Corrigendum to “Discovery of benzofuran propanoic acid GPR120 agonists: From uHTS hit to mechanism-based pharmacodynamic effects” [Bioorg. Med. Chem. Lett. 26 (2016) 5724–5728](S0960894X16310927)(10.1016/j.bmcl.2016.10.054);Discovery of benzofuran propanoic acid GPR120 agonists: From uHTS hit to mechanism-based pharmacodynamic effects

Bioorganic and Medicinal Chemistry Letters

Volumn 26, Issue 23, 2016, Pages 5724-5728

  Lombardo, Matthew ^a   Bender, Kate ^a   London, Clare ^a   Kirkland, Melissa ^a   Mane, Joel ^a   Pachanski, Michele ^a   Geissler, Wayne ^a   Cummings, John ^a   Habulihaz, Bahanu ^a   Akiyama, Taro E ^a   Di Salvo, Jerry ^a   Madeira, Maria ^a   Pols, Joanna ^a   Powles, Mary Ann ^a   Finley, Michael F ^a   Johnson, Eric ^a   Roussel, Thomas ^a   Uebele, Victor N ^a   Crespo, Alejandro ^a   Leung, Dennis ^a   Alleyne, Candice ^a   Trusca, Dorina ^a   Lei, Ying ^a   Howard, Andrew D ^a   Ujjainwalla, Feroze ^a   Tata, James R ^a   Sinz, Christopher J ^a   more..

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Aryloxybutanoic acid; Benzofuran propanoic acid; FFAR4; GPR120; Type 2 diabetes; Ultra high throughput screening

Indexed keywords

AGENTS INTERACTING WITH TRANSMITTER, HORMONE OR DRUG RECEPTORS; BENZOFURAN DERIVATIVE; G PROTEIN COUPLED RECEPTOR 120; PROPIONIC ACID DERIVATIVE; ANTIDIABETIC AGENT; G PROTEIN COUPLED RECEPTOR; GLUCOSE BLOOD LEVEL; O3FAR1 PROTEIN, HUMAN; PROPIONIC ACID;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG EFFICACY; DRUG SYNTHESIS; EC50; FEMALE; HIGH THROUGHPUT SCREENING; HORNER WADSWORTH EMMONS REACTION; HYDROGENATION; HYDROLYSIS; IC50; IN VIVO STUDY; MOUSE; NONHUMAN; ORAL GLUCOSE TOLERANCE TEST; PLASMA CLEARANCE; STRUCTURE ACTIVITY RELATION; SUZUKI REACTION; AGONISTS; ANALYSIS; ANIMAL; BLOOD; CHEMISTRY; DIABETES MELLITUS, TYPE 2; GLUCOSE BLOOD LEVEL; HUMAN; METABOLISM; PRECLINICAL STUDY;

ANIMALS; BENZOFURANS; BLOOD GLUCOSE; DIABETES MELLITUS, TYPE 2; DRUG EVALUATION, PRECLINICAL; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; HYPOGLYCEMIC AGENTS; MICE; PROPIONATES; RECEPTORS, G-PROTEIN-COUPLED;

EID: 84996564417     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2017.01.082     Document Type: Erratum

References (31)

1. [1] Olokoba, A.B., Obateru, O.A., Olokoba, L.B., Oman Med. J., 27, 2012, 269.
2. [2] Alberti, K.G.M.M., Zimmet, P.Z., Diabet. Med., 15, 1998, 539.
3. [3] Lau, D.C.W., Canadian J. Diabetes, 35, 2011, 314.
4. [4] Halder, S., Kumar, S., Sharma, R., Expert Opin. Ther. Patents, 23, 2013, 1581.
5. [5] Sun, Q., Hirasawa, A., Hara, T., Kimura, I., Adachi, T., Awaji, T., Isgiguro, M., Suzuki, T., Miyata, N., Tsujimoto, G., Mol. Pharmacol., 78, 2010, 804.
6. [6] Ulben, T., Christiansen, E., Annu. Rev. Nutr., 35, 2015, 239.
7. [7](a) Oh, D.Y., Talukdar, S., Bae, E.J., Imamura, T., Morinaga, H., Fan, W., Li, P., Lu, W.J., Watkins, S.M., Olefsky, J.M., Cell, 142, 2010, 687.
8. [7](b) Ichimura, A., Hirasawa, A., Poulain-Godefroy, O., Bonnefond, A., Hara, T., Yengo, L., Kimura, I., Leloire, A., Liu, N., Iida, K., Choquet, H., Besnard, P., Lecoeur, C., Vivequin, S., Ayukawa, K., Takeuchi, M., Ozawa, K., Tauber, M., Maffeis, C., Morandi, A., Buzzetti, R., Elliott, P., Pouta, A., Jarvelin, M.-R., Körner, A., Kiess, W., Pigeyre, M., Caiazzo, R., Van Hul, W., Van Gaal, L., Horber, F., Balkau, B., Lévy-Marchal, C., Rouskas, K., Kouvatsi, A., Hebebrand, J., Hinney, A., Scherag, A., Pattou, F., Meyre, D., Koshimizu, T.-A., Wolowczuk, I., Tsujimoto, G., Froguel, P., Nature, 483, 2012, 350.
9. [7](c) Oh, D.Y.Oh., Walenta, E., Akiyama, T.E., Lagakos, W.S., Lackey, D., Pessentheiner, A.R., Sasik, R., Hah, N., Chi, T.J., Cox, J.M., Powles, M., Di Salvo, J., Sinz, C.J., Watkins, S.M., Armando, A.M., Chung, H., Evans, R.M., Quehenberger, O., McNelis, J., Bogner-Strauss, J.G., Olefsky, J.M., Nat. Med., 20, 2014, 942.
10. [8](a) Shimpukade, B., Hudson, B.D., Hovgaard, C.K., Milligan, G., Ulven, T., J. Med. Chem., 55, 2012, 4511.
11. [8](b) Sparks, S.M., Chen, G., Collins, J.L., Danger, D., Dock, S.T., Jayawickreme, C., Jenkinson, S., Laudeman, C., Leesnitzer, M.A., Liang, X., et al. Bioorg. Med. Chem. Lett., 24, 2014, 3100.
12. [8](c) Winters, M.P., Lanter, J., Wall, M.J., Sui, Z., Leonard, J., Gunnet, J., Wang, Y., Hua, H., Yan, W., Suckow, A., et al. Abstract of papers. 250th ACS National Meeting & Exposition, Boston, MA, 2015, American Chemical Society, Washington, DC Abstract 478.
13. [8](d) Zhang, X., Cai, C., Sui, Z., Macielag, M.J., Wang, Y., Yan, W., Suckow, A., Hua, H., Bell, A., Haug, P., et al. Abstract of papers. 250th ACS National Meeting & Exposition, Boston, MA, 2015, American Chemical Society, Washington, DC Abstract 472.
14. [8](e) Zhang, X., Cai, C., Winters, M.P., Sui, Z., Wang, Y., Yan, W., Jenkinson, C., Gunnet, J., Leonard, J., Murray, W.V., Abstract of papers. 250th ACS National Meeting & Exposition, Boston, MA, 2015, American Chemical Society, Washington, DC Abstract 471.
15. [8](f) Subasinghe, N.L., Lanter, J., Lawson, E.C., Sui, Z., Wang, Y., Gunnet, J., Hua, H., Suckow, A., Jenkinson, C., Haug, P., et al. Abstract of papers. 250th ACS National Meeting & Exposition, Boston, MA, 2015, American Chemical Society, Washington, DC Abstract 138.
16. [9] During the preparation of this manuscript, a patent claiming related chemical matter appeared, Kim, Y. K.; Park, S. Y.; Joo, H. W.; Choi, E. S. U.S. Patent US2016/168096 (A1), 2016.
17. [10](a) For recent reviews of GPR120 pharmacology, please see:Talukdar, S., Olefsky, J.M., Osborn, O., Trends Pharmacol. Sci., 32, 2011, 543.
18. [10](b) Zhang, D., Leung, P.S., Drug Des. Dev. Ther., 1013, 2014, 8.
19. [10](c) Cornall, L.M., Mathai, M.L., Hryciw, D.H., McAinch, A.J., Drug Discovery Today, 19, 2014, 670.
20. [10](d) For a recent chemical review of GPR120, please see.Milligan, G., Shimpukade, B., Ulven, T., Hudson, B.D., Chem. Rev., 2016, 10.1021/acs.chemrev.6b00056 published online June 14.
21. [11](a) Itoh, Y., Kawamata, Y., Harada, M., Kobayashi, M., Fujii, R., Fukusumi, S., Ogi, K., Hosoya, M., Tanaka, Y., Uejima, H., Tanaka, H., Maruyama, M., Satoh, R., Okubo, S., Kizawa, H., Komatsu, H., Matsumura, F., Noguchi, Y., Shinohara, T., Hinuma, S., Fujisawa, Y., Fujino, M., Nature, 422, 2003, 173.
22. [11](b) Stoddart, L.A., Brown, A.J., Milligan, G., Mol. Pharmacol., 71, 2007, 994.
23. [12] All compounds were tested at 5 μM concentration. The primary and confirmation screen utilized Fluo-4 calcium detection on the FLIPR Tetra in 1536-well format. For the primary and confirmation screen, a CHO-NFAT cell line stably expressing human GPR120 was used. From the 1.9 million compounds screened, a 3-sigma cut off by plate, row and column resulted in 42337 compounds. A counter screen utilizing wild-type CHO-K1 cells on the FLIPR Tetra was performed. Hits were then selected based upon confirmed agonist activity in hGPR120 (>11% activation) and <10% activation in wild-type CHO-K1 cells. Based on these criteria, 5516 compounds were tested at 8 different concentrations in three assays: the Fluo-4 calcium detection assay used in the primary and confirmation screen, an HTRF IP1 detection assay and a DiscoveRx PathHunter assay (both measured on ViewLux). All three concentration-response assays were performed in triplicate. Compounds active in all 3 assays were further filtered and ∼390 compounds were characterized. From the hits ultimately generated, one of the hits was compound 1.
24. 50 were determined for each test compound.
25. [14] (a) Mouse PK experiment details for compound 1 are as follows: iv dose: 2 mg/kg (n = 2), formulation: 0.5 mg/mL EtOH:PEG:water (10:40:50); po dose: 10 mg/kg (n = 3), formulation: 1.0 mg/mL EtOH:PEG:water (10:40:50). (b) Mouse PK experiment details for compound 6 are as follows: iv dose: 2 mg/kg (n = 3), formulation: 0.5 mg/mL EtOH:PEG:water (10:40:50); po dose: 10 mg/kg (n = 3), formulation: 1.0 mg/mL EtOH:PEG:water (10:40:50). (c) Mouse PK experiment details for compounds 23 and 37 are as follows: iv dose: 2 mg/kg (n = 3), formulation: 0.5 mg/mL EtOH:PEG:water (10:40:50); po dose: 10 mg/kg (n = 3), formulation: 2.0 mg/mL EtOH:PEG:water (10:40:50).
26. [15](a) Miyaura, N., Suzuki, A., Chem. Rev., 95, 1995, 2457.
27. [15](b) Walker, S.D., Barder, T.E., Martinelli, J.R., Buchwald, S.L., Angew. Chem. Int. Ed., 2004, 1871, 43.
28. [16](a) Horner, L., Hoffman, H., Wippel, H.G., Klahre, G., Chem. Ber., 92, 1959, 2499.
29. [16](b) Wadsworth, W.S. Jr., Emmons, W.D., J. Am. Chem. Soc., 83, 1961, 1733.
30. [17] Andrikopoulos, S., Blair, A.R., Deluca, N., Fam, B.C., Proietto, J., Am. J. Physiol. Endocrinol. Metab., 295, 2008, 1323.
31. 50 = 43 nM). Estimated target engagement is as follows: 30 mpk: 40% target engagement, 100 mpk: 68% target engagement.