Structural insights into xenobiotic and inhibitor binding to human Aldehyde Oxidase
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1 Suppementary Information Structura insights into xenobiotic and inhibitor binding to human Adehyde Oxidase Catarina Coeho 1, Aessandro Foti 2, Tobias Hartmann 2, Teresa Santos-Siva 1, Sike Leimküher 2 and Maria João Romão 1 1 UCIBIO@REQUIMTE Departamento de Química, Facudade de Ciências e Tecnoogia, Universidade Nova de Lisboa, Caparica, Portuga 2 Institute of Biochemistry and Bioogy, Department of Moecuar Enzymoogy, University of Potsdam, D Potsdam, Germany
2 Suppementary Tabe1: PDB identification of the 31 XO and XDH structures anayzed. PDB ID Xanthine Oxidase (XO) Xanthine Dehydrogenase (XDH) 1FIQ; 3EUB; 3AX7; 3NVY; 3NVW; 3ETR; 3NVZ; 3NRZ; 3B9J; 3NVV; 3NS1; 2CKJ; 1SB3; 1RM6; 2E3T; 3SR6; 3AMZ; 3AX9; 2E1Q. 1FO4; 3UNI; 3UNA; 3AM9; 3UNC; 1WYG; 3BDJ; 1N5X; 1VDV; 1V97; 3AN1; 2W54.
3 Suppementary Tabe2: Data coection and refinement statistics -Pht-Thi Data coection Space group P Ce dimensions a = b, c (Å) , , Resoution (Å) ( ) ( ) R merge 0.18 (2.73) 0.08 (1.08) I / s(i) (1.50) (1.60) Competeness (%) (100.00) (98.70) Redundancy (15.80) (6.50) Refinement Resoution (Å) No. refections (4476) (4556) R work / R free 18.8 / / 24.4 No. atoms Protein Ligand/ion Water B-factors Protein Ligand/ion Water R.m.s. deviations Bond engths (Å) Bond anges ( ) *Vaues in parentheses are for highest-resoution she
4 FAD I440 T1230 Q1235 Q430 FeSII :430QAQRQENALAI440 :430QAPRQQNAFAT440 bxo/bxdh:423qasrreddiak433 bxo/bxdh:423**s*::::i*k433 FAD Variabe oop Suppementary Figure1: Superposition of (4uhw, in bue), (3zyv, in gray), bxo (1fiq, in pink) and bxdh (1fo4, in orange) crysta structures at the FAD binding site, viewed from the sovent. The FAD and the FeS II are represented coor-coded and correspond to the crysta structure. Note the drastic change in the oop T1230-Q1235 ( numbering) when comparing to and bxo/bxdh proteins.
5 Thi-A Thi-B (R)-thioridazine (S)-thioridazine Suppementary Figure2: Bottom view of the surface representation of the homodimer highighting the inhibitor thioridazine binding pocket. Thioridazine is represented in space-fiing-mode. At the bottom, the eectron density of thioridazine is contoured at 1σ in the 2mFo DFc eectron density map of the compex.
6 S100B_Ch (3k0) MALT1_Thi (4i1r) Pim1_Thi (4iaa) PrP_Ch (4ma8) _Ph_Thi (4uhx, this work) P450_Thi (substrate) (4wnw) Suppementary Figure3: Structures of compexes with phenothiazine-reated drugs, reported in the PDB (top to bottom, eft to right): Compexes with inhibitors: S100B-p53 31 with chorpromazine (3k0); caspase-ig3 (human MALT1 compexed with Thi, (4i1r) 30, Ser/Thr kinase Pim1 with thioridazine (4iaa), prion protein PrP with chorpromazine (4ma8) 26, _Ph_Thi (4uhx, this work). Compex with substrate: Cytochrome P450 with thioridazine 32 (4wnw).
![1/V 1/Vmax app 1/V 1/V Intercept (1/Vmax ) a) 0.01 0-4 0 4 8 12 16 20 [ thioridazine] μm 0.4 0.3 0.2 0.1 0-0.4-0.2 0 0.2 0.4 0.6 0.8 1-0.1 1/[phthaazine] (μm -1 ) -0.2 1/Vmax app b) 0.15 0.05 0.04 0.](/docs-images/94/120788271/images/7-0.jpg "03 0.1 0.01 0-20 -10 0 10 20 0.05 [ thioridazine] μm 0-0.2-0.15-0.1-0.05 0 0.05 0.1 0.15 0.2 1/[phthaazine] (μm -1 ) -0.05 c) 0.14 5 0.12 0.1 0.08 0.015 0.06 0.01 0.04 0.")
7 1/V 1/Vmax app 1/V 1/V Intercept (1/Vmax ) a) [ thioridazine] μm /[phthaazine] (μm -1 ) /Vmax app b) [ thioridazine] μm /[phthaazine] (μm -1 ) c) [ thioridazine] μm bxo /[xanthine] (μm -1 ) d) :570IGPKQHPEDPIG ( ) IQVVSRELRMPMSNVHLRGTS1076 :570VDFQQPLQDPIG ( ) IQVASRELKIPMSYIHLDEMS1072 e) I570 G580 L1063 bxo:563vpngqskedtvg ( ) VQVASKALKIPISKIYISETS1067 bxo:563:xxx*xx:*::* ( ) :**:*::*::*:*K:::S::* Suppementary Figure4: Kinetics of phthaazine-thioridazine inhibition of (a), (b) and xanthine-thioridazine inhibition of bxo (c). Lineweaver-burk pots for substrate-eectron acceptor reaction of, and bxo in the presence of thioridazine. a) inhibition of μm using 1, 1.5, 2.5, 3.75, 5, 10, 20, 40 µm phthaazine and 0.1, 0.5, 1, 2.5, 5, 7.5, 10, 15 μm thioridazine in the presence 1 mm ferricyanide as eectron acceptor. Inset: the Ki vaue was obtained from the secondary pot of the apparent 1/Vmax of the Linewaever-Burk pot. b) inhibition of µm using 1, 5, 10, 20, 40 µm phthaazine and 1, 5, 10, 15, 25 μm of thioridazine in the presence 1 mm ferricyanide as eectron acceptor. Inset: the Ki vaue was obtained from the secondary pot of the apparent 1/Vmax of the Linewaever-Burk pot. c) inhibition of 0.1 µm bxo using using 5, 10, 25, 10, 200 µm xanthine and 10, 25, 35, 50 μm thioridazine in the presence of moecuar oxygen as eectron acceptor. Inset: the K i and K ii vaues were obtained from the secondary pot of the sope apparent 1/Vmax of the Linewaever-Burk pot, respectivey. Data are mean vaues from three independent measurements (± S.D.) Aignment of the residues constituting the thioridazine binding pocket (d) and structure of the surrounding region for (4uhx, in bue), (3zyv, in grey) and bxo (1fo4, in pink) (e).
8 GATE GATE Suppementary Figure5: Comparison of the amino acid sequence of human AOX1 and mouse AOX1, AOX3, AOX2 and AOX4 proteins. The Gate 1 and Gate 2 are highighted in a red box and the important active site residues are marked in orange. The aignment was created with using the custaw2 server and represented using the Jaview program.
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