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1 Chloromethylhalicyclamine B, a Marine-Derived Protein Kinase CK1δ/ε Inhibitor Germana Esposito, Marie-Lise Bourguet-Kondracki, * Linh H. Mai, Arlette Longeon, Roberta Teta, Laurent Meijer, Rob Van Soest, Alfonso Mangoni, Valeria Costantino * Laboratoire Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS, Muséum National d Histoire Naturelle, 57 rue Cuvier (C.P. 54), Paris, France The NeaNat Group, Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, via D. Montesano 49, Napoli, Italy ManRos Therapeutics, Perharidy Research Center, Roscoff, France Naturalis Biodiversity Center, P.O. Box 9517, 2300 RA Leiden, The Netherlands Table of contents Supporting Information Table S1. Activity of compounds 1 and 2 against a panel of 14 kinases.... S2 Figure S1. Inhibition of CK1δ/ε by compound 1... S2 Figure S2. Average interproton distances and NOEs of compound 1... S3 1 H-NMR spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)... S4 DEPTQ spectrum of chloromethylhalicyclamine B (1) (150 MHz, CD 3 OD)... S5 COSY spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)... S6 NOESY spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)... S7 HSQC spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)... S8 HMBC spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)... S9 Table S1. Cartesian coordinates of the 20 lowest-energy conformers of 1 in the CFF91 force field.... S10
2 S2 Table S1. Activity of compounds 1 and 2 against a panel of 14 kinases. IC 50 (μm) Compound 1 Compound 2 CDK2/cyclin A inactive a not tested CDK5/p25 inactive a inactive a CDK9/cyclin T inactive a inactive a CK1δ/ε 6 μm inactive a LmCK1 inactive a not tested CLK1 inactive a inactive a CLK2 inactive a not tested CLK3 inactive a not tested CLK4 inactive a not tested DYRK1A inactive a inactive a DYRK1B inactive a not tested DYRK2 inactive a not tested DYRK3 inactive a not tested GSK3 inactive a inactive a a Not significantly active at 10 μm Figure S1. Inhibition of CK1δ/ε by compound 1. Data are expressed as SD of mean (n = 2).
3 S3 Figure S2. Average interproton distances for compound 1 calculated by a molecular dynamics simulation, and NOEs detected from the NOESY spectrum. Because of chemical shift degeneracy, NOESY cross peaks were assigned in an iterative process: only unambiguous NOESY peaks were used at the initial stage to validate the interproton distances generated by MD calculations; after this, average distances themselves were used as a guide to assign the ambiguous NOESY peaks. Only calculated distances < 3.5 Ǻ are shown in the table. The table is color coded. Distances between geminal protons are in blue digits; distances between vicinal protons are in red digits; distances between distal protons are in black digits; distances > 3.5 Ǻ between protons showing NOE are in white digits. A light blue background indicates the presence of NOE. A pink background indicates that the presence (or absence) of NOE was not experimentally accessible, either because the protons involved have very close chemical shifts, or because the correlation would be overlapped with a very strong geminal NOE. A yellow background indicates absence of NOE with a calculated interproton distance < 3.0 Ǻ.
4 S4 1 H-NMR spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)
5 S5 DEPTQ spectrum of chloromethylhalicyclamine B (1) (150 MHz, CD 3 OD)
6 S6 COSY spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)
7 S7 NOESY spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)
8 S8 HSQC spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)
9 S9 HMBC spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)
10 S10 Table S1. Cartesian coordinates of the 20 lowest-energy conformers of 1 in the CFF91 force field Conformer #1 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
11 S11 Conformer #2 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
12 S12 Conformer #3 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
13 S13 Conformer #4 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
14 S14 Conformer #5 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
15 S15 Conformer #6 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
16 S16 Conformer #7 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
17 S17 Conformer #8 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
18 S18 Conformer #9 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
19 S19 Conformer #10 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
20 S20 Conformer #11 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
21 S21 Conformer #12 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
22 S22 Conformer #13 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
23 S23 Conformer #14 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
24 S24 Conformer #15 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
25 S25 Conformer #16 Energy: kcal/mol N C C C C C C C Cl C C H C C N C C C C C C H C H C C C C C C C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H
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