Discovery of novel, high potent, ABC type PTP1B inhibitors with TCPTP selectivity and cellular activity

European Journal of Medicinal Chemistry

Volumn 118, Issue , 2016, Pages 27-33

  Liu, Peihong ^a   Du, Yongli ^a   Song, Lianhua ^a   Shen, Jingkang ^b   Li, Qunyi ^c  

^a QILU UNIVERSITY OF TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^c FUDAN UNIVERSITY   (China)

Author keywords

ABC type PTP1B inhibitor; Methyl salicylate derivatives; Type 2 diabetes mellitus

Indexed keywords

2 BENZYLOXY 5 [[4 (METHANESULFONYLMETHOXYCARBONYLMETHYL AMINO) BENZYL] PHENYLMETHANESULFONYL AMINO] BENZOIC ACID METHYL ESTER; 2 BUTOXY 5 [[4 (METHANESULFONYL METHOXYCARBONYLMETHYL AMINO) BENZYL] PHENYLMETHANESULFONYL AMINO] BENZOIC ACID METHYL ESTER; 2 ETHOXY 5 [[4 (METHANESULFONYL METHOXYCARBONYLMETHYL AMINO) BENZYL] PHENYLMETHANESULFONYL AMINO] BENZOIC ACID METHYL ESTER; 5 [[4 (METHANESULFONYL METHOXYCARBONYLMETHYL AMINO) BENZYL] PHENYLMETHANESULFONYL AMINO] 2 (3 METHYL BENZYLOXY) BENZOIC ACID METHYL ESTER; 5 [[4 (METHANESULFONYL METHOXYCARBONYLMETHYL AMINO) BENZYL] PHENYLMETHANESULFONYL AMINO] 2 (4 METHYL BENZYLOXY) BENZOIC ACID METHYL ESTER; 5 [[4 (METHANESULFONYL METHOXYCARBONYLMETHYL AMINO) BENZYL] PHENYLMETHANESULFONYL AMINO] 2 PROPOXY BENZOIC ACID METHYL ESTER; ANTIDIABETIC AGENT; ANTIOBESITY AGENT; INSULIN MEDIATED INSULIN RECEPTOR BETA; INSULIN RECEPTOR; NON RECEPTOR PROTEIN TYROSINE PHOSPHATASE 2; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; UNCLASSIFIED DRUG; [[4 [[(4 BENZYLOXY PHENYL) PHENYLMETHANESULFONYL AMINO]METHYL] PHENYL] METHANESULFONYL AMINO] ACETIC ACID METHYL ESTER; ENZYME INHIBITOR; GLUCOSE; PROTEIN TYROSINE PHOSPHATASE 1B; PROTEIN TYROSINE PHOSPHATASE SHP 1; PROTEIN TYROSINE PHOSPHATASE SHP 2; PTPN11 PROTEIN, HUMAN;

ANIMAL CELL; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL ACTIVITY; CELL FRACTIONATION; CHO CELL LINE; CONTROLLED STUDY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; FEMALE; GLUCOSE TOLERANCE; GLUCOSE TRANSPORT; IC50; INSULIN SENSITIVITY; MOLECULAR DOCKING; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; OBESITY; PROTEIN PHOSPHORYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY; CRICETULUS; DRUG DESIGN; ENZYME SPECIFICITY; HAMSTER; HUMAN; METABOLISM; PROTEIN CONFORMATION;

ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; DRUG DESIGN; ENZYME INHIBITORS; GLUCOSE; HUMANS; MOLECULAR DOCKING SIMULATION; PROTEIN CONFORMATION; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 11; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 2; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 6; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 84964465728     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2016.04.014     Document Type: Article

References (31)

1. J. Korner L.J. Aronne The emerging science of body weight regulation and its impact on obesity treatment J. Clin. Investig. 111 2003 565 570
2. Moller New drug targets for type 2 diabetes and the metabolic syndrome Nature 414 2001 821 827
3. I.K. Lund J.A. Hansen H.S. Andersen N.P. Moller N. Billestrup Mechanism of protein tyrosine phosphatase 1B-mediated inhibition of leptin signalling J. Mol. Endocrinol. 34 2005 339 351
4. A. Salmeen J.N. Andersen M.P. Myers N.K. Tonks D. Barford Molecular basis for the dephosphorylation of the activation segment of the insulin receptor by protein tyrosine phosphatase 1B Mol. Cell. 6 2000 1401 1412
5. M. Elchebly P. Payette E. Michaliszyn W. Cromlish S. Collins A.L. Loy D. Normandin A. Cheng J. Himms-Hagen C.-C. Chan C. Ramachandran M.J. Gresser M.L. Tremblay B.P. Kennedy Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene Science 283 1999 1544 1548
6. L.D. Klaman O. Boss O.D. Peroni J.K. Kim J.L. Martino J.M. Zabolotny N. Moghal M. Lubkin Y.-B. Kim A.H. Sharpe A. Stricker-Krongrad G.I. Shulman B.G. Neel B.B. Kahn Increased energy expenditure, decreased adiposity, and tissue-specific insulin sensitivity in protein-tyrosine phosphatase 1B-deficient mice Mol. Cell. Biol. 20 2000 5479 5489
7. K.E. You-Ten E.S. Muise A. Itié E. Michaliszyn J. Wagner S. Jothy W.S. Lapp M.L. Tremblay Impaired bone marrow microenvironment and immune function in T cell protein tyrosine phosphatase-deficient mice J. Exp. Med. 186 1997 683 693
8. T.O. Johnson J. Ermolieff M.R. Jirousek Protein tyrosine phosphatase 1B inhibitors for diabetes Nat. Rev. Drug Discov. 1 2002 696 709
9. R. He L.F. Zeng Y. He S. Zhang Z.Y. Zhang Small molecule tools for functional interrogation of protein tyrosine phosphatases FEBS J. 280 2013 731 750
10. A.K. Tamrakar C.K. Maurya A.K. Rai PTP1B inhibitors for type 2 diabetes treatment: a patent review (2011-2014) Expert Opin. Ther. Pat. 24 2014 1 15
11. A.J. Barr Protein tyrosine phosphatases as drug targets: strategies and challenges of inhibitor development Future Med. Chem. 2 2010 1563 1576
12. L.F. Iversen K.B. Møller A.K. Pedersen G.H. Peters A.S. Petersen H.S. Andersen S. Branner S.B. Mortensen N.P.H. Møller Structure determination of T cell protein-tyrosine phosphatase J. Biol. Chem. 277 2002 19982 19990
13. P. Liu Y. Du L. Song J. Shen Q. Li Novel, potent, selective and cellular active ABC type PTP1B inhibitors containing (methanesulfonyl-phenyl-amino)-acetic acid methyl ester phosphotyrosine mimetic Bioorg. Med. Chem. 23 2015 7079 7088
14. Z. Jia Q. Ye A.N. Dinaut Q. Wang D. Waddleton P. Payette C. Ramachandran B. Kennedy G. Hum S.D. Taylor Structure of protein tyrosine phosphatase 1B in complex with inhibitors bearing two phosphotyrosine mimetics J. Med. Chem. 44 2001 4584 4594
15. A.A. Kulkarni N.T. Nivangune V.S. Kalyani R.A. Joshi R.R. Joshi Continuous flow nitration of salicylic acid Org. Process Res. Dev. 12 2008 995 1000
16. 3+-β-diketonate complexes: comparison of theoretical and experimental photophysical properties Dalton Trans. 40 2011 3257 3268
17. T.V. Khasanova O. Khakshoor J.S. Nowick Functionalized analogues of an unnatural amino acid that mimics a tripeptide β-strand Org. Lett. 10 2008 5293 5296
18. Y. Takeuchi T. Oda M. Chang Y. Okamoto J. Ono, et al. Synthesis and antitumor activity of fused quinoline derivatives. IV. Novel 11-aminoindolo[3.2-b]quinolines Chem. Pharm. Bull. 45 1997 406 411
19. V.A. Rassadin D.S. Grosheva I.A. Arefeva A.A. Tomashevskiy V.V. Sokolov A. Meijere Access to a wide range of sultams by cyclodialkylation of α-substituted methanesulfonanilides Eur. J. Org. Chem. 9 2012 5028 5037
20. R. Lis A.J. Marisca Methanesulfonanilides and the Mannich reaction J. Org. Chem. 52 1987 4377 4379
21. A. Quattropani J. Dorbais D. Covini, et al. Discovery and development of a new class of potent, selective, orally active oxytocin receptor antagonists J. Med. Chem. 48 2005 7882 7905
22. R. Cao P. Müller S.J. Lippard Tripodal tris-tacn and tris-dpa platforms for assembling phosphate-templated trimetallic centers J. Am. Chem. Soc. 132 2010 17366 17369
23. H. Koshio F. Hirayama T. Ishihara Y. Taniuchi K. Sato Y. Sakai-Moritani S. Kaku T. Kawasaki Y. Matsumoto S. Sakamoto S. Tsukamoto Synthesis and biological activity of novel 1,4-diazepane derivatives as factor Xa inhibitor with potent anticoagulant and antithrombotic activity Bioorg. Med. Chem. 12 2004 2179 2191
24. E. Panzhinskiy J. Ren S. Nair Pharmacological inhibition of protein tyrosine phosphatase 1B: a promising strategy for the treatment of obesity and type 2 diabetes mellitus Curr. Med. Chem. 20 2013 2609 2625
25. A. Maeda K. Kai M. Ishii T. Ishii M. Akagawa Safranal, a novel protein tyrosine phosphatase 1B inhibitor, activates insulin signaling in C2C12 myotubes and improves glucose tolerance in diabetic KK-Ay mice Mol. Nutr. Food. Res. 58 2014 1177 1189
26. B.A. Zinker C.M. Rondinone J.M. Trevillyan R.J. Gum J.E. Clampit J.F. Waring N. Xie D. Wilcox P. Jacobson L. Frost P.E. Kroeger R.M. Reilly S. Koterski T.J. Opgenorth R.G. Ulrich S. Crosby M. Butler S.F. Murray R.A. McKay S. Bhanot B.P. Monia M.R. Jirousek PTP1B antisense oligonucleotide lowers PTP1B protein, normalizes blood glucose, and improves insulin sensitivity in diabetic mice Proc. Natl. Acad. Sci. U. S. A. 99 2002 11357 11362
27. S. Fukuda T. Ohta S. Sakata H. Morinaga M. Ito Y. Nakagawa M. Tanaka M. Matsushita Pharmacological profiles of a novel protein tyrosine phosphatase 1B inhibitor, JTT-551 Diabetes Obes. Metab. 12 2010 299 306
28. K. Otake S. Azukizawa M. Fukui K. Kunishiro H. Kamemoto M. Kanda T. Miike M. Kasai H. Shirahase Novel (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids: peroxisome proliferator-activated receptor 3 selective agonists with protein-tyrosine phosphatase 1B inhibition Bioorg. Med. Chem. 20 2012 1060 1075
29. N. Lakshminarayana Y.R. Prasad L. Gharat A. Thomas S. Narayanan A. Raghuram C.V. Srinivasan B. Gopalan Synthesis and evaluation of some novel dibenzo[b,d]furan carboxylic acids as potential anti-diabetic agents Eur. J. Med. Chem. 45 2010 3709 3718
30. J. Qiu K. Maekawa Y. Kitamura Y. Miyata K. Tanaka T. Tanaka M. Soga T. Tsuda T. Matsui Stimulation of glucose uptake by theasinensins through the AMP-activated protein kinase pathway in rat skeletal muscle cells Biochem. Pharmacol. 87 2014 344 351
31. L. Chen Q.Y. Li X.J. Shi S.L. Mao Y.L. Du J. Agric 6-Hydroxydaidzein enhances adipocyte differentiation and glucose uptake in 3T3-L1 cells Food Chem. 61 2013 10714 10719