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65646-68-6

65646-68-6 structure
65646-68-6 structure
  • Name: Fenretinide
  • Chemical Name: 4-hydroxyphenyl retinamide
  • CAS Number: 65646-68-6
  • Molecular Formula: C26H33NO2
  • Molecular Weight: 391.546
  • Catalog: Signaling Pathways Autophagy Autophagy
  • Create Date: 2018-06-10 23:08:12
  • Modify Date: 2024-01-02 07:19:18
  • Fenretinide is a synthetic retinoid deriverative, binding to the retinoic acid receptors (RAR) at concentrations necessary to induce cell death.
Name 4-hydroxyphenyl retinamide
Synonyms 4-Hydroxyphenyl retinamide
Fenretinide
4-HPR
15-[(4-Hydroxyphenyl)amino]retinal
fenretinida
Retinal, 15-[(4-hydroxyphenyl)amino]-
fenretinidum
MFCD00792674
Description Fenretinide is a synthetic retinoid deriverative, binding to the retinoic acid receptors (RAR) at concentrations necessary to induce cell death.
Related Catalog
In Vitro Fenretinide 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].
In Vivo Fenretinide (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].
Cell Assay 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).
Animal Admin 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.
References

[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.

[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.

[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.

[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.
Density 1.1±0.1 g/cm3
Boiling Point 597.6±42.0 °C at 760 mmHg
Melting Point 162-163°C
Molecular Formula C26H33NO2
Molecular Weight 391.546
Flash Point 315.2±27.9 °C
Exact Mass 391.251129
PSA 49.33000
LogP 7.41
Vapour Pressure 0.0±1.8 mmHg at 25°C
Index of Refraction 1.607
Storage condition −20°C
Stability Light Sensitive - Protect from Light Exposure

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VH6420000
CHEMICAL NAME :
Retinamide, N-(4-hydroxyphenyl)-
CAS REGISTRY NUMBER :
65646-68-6
LAST UPDATED :
199712
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C26-H33-N-O2
MOLECULAR WEIGHT :
391.60

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
180 mg/kg/18D-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - retinal changes (pigmentary depositions, retinitis, other)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
210 mg/kg/2W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - retinal changes (pigmentary depositions, retinitis, other)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
8388 mg/kg/21D-I
TOXIC EFFECTS :
Blood - changes in other cell count (unspecified)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2138 mg/kg/21D-I
TOXIC EFFECTS :
Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
600 mg/kg
SEX/DURATION :
female 10-11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
400 mg/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system

MUTATION DATA

TYPE OF TEST :
Morphological transformation
TEST SYSTEM :
Rodent - mouse Mammary gland
DOSE/DURATION :
10 umol/L
REFERENCE :
NUCADQ Nutrition and Cancer. (Franklin Institute Press, POB 2266, Phildelphia, PA 19103) V.1- 1978- Volume(issue)/page/year: 7,105,1985
Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Danger
Hazard Statements H302 + H312 + H332-H315-H319-H335-H360
Precautionary Statements P201-P261-P280-P305 + P351 + P338-P308 + P313
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T: Toxic;
Risk Phrases R60;R61;R20/21/22;R36/37/38
Safety Phrases S53-S26-S36/37/39-S45
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS VH6420000
302-79-4 structure

302-79-4
123-30-8 structure

123-30-8

~82%

65646-68-6 structure

65646-68-6
Literature: Sangmam, Charles; Winum, Jean-Yves; Lucas, Marc; Montero, Jean-Louis; Chavis, Claude Synthetic Communications, 1998 , vol. 28, # 16 p. 2945 - 2958
53839-60-4 structure

53839-60-4
123-30-8 structure

123-30-8

~%

65646-68-6 structure

65646-68-6
Literature: Journal of Pharmaceutical Sciences, , vol. 73, # 6 p. 745 - 751
302-79-4 structure

302-79-4

~%

65646-68-6 structure

65646-68-6
Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 17, # 3 p. 836 - 840
Precursor  3

DownStream  1


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