Decanal, 2-ethylidene- | 73257-80-4 | antitumor

RV 538
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 581775

CAS#: 73257-80-4

Description: RV 538 is also known as DL-PDMP. It is a ceramide analog first prepared in a search for inhibitors of UGCG (glucosylceramide synthase). PDMP closely resembles the natural sphingolipid substrate of brain glucosyltransferase and acts as a potent and competitive inhibitor of this enzyme. Blocks the outgrowth of neurites and inhibits glycolipid synthesis in cultured NIH/3T3 cells.

Chemical Structure

RV 538

CAS# 73257-80-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 581775
Name: RV 538
CAS#: 73257-80-4
Chemical Formula: C23H39ClN2O3
Exact Mass: 426.26
Molecular Weight: 427.030
Elemental Analysis: C, 64.69; H, 9.21; Cl, 8.30; N, 6.56; O, 11.24

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 210
25mg	USD 370
50mg	USD 600
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: RV 538; DAMPP; PDMP; DL-PDMP.

IUPAC/Chemical Name: Decanamide, N-(2-hydroxy-1-(4-morpholinylmethyl)-2-phenylethyl)-, hydrochloride

InChi Key: HVJHJOYQTSEKPK-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H38N2O3.ClH/c1-2-3-4-5-6-7-11-14-22(26)24-21(19-25-15-17-28-18-16-25)23(27)20-12-9-8-10-13-20;/h8-10,12-13,21,23,27H,2-7,11,14-19H2,1H3,(H,24,26);1H

SMILES Code: CCCCCCCCCC(NC(CN1CCOCC1)C(O)C2=CC=CC=C2)=O.[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

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Product Data:

Product Data

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Biological target:	RV 538 inhibits glucosylceramide synthase, primarily through its D-threo (1R,2R) enantiomer, and inhibits β-1,4-galactosyltransferase 6, preventing lactosylceramide synthesis. RV 538 enhances the effectiveness of curcumin in inhibiting proliferation, activating JNK, inhibiting Akt, and inducing apoptosis in melanoma cells.
In vitro activity:	High concentrations of RV 538 were observed to target lysosomes in Chinese hamster ovary (CHO) cells, leading to lysosomal enlargement after overnight incubation. RV 538exhibited toxicity at concentrations exceeding 30 microM. This property was leveraged to select RV 538-resistant CHO cells that demonstrated approximately twice the resistance to RV 538 compared to parental cells. RV 538 resistant cells also displayed resistance to other lipophilic drugs with titratable amino groups, indicating a distinct multidrug resistance mechanism from cells overproducing P-glycoprotein, which were found to be highly sensitive to RV 538. Reference: J Lipid Res. 1994 Jul;35(7):1232-40. https://pubmed.ncbi.nlm.nih.gov/7964184/
In vivo activity:	Polymer-encapsulated RV 538 demonstrated significantly increased residence time in mice. This prolonged in vivo longevity substantially improved its efficacy in interfering with atherosclerosis and cardiac hypertrophy in mice with a high-fat and high-cholesterol diet-induced condition. RV 538 is a promising therapeutic option for diseases associated with abnormal glycosphingolipid biosynthesis. Reference: Biomaterials. 2015 Sep;64:125-135. https://pubmed.ncbi.nlm.nih.gov/26111596/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	25.0	58.54
	DMSO	30.0	70.26
	Ethanol	50.0	117.09

Preparing Stock Solutions

The following data is based on the product molecular weight 427.03 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. Rosenwald AG, Pagano RE. Effects of the glucosphingolipid synthesis inhibitor, PDMP, on lysosomes in cultured cells. J Lipid Res. 1994 Jul;35(7):1232-40. PMID: 7964184. 2. Meuillet EJ, Mania-Farnell B, George D, Inokuchi JI, Bremer EG. Modulation of EGF receptor activity by changes in the GM3 content in a human epidermoid carcinoma cell line, A431. Exp Cell Res. 2000 Apr 10;256(1):74-82. doi: 10.1006/excr.1999.4509. PMID: 10739654. 3. Mishra S, Bedja D, Amuzie C, Foss CA, Pomper MG, Bhattacharya R, Yarema KJ, Chatterjee S. Improved intervention of atherosclerosis and cardiac hypertrophy through biodegradable polymer-encapsulated delivery of glycosphingolipid inhibitor. Biomaterials. 2015 Sep;64:125-135. doi: 10.1016/j.biomaterials.2015.06.001. Epub 2015 Jun 3. PMID: 26111596; PMCID: PMC4557963. 4. Saito M, Fukushima Y, Tatsumi K, Bei L, Fujiki Y, Iwamori M, Igarashi T, Sakakihara Y. Molecular cloning of Chinese hamster ceramide glucosyltransferase and its enhanced expression in peroxisome-defective mutant Z65 cells. Arch Biochem Biophys. 2002 Jul 15;403(2):171-8. doi: 10.1016/s0003-9861(02)00216-3. PMID: 12139966.
In vitro protocol:	1. Rosenwald AG, Pagano RE. Effects of the glucosphingolipid synthesis inhibitor, PDMP, on lysosomes in cultured cells. J Lipid Res. 1994 Jul;35(7):1232-40. PMID: 7964184. 2. Meuillet EJ, Mania-Farnell B, George D, Inokuchi JI, Bremer EG. Modulation of EGF receptor activity by changes in the GM3 content in a human epidermoid carcinoma cell line, A431. Exp Cell Res. 2000 Apr 10;256(1):74-82. doi: 10.1006/excr.1999.4509. PMID: 10739654.
In vivo protocol:	1. Mishra S, Bedja D, Amuzie C, Foss CA, Pomper MG, Bhattacharya R, Yarema KJ, Chatterjee S. Improved intervention of atherosclerosis and cardiac hypertrophy through biodegradable polymer-encapsulated delivery of glycosphingolipid inhibitor. Biomaterials. 2015 Sep;64:125-135. doi: 10.1016/j.biomaterials.2015.06.001. Epub 2015 Jun 3. PMID: 26111596; PMCID: PMC4557963. 2. Saito M, Fukushima Y, Tatsumi K, Bei L, Fujiki Y, Iwamori M, Igarashi T, Sakakihara Y. Molecular cloning of Chinese hamster ceramide glucosyltransferase and its enhanced expression in peroxisome-defective mutant Z65 cells. Arch Biochem Biophys. 2002 Jul 15;403(2):171-8. doi: 10.1016/s0003-9861(02)00216-3. PMID: 12139966.

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1: Yamane M, Moriya S, Kokuba H. Visualization of ceramide channels in lysosomes following endogenous palmitoyl-ceramide accumulation as an initial step in the induction of necrosis. Biochem Biophys Rep. 2017 Mar 13;11:174-181. doi: 10.1016/j.bbrep.2017.02.010. eCollection 2017 Sep. PubMed PMID: 28955782; PubMed Central PMCID: PMC5614681.

2: Tang YC, Yuwen H, Wang K, Bruno PM, Bullock K, Deik A, Santaguida S, Trakala M, Pfau SJ, Zhong N, Huang T, Wang L, Clish CB, Hemann MT, Amon A. Aneuploid Cell Survival Relies upon Sphingolipid Homeostasis. Cancer Res. 2017 Oct 1;77(19):5272-5286. doi: 10.1158/0008-5472.CAN-17-0049. Epub 2017 Aug 3. PubMed PMID: 28775166; PubMed Central PMCID: PMC5772763.

3: Yamane M. Palmitoyl-ceramide accumulation with necrotic cell death in A549 cells, followed by a steep increase in sphinganine content. Biochim Open. 2015 Jun 21;1:11-27. doi: 10.1016/j.biopen.2015.06.001. eCollection 2015. PubMed PMID: 29632826; PubMed Central PMCID: PMC5889477.

4: Yamane M, Miyazawa K, Moriya S, Abe A, Yamane S. D,L-Threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (DL-PDMP) increases endoplasmic reticulum stress, autophagy and apoptosis accompanying ceramide accumulation via ceramide synthase 5 protein expression in A549 cells. Biochimie. 2011 Sep;93(9):1446-59. doi: 10.1016/j.biochi.2011.04.016. Epub 2011 May 7. PubMed PMID: 21571032.

5: Alphonse G, Bionda C, Aloy MT, Ardail D, Rousson R, Rodriguez-Lafrasse C. Overcoming resistance to gamma-rays in squamous carcinoma cells by poly-drug elevation of ceramide levels. Oncogene. 2004 Apr 8;23(15):2703-15. PubMed PMID: 15048093.

6: Alphonse G, Aloy MT, Broquet P, Gerard JP, Louisot P, Rousson R, Rodriguez-Lafrasse C. Ceramide induces activation of the mitochondrial/caspases pathway in Jurkat and SCC61 cells sensitive to gamma-radiation but activation of this sequence is defective in radioresistant SQ20B cells. Int J Radiat Biol. 2002 Sep;78(9):821-35. PubMed PMID: 12428923.

7: Rodriguez-Lafrasse C, Alphonse G, Aloy MT, Ardail D, Gérard JP, Louisot P, Rousson R. Increasing endogenous ceramide using inhibitors of sphingolipid metabolism maximizes ionizing radiation-induced mitochondrial injury and apoptotic cell killing. Int J Cancer. 2002 Oct 20;101(6):589-98. PubMed PMID: 12237902.

8: Sietsma H, Nijhof W, Dontje B, Vellenga E, Kamps WA, Kok JW. Inhibition of hemopoiesis in vitro by neuroblastoma-derived gangliosides. Cancer Res. 1998 Nov 1;58(21):4840-4. PubMed PMID: 9809988.

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RV 538 featured