CN103204899A - Polypeptide cyclizing method based on combination of histidine and metal iridium complex - Google Patents

Polypeptide cyclizing method based on combination of histidine and metal iridium complex Download PDF

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CN103204899A
CN103204899A CN2013100776342A CN201310077634A CN103204899A CN 103204899 A CN103204899 A CN 103204899A CN 2013100776342 A CN2013100776342 A CN 2013100776342A CN 201310077634 A CN201310077634 A CN 201310077634A CN 103204899 A CN103204899 A CN 103204899A
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polypeptide
histidine
metal iridium
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iridium complex
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费浩
马晓川
王小波
贾俊丽
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Suzhou Institute of Nano Tech and Nano Bionics of CAS
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Priority to CN201710308188.XA priority patent/CN107129519B/en
Priority to CN201410079377.0A priority patent/CN104045683A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K2319/00—Fusion polypeptide
    • C07K2319/55—Fusion polypeptide containing a fusion with a toxin, e.g. diphteria toxin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

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Abstract

A polypeptide cyclizing method based on combination of histidine and metal iridium complex includes: providing a ring metal iridium coordination compound composed of two identical C^N bidentate ligands and two solvent molecules in a coordination and complexing manner, subjecting the ring metal iridium coordination compound and two histidines in a polypeptide chain to coordination and realizing polypeptide cyclizing. The chemical formula of the ring metal iridium coordination compound is (L<C^N>)2Ir(L<solv>)2(OTf), wherein the L<C^N> is C^N bidentate ligands, the L<solv> are solvent molecules, and the OTf is trifluoromethane sulfonic acid. Polypeptide cycling is completed by coordination of the non-fluorescent ring metal iridium coordination compound and the two histidines in the polypeptide chain, and polypeptide performance is optimized, and excitable fluorophores can be formed, so that polypeptide molecules are marked by fluorescence and can be used for analyzing, detecting and fluorescent imaging and the like. The polypeptide cyclizing method is simple and quick in technique, moderate in reaction conditions, stable in product performance, non-remarkable in biotoxicity, beneficial for further complicated design, decoration and assembly, and has wide application prospect.

Description

A kind of polypeptide cyclization method of being combined with metal iridium complex based on Histidine
Technical field
The present invention relates to a kind of novel polypeptide cyclization method, particularly a kind ofly be combined the polypeptide cyclization method of being combined with metal iridium complex based on Histidine that generates the complex of iridium of fluorophor and realize with Histidine based on a class.
Background technology
In recent years, polypeptide and various small molecular protein are widely used in multiple treatment of diseases owing to have superior biocompatibility and plasticity-.As the executive of most of signal path in the cell, these crucial peptide molecules can provide the action target spot of medicine by the signal path of regulation and control with disease-related.In addition, as bioactive molecules, the polypeptide wide material sources are easy to synthesize, and different polypeptide can provide and wear film, target, and multiple functions such as treatment become one of the important tool in contemporary medical science and life science field day by day.
The cyclisation polypeptide is widely distributed at occurring in nature, and plant, animal, marine organisms, microorganism, bacterium and germ etc. such as low all contain the cyclisation polypeptide of trace.Though the content of these cyclic peptide is low, wherein much have tangible physiologically active, also therefore be subjected to the attention of domestic and international many chemists, biologist and pharmacy man.Therefore the cyclisation of peptide becomes a kind of important peptide molecule method of design, and cyclisation can reduce the degree of freedom of ring component, and the specific secondary structure of stabilized peptide.Studies show that the conformation of restriction polypeptide can increase avidity and the selectivity with receptors bind, the every performance under its cyclisation state all obviously is better than its linear condition.For example, RGD tripeptide sequence (arginine, glycine, aspartic acid) can be combined with the plain specificity of multiple integration, can promote cell to the adhesion of biomaterial effectively, reaches the purpose of the plain high expressing cell of targeted integration.Studies show that after its cyclisation, in stability, targeting and avidity everyway obviously are better than linear RGD.
Existing linear polypeptide cyclization method has 2 kinds: a class is the condensation by amino and carboxyl, forms peptide bond.This traditional head and the tail cyclization method relates to part or all of protection with the deprotection strategy and needs condensation reagent to carry out ring closure reaction mutually, the process complexity, and be difficult to do the extension of structure after the cyclisation, can't do more complicated design and functionalization.Another kind ofly by introducing disulfide linkage (s-s) biologically active peptides is carried out cyclisation.Usually synthesize the line style peptide precursor that has sulfhydryl protected halfcystine (Cys) residue earlier; slough the protecting group of Cys then; be oxidized to Cheng Huan behind the disulfide linkage; or directly will be oxidized into the s-s key with the Cys of protecting group; but the S-S key is unstable under reducing environment, has limited the further application of this class biological activity cyclisation polypeptide greatly.
Summary of the invention
Main purpose of the present invention is to provide a kind of polypeptide cyclization method of being combined with metal iridium complex based on Histidine, its technology is simple, quick, easy to implement, and obtained product has hypotoxicity, characteristics such as high stability, thus overcome deficiency of the prior art.
For achieving the above object, the present invention has adopted following technical scheme:
A kind of polypeptide cyclization method of being combined with metal iridium complex based on Histidine is characterized in that, comprising:
Main Cyclometalated iridium coordination compound by two identical C^N bidentate ligands and two solvent molecule ligand complexes is provided, and makes 2 Histidine generation coordination reactions in described Cyclometalated iridium coordination compound and the polypeptide peptide chain, realize the polypeptide cyclisation.
Particularly, the chemical molecular formula of described Cyclometalated iridium coordination compound is (L C^N) 2Ir (L Solv) 2[OTf], its structural formula is as follows:
Wherein, L C^NBe C^N bidentate ligand, L SolvBe solvent molecule, OTf is the trifluoromethane sulfonic acid root.
Further, described C^N bidentate ligand L C^NOptional but be not limited to the 2-phenylpyridine.
Described solvent molecule can be selected from but be not limited to water, acetonitrile etc.
As one of embodiment preferred comparatively, described polypeptide peptide chain contains two above Histidines, wherein in order to be distributed in two different select locations on the polypeptide peptide chain with two Histidines that Cyclometalated iridium coordination compound carries out coordination reaction.
As one of embodiment preferred comparatively, in the described polypeptide peptide chain in order to and Cyclometalated iridium coordination compound carry out between two Histidines of coordination reaction 1-5 amino acid at interval.
For example, described polypeptide is optional but be not limited to RGD etc.
Postscript, described coordination reaction are to carry out in buffer solution system, and described buffer solution system can be selected from but be not limited to phosphoric acid buffer (PBS), Tris damping fluid, Bis-Tris damping fluid, MES damping fluid or HEPES damping fluid etc.
Compared with prior art, advantage of the present invention is at least:
(1) the invention provides a kind of polypeptide cyclisation mode of novelty, it passes through 2 histidine residues (Histidine) combination in Cyclometalated iridium coordination compound and the polypeptide peptide chain, make the peptide sequence cyclisation between the Histidine, realize fluorescent mark simultaneously, and, even if the sequence difference of polypeptide, namely can finish the cyclisation of peptide sequence therebetween as long as contain 2 histidine residues in the peptide chain, reaction process is quick, easy, the reaction conditions gentleness, and cyclisation product is stable, irreversible, nontoxicity in living things system, be convenient to proceed complicated modification and assembling process, can be widely used in analyzing and testing, technical fields such as fluorescence imaging.
(2) cyclization of the present invention can be at normal temperatures, carry out in the buffered soln commonly used, do not need extra cross-linking reagent, the reaction conditions gentleness, operation steps is simple, and is with low cost;
(3) Cyclometalated iridium coordination compound used in the present invention was not possessing fluorescence before the histidine residues of polypeptide is combined, the mixture that forms in the labeling process just has tangible fluorescence to strengthen, thereby a step is finished the optimization (cyclisation) of structure and the mark of fluorescence, produced simultaneously fluorescence also can prove the success or not of polypeptide cyclisation accurately, and, Cyclometalated iridium coordination compound of the present invention also has light stability preferably, long photophysics characteristic and chemical stabilities such as fluorescence lifetime can be preserved for a long time with solid or solution form under normal condition.
Description of drawings
Fig. 1 is the structural representation of polypeptide cyclisation in the preferable concrete application examples of the present invention one;
Fig. 2 A and Fig. 2 B are the structural representations of polypeptide cyclisation in the embodiment of the invention 1, and wherein Fig. 2 A is the synoptic diagram of HRGDH and iridium complex compound coordination, and Fig. 2 B is HRGDH-(KLAKLAK) 2Synoptic diagram with the iridium complex compound coordination;
Fig. 3 is iridium complex compound and polypeptide HRGDH in the embodiment of the invention 1, HRGDH-(KLAKLAK) 2Fluorescence emission spectrogram (ex:328nm) before and after the coordination cyclisation;
Fig. 4 is HRGDH-in the embodiment of the invention 2 (KLAKLAK) 2Sign collection of illustrative plates with trigger cell apoptotic process after the iridium complex compound coordination cyclisation.
Embodiment
As previously mentioned, in view of deficiency of the prior art, one aspect of the present invention aims to provide a kind of polypeptide cyclization method of being combined with metal iridium complex based on Histidine, and it mainly is based on a class and is combined with Histidine and generates the complex of iridium of fluorophor and realize.
Further say, as an embodiment preferred comparatively of the present invention, should be combined by 2 histidine residues of the non-blooming Cyclometalated iridium coordination compound of a class self on polypeptide based on the polypeptide cyclization method system that Histidine is combined with metal iridium complex, finish the polypeptide cyclisation, form the fluorophor that can be excited when optimizing the polypeptide performance, be able to the labeling polypeptide molecule, and be used for analyzing and testing and fluorescence imaging.The process of polypeptide cyclisation is simple, quick, efficient among the present invention, the reaction conditions gentleness, polypeptide stable in properties after the cyclisation, do not have obvious bio-toxicity, can be applicable to further complicated the modification and assembling process, and have green fluorescence and be convenient to spike, in fields such as life sciences wide application prospect is arranged, for example, its range of application can be including, but not limited to the assembling of biomolecule detection, cell dyeing, animal tissues's mark and polypeptide, experiments such as mark and spike.
Wherein, Cyclometalated iridium coordination compound preferably adopts the Cyclometalated iridium coordination compound by two identical C^N bidentate ligands and two solvent molecule ligand complexes, and its chemical molecular formula can be (L C^N) 2Ir (L Solv) 2[OTf], its structural formula can for:
Figure 309430DEST_PATH_IMAGE002
Wherein, L C^NRepresent bidentate ligand, L SolvRepresent solvent molecule, OTf represents the trifluoromethane sulfonic acid root.
Further, aforementioned C^N bidentate ligand L C^NCan be including, but not limited to the 2-phenylpyridine.
The aforementioned solvents molecule can include but not limited to water, acetonitrile.
For example, the structural formula of aforementioned Cyclometalated iridium coordination compound can for:
Wherein ppy represents the 2-pyridine(2-phenylpyridine), OTf-represents Trifluoromethanesulfonate (trifluoromethane sulfonic acid root), L SolvRepresentative is easy to from the solvent molecule of central metal disengaging, such as water or acetonitrile.
Again for example, the process of aforementioned Cyclometalated iridium coordination compound and polypeptide reaction can be with reference to figure 1.
Below in conjunction with some preferred embodiments technical scheme of the present invention is further described.
Embodiment 1: the cyclization of polypeptide HRGDH
[(ppy) 2Ir (H 2O) 2] (OTf) respectively react (consulting Fig. 2 A) with the polypeptide HRGDH of a Histidine with head and the tail, [(ppy) 2Ir (H 2O) 2] (OTf) mol ratio with the reaction density of polypeptide be 1:1, be reflected at PBS(pH7.4) in carry out, 37 ℃ of concussions were spent the night in 2 hours or 4 ℃.Consult Fig. 4, under UV-light (365nm) irradiation, the polypeptide after the cyclisation can produce green fluorescence.Fig. 3 has shown the fluorescence emission spectrum (ex:328nm) before and after iridium complex compound and the polypeptide HRGDH coordination cyclisation.In the present embodiment after the cyclisation MTT detected result of polypeptide show that to finish the polypeptide cytotoxicity that cyclisation causes by this type of cyclization method low, IC50 is greater than 200 μ M, the result is as shown in table 1.
Embodiment 2: polypeptide HRGDH-(KLAKLAK) 2Cytotoxicity optimization after the cyclisation
Polypeptide cyclization process and embodiment one are basic identical, and difference is that the polypeptide in the present embodiment has connected cytotoxic polypeptide (KLAKLAK) outside the cyclisation part 2(shown in Fig. 2 B) (KLAKLAK) 2This because going into born of the same parents' difficulty, can't enter cell and bring out apoptosis under the monomer situation.And by being connected with HRGDH after the cyclisation, promoted the adhesion of itself and cell surface, effectively help it to go into born of the same parents and bring into play toxicity.Simultaneously, because the present invention is green fluorescence on the cyclisation polypeptide marker also, make the polypeptide HRGDH-(KLAKLAK) after the cyclisation in the present embodiment when finishing the polypeptide cyclisation 2The process of trigger cell apoptosis is characterized (Fig. 4).In the present embodiment relevant fluorescence emission spectrum result as shown in Figure 3, cytotoxicity MTT detected result is as shown in table 1.
Table 1 polypeptide HRGDH, HRGDH-(KLAKLAK) 2With the cytotoxicity MTT experimental result before and after the iridium complex compound coordination cyclisation.
It is pointed out that disclosed is one or more of preferred embodiment, the change of every part or modification and come from technological thought of the present invention and be have the knack of this technology the people was easy to know by inference, all do not break away from patent right scope of the present invention.

Claims (8)

1. a polypeptide cyclization method of being combined with metal iridium complex based on Histidine is characterized in that, comprising:
Main Cyclometalated iridium coordination compound by two identical C^N bidentate ligands and two solvent molecule ligand complexes is provided, and makes 2 Histidine generation coordination reactions in described Cyclometalated iridium coordination compound and the polypeptide peptide chain, realize the polypeptide cyclisation.
2. polypeptide cyclization method of being combined with metal iridium complex based on Histidine according to claim 1 is characterized in that, the chemical molecular formula of described Cyclometalated iridium coordination compound is (L C^N) 2Ir (L Solv) 2[OTf], its structural formula is as follows:
Figure 2013100776342100001DEST_PATH_IMAGE001
Wherein, L C^NBe C^N bidentate ligand, L SolvBe solvent molecule, OTf is the trifluoromethane sulfonic acid root.
3. polypeptide cyclization method of being combined with metal iridium complex based on Histidine according to claim 1 and 2 is characterized in that, described C^N bidentate ligand L C^NOptional but be not limited to the 2-phenylpyridine.
4. polypeptide cyclization method of being combined with metal iridium complex based on Histidine according to claim 1 and 2 is characterized in that described solvent molecule comprises water, acetonitrile, DMF or DMSO.
5. polypeptide cyclization method of being combined with metal iridium complex based on Histidine according to claim 1, it is characterized in that, described polypeptide peptide chain contains two above Histidines, wherein in order to be distributed in two different select locations on the polypeptide peptide chain with two Histidines that Cyclometalated iridium coordination compound carries out coordination reaction.
6. polypeptide cyclization method of being combined with metal iridium complex based on Histidine according to claim 5 is characterized in that, in the described polypeptide peptide chain in order to and Cyclometalated iridium coordination compound carry out between two Histidines of coordination reaction 1-5 amino acid at interval.
7. according to claim 1 or 5 or 6 described polypeptide cyclization methods of being combined with metal iridium complex based on Histidine, it is characterized in that described polypeptide comprises RGD.
8. polypeptide cyclization method of being combined with metal iridium complex based on Histidine according to claim 1, it is characterized in that, described coordination reaction is to carry out in buffer solution system, and described buffer solution system comprises phosphoric acid buffer, Tris damping fluid, Bis-Tris damping fluid, MES damping fluid or HEPES damping fluid.
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CN103665096A (en) * 2013-04-19 2014-03-26 中国科学院苏州纳米技术与纳米仿生研究所 Method for forming stable nail peptide based on iridium complex
CN104045683A (en) * 2013-03-12 2014-09-17 中国科学院苏州纳米技术与纳米仿生研究所 Iridium complex-based polypeptide fluorescent cyclisation method and cyclized polypeptide
CN104974227A (en) * 2014-04-04 2015-10-14 中国科学院苏州纳米技术与纳米仿生研究所 Cation amphiphilic membrane targeted alpha-helix polypeptides and application thereof
CN114617974A (en) * 2020-12-10 2022-06-14 中国科学院苏州纳米技术与纳米仿生研究所 Polypeptide albumin nanoparticle and preparation method and application thereof

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CN104045683A (en) * 2013-03-12 2014-09-17 中国科学院苏州纳米技术与纳米仿生研究所 Iridium complex-based polypeptide fluorescent cyclisation method and cyclized polypeptide
CN107129519A (en) * 2013-03-12 2017-09-05 中国科学院苏州纳米技术与纳米仿生研究所 Polypeptide fluorescence cyclization method and cyclized polypeptide based on metal iridium complex
CN103665096A (en) * 2013-04-19 2014-03-26 中国科学院苏州纳米技术与纳米仿生研究所 Method for forming stable nail peptide based on iridium complex
CN104974227A (en) * 2014-04-04 2015-10-14 中国科学院苏州纳米技术与纳米仿生研究所 Cation amphiphilic membrane targeted alpha-helix polypeptides and application thereof
CN104974227B (en) * 2014-04-04 2019-04-23 中国科学院苏州纳米技术与纳米仿生研究所 The amphiphilic film targeting alpha-helix polypeptide of cation and its application
CN114617974A (en) * 2020-12-10 2022-06-14 中国科学院苏州纳米技术与纳米仿生研究所 Polypeptide albumin nanoparticle and preparation method and application thereof
CN114617974B (en) * 2020-12-10 2023-10-03 中国科学院苏州纳米技术与纳米仿生研究所 Polypeptide albumin nanoparticle and preparation method and application thereof

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