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Key Documents

SML3893

Sigma-Aldrich

LCL521 dihydrochlroide

new

≥95% (HPLC)

Synonym(s):

(1R,2R)-2-N-(Tetradecanoylamino)-1-(40-nitrophenyl)-propyl-1,3-O,O-di-(N,N-dimethylamino) acetate dihydrochloride, 1,3-DMG-B13, 1,3-O,O-DMG-B13•2HCl, 1,3-di-DMG-B13, B13: (1R,2R)-2-(tetradecanoylamino)-1-(4′-nitrophenyl)-1,3-propandiol), LCL 521, LCL-521

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About This Item

Empirical Formula (Hill Notation):
C31H52N4O7·2HCl
CAS Number:
Molecular Weight:
665.69
MDL number:
UNSPSC Code:
51111800
UNSPSC Code:
12352200

Quality Level

Assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

CN(C)CC(O[C@H](C1=CC=C(C=C1)[N+]([O-])=O)[C@@H](COC(CN(C)C)=O)NC(CCCCCCCCCCCCC)=O)=O.[2HCl]

Biochem/physiol Actions

N,N-dimethyl glycine (DMG) diester prodrug form of the selective acid ceramidase (ACDase) inhibitor B13 for enhanced lysosomal delivery and cellular potency.



LCL521 is the N,N-dimethyl glycine (DMG) diester prodrug form of the selective acid ceramidase (ACDase) inhibitor B13 (no inhibition against NCDase/ASAH2 or AlkCDase/ACER2). The DMG enables efficient and targeted B13 lysosomal delivery, resulting in enhanced cellular ACDase inhibitory potency (by 70% vs 12% in MCF7, respectively, post 1h treatment by 1 μM LCL521 or 10 μM B13) and effective blockage of ceramide (Cer) to sphingosine (Sph) processing (80% vs 0% Sph level drop in MCF7, respectively, post 1h treatment by 1 μM LCL521 or 10 μM B13).

Caution

Hygroscopic

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Shai White-Gilbertson et al.
Journal of lipid research, 60(7), 1225-1235 (2019-04-17)
Radiation treatment failure or relapse after initial response to chemotherapy presents significant clinical challenges in cancer patients. Escape from initial courses of treatment can involve reactivation of embryonic developmental stages, with the formation of polynuclear giant cancer cells (PGCCs). This
Shai White-Gilbertson et al.
Cancer medicine, 9(9), 3142-3152 (2020-03-07)
Polyploid giant cancer cells (PGCC) represent a poorly understood, small subpopulation of tumor cells that are increasingly being recognized for their critical role in therapy resistance, metastasis, and cancer recurrence. PGCC have the potential to generate progeny through primitive or
Mladen Korbelik et al.
International journal of cancer, 139(6), 1372-1378 (2016-05-04)
Acid ceramidase has been identified as a promising target for cancer therapy. One of its most effective inhibitors, LCL521, was examined as adjuvant to photodynamic therapy (PDT) using mouse squamous cell carcinoma SCCVII model of head and neck cancer. Lethal
Rachael E Clifford et al.
Cells, 9(12) (2020-12-19)
Previous work utilizing proteomic and immunohistochemical analyses has identified that high levels of acid ceramidase (AC) expression confers a poorer response to neoadjuvant treatment in locally advanced rectal cancer. We aimed to assess the radiosensitising effect of biological and pharmacological
Anticancer actions of lysosomally targeted inhibitor, LCL521, of acid ceramidase
PLoS ONE, 12(6) (2017)

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