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Fenretinide

Fenretinide

  • CAT Number: I004475
  • CAS Number: 65646-68-6
  • Molecular Formula: C26H33NO2
  • Molecular Weight: 391.6
  • Purity: ≥95%
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Fenretinide (Cat No.:I004475) is a synthetic retinoid derivative that exhibits properties similar to retinoic acid. It has been found to bind to retinoic acid receptors (RAR) at concentrations required to induce cell death. By interacting with RAR, 4-HPR can modulate gene expression and cellular processes associated with differentiation, proliferation, and apoptosis. This retinoid derivative has shown promise in preclinical and clinical studies for its potential anticancer and chemopreventive activities.

Catalog Number I004475
CAS Number 65646-68-6
Molecular Formula

C26H33NO2

Purity 95%
Target RAR/RXR
Solubility 10 mM in DMSO
Storage Store at -20°C
IUPAC Name (2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
InChI InChI=1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+
InChIKey AKJHMTWEGVYYSE-FXILSDISSA-N
SMILES CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)NC2=CC=C(C=C2)O)C)C
Reference

</br>1:Inhibitory effects of fenretinide metabolites N-[4-methoxyphenyl]retinamide (MPR) and 4-oxo-N-(4-hydroxyphenyl)retinamide (3-keto-HPR) on fenretinide molecular targets β-carotene oxygenase 1, stearoyl-CoA desaturase 1 and dihydroceramide Δ4-desaturase 1. Poliakov E, Samuel W, Duncan T, Gutierrez DB, Mata NL, Redmond TM.PLoS One. 2017 Apr 27;12(4):e0176487. doi: 10.1371/journal.pone.0176487. eCollection 2017. PMID: 28448568 Free PMC Article</br>2:Clinical development of fenretinide as an antineoplastic drug: Pharmacology perspectives. Cooper JP, Reynolds CP, Cho H, Kang MH.Exp Biol Med (Maywood). 2017 Jan 1:1535370217706952. doi: 10.1177/1535370217706952. [Epub ahead of print] PMID: 28429653 </br>3:Phase I Study of Fenretinide Delivered Intravenously in Patients with Relapsed or Refractory Hematologic Malignancies: a California Cancer Consortium Trial. Mohrbacher A, Yang AS, Groshen S, Kummar S, Gutierrez ME, Kang MH, Tsao-Wei D, Reynolds CP, Newman E, Maurer BJ.Clin Cancer Res. 2017 Apr 18. pii: clincanres.0234.2017. doi: 10.1158/1078-0432.CCR-17-0234. [Epub ahead of print] PMID: 28420721 </br>4:P450 inhibitor ketoconazole increased the intratumor drug levels and antitumor activity of fenretinide in human neuroblastoma xenograft models. Lopez-Barcons L, Maurer BJ, Kang MH, Reynolds CP.Int J Cancer. 2017 Mar 24. doi: 10.1002/ijc.30706. [Epub ahead of print] PMID: 28340497 </br>5:Synthesis of short retinoidal amides related to fenretinide: antioxidant activities and differentiation-inducing ability. Anzaldi M, Viale M, Macciò C, Castagnola P, Oliveri V, Rosano C, Balbi A.Cancer Chemother Pharmacol. 2017 Apr;79(4):725-736. doi: 10.1007/s00280-017-3265-1. Epub 2017 Mar 9. PMID: 28275870 </br>6:Elevated Fibroblast growth factor 21 (FGF21) in obese, insulin resistant states is normalised by the synthetic retinoid Fenretinide in mice. Morrice N, Mcilroy GD, Tammireddy SR, Reekie J, Shearer KD, Doherty MK, Delibegović M, Whitfield PD, Mody N.Sci Rep. 2017 Mar 3;7:43782. doi: 10.1038/srep43782. PMID: 28256636 Free PMC Article</br>7:Fumonisin B1 Inhibits Endoplasmic Reticulum Stress Associated-apoptosis After FoscanPDT Combined with C6-Pyridinium Ceramide or Fenretinide. Boppana NB, Kraveka JM, Rahmaniyan M, Li LI, Bielawska A, Bielawski J, Pierce JS, Delor JS, Zhang K, Korbelik M, Separovic D.Anticancer Res. 2017 Feb;37(2):455-463. PMID: 28179290 </br>8:Reactive Oxygen Species-Mediated Synergism of Fenretinide and Romidepsin in Preclinical Models of T-cell Lymphoid Malignancies. Makena MR, Koneru B, Nguyen TH, Kang MH, Reynolds CP.Mol Cancer Ther. 2017 Apr;16(4):649-661. doi: 10.1158/1535-7163.MCT-16-0749. Epub 2017 Jan 23. PMID: 28119491 </br>9:Results of a phase I-II study of fenretinide and rituximab for patients with indolent B-cell lymphoma and mantle cell lymphoma. Cowan AJ, Stevenson PA, Gooley TA, Frayo SL, Oliveira GR, Smith SD, Green DJ, Roden JE, Pagel JM, Wood BL, Press OW, Gopal AK.Br J Haematol. 2017 Feb;176(4):583-590. doi: 10.1111/bjh.14451. Epub 2017 Jan 5. PMID: 28055107 </br>10:The involvement of M2 macrophage polarization inhibition in fenretinide-mediated chemopreventive effects on colon cancer. Dong R, Gong Y, Meng W, Yuan M, Zhu H, Ying M, He Q, Cao J, Yang B.Cancer Lett. 2017 Mar 1;388:43-53. doi: 10.1016/j.canlet.2016.11.029. Epub 2016 Nov 30. PMID: 27913199

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