LCL521 dihydrochloride | CAS#1226759-47-2 | ACDase inhibitor

MedKoo Cat#: 462427 | Name: LCL521 dihydrochloride

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

LCL521 dihydrochloride is an acid ceramidase (ACDase) inhibitor. LCL521 also inhibits the lysosomal acid sphingomyelinase (ASMase).

Chemical Structure

LCL521 dihydrochloride

CAS#1226759-47-2 (2HCl)

Theoretical Analysis

MedKoo Cat#: 462427

Name: LCL521 dihydrochloride

CAS#: 1226759-47-2 (2HCl)

Chemical Formula: C31H54Cl2N4O7

Exact Mass: 664.3370

Molecular Weight: 665.69

Elemental Analysis: C, 55.93; H, 8.18; Cl, 10.65; N, 8.42; O, 16.82

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 530.00	2 Weeks
10mg	USD 850.00	2 Weeks

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Related CAS #

1226759-47-2 (2HCl) 1226851-11-1 (free base)

Synonym

LCL-521 dihydrochloride; LCL521 dihydrochloride; LCL 521 dihydrochloride

IUPAC/Chemical Name

(1R,2R)-1-(4-nitrophenyl)-2-tetradecanamidopropane-1,3-diyl bis(2-(dimethylamino)acetate) dihydrochloride

InChi Key

RGUSRMLMLNVDSF-QJCVVZHISA-N

InChi Code

InChI=1S/C31H52N4O7.2ClH/c1-6-7-8-9-10-11-12-13-14-15-16-17-28(36)32-27(24-41-29(37)22-33(2)3)31(42-30(38)23-34(4)5)25-18-20-26(21-19-25)35(39)40;;/h18-21,27,31H,6-17,22-24H2,1-5H3,(H,32,36);2*1H/t27-,31-;;/m1../s1

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

LCL521 dihydrochloride is an acid ceramidase (ACDase) inhibitor.

In vitro activity:

In summary, LCL521 acted as a specific inhibitor of the cellular ACDase, whereas the mono DMG-B13 prodrugs, similarly as B13, affected also the cellular neutral and alkaline ceramidases, but with a low efficiency. Moreover, LCL521 acted as inhibitor of the lysosomal ACDase and ASMase whereas LCL522 and LCL596 may be specific to the lysosomal ACDase. Reference: Bioorg Med Chem. 2014 Dec 15;22(24):6933-44. https://pubmed.ncbi.nlm.nih.gov/25456083/

In vivo activity:

The therapeutic benefit with adjuvant LCL521 was also achieved with SCCVII tumors treated with standard PDT when using immunocompetent mice but not with immunodeficient hosts. The interaction of LCL521 with PDT-based antitumor mechanisms is dominated by immune system contribution that includes overriding the effects of immunoregulatory cells, but could also include a tacit contribution from boosting direct tumor cell kill. Reference: Int J Cancer. 2016 Sep 15;139(6):1372-8. https://pubmed.ncbi.nlm.nih.gov/27136745/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.8	31.29
	Water	100.0	150.22

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 665.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. White-Gilbertson S, Lu P, Esobi I, Echesabal-Chen J, Mulholland PJ, Gooz M, Ogretmen B, Stamatikos A, Voelkel-Johnson C. Polyploid giant cancer cells are dependent on cholesterol for progeny formation through amitotic division. Sci Rep. 2022 May 27;12(1):8971. doi: 10.1038/s41598-022-12705-4. PMID: 35624221; PMCID: PMC9142539. 2. Bai A, Szulc ZM, Bielawski J, Pierce JS, Rembiesa B, Terzieva S, Mao C, Xu R, Wu B, Clarke CJ, Newcomb B, Liu X, Norris J, Hannun YA, Bielawska A. Targeting (cellular) lysosomal acid ceramidase by B13: design, synthesis and evaluation of novel DMG-B13 ester prodrugs. Bioorg Med Chem. 2014 Dec 15;22(24):6933-44. doi: 10.1016/j.bmc.2014.10.025. Epub 2014 Oct 22. PMID: 25456083; PMCID: PMC4443482. 3. Korbelik M, Banáth J, Zhang W, Saw KM, Szulc ZM, Bielawska A, Separovic D. Interaction of acid ceramidase inhibitor LCL521 with tumor response to photodynamic therapy and photodynamic therapy-generated vaccine. Int J Cancer. 2016 Sep 15;139(6):1372-8. doi: 10.1002/ijc.30171. Epub 2016 May 18. PMID: 27136745.

In vitro protocol:

In vivo protocol:

1. Korbelik M, Banáth J, Zhang W, Saw KM, Szulc ZM, Bielawska A, Separovic D. Interaction of acid ceramidase inhibitor LCL521 with tumor response to photodynamic therapy and photodynamic therapy-generated vaccine. Int J Cancer. 2016 Sep 15;139(6):1372-8. doi: 10.1002/ijc.30171. Epub 2016 May 18. PMID: 27136745.

1: Bai A, Szulc ZM, Bielawski J, et al. Targeting (cellular) lysosomal acid ceramidase by B13: design, synthesis and evaluation of novel DMG-B13 ester prodrugs. Bioorg Med Chem. 2014;22(24):6933-6944. doi:10.1016/j.bmc.2014.10.025