Art. -Nr.: HY-15373

Fenretinide

(Synonyms: 4-HPR; ISLA-101)

9 Cited Publications

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Based on 9 publication(s) in Google Scholar

Fenretinide (4-HPR) is a synthetic retinoid deriverative, binding to the retinoic acid receptors (RAR) at concentrations necessary to induce cell death.

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Reinheit: 98.34%
CAS. Nr.: 65646-68-6
Formel: C₂₆H₃₃NO₂
Molecular Weight:391.55

Speicherung:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year

Fenretinide Chemical Structure

CAS. Nr.: 65646-68-6

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Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
- In Vivo
- Clinical Trial
Chemical Information
Publications (9)
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Protokoll
Reinheit & Dokumentation
Verweise
Help & FAQs
Bioz

Biologische Aktivität

Beschreibung

Fenretinide (4-HPR) is a synthetic retinoid deriverative, binding to the retinoic acid receptors (RAR) at concentrations necessary to induce cell death.

Alle RAR/RXR Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
Astrocyte	EC₅₀	2.399 μM Compound: 11	Antiproliferative activity against mouse astrocyte cells by MTT assay Antiproliferative activity against mouse astrocyte cells by MTT assay	[PMID: 17417631]
BHK-21	CC₅₀	31.5 μM Compound: 192	Cytotoxicity against BHK21 cells in presence of ATP by Celltiter-Glo assay Cytotoxicity against BHK21 cells in presence of ATP by Celltiter-Glo assay	[PMID: 28689975]
CWR22R	GI₅₀	3.23 μM Compound: 4-HPR, fenretinide	Growth inhibition of human CWR22Rv1 cells by MTT assay Growth inhibition of human CWR22Rv1 cells by MTT assay	[PMID: 25634130]
Daoy	GI₅₀	5 μM Compound: Fenretinide	Antiproliferative activity against human Daoy cells assessed as inhibition of cell growth incubated for 24 to 96 hrs by MTT assay Antiproliferative activity against human Daoy cells assessed as inhibition of cell growth incubated for 24 to 96 hrs by MTT assay	[PMID: 33636537]
G-401	IC₅₀	5 μM Compound: 1	Cytotoxicity against human G401 cells assessed as cell survival after 3 days by MTS assay Cytotoxicity against human G401 cells assessed as cell survival after 3 days by MTS assay	[PMID: 18556204]
HEK-293T	IC₅₀	18.7 μM Compound: Fenretinide	Inhibition of mouse Ido2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation after 45 mins by spectrophotometric analysis Inhibition of mouse Ido2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation after 45 mins by spectrophotometric analysis	[PMID: 23122865]
HEK-293T	IC₅₀	59.9 μM Compound: Fenretinide	Inhibition of mouse Ido1 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation after 45 mins by spectrophotometric analysis Inhibition of mouse Ido1 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation after 45 mins by spectrophotometric analysis	[PMID: 23122865]
HuCCT-1	IC₅₀	6 μM Compound: 3, Fenretinide	Cytotoxicity against human HuCCT1 cells after 72 hrs by MTT assay Cytotoxicity against human HuCCT1 cells after 72 hrs by MTT assay	[PMID: 22440084]
Huh-7	CC₅₀	<=10 μM Compound: 4-HPR	Cytotoxicity against human Huh-7 cells assessed as reduction in cell viability measured after 48 hrs by Celltiter-glo assay Cytotoxicity against human Huh-7 cells assessed as reduction in cell viability measured after 48 hrs by Celltiter-glo assay	[PMID: 37159959]
LNCaP	GI₅₀	2.69 μM Compound: 4-HPR, fenretinide	Growth inhibition of human LNCAP cells by MTT assay Growth inhibition of human LNCAP cells by MTT assay	[PMID: 25634130]
LNCaP	IC₅₀	7.5 μM Compound: 4-HPR	Growth inhibition of human LNCaP cells after 6 days by MTT assay Growth inhibition of human LNCaP cells after 6 days by MTT assay	[PMID: 15615521]
MCF7	GI₅₀	4.65 μM Compound: 4-HPR, fenretinide	Growth inhibition of human MCF7 cells by MTT assay Growth inhibition of human MCF7 cells by MTT assay	[PMID: 25634130]
MCF7	IC₅₀	0.15 μM Compound: 4-HPR	Growth inhibition of human MCF7 cells after 6 days by MTT assay Growth inhibition of human MCF7 cells after 6 days by MTT assay	[PMID: 15615521]
MDA-MB-231	GI₅₀	11.05 μM Compound: 4-HPR, fenretinide	Growth inhibition of human MDA-MB-231 cells by MTT assay Growth inhibition of human MDA-MB-231 cells by MTT assay	[PMID: 25634130]
MDA-MB-231	IC₅₀	7.7 μM Compound: 4-HPR	Growth inhibition of human MDA-MB-231 cells after 6 days by MTT assay Growth inhibition of human MDA-MB-231 cells after 6 days by MTT assay	[PMID: 15615521]
MDA-MB-468	GI₅₀	6.02 μM Compound: 4-HPR, fenretinide	Growth inhibition of human MDA-MB-468 cells by MTT assay Growth inhibition of human MDA-MB-468 cells by MTT assay	[PMID: 25634130]
Medulloblastoma cell	EC₅₀	0.204 μM Compound: 11	Antiproliferative activity against mouse medulloblastoma cells harboring heterozygous ptch1 gene by MTT assay Antiproliferative activity against mouse medulloblastoma cells harboring heterozygous ptch1 gene by MTT assay	[PMID: 17417631]
MIA PaCa-2	IC₅₀	7 μM Compound: 3, Fenretinide	Cytotoxicity against human MIAPaCa2 cells after 72 hrs by MTT assay Cytotoxicity against human MIAPaCa2 cells after 72 hrs by MTT assay	[PMID: 22440084]
ONS-76	GI₅₀	2 μM Compound: Fenretinide	Antiproliferative activity against human ONS-76 cells assessed as inhibition of cell growth incubated for 24 to 96 hrs by MTT assay Antiproliferative activity against human ONS-76 cells assessed as inhibition of cell growth incubated for 24 to 96 hrs by MTT assay	[PMID: 33636537]
PC-3	GI₅₀	2 μM Compound: 43	Cytotoxicity against human PC3 cells after 72 hrs by MTT assay Cytotoxicity against human PC3 cells after 72 hrs by MTT assay	[PMID: 26780304]
PC-3	GI₅₀	3.54 μM Compound: 4-HPR, fenretinide	Growth inhibition of human PC3 cells by MTT assay Growth inhibition of human PC3 cells by MTT assay	[PMID: 25634130]
PC-3	IC₅₀	3.6 μM Compound: 4-HPR	Growth inhibition of human PC3 cells after 6 days by MTT assay Growth inhibition of human PC3 cells after 6 days by MTT assay	[PMID: 15615521]
SK-BR-3	GI₅₀	3.98 μM Compound: 4-HPR, fenretinide	Growth inhibition of human SKBR3 cells by MTT assay Growth inhibition of human SKBR3 cells by MTT assay	[PMID: 25634130]

In Vitro

Fenretinide (4-HPR) exerts not just acute but also long term antitumor activity in selected T-ALL cell lines. Fenretinide inhibits DES activity in CCRF-CEM leukemia cells in a dose and time dependent manner, leading to a concomitant increase of the endogenous cellular dhCer content. Fenretinide (3 μM)-induced dhCer accumulation in both CCRF-CEM and Jurkat cells^[1]. Ceramide inhibition with fenretinide protects insulin signaling. Fenretinide prevents lipid-induced reductions in insulin-stimulated glucose uptake^[2]. Fenretinide inhibits OVCAR-5 cell proliferation and viability at concentrations higher than 1 microM, with 70-90% growth inhibition at 10 microM. Fenretinide (1 microM) significantly inhibits OVCAR-5 invasion after 3 days preincubation. Endothelial cells treated with 1 microM 4-HPR fails to form tubes, but forms small cellular aggregates^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Fenretinide (4-HPR) (10 mg/kg, i.p.) selectively inhibits ceramide accumulation HFD-fed male C57Bl/6 mice. Fenretinide treatment improves glucose tolerance and insulin sensitivity as determined by both glucose and insulin tolerance tests^[2]. Addition of 25 mg/kg ketoconazole to Fenretinide in NOD/SCID mice increased 4-HPR plasma levels^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase A549
NCT01329991	Plexxikon\|		2011-05	PHASE1

Chemical Information

CAS. Nr. 65646-68-6
Appearance Solid
Molecular Weight 391.55
Formel C₂₆H₃₃NO₂
Color Light yellow to yellow
SMILES

CC(/C=C/C=C(/C=C/C1=C(CCCC(C)1C)C)C)=C\C(NC2=CC=C(O)C=C2)=O
Synonyms

4-HPR; ISLA-101
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	2 years
	-20°C	1 year

Publications (9)

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Journal Impact Factor

Signal Transduct Target Ther

Dysregulated ceramides metabolism by fatty acid 2-hydroxylase exposes a metabolic vulnerability to target cancer metastasis. [Abstract]

2022 Oct 24;7(1):370. PMID: 36274060
Biomed Pharmacother

Fenretinide attenuates lipopolysaccharide (LPS)-induced blood-brain barrier (BBB) and depressive-like behavior in mice by targeting Nrf-2 signaling. [Abstract]

2020 May;125:109680. PMID: 32106372
Oncol Rep

Fenretinide inhibits the proliferation and migration of human liver cancer HepG2 cells by downregulating the activation of myosin light chain kinase through the p38‑MAPK signaling pathway. [Abstract]

2018 Jul;40(1):518-526. PMID: 29767236

Fenretinide purchased from MedChemExpress. Usage Cited in: Oncol Rep. 2018 Jul;40(1):518-526. [Abstract]

Western blot analyses reveal that the phosphorylation of p38 is significantly increased. Lane 1, cell control; lane 2, DMSO; lane 3, 5 μM ATRA; lane 4, 10 μM ATRA; lane 5, 5 μM 4-HPR; and lane 6, 10 μM 4-HPR.
Clin Exp Med

The association between 4-HPR-mediated LCN2 suppression and reduced intestinal cell senescence in ulcerative colitis. [Abstract]

2025 Aug 21;25(1):297. PMID: 40839227
J Cancer

Fenretinide-induced Apoptosis of Acute Myeloid Leukemia Cells via NR4A1 Translocation into Mitochondria and Bcl-2 Transformation. [Abstract]

2019 Nov 1;10(27):6767-6778. PMID: 31839811
Cell Biochem Biophys

Dihydroceramide Desaturase Functions as an Inducer and Rectifier of Apoptosis: Effect of Retinol Derivatives, Antioxidants and Phenolic Compounds. [Abstract]

2021 Sep;79(3):461-475. PMID: 33991313
Cornea

Fenretinide Inhibits Neutrophil Recruitment and IL-1β Production in Aspergillus fumigatus Keratitis. [Abstract]

2018 Dec;37(12):1579-1585. PMID: 30211745

Fenretinide purchased from MedChemExpress. Usage Cited in: Cornea. 2018 Dec;37(12):1579-1585. [Abstract]

Fenretinide pretreatment reduces neutrophils recruitment and MPO activity in the mouse Aspergillus fumigatus keratitis model. Positive staining (green) of NIMP-R14 in the corneas of pretreated mice is indicative of a decreased presence of neutrophils compared with control mice at 1 day after infection.

Fenretinide purchased from MedChemExpress. Usage Cited in: Cornea. 2018 Dec;37(12):1579-1585. [Abstract]

Compared with infected controls, LOX-1, phosphorylated JNK, and pro-IL-1b protein levels in corneas are significantly lower at 1 day after infection in fenretinide-pretreated mice.

Fenretinide purchased from MedChemExpress. Usage Cited in: Cornea. 2018 Dec;37(12):1579-1585. [Abstract]

Compared with stimulated controls, LOX-1, JNK, phosphorylated JNK, and pro-IL-1b protein levels in fenretinide-pretreated THP-1 macrophages are significantly lower at 16 hours with A. fumigatus stimulation. JNK was not affected by fenretinide pretreatment.

Fenretinide purchased from MedChemExpress. Usage Cited in: Cornea. 2018 Dec;37(12):1579-1585. [Abstract]

BAX, cytochrome c, cleaved-caspase-8, cleaved-caspase-9, and cleaved-caspase-3 protein levels in fenretinide-pretreated mice corneas are found to be significantly increased.
Patent

20200038327A1.
Wayne State University

2015 Jan.

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : ≥ 100 mg/mL (255.40 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

* "≥" means soluble, but saturation unknown.

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.5540 mL

12.7698 mL

25.5395 mL

5 mM

0.5108 mL

2.5540 mL

5.1079 mL

10 mM

0.2554 mL

1.2770 mL

2.5540 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 2.5 mg/mL (6.38 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: ≥ 2.5 mg/mL (6.38 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.5 mg/mL (6.38 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Protokoll

Cell Assay^[1]

Standard XTT assay is used to determine cell viability. For fenretinide-only treatments, cells are plated in 96-well plates at 750,000 cells/mL and 100 μL/well. After 4 h, treatments are added on 50 μL/well obtaining a final density of 500,000 cells/mL and final volume of 150 μL/well. Four replicates are used per experimental condition. XTT reagent mixture is added 4 h before the end of selected treatment period and absorbance at 490 nm is determined per each well. A slightly modified protocol is used for analysis of the effect of myriocin (final concentration of 100 nM) or antioxidant on Fenretinide treatment. Briefly, cells are seeded on 60 mm culture dishes and myriocin or antioxidants added after 4 h. Fenretinide treatment is added 2 h later and cells are plated in quadruplicates in 96 well plates (150 μL/well).

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Administration^[2]

Male mice (C57Bl6) are fed a standard chow or a high-fat diet (HFD) from 5 to 17 weeks, at which point half of the HFD-fed mice begin receiving fenretinide in drinking water for 4 weeks. Fenretinide is dissolved in 100% ethanol and diluted in water to 10 μg/mL. Control treatment water receives an equal amount of ethanol (0.5%). FEN water is prepared in low-light conditions and administered in light-protective bottles. Water is replaced every 1-2 days, and no precipitation of FEN is noted at any time. Animal weights are recorded at the beginning and end of the treatment period. Following a 4-week FEN treatment, mice undergo intraperitoneal glucose and insulin tolerance tests. For both tests, mice are fasted for 6 h andreceive an injection of either glucose (1 g/kg of body weight) or insulin (0.75 units/kg of body weight). Blood glucose is determined at the times indicated by the Bayer Contour^® glucose meter, and insulin is measured with the rat/mouse insulin ELISA kit. The insulin resistance index is assessed by using fasting blood glucose and insulin levels to compute the homeostatic model assessment of insulin resistance (HOMA-IR), where a higher number represents greater insulin resistance.

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (276 KB)
SDS (419 KB)
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COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Apraiz, Aintzane., et al. Dihydroceramide accumulation and reactive oxygen species are distinct and nonessential events in 4-HPR-mediated leukemia cell death. Biochemistry and Cell Biology (2012), 90(2), 209-223. [Content Brief]

[2]. Bikman, Benjamin T., et al. Fenretinide Prevents Lipid-induced Insulin Resistance by Blocking Ceramide Biosynthesis. Journal of Biological Chemistry (2012), 287(21), 17426-17437. [Content Brief]

[3]. Cooper JP, et al. Fenretinide metabolism in humans and mice: utilizing pharmacological modulation of its metabolic pathway to increase systemic exposure. Br J Pharmacol. 2011 Jul;163(6):1263-75. [Content Brief]

[4]. Golubkov V, et al. Action of fenretinide (4-HPR) on ovarian cancer and endothelial cells. Anticancer Res. 2005 Jan-Feb;25(1A):249-53. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.5540 mL	12.7698 mL	25.5395 mL	63.8488 mL
	5 mM	0.5108 mL	2.5540 mL	5.1079 mL	12.7698 mL
	10 mM	0.2554 mL	1.2770 mL	2.5540 mL	6.3849 mL
	15 mM	0.1703 mL	0.8513 mL	1.7026 mL	4.2566 mL
	20 mM	0.1277 mL	0.6385 mL	1.2770 mL	3.1924 mL
	25 mM	0.1022 mL	0.5108 mL	1.0216 mL	2.5540 mL
	30 mM	0.0851 mL	0.4257 mL	0.8513 mL	2.1283 mL
	40 mM	0.0638 mL	0.3192 mL	0.6385 mL	1.5962 mL
	50 mM	0.0511 mL	0.2554 mL	0.5108 mL	1.2770 mL
	60 mM	0.0426 mL	0.2128 mL	0.4257 mL	1.0641 mL
	80 mM	0.0319 mL	0.1596 mL	0.3192 mL	0.7981 mL
	100 mM	0.0255 mL	0.1277 mL	0.2554 mL	0.6385 mL

Keywords

Fenretinide

9 Cited Publications

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Publications Citing Use of MedChemExpress (MCE) Fenretinide

Alle RAR/RXR Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Publications (9)

Lösungsmittel & Löslichkeit

Protokoll

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Fenretinide Related Classifications

Art. -Nr.: HY-15373