrazone class provided by the invention is that self assembly can generate in water after amphipathic molecule switchs
The E-Z isomers transformation of high conversion can also occur under light illumination for nano vesicle, this vesica.Nano vesicle can include loading
Anticancer drug such as procarbazine, can making it, solubility increases by 225 times in water.Under light illumination, the procarbazine energy of inclusion
It is enough to be released out of vesica, realize the loading and controlled release of drug.
Detailed description of the invention
Fig. 1 is that the E- isomers of molecular switch I of the present invention is converted into the conversion schematic diagram of Z- isomers under light illumination；
Fig. 2 is molecular switch I1H-NMR spectrum；
Fig. 3 is molecular switch I13C-NMR spectrum；
Fig. 4 is the high resolution mass spectrum of molecular switch I；
Fig. 5 is I before and after molecular switch illumination1H-NMR spectrum；
Fig. 6 is variation of the molecular switch uv-vis spectra with light application time；
Fig. 7 is molecular switch and anticancer drug procarbazine mixture aqueous solution grain size analysis diagram and photograph before and after illumination
Piece；
Fig. 8 is molecular switch and anticancer drug procarbazine mixture aqueous solution the FE-SEM photo before and after illumination.
Specific embodiment
In order to make the objectives, technical solutions, and advantages of the present invention clearer, with reference to the accompanying drawings and embodiments, right
The present invention is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, and
It is not used in the restriction present invention.As long as in addition, technical characteristic involved in the various embodiments of the present invention described below
Not constituting a conflict with each other can be combined with each other.
The drug provided by the invention that can be used for is loaded with the compound of controlled release with structure shown in following formula (I):
Wherein, substituent group is set in the general formula so that the adjacent both sides steric hindrance of its acylhydrazone imine group is larger, keeps its E- different
Structure body stability reduces, and is easy to be converted into Z- isomers from E- isomers under light illumination.
In some embodiments:
R1、R2、R3It is each independently H, alkyl or multicondensed ethylene glycol ether etc.；
R4Substituent group is alkyl；It is preferred that the alkyl for being 1-20 containing carbon number.
R5Substituent group is H, alkenyl, imido grpup or phenyl etc..
R6For alkyl, alkoxy or multicondensed ethylene glycol ether etc., wherein alkyl is preferably 1-20 containing carbon number.
Wherein multicondensed ethylene glycol ether is expressed as-(OCH2CH2)nOH, n are the integer of 3-30, the preferably integer of 3-10.
Above compound can be synthesized by following route:
Formula (II) compound (0.2-2g) and ethyl alcohol (10-50mL) are added in round-bottomed flask, formula (III) then is added
Ethyl alcohol (10-50mL) solution of compound (0.3-5g).At 40-80 DEG C after heating stirring 1-10min, filtering.That collects consolidates
Body ethanol washing, obtains formula (I) compound, and yield is greater than 95%.Substituent group value range is same as above in formula.
Structure determination: by NMR, HRMS, IR, the means of testing such as Mp, UV-Vis determine structure.
Formula (I) compound proposed by the present invention can be condensed by 2- methoxyl group naphthaldehyde with benzoyl hydrazine.The present invention mentions
Formula (I) compound out can be used for loading and controlled release for drug, and the novel acylhydrazone of the loading and controlled release for drug is made
Photic molecular switch.The group that the adjacent both sides of acylhydrazone imine group have steric hindrance big in the compound that the present invention synthesizes, E- are different
Structure body is easy to be converted into Z- isomers under light illumination, converts schematic diagram as shown in Figure 1, its transformation efficiency greatly improves.The present invention
Formula (I) general formula compound of proposition, the transformation efficiency of E-Z isomers may be up to 99%, and quantum yield is up to 89%.It is made
After switching at amphipathic molecule, self assembly nano vesicle can be generated in water, height can also occur under light illumination for this vesica
The E-Z isomers of conversion ratio changes.Vesica can include loading anticancer drug, such as procarbazine, make the drug in water
Solubility increases by 225 times.Under light illumination, the procarbazine of inclusion can be released out of vesica.
The following are embodiments:
Embodiment 1
Molecular switch I (in logical formula (I), R1=R2=R3=-(OCH2CH2)5OH；R4=CH3；R5=H；R6=-OCH2
(CH2)12CH3) synthesis:
Formula (II) compound (0.2-2g) and ethyl alcohol (10-50mL) are added in round-bottomed flask, formula (III) then is added
Ethyl alcohol (10-50mL) solution of compound (0.3-5g).At 40-80 DEG C after heating stirring 1-10min, filtering.That collects consolidates
Body ethanol washing, obtains formula (I) compound, and yield is greater than 95%.
Formula (I) compound is in DMSO-d61H-NMR spectrum is shown in Fig. 2,13C-NMR spectrum is shown in Fig. 3, and HRMS spectrum is shown in Fig. 4.
Embodiment 2
By compound of formula I (in general formula (I), R1=R2=R3=-(OCH2CH2)5OH；R4=CH3；R5=H；R6=-
OCH2(CH2)12CH3) be dissolved in water, the obtained aqueous solution light of portable ultraviolet lamp 365nm irradiates, after measuring illumination1H-
H NMR spectroscopy has the conversion of 90%E- isomers for Z- isomers.It is in D2In O before and after illumination1H-NMR spectrum, is shown in Fig. 5 a and Fig. 5 b.
Embodiment 3
By formula (I) compound (in general expression I, R1=R2=R3=-(OCH2CH2)5OH；R4=CH3；R5=H；R6=-
OCH2(CH2)12CH3) be dissolved in DMSO, with the ultraviolet lighting different time of 388nm, measuring the ultraviolet of different light application times can
Light-exposed spectrum, is shown in Fig. 6 (a)；It was found that the absorption band in 377nm gradually weakens, and the absorption band in 273nm gradually increases, and sees Fig. 6
(b)。
Fig. 6 be formula (I) compound (in general expression I, R1=R2=R3=-(OCH2CH2)5OH；R4=CH3；R5=H；R6
=-OCH2(CH2)12CH3) the visible external spectrum of purple in DMSO is with the variation (a) of light application time and at 377nm and 273nm
Absorbance with light application time variation (b).[Formulas I]=6.0 × 10-5M, light source 388nm light.
Embodiment 4
Anticarcinogen procarbazine in water solubility be 0.002mg/mL, but be added formula (I) compound (in general expression I,
R1=R2=R3=-(OCH2CH2)5OH；R4=CH3；R5=H；R6=-OCH2(CH2)12CH3) after, make the concentration of formula (I) compound
For 5mM, procarbazine solubility is 0.45mg/mL, and solubility increases 225 times.Obtained clear solution, has through grain size analysis
The particle that diameter is 110-170nm exists, and FE-SEM photo shows that particle diameter is 150nm or so, and clear solution can stablize 1
A month or more.But after the irradiation of the light of portable ultraviolet lamp 365nm, clear solution becomes white opacity, and SEM photograph shows that particle is straight
Diameter is 1.10-1.60 μm, and after illustrating illumination, procarbazine is precipitated from the vesica that formula (I) compound is formed, and due in water
Solubility very little and be gathered into big particle.See Fig. 7 and Fig. 8.
Fig. 7 be procarbazine and formula (I) compound (in general expression I, R1=R2=R3=-(OCH2CH2)5OH；R4=
CH3；R5=H；R6=-OCH2(CH2)12CH3) mixture dynamic light scattering diagram in water.(A) before the irradiation of 365nm light, (B)
After the irradiation of 365nm light.Illustration, the photo of solution before and after illumination.[Formulas I]=5mM, [procarbazine]=0.45mg/mL.
Fig. 8 be procarbazine and formula (I) compound (in general expression I, R1=R2=R3=-(OCH2CH2)5OH；R4=
CH3；R5=H；R6=-OCH2(CH2)12CH3) mixture aqueous solution FE-SEM figure.(A) before the irradiation of 365nm light, (B) 365nm
After light irradiation.
As it will be easily appreciated by one skilled in the art that the foregoing is merely illustrative of the preferred embodiments of the present invention, not to
The limitation present invention, any modifications, equivalent substitutions and improvements made within the spirit and principles of the present invention should all include
Within protection scope of the present invention.
Claims (6)
1. the compound with the general structure as described in formula (I):
Wherein:
R1、R2And R3It is each independently H, alkyl or multicondensed ethylene glycol ether；
R4For alkyl；
R5For H, alkenyl, imido grpup or phenyl；
R6For alkyl, alkoxy or multicondensed ethylene glycol ether.
2. compound as described in claim 1, which is characterized in that the multicondensed ethylene glycol ether is expressed as-(OCH2CH2)nOH, wherein n is the integer of 3-30.
3. the preparation method of compound as claimed in claim 1 or 2, which is characterized in that it is by 2- methoxyl group naphthaldehyde and benzene first
Hydrazides is condensed.
4. preparation method as claimed in claim 3, which is characterized in that specifically comprise the following steps: formula (II) compound
After the mixing of the ethanol solution of ethanol solution and formula (III) compound, at 40-80 DEG C after heating stirring 1-10min, solid-liquid point
From obtaining formula (I) described compound to the solid ethanol washing being collected into；Wherein:
The proportion of formula (II) compound, formula (III) compound and ethyl alcohol are as follows: 0.2-2g:0.3-5g:10-50mL；
Formula (II) compound structure general formula is as follows:
Formula (III) compound structure general formula is as follows:
R1、R2And R3It is each independently H, alkyl or multicondensed ethylene glycol ether；
R4For alkyl；
R5For H, alkenyl, imido grpup or phenyl；
R6For alkyl, alkoxy or multicondensed ethylene glycol ether.
5. the application of compound as claimed in claim 1 or 2, which is characterized in that loading and controlled release for drug.
6. a kind of photic molecular switch loaded for drug with controlled release, which is characterized in that containing as claimed in claim 1 or 2
Compound.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104177624A (en) * | 2014-08-14 | 2014-12-03 | 天津大学 | Dual sensitive amphiphilic triblock copolymer containing disulfide bond and acylhydrazone bond and preparation method and application of dual sensitive amphiphilic triblock copolymer |
| CN104877127A (en) * | 2015-06-23 | 2015-09-02 | 厦门赛诺邦格生物科技有限公司 | Eight-armed polyethylene glycol derivative, preparation method and related biological substance modified by derivative |
| WO2017100644A1 (en) * | 2015-12-09 | 2017-06-15 | Case Western Reserve University | Method of modulating ribonucleotide reductase |
| CN107029243A (en) * | 2017-06-08 | 2017-08-11 | 厦门大学 | A kind of double acylhydrazone connecting keys of polypeptide bridging are applied to the delivering of aldehyde drug derivative |
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- 2018-10-19 CN CN201811222654.3A patent/CN109467517B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104177624A (en) * | 2014-08-14 | 2014-12-03 | 天津大学 | Dual sensitive amphiphilic triblock copolymer containing disulfide bond and acylhydrazone bond and preparation method and application of dual sensitive amphiphilic triblock copolymer |
| CN104877127A (en) * | 2015-06-23 | 2015-09-02 | 厦门赛诺邦格生物科技有限公司 | Eight-armed polyethylene glycol derivative, preparation method and related biological substance modified by derivative |
| WO2017100644A1 (en) * | 2015-12-09 | 2017-06-15 | Case Western Reserve University | Method of modulating ribonucleotide reductase |
| CN107029243A (en) * | 2017-06-08 | 2017-08-11 | 厦门大学 | A kind of double acylhydrazone connecting keys of polypeptide bridging are applied to the delivering of aldehyde drug derivative |
Non-Patent Citations (1)
| Title |
|---|
| DERK JAN VAN DIJKEN等: "Acylhydrazones as Widely Tunable Photoswitches", 《J. AM. CHEM. SOC.》 * |
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