Gold-copper alkynyl phosphine complexes as luminescent labels for fluorescence microscopy

FIELD: chemistry.

SUBSTANCE: invention relates to chemistry of organometallic compounds, particularly to alkynyl phosphine gold-copper complexes which dissociate in a solution to form ions. The gold-copper alkynyl phosphine complexes are capable of forming covalent conjugates with proteins, thereby turning into a water-soluble form, exhibit luminescent properties and can be used as labels for fluorescence microscopy and in luminescent analysis.

EFFECT: improved properties of the compounds.

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The invention relates to the field of chemistry of ORGANOMETALLIC compounds, in particular to heterometallic gold-copper complexes that exhibit fluorescent properties and can be used as labels for fluorescence microscopy and fluorescent analysis. The invention can find application in analytical chemistry, molecular biology, biotechnology, pharmacology and medicine for in vitro assays.

Currently known complexes of transition metals (CTV), which show luminescence properties and are used as labels in fluorescence microscopy [1]. Such complexes have a number of advantages compared to, for example, with labels on the basis of organic phosphors: their luminescence is characterized by a large Stokes shifts and large lifetimes of the excited state. A large Stokes shift simplifies the separation of signals luminescence and excitation radiation and reduces somatuline in solution. Increasing the lifetime of the excited state of the fluorescent QPM allows using the registration of the decay time of the luminescence of the sample (FLIM, fluorescence life time imaging) to cut off autofluorescence biological samples, and thus improve the image contrast and sensitivity of detection.

For the practical application of most interest what was the complexes, capable of specific binding with specific biomolecules or cellular structures, and one of the tag types on the basis of the PMC are labels for covalent binding proteins [2].

Significant disadvantages of using at the time labels on the basis of PCM is that the luminescence of the vast majority of such phosphors are susceptible to quenching by molecular oxygen and in the presence of air quantum yield of luminescence decreases appreciably compared to the degassed solution.

Known gold-copper alkylphosphine complexes, which solved the technical problem are the closest to the claimed invention and taken as a prototype [3]. In common with the claimed invention is that the complexes prototypes have intense luminescence, microsecond lifetimes and luminescence of complexes is slightly reduced in the presence of oxygen.

The disadvantage of these systems is relatively narrow area of application due to their insolubility in water and physiological media, as well as the impossibility of linking them with the protein.

The technical result of the invention is the expansion of the scope due to the possibility of protein binding. Important in the present invention is Mor is Annie intense luminescence, including in the presence of molecular oxygen.

This technical result is achieved by the fact that alkylphosphine gold-copper complexes dissociate in solution with the formation of ions that can form covalent adducts with amino groups, in particular amino groups of proteins

which allows their use as fluorescent labels for fluorescence microscopy.

The essence of the invention is illustrated by examples of specific implementations that are illustrated in Fig. 1-5.

In Fig. 1 presents a scheme of the synthesis of the complex [AuC2C6H4-4-COONC4H4O2].

In Fig. 2 presents the scheme of the synthesis of the complex [Au2(C2With6H4-4-COONC4H4O2)2PPh2C6H4PPh2].

In Fig. 3 presents a scheme of the synthesis of the complex [Au6Cu2(C2With6H4-4-COONC4H4O2)6(PPh2C6H4PPh2)3](PF6)2..

In Fig. 4 and 5 presents the spectra of luminescence.

The claimed invention was tested in St. Petersburg state University in real time, and the results of testing are given in the form of specific examples.

Example 1.

The complex [Au6Cu2(C2 6H4-4-COONC4H4O2)6(PPh2C6H4PPh2)3](PF6)2.

The complex [AuC2C6H4-4-COONC4H4O2] (Fig. 1). To a suspension of 0.45 mmol of the complex [Au(tetrahydrothiophene)C1] 2 ml of acetone was added a solution of 0.56 mmol 2,5-dioxopiperidin-1-yl-4-ethynylbenzoate in 2 ml of acetone and 10 drops of triethylamine, after which the reaction mixture was stirred in the dark before the formation of white precipitate. The precipitate was separated by centrifugation and washed with water-ethanol mixture 1:1 by volume, ethanol and pentane. Yield 97%.

The complex [Au2(C2C6H4-4-COONC4H4O2)2PPh2C6H4PPh2] (Fig.2). In a solution of 0.15 mmol of 1,4-bis(diphenylphosphino)benzene in 5 ml of dichloromethane was added 0.32 mmol [AuC2C6H4-4-COONC4H4O2] and stirred until complete dissolution of the precipitate, then added 2.5 ml of toluene, after which the solution was passed through a column of neutral alumoweld and drove the solvent. Yield 65%.

The complex [Au6Cu2(C2C6H4-4-COONC4H4O2)6(PPh2C6H4PPh2)3](PF6)2(Fig.3) (1)

To a solution of 0.33 mmol [Au2(C2C6H4-4-COONC4H4O2)2PPh2C6H4PPh2] 3 m is dichloromethane was added 0.22 mmol [Cu(NCMe) 4]PF6and stirred the reaction mixture before formation of yellow-orange solution, then this solution will pass through celite, drove the solvent and recrystallized by the method of vapor diffusion of pentane in acetone. Yield 81%.31P NMR (D[6]-acetone): 44.4 (C, 6), -144.8 (cept 2P, PF6I , JPF712 Hz). 1H NMR (D[6]-acetone): 8.00 (DM, JHH=7.2 Hz, JPH13 Hz, 24N, H-ortho), 7.85 (m, N, {P-C6H4-P}), 7.67 (t, JHH7.4 Hz, N, N-pair), 7.51 (DD, JHH7.4 Hz, 24N, H-meta), 7.56 (d, JHH8.3 Hz, N, C6H4), 7.05 (d, JHH8.3 Hz, N, C6H4), 2.95 (s, 24N, CH2CH2). ESI-mass spectrum (m/z): 2060 (M2+).

Example 2.

Complexsynthesized as described in example 1, using 1-ethinyl-4-isothiocyanatobenzene as acetylene ligand.

31P NMR (D[6]-acetone): 44.6 (C, 6), -144.8 (cept 2P, PF6I , JPF712 Hz). 1H NMR (D[6]-acetone): 7.87 (DM, JHH=7 Hz, JPH=13 Hz, 24N, ortho-H), 7.58 (m, 24N, {P-C6H4-P}, para-H), 7.41 (m, 24N, meta-H), 6.67 (d, JHH=7.4 Hz, N,6H4), 6.56 (s, JHH=7.4 Hz, N,6H4).

Example 3.

Complexsynthesized as described in example 1, using 4-ethynylbenzaldehyde as acetylene ligand.

31P NMR (D[6]-acetone): 44.9 (C, 6), -144.8 (cept 2P, PF6I , JPF712 is). 1H NMR (D[6]-acetone): 9.83 (s, 6N, SNO), 8.02 (DM, JHH=7.2 Hz, JPH14 Hz, 24N, H-ortho), 7.88 (m, N, {P-C6H4-R}), 7.67 (t, JHH7.4 Hz, N, N-pair), 7.49 (DD, JHH7.4 Hz, 24N, H-meta), 7.35 (d, JHH8.4 Hz, N, C6H4), 7.02 (d, JHH8.4 Hz, N,6H4).

For complexes (1)-(3) were measured photophysical properties, namely at room temperature were measured by the electronic absorption spectra and luminescence spectra and the lifetimes of excited States and quantum yields of luminescence (table 1). Compounds (1) to(3) show high quantum yields of luminescence and the lifetimes of luminescence in the range of 2.4-3.3 µs, similar to the prototype.

Table 1
Photophysical properties of complexes
ConnectionSolventλwillnmλsosbudnmλEmissnmτ, microsecQuantum yield, %
12345 67
(1)CH2Cl2265, 300 dps, 317, 350 dps, 409330, 350 dps, 4085703.350
Acetone353 sq, 408331, 4145803.0
Borate buffer265, 348, 412300, 330, 4035800.5 (36%), 3.4 (64%)
1234567
(2)CH2Cl2267, 316, 355 sq, 410310, 345, 4075962.423
(3)CH2Cl2266, 324, 338 sq, 360, 414265, 335, 358 is l, 4115842.554

It was demonstrated that the complexes (1)-(3) are able to form covalent conjugates with proteins. Synthesis of conjugates was carried out in 0.01 M Na-borate buffer solution, pH 8.4, for 1 hour. Removing unbound label was carried out by gel-chromatography using as the stationary phase gel Sephadex-G75. Table 2 presents the results of retrieval of conjugates of proteins, namely soybean trypsin inhibitor (CITR), serum albumin human (CSA), antibodies to CSA. While the resulting conjugates are soluble in water and buffer solutions, in contrast to the original labels.

Table 2
Molar ratio of protein/complex in the formation of conjugates
ProteinThe molar ratio of protein/complex taken to obtain conjugateThe molar ratio of protein/complex in the resulting conjugate
(1)(2)(3)
SITR 1:31.0:1.31.0:2.11.0:1.7
SITR1:51.0:1.91.0:3.21.0:2.9
CSA1:31.0:1.31.0:1.81.0:1.8
CSA1:51.0:2.11.0:3.21.0:3.3
Antibodies to CSA1:51.0:2.61.0:3.31.0:3.0
Antibodies to CSA1:71.0:3.41.0:4.51.0:4.0
Antibodies to CSA1:101.0:4.81.0:6.71.0:6.0

In the formation of covalent conjugates with proteins luminescence spectra of the labels are virtually unchanged. For example, in Fig.4 presents the spectra of the luminescence of the free complex (1) and its conjugates with protein is I. In Fig.4: 1 complex (1) in acetone, 2 - conjugate 1 CSA in borate buffer, 3 - conjugate 1-antics in borate buffer and 4 - conjugate 1-SITR in borate buffer.

As for the labels of the prototypes, the luminescence of the complexes (1)-(3) does not undergo a substantial reduction in the presence of oxygen. For example, in Fig.5 shows luminescence spectra of the conjugate (1) with CSA in degassed (curve 1) and aerated (curve 2) solutions.

Proteins in the formation of conjugates with complexes also maintain their structure and biological activity, as was demonstrated on the example of the formation of the specific complex of trypsin-trypsin inhibitor" model and hydrolysis by trypsin specific substrate 4-nitroaniline N-benzoyl-L-tyrosine in the presence of native SITR and SITR labeled complexes (1)-(3). The inhibition constants were determined by the method of Dixon and is presented in table 3.

Table 3
The inhibition constants when using SITR and its conjugates with complexes
The form of the inhibitorThe inhibition constant (Ki), nm
Native SITR88
Conjugate SITR complex (1)220
Conjugate SITR complex (2)160
Conjugate SITR complex (3)145

Of Michaelis constant and the specific activity of the enzyme hydrolysis are presented in table 4.

Table 4
The specific activity and Michaelis constants for enzymatic hydrolysis in the presence of SITR and its conjugates with complexes
Enzymatic hydrolysisThe Michaelis constant (KMmm)Specific activity, µmol/(min·mg)
Without inhibitor0.371.01
In the presence of SITR0.340.54
In the presence of conjugate0.360.62
SITR with complex (1)
In the presence of conjugate 0.350.58
SITR with complex (2)
In the presence of conjugate0.340.56
SITR with complex (3)

The data obtained indicate that covalent attachment (1)-(3) to the protein does not interfere with specific binding affinity partner.

Technical and economic efficiency of the claimed invention is, as shown by the results of the above examples of specific implementations in a significant expansion of the scope of the claimed complexes as labels for fluorescence microscopy due to the possibility of protein binding. Important in the present invention is the preservation of the luminescence intensity in the presence of molecular oxygen.

The claimed complexes exhibit luminescence with high quantum yield and microsecond lifetimes. The luminescence of the complexes is not exposed to significant quenching by oxygen of air, i.e. the claimed complexes exhibit luminescence characteristics not worse than the prototype. A significant advantage of the proposed set is xov compared with the prototype is they are able to form covalent conjugates with proteins, moving in water-soluble form. If this is not observed any significant changes in the luminescence of the complex, no loss of protein biological activity, which allows the use of these complexes as specific labels in fluorescent analysis and fluorescence microscopy.

The list of the used sources of information

1. K. K.-W. Lo, A. W.-T. Choi, W. H.-T. Law. // Dalton Trans. 2012. V. 41. P. 6021-6047; Q. Zhao, C. Huang, F. Li. // Chem. Soc. ReV. 2011. V. 40. P. 2508-2524; V. Fernandez-Moreira, F. L. Thorp-Greenwood, M. P. Coogan. // Chem. Commun. 2010. V. 46. P. 186-202; K. L. Haas, K. J. Franz. // Chem. Rev. 2009. V. 109. P. 4921-4960; F. L. Thorp-Greenwood. // Organometallics 2012. V. 31. P. 5686-5692.

2. E. Ferri, D. Donghi, M. Panigati, G. Prencipe, L. D'alfonso, I. Zanoni, C. Baldoli, S. Maiorana, G. D'alfonso, E. Licandro. // Chem. Commun. 2010. V. 46. P. 6255-6257; K. W. Hubel, B. E. Henri // US 3280017 (A) 1966-10-18], iridium [D.-L. Ma, H.-J. Zhong, W.-C. Fu, D. S.-H. Chan, H.-Y. Kwan, W.-F. Fong, L.-H. Chung, C.-Y. Wong, C.-H. Leung. // PLoS ONE 2013. V. 8. P. e55751], platinum [D. R. McMillin, J. J. Moore. // Coordination Chemistry Reviews 2002. V. 229. P. 113-121; J. F. Hainfeld, F. R. Furuya, R. D. Powell // US 2005130207 (A1) 2005-06-16], and also complexes of lanthanides [S. Mizukami, T. Yamamoto, A. Yoshimura, S. Watanabe, K. Kikuchi. // Angew. Chem. Int. Ed. 2011. V. 50. P. 8750-8752; K. N. Raymond, S. Petoud, S. Cohen, J. Xu // EP 1154991 (A1) 2001-11-21.

3. Koshevoy I. O., etc. Intensely luminescent alkynyl - Phosphine Gold(l)-Copper(l) complexes: Synthesis, characterization, photophysical and computational studies // Inorg. Chem. 2009. T. 48. No. 5. S. 2094-2102 (prototype).

1. Alkylphosphine gold-copper complexes dissociate in solution with ions

as fluorescent labels for fluorescence microscopy.



 

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