1-(5-Chloronaphthalenesulfonyl)-1H-hexahydro-1,4-diazepine, Hydrochloride

  • CAT Number: R020650
  • CAS Number: 105637-50-1
  • Molecular Formula: C15H18Cl2N2O2S
  • Molecular Weight: 361.281
  • Purity: ≥95%
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ML 9 a is myosin light chain kinase (MLCK) inhibitor. ML-9 enhances the anticancer activity of docetaxel, suggesting its potential application as an adjuvant to existing anticancer chemotherapy. The complex effect of ML-9 on autophagy and indentified ML-9 as an attractive tool for targeting autophagy in cancer therapy through dual inhibition of both the Akt pathway and the autophagy.


Catalog Number R020650
CAS Number 105637-50-1
Synonyms

ML-9

Molecular Formula C15H18Cl2N2O2S
Purity ≥95%
Target Myosin
Solubility Soluble in DMSO > 10 mM
Storage Desiccate at RT
IUPAC Name 1-(5-chloronaphthalen-1-yl)sulfonyl-1,4-diazepane;hydrochloride
InChI InChI=1S/C15H17ClN2O2S.ClH/c16-14-6-1-5-13-12(14)4-2-7-15(13)21(19,20)18-10-3-8-17-9-11-18;/h1-2,4-7,17H,3,8-11H2;1H
InChIKey ZNRYCIVTNLZOGI-UHFFFAOYSA-N
SMILES C1CNCCN(C1)S(=O)(=O)C2=CC=CC3=C2C=CC=C3Cl.Cl
Reference

</br>1: Kondratskyi A, Yassine M, Slomianny C, Kondratska K, Gordienko D, Dewailly E, Lehen/’kyi V, Skryma R, Prevarskaya N. Identification of ML-9 as a lysosomotropic agent targeting autophagy and cell death. Cell Death Dis. 2014 Apr 24;5:e1193. doi: 10.1038/cddis.2014.156. PubMed PMID: 24763050; PubMed Central PMCID: PMC4001310.</br> 2: Ito S, Kume H, Honjo H, Kodama I, Katoh H, Hayashi H, Shimokata K. ML-9, a myosin light chain kinase inhibitor, reduces intracellular Ca2+ concentration in guinea pig trachealis. Eur J Pharmacol. 2004 Feb 23;486(3):325-33. PubMed PMID: 14985055.</br> 3: Honjo M, Inatani M, Kido N, Sawamura T, Yue BY, Honda Y, Tanihara H. A myosin light chain kinase inhibitor, ML-9, lowers the intraocular pressure in rabbit eyes. Exp Eye Res. 2002 Aug;75(2):135-42. PubMed PMID: 12137759.</br> 4: Kokubu K, Tani E, Nakano M, Minami N, Shindo H. Effects of ML-9 on experimental delayed cerebral vasospasm. J Neurosurg. 1989 Dec;71(6):916-22. PubMed PMID: 2585084.</br> 5: Shi J, Takahashi S, Jin XH, Li YQ, Ito Y, Mori Y, Inoue R. Myosin light chain kinase-independent inhibition by ML-9 of murine TRPC6 channels expressed in HEK293 cells. Br J Pharmacol. 2007 Sep;152(1):122-31. Epub 2007 Jul 2. PubMed PMID: 17603544; PubMed Central PMCID: PMC1978268.</br> 6: Kishi H, Bao J, Kohama K. Inhibitory effects of ML-9, wortmannin, and Y-27632 on the chemotaxis of vascular smooth muscle cells in response to platelet-derived growth factor-BB. J Biochem. 2000 Nov;128(5):719-22. PubMed PMID: 11056381.</br> 7: Coling DE, Bartolami S, Rhee D, Neelands T. Inhibition of calcium-dependent motility of cochlear outer hair cells by the protein kinase inhibitor, ML-9. Hear Res. 1998 Jan;115(1-2):175-83. PubMed PMID: 9472746.</br> 8: Yamamoto-Yamaguchi Y, Makishima M, Kanatani Y, Kasukabe T, Honma Y. Reversible differentiation of human monoblastic leukemia U937 cells by ML-9, an inhibitor of myosin light chain kinase. Exp Hematol. 1996 May;24(6):682-9. PubMed PMID: 8635523.</br> 9: Barros LF, Marchant RB, Baldwin SA. Dissection of stress-activated glucose transport from insulin-induced glucose transport in mammalian cells using wortmannin and ML-9. Biochem J. 1995 Aug 1;309 ( Pt 3):731-6. PubMed PMID: 7639686; PubMed Central PMCID: PMC1135693.</br> 10: Inoue G, Kuzuya H, Hayashi T, Okamoto M, Yoshimasa Y, Kosaki A, Kono S, Okamoto M, Maeda I, Kubota M, et al. Effects of ML-9 on insulin stimulation of glucose transport in 3T3-L1 adipocytes. J Biol Chem. 1993 Mar 5;268(7):5272-8. PubMed PMID: 7680348.</br> 11: Isemura M, Mita T, Satoh K, Narumi K, Motomiya M. Myosin light chain kinase inhibitors ML-7 and ML-9 inhibit mouse lung carcinoma cell attachment to the fibronectin substratum. Cell Biol Int Rep. 1991 Oct;15(10):965-72. PubMed PMID: 1773444.</br> 12: Nakanishi A, Yoshizumi M, Hamano S, Morita K, Oka M. Myosin light-chain kinase inhibitor, 1-(5-chlornaphthalene-1-sulfonyl)-1H-hexahydro-1,4-diazepine (ML-9), inhibits catecholamine secretion from adrenal chromaffin cells by inhibiting Ca2+ uptake into the cells. Biochem Pharmacol. 1989 Aug 15;38(16):2615-9. PubMed PMID: 2764985.</br> 13: Ito M, Tanabe F, Sato A, Ishida E, Takami Y, Shigeta S. Inhibition of natural killer cell-mediated cytotoxicity by ML-9, a selective inhibitor of myosin light chain kinase. Int J Immunopharmacol. 1989;11(2):185-90. PubMed PMID: 2703279.</br> 14: Ishikawa T, Chijiwa T, Hagiwara M, Mamiya S, Saitoh M, Hidaka H. ML-9 inhibits the vascular contraction via the inhibition of myosin light chain phosphorylation. Mol Pharmacol. 1988 Jun;33(6):598-603. PubMed PMID: 3380076.</br></br>

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