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MedKoo Cat#: 112111 | Name: Nemorosone
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Description:

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

Nemorosone induces apoptosis, abolishes the mitochondrial membrane potential, and increases cytosolic calcium concentration in pancreatic cancer cells. Nemorosone also reduces tumor growth in an MIA-PaCa-2 mouse xenograft model.

Chemical Structure

Nemorosone
Nemorosone
CAS#351416-47-2

Theoretical Analysis

MedKoo Cat#: 112111

Name: Nemorosone

CAS#: 351416-47-2

Chemical Formula: C33H42O4

Exact Mass: 502.3083

Molecular Weight: 502.70

Elemental Analysis: C, 78.85; H, 8.42; O, 12.73

Price and Availability

Size Price Availability Quantity
1mg USD 240.00 2 Weeks
5mg USD 540.00 2 Weeks
10mg USD 830.00 2 Weeks
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Related CAS #
No Data
Synonym
Nemorosone
IUPAC/Chemical Name
(1R,5S,7S)-5-benzoyl-4-hydroxy-6,6-dimethyl-1,3,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione
InChi Key
NXZAENPZCAUREW-RFQWPUQQSA-N
InChi Code
InChI=1S/C33H42O4/c1-21(2)14-16-25-20-32(19-18-23(5)6)28(35)26(17-15-22(3)4)29(36)33(30(32)37,31(25,7)8)27(34)24-12-10-9-11-13-24/h9-15,18,25,36H,16-17,19-20H2,1-8H3/t25-,32+,33-/m0/s1
SMILES Code
OC1=C(C([C@]2(C[C@@H](C(C)([C@]1(C(C3=CC=CC=C3)=O)C2=O)C)C/C=C(C)\C)C/C=C(C)\C)=O)C/C=C(C)\C
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info
Solvent mg/mL mM
Solubility
DMF 30.0 59.68
DMSO 30.0 59.68
Ethanol 30.0 59.68
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 502.70 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
1: Frión-Herrera Y, Gabbia D, Cuesta-Rubio O, De Martin S, Carrara M. Nemorosone inhibits the proliferation and migration of hepatocellular carcinoma cells. Life Sci. 2019 Oct 15;235:116817. doi: 10.1016/j.lfs.2019.116817. Epub 2019 Aug 30. PMID: 31476309. 2: Wolf RJ, Hilger RA, Hoheisel JD, Werner J, Holtrup F. In vivo activity and pharmacokinetics of nemorosone on pancreatic cancer xenografts. PLoS One. 2013 Sep 5;8(9):e74555. doi: 10.1371/journal.pone.0074555. PMID: 24040280; PMCID: PMC3764110. 3: Pardo-Andreu GL, Nuñez-Figueredo Y, Tudella VG, Cuesta-Rubio O, Rodrigues FP, Pestana CR, Uyemura SA, Leopoldino AM, Alberici LC, Curti C. The anti-cancer agent nemorosone is a new potent protonophoric mitochondrial uncoupler. Mitochondrion. 2011 Mar;11(2):255-63. doi: 10.1016/j.mito.2010.10.008. Epub 2010 Oct 31. PMID: 21044702. 4: Popolo A, Piccinelli AL, Morello S, Sorrentino R, Osmany CR, Rastrelli L, Pinto A. Cytotoxic activity of nemorosone in human MCF-7 breast cancer cells. Can J Physiol Pharmacol. 2011 Jan;89(1):50-7. doi: 10.1139/y10-100. Erratum in: Can J Physiol Pharmacol. 2011 Feb;89(2):149. Aldo, Pinto [corrected to Pinto, Aldo]. PMID: 21186377. 5: Kapoor S. Nemorosone and its emerging anti-neoplastic effects. Graefes Arch Clin Exp Ophthalmol. 2013 Oct;251(10):2487. doi: 10.1007/s00417-013-2395-3. Epub 2013 Jun 12. PMID: 23760655. 6: Díaz-Carballo D, Malak S, Freistühler M, Elmaagacli A, Bardenheuer W, Reusch HP. Nemorosone blocks proliferation and induces apoptosis in leukemia cells. Int J Clin Pharmacol Ther. 2008 Aug;46(8):428-39. doi: 10.5414/cpp46428. PMID: 18793585. 7: Frión-Herrera Y, Gabbia D, Díaz-García A, Cuesta-Rubio O, Carrara M. Chemosensitizing activity of Cuban propolis and nemorosone in doxorubicin resistant human colon carcinoma cells. Fitoterapia. 2019 Jul;136:104173. doi: 10.1016/j.fitote.2019.104173. Epub 2019 May 11. PMID: 31085307. 8: Frión-Herrera Y, Gabbia D, Scaffidi M, Zagni L, Cuesta-Rubio O, De Martin S, Carrara M. The Cuban Propolis Component Nemorosone Inhibits Proliferation and Metastatic Properties of Human Colorectal Cancer Cells. Int J Mol Sci. 2020 Mar 6;21(5):1827. doi: 10.3390/ijms21051827. PMID: 32155848; PMCID: PMC7084755. 9: Simpkins NS, Holtrup F, Rodeschini V, Taylor JD, Wolf R. Comparison of the cytotoxic effects of enantiopure PPAPs, including nemorosone and clusianone. Bioorg Med Chem Lett. 2012 Oct 1;22(19):6144-7. doi: 10.1016/j.bmcl.2012.08.023. Epub 2012 Aug 11. PMID: 22944119. 10: Camargo MS, Oliveira MT, Santoni MM, Resende FA, Oliveira-Höhne AP, Espanha LG, Nogueira CH, Cuesta-Rubio O, Vilegas W, Varanda EA. Effects of nemorosone, isolated from the plant Clusia rosea, on the cell cycle and gene expression in MCF-7 BUS breast cancer cell lines. Phytomedicine. 2015 Jan 15;22(1):153-7. doi: 10.1016/j.phymed.2014.11.007. Epub 2014 Nov 22. PMID: 25636884. 11: Díaz-Carballo D, Malak S, Bardenheuer W, Freistuehler M, Reusch HP. Cytotoxic activity of nemorosone in neuroblastoma cells. J Cell Mol Med. 2008 Dec;12(6B):2598-608. doi: 10.1111/j.1582-4934.2008.00232.x. PMID: 18194446; PMCID: PMC3828876. 12: Holtrup F, Bauer A, Fellenberg K, Hilger RA, Wink M, Hoheisel JD. Microarray analysis of nemorosone-induced cytotoxic effects on pancreatic cancer cells reveals activation of the unfolded protein response (UPR). Br J Pharmacol. 2011 Mar;162(5):1045-59. doi: 10.1111/j.1476-5381.2010.01125.x. PMID: 21091652; PMCID: PMC3051378.

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