2074614-60-9
Chemical Structure
MSDH
Synonym(s): O-Methyl-serine dodecylamide hydrochloride
- CAS No.: 2074614-60-9
- Formula:C16H35ClN2O2
- Molecular Weight:322.92
IUPAC Name: (S)-2-amino-N-dodecyl-3-methoxypropanamide hydrochloride
InChIKey: KEFSFBIMLKNBML-RSAXXLAASA-N
SMILES: C(NCCCCCCCCCCCC)([C@H](COC)N)=O.Cl
Biological Activity: MSDH (O-Methyl-serine dodecylamide hydrochloride) is a lysosomotropic detergent that targets the lysosomal membrane. MSDH enters cells via endocytosis, accumulates in lysosomes and becomes protonated, forming physiological pH vesicles that dissociate at acidic pH, and acts as a micellar detergent. MSDH induces lysosomal membrane permeabilization, deacidification, release of cathepsin D/B and β-N-acetylglucosaminidase, and translocation of galectins to lysosomes. MSDH induces apoptosis, necrosis, caspase-3 activation, a decrease in mitochondrial transmembrane potential, and elevated p62/LC3BII levels. MSDH can be used in research on non-alcoholic steatohepatitis and head and neck squamous cell carcinoma[1][2][3][4][5][6][7][8][9].
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MSDH | MSDH (O-Methyl-serine dodecylamide hydrochloride) is a lysosomotropic detergent that targets the lysosomal membrane. MSDH enters cells via endocytosis, accumulates in lysosomes and becomes protonated, forming physiological pH vesicles that dissociate at acidic pH, and acts as a micellar detergent. MSDH induces lysosomal membrane permeabilization, deacidification, release of cathepsin D/B and β-N-acetylglucosaminidase, and translocation of galectins to lysosomes. MSDH induces apoptosis, necrosis, caspase-3 activation, a decrease in mitochondrial transmembrane potential, and elevated p62/LC3BII levels. MSDH can be used in research on non-alcoholic steatohepatitis and head and neck squamous cell carcinoma. | |||||||||||||||||||||
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References
- [1]. Fucho R, et al. ASMase regulates autophagy and lysosomal membrane permeabilization and its inhibition prevents early stage non-alcoholic steatohepatitis. Journal of hepatology. 2014 Nov;61(5):1126-34.
- [2]. Eriksson I, et al. The histone deacetylase inhibitor trichostatin A reduces lysosomal pH and enhances cisplatin-induced apoptosis. Experimental cell research. 2013 Jan 01;319(1):12-20.
- [3]. Hu M, et al. Repurposing Cationic Amphiphilic Drugs and Derivatives to Engage Lysosomal Cell Death in Cancer Treatment. Frontiers in oncology. 2020;10:605361.
- [4]. Appelqvist H, et al. Sensitivity to lysosome-dependent cell death is directly regulated by lysosomal cholesterol content. PloS one. 2012;7(11):e50262.
- [5]. Ma Z, et al. Pharmacophore hybridisation and nanoscale assembly to discover self-delivering lysosomotropic new-chemical entities for cancer therapy. Nature communications. 2020 Sep 15;11(1):4615.
- [6]. Gaspar J, et al. 2-Hydroxypropyl-beta-cyclodextrin (HPβCD) reduces age-related lipofuscin accumulation through a cholesterol-associated pathway. Scientific reports. 2017 May 19;7(1):2197.
- [7]. Li W, et al. Induction of cell death by the lysosomotropic detergent MSDH. FEBS letters. 2000 Mar 17;470(1):35-9.
- [8]. Villamil Giraldo AM, et al. Interactions of the Lysosomotropic Detergent O-Methyl-Serine Dodecylamide Hydrochloride (MSDH) with Lipid Bilayer Membranes-Implications for Cell Toxicity. International journal of molecular sciences. 2020 Apr 29;21(9):3136.
- [9]. Appelqvist H, et al. Attenuation of the lysosomal death pathway by lysosomal cholesterol accumulation. The American journal of pathology. 2011 Feb;178(2):629-39.
