4-Oxo-4-HPR

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

MedKoo CAT#: 563704

CAS#: 865536-65-8

Description: 4-Oxo-4-HPR is an inhibitor of tubulin polymerization, inducing marked G2-M cell cycle arrest and apoptosis in fenretinide-sensitive and fenretinide-resistant cell lines. It is also a fenretinide metabolite.


Chemical Structure

img
4-Oxo-4-HPR
CAS# 865536-65-8

Theoretical Analysis

MedKoo Cat#: 563704
Name: 4-Oxo-4-HPR
CAS#: 865536-65-8
Chemical Formula: C26H31NO3
Exact Mass: 405.2304
Molecular Weight: 405.53
Elemental Analysis: C, 77.01; H, 7.71; N, 3.45; O, 11.84

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: 4-Oxo-4-HPR; 4 Oxo 4 HPR; 4Oxo4HPR; 3-Keto fenretinide; 4-Oxo Fenretinide; 4-Keto-4-HPR;

IUPAC/Chemical Name: (2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)nona-2,4,6,8-tetraenamide

InChi Key: NZVOGZATHCUFRC-KFJFTADJSA-N

InChi Code: InChI=1S/C26H31NO3/c1-18(9-14-23-20(3)24(29)15-16-26(23,4)5)7-6-8-19(2)17-25(30)27-21-10-12-22(28)13-11-21/h6-14,17,28H,15-16H2,1-5H3,(H,27,30)/b8-6+,14-9+,18-7+,19-17+

SMILES Code: O=C(NC1=CC=C(O)C=C1)/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(CCC2(C)C)=O

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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 405.53 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.

Recalculate based on batch purity %
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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Tiberio P, Cavadini E, Cleris L, Dallavalle S, Musso L, Daidone MG, Appierto V. Sodium 4-Carboxymethoxyimino-(4-HPR) a Novel Water-Soluble Derivative of 4-Oxo-4-HPR Endowed with In Vivo Anticancer Activity on Solid Tumors. Front Pharmacol. 2017 Apr 26;8:226. doi: 10.3389/fphar.2017.00226. eCollection 2017. PubMed PMID: 28491037; PubMed Central PMCID: PMC5405676.

2: Poliakov E, Samuel W, Duncan T, Gutierrez DB, Mata NL, Redmond TM. 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. PLoS One. 2017 Apr 27;12(4):e0176487. doi: 10.1371/journal.pone.0176487. eCollection 2017. PubMed PMID: 28448568; PubMed Central PMCID: PMC5407626.

3: Lopez-Barcons L, Maurer BJ, Kang MH, Reynolds CP. P450 inhibitor ketoconazole increased the intratumor drug levels and antitumor activity of fenretinide in human neuroblastoma xenograft models. Int J Cancer. 2017 Jul 15;141(2):405-413. doi: 10.1002/ijc.30706. Epub 2017 May 9. PubMed PMID: 28340497.

4: Cho HE, Min HK. Analysis of fenretinide and its metabolites in human plasma by liquid chromatography-tandem mass spectrometry and its application to clinical pharmacokinetics. J Pharm Biomed Anal. 2017 Jan 5;132:117-124. doi: 10.1016/j.jpba.2016.09.046. Epub 2016 Sep 29. PubMed PMID: 27701038; PubMed Central PMCID: PMC5231410.

5: Musso L, Tiberio P, Appierto V, Cincinelli R, Cavadini E, Cleris L, Daidone MG, Dallavalle S. Water-soluble derivatives of 4-oxo-N-(4-hydroxyphenyl) retinamide: synthesis and biological activity. Chem Biol Drug Des. 2016 Oct;88(4):608-14. doi: 10.1111/cbdd.12781. Epub 2016 Jun 6. PubMed PMID: 27135197.

6: Holpuch AS, Phelps MP, Desai KG, Chen W, Koutras GM, Han BB, Warner BM, Pei P, Seghi GA, Tong M, Border MB, Fields HW, Stoner GD, Larsen PE, Liu Z, Schwendeman SP, Mallery SR. Evaluation of a mucoadhesive fenretinide patch for local intraoral delivery: a strategy to reintroduce fenretinide for oral cancer chemoprevention. Carcinogenesis. 2012 May;33(5):1098-105. doi: 10.1093/carcin/bgs122. Epub 2012 Mar 15. PubMed PMID: 22427354; PubMed Central PMCID: PMC3334520.

7: Rahmaniyan M, Curley RW Jr, Obeid LM, Hannun YA, Kraveka JM. Identification of dihydroceramide desaturase as a direct in vitro target for fenretinide. J Biol Chem. 2011 Jul 15;286(28):24754-64. doi: 10.1074/jbc.M111.250779. Epub 2011 May 4. PubMed PMID: 21543327; PubMed Central PMCID: PMC3137051.

8: Cooper JP, Hwang K, Singh H, Wang D, Reynolds CP, Curley RW Jr, Williams SC, Maurer BJ, Kang MH. 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. doi: 10.1111/j.1476-5381.2011.01310.x. PubMed PMID: 21391977; PubMed Central PMCID: PMC3144539.

9: Illingworth NA, Boddy AV, Daly AK, Veal GJ. Characterization of the metabolism of fenretinide by human liver microsomes, cytochrome P450 enzymes and UDP-glucuronosyltransferases. Br J Pharmacol. 2011 Feb;162(4):989-99. doi: 10.1111/j.1476-5381.2010.01104.x. PubMed PMID: 21054342; PubMed Central PMCID: PMC3042207.

10: Tiberio P, Cavadini E, Abolafio G, Formelli F, Appierto V. 4-oxo-N-(4-hydroxyphenyl)retinamide: two independent ways to kill cancer cells. PLoS One. 2010 Oct 14;5(10):e13362. doi: 10.1371/journal.pone.0013362. PubMed PMID: 20976277; PubMed Central PMCID: PMC2954786.

11: Valsecchi M, Aureli M, Mauri L, Illuzzi G, Chigorno V, Prinetti A, Sonnino S. Sphingolipidomics of A2780 human ovarian carcinoma cells treated with synthetic retinoids. J Lipid Res. 2010 Jul;51(7):1832-40. doi: 10.1194/jlr.M004010. Epub 2010 Mar 1. PubMed PMID: 20194109; PubMed Central PMCID: PMC2882740.

12: Appierto V, Tiberio P, Cavadini E, Casalini P, Cappelletti G, Formelli F. Antimitotic effect of the retinoid 4-oxo-fenretinide through inhibition of tubulin polymerization: a novel mechanism of retinoid growth-inhibitory activity. Mol Cancer Ther. 2009 Dec;8(12):3360-8. doi: 10.1158/1535-7163.MCT-09-0798. PubMed PMID: 19996280.

13: Formelli F, Cavadini E, Luksch R, Garaventa A, Villani MG, Appierto V, Persiani S. Pharmacokinetics of oral fenretinide in neuroblastoma patients: indications for optimal dose and dosing schedule also with respect to the active metabolite 4-oxo-fenretinide. Cancer Chemother Pharmacol. 2008 Sep;62(4):655-65. Epub 2007 Dec 8. PubMed PMID: 18066548.

14: Villani MG, Appierto V, Cavadini E, Bettiga A, Prinetti A, Clagett-Dame M, Curley RW, Formelli F. 4-oxo-fenretinide, a recently identified fenretinide metabolite, induces marked G2-M cell cycle arrest and apoptosis in fenretinide-sensitive and fenretinide-resistant cell lines. Cancer Res. 2006 Mar 15;66(6):3238-47. PubMed PMID: 16540676.

15: Villani MG, Appierto V, Cavadini E, Valsecchi M, Sonnino S, Curley RW, Formelli F. Identification of the fenretinide metabolite 4-oxo-fenretinide present in human plasma and formed in human ovarian carcinoma cells through induction of cytochrome P450 26A1. Clin Cancer Res. 2004 Sep 15;10(18 Pt 1):6265-75. PubMed PMID: 15448016.