Intensity ion fading SALDI MS approach for searching inhibitors of tyrosinase in complex mixtures
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1 Université d'orléans Institut de Chimie Organique et Analytique Intensity ion fading SALDI MS approach for searching inhibitors of tyrosinase in complex mixtures Aleksander Salwiński Prof. Benoit Maunit, Prof. Raphaël Delépée 29 èmes Journées Françaises de Spectrométrie de Masse, sept. 2012, Orléans (France)
2 General outlook of the new approach 1 st step: finding prospective inhibitors extraction PLANT EXTRACT (PE) No pretreatment Enzyme coupled nanoparticle assisted LDI (ENALDI) experiment active enzyme comparison denaturated enzyme Finding the inhibitor candidate 3 rd step: characterisation of the inhibitor: determination its structure, enzymatic test: K I, type of inhibition 2 nd step: PE separation in LC/MS mode; searching for the peak of prospective inhibitor on the chromatogram and its purification SA 1 [min mg μmol 1 ] 3.2E+00 [KA] = 0 um [KA] = 11 um 2.7E+00 [KA] = 21 um 2.2E E E E E E E 01 E E E 02 C 1 L Tyr [um 1 ] Intens. [mau] Time [min] X004285AS.d: UV Chromatogram, 280 nm X004285AS.d: EIC ±1 -All MS X004285AS.d: EIC ±1 -All MS 22 23
3 Enzyme coupled nanoparticle assisted LDI (ENALDI) principle EtOH Tyrosinase active/denaturated Denaturated enzyme (control) non interacting compounds substrate inhibitor product Active enzyme binding/drying drying LASER shot denaturation on the MALDI spot after drying by deposition 0.1% FA = release of previously bound ligand
4 s characterisation Stability: Relative activity 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% days after the immobilization -s-tyrosinase Free tyrosinase Free tyrosinase looses 55% of the initial activity within approx days [1,2] when stored at 4 C. s immobilized tyrosinase looses 55% of initial activity up to days. Protein binding capacity: 245 mg of BSA/g of s [1] A.M. Girelli, E. Mattei, A. Messina, D. Papaleo, Sensors and Actuators B, 2007,125, [2] M. Y. Arıca, G. Bayramoglu, N. Bıçak, Process Biochemistry, 2004,39,
5 Enzyme coupled nanoparticle-assisted LDI (ENALDI) highligts LASER shot On a single spot: Total amount of s: 3.47 µg; amount of tyrosinase enzyme bound to s: approx. 800 ng (6.5 pmol); amount of plant extract (equivalent of dry mass of plant powder): ng; Dual function of magnetic nanoparticles: enzyme carrier; energy absorber: nanoparticle assisted ionization is believed to be generated by heat released upon the laser shot Experimental: Bruker Autoflex with MTP 384 standard target plate (polished steel) number of LASER shots: 300 MS spectra collected in a negative mode
6 Exemplary ENALDI spectra of raw aqueous extract of licorice (Glycyrrhiza glabra) root Intens. [a.u.] x CO s-denaturated tyrosinase x Intens. [a.u.] x s-active tyrosinase x significant drop of the ion response for and ions
7 Enzyme coupled nanoparticle assisted LDI (ENALDI) principle EtOH Tyrosinase active/denaturated Denaturated enzyme (control) non interacting compounds substrate product inhibitor Active enzyme binding/drying drying LASER shot denaturation on the MALDI spot after drying by deposition 0.1% FA = release of previously bound ligand
8 Exemplary ENALDI spectra of raw aqueous extract of licorice (Glycyrrhiza glabra) root Intens. [a.u.] x Td_reg_300_25LP 0:C7 MS Raw s denaturated tyrosinase Intens. [a.u.] 0 x Ta_reg_300_25LP 0:C4 MS Raw s active tyrosinase Inten s. [a.u.] 0 x Ta_reg_acid_300_25LP 0:C10 MS Raw s active tyrosinase (desorption) re appearance of the ion [M H] : after treatment of s with 0.1% solution of formic acid directly on the spot
9 Statistical description of the data S/N is calculated as the ratio of the intensity of given peak and the adjacent baseline Student s t test p >= 5% (S/N not significantly different) p < 5% and p >= 1% (S/N significantly different) p < 1% (S/N highly significantly different) S/N DENATURATED ACTIVE (a) (b) DENATURATED ACTIVE Raw aqueous extract of licorice 4.0 S/N Raw methanol extract of licorice
10 Searching for the inhibitor S/N DENATURATED ACTIVE? 1.0 Isoliquiritigenin, known tyrosinase inhibitor [1] Liquiritin apioside Liquiritigenin Isoviolanthin L tyrosine [1] J Agric Food Chem. 2003, 51, Licuraside
11 Structural identification of the inhibitor DENATURATED ACTIVE Intens. [mau] S/N PE separation in LC/MS mode; localizing the inhibitor candidate; purification Time [min] X004285AS.d: UV Chromatogram, 280 nm X004285AS.d: EIC ±1 -All MS X004285AS.d: EIC ±1 -All MS Structure identification by NMR study ( 1 H, 13 C, HSQC, COSY) R H O 11
12 Kinetic test of purified compound [Inh] = 0 um 1.4 [Inh] = 260 um 1.2 [Inh] = 649 um C 1 L Tyr [um 1 ] SA 1 [min mg μmol 1 ] K I = 291 μm 12
13 Conclusions Advantages of ENALDI approach: simplified study of complex extracts (no pre treatment, purification is limited to prospective inhibitors, no laborious fractionation required); high stability of s (45% of initial activity after 80 days of storage in 4 C); high homogeneity of the sample: no sweet spots on the MALDI plate; possibility to distinguish substrate and inhibitor; magnetic properties of beads: easy purification, no centrifuge required; low protein consumption per analysis (approx. 6.5 pmol) Further development improvement of S/N ratio in low mass range
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