Bruceantin | CAS#41451-75-6 | Natural diverse quassinoid

MedKoo Cat#: 584282 | Name: Bruceantin

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Description:

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

Bruceantin is a quassinoid originally isolated from B. antidysenterica that has diverse biological activities. It inhibits protein synthesis in HeLa cells, reticulocytes, and reticulocyte lysates (IC50s = 30, 40, and 1,600 nM, respectively). Bruceantin is active against chloroquine-sensitive and -resistant strains of P. falciparum (IC50s = 8 and 13 nM, respectively). It induces apoptosis in HL-60 leukemia and RPMI-8226 multiple myeloma cells (IC50s = 12.2 and 12.8 nM, respectively). Bruceantin (5 mg/kg) induces tumor regression in an RPMI-8226 mouse xenograft model.

Chemical Structure

Bruceantin

CAS#41451-75-6

Theoretical Analysis

MedKoo Cat#: 584282

Name: Bruceantin

CAS#: 41451-75-6

Chemical Formula: C28H36O11

Exact Mass: 548.2258

Molecular Weight: 548.59

Elemental Analysis: C, 61.30; H, 6.61; O, 32.08

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 Weeks
5mg	USD 850.00	2 Weeks

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Related CAS #

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Synonym

Bruceantin; (–)-Bruceantin; (–) Bruceantin; NCI 165563; NCI165563; NCI-165563; NSC 165563; NSC165563; NSC-165563;

IUPAC/Chemical Name

Picras-3-en-21-oic acid, 15-((3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester, (11beta,12alpha,15beta(E))- (9CI)

InChi Key

IRQXZTBHNKVIRL-GOTQHHPNSA-N

InChi Code

InChI=1S/C28H36O11/c1-11(2)12(3)7-17(30)39-20-22-27-10-37-28(22,25(35)36-6)23(33)19(32)21(27)26(5)9-15(29)18(31)13(4)14(26)8-16(27)38-24(20)34/h7,11,14,16,19-23,31-33H,8-10H2,1-6H3/b12-7+/t14-,16+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1

SMILES Code

CC([C@](C[C@@](O1)2[H])3[H])=C(O)C(C[C@]3(C)[C@]4([H])[C@]2(CO[C@@]5([C@@H](O)[C@@H]4O)C(OC)=O)[C@@]5([H])[C@@H](OC(/C=C(C)/C(C)C)=O)C1=O)=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

>2 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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Bruceantin (NSC165563) is first isolated from Brucea antidysenterica, a tree used in Ethiopia for the treatment of cancer, and activity was observed against B16 melanoma, colon 38, and L1210 and P388 leukemia in mice.

In vitro activity:

In addition, BCT (bruceantin) induced apoptosis in 22RV1 cells in a time-dependent manner (Figure 1G and Figure S2B). BCT also strongly suppressed the migration and invasion of 22RV1 cells (Figure 1H). Moreover, BCT reduced the size and number of prostaspheres in sphere formation assays using 22RV1 cells (Figure 1I), indicating that BCT can inhibit the self-renewal of stem-like CRPC cells. Collectively, these results revealed that BCT could potently inhibit the growth of AR-positive PCa cells (including both androgen-sensitive and CRPC cells) with less effect on normal prostate cells and AR-negative PCa cells and suppress in vitro metastatic properties of CRPC cells. Reference: Theranostics. 2021; 11(2): 958–973. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7738850/

In vivo activity:

Differences in the growth rate of tumors during the treatment period between the control and the treated group were statistically significant (P = 0.0179). At day 60, 6-week-old males treated with the vehicle had a tumor volume that increased to 318% (95% CI, 0–974%), compared with 100% at day 35, whereas the tumor volume of mice treated with bruceantin (2.5 mg/kg) decreased to 30% (95% CI, 0–130%). Reference: Clin Cancer Res. 2004 Feb 1;10(3):1170-9. https://clincancerres.aacrjournals.org/content/10/3/1170.long

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	182.29

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 548.59 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.

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

Formulation protocol:

1. Moon SJ, Jeong BC, Kim HJ, Lim JE, Kim HJ, Kwon GY, Jackman JA, Kim JH. Bruceantin targets HSP90 to overcome resistance to hormone therapy in castration-resistant prostate cancer. Theranostics. 2021 Jan 1;11(2):958-973. doi: 10.7150/thno.51478. PMID: 33391515; PMCID: PMC7738850. 2. Issa ME, Berndt S, Carpentier G, Pezzuto JM, Cuendet M. Bruceantin inhibits multiple myeloma cancer stem cell proliferation. Cancer Biol Ther. 2016 Sep;17(9):966-75. doi: 10.1080/15384047.2016.1210737. Epub 2016 Jul 19. PMID: 27434731; PMCID: PMC5036415. 3. Cuendet M, Christov K, Lantvit DD, Deng Y, Hedayat S, Helson L, McChesney JD, Pezzuto JM. Multiple myeloma regression mediated by bruceantin. Clin Cancer Res. 2004 Feb 1;10(3):1170-9. doi: 10.1158/1078-0432.ccr-0362-3. PMID: 14871997.

In vitro protocol:

In vivo protocol:

1. Cuendet M, Christov K, Lantvit DD, Deng Y, Hedayat S, Helson L, McChesney JD, Pezzuto JM. Multiple myeloma regression mediated by bruceantin. Clin Cancer Res. 2004 Feb 1;10(3):1170-9. doi: 10.1158/1078-0432.ccr-0362-3. PMID: 14871997.

1: Jöhrer K, Ҫiҫek SS. Multiple Myeloma Inhibitory Activity of Plant Natural Products. Cancers (Basel). 2021 May 29;13(11):2678. doi: 10.3390/cancers13112678. PMID: 34072312; PMCID: PMC8198565. 2: Burgers LD, Fürst R. Natural products as drugs and tools for influencing core processes of eukaryotic mRNA translation. Pharmacol Res. 2021 May 29;170:105535. doi: 10.1016/j.phrs.2021.105535. Epub ahead of print. PMID: 34058326. 3: Jakhmola S, Hazarika Z, Jha AN, Jha HC. In silico analysis of antiviral phytochemicals efficacy against Epstein-Barr virus glycoprotein H. J Biomol Struct Dyn. 2021 Jan 13:1-14. doi: 10.1080/07391102.2020.1871074. Epub ahead of print. PMID: 33438528. 4: Moon SJ, Jeong BC, Kim HJ, Lim JE, Kim HJ, Kwon GY, Jackman JA, Kim JH. Bruceantin targets HSP90 to overcome resistance to hormone therapy in castration-resistant prostate cancer. Theranostics. 2021 Jan 1;11(2):958-973. doi: 10.7150/thno.51478. PMID: 33391515; PMCID: PMC7738850. 5: Ren Y, Kinghorn AD. Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones. J Med Chem. 2020 Dec 24;63(24):15410-15448. doi: 10.1021/acs.jmedchem.0c01449. Epub 2020 Dec 8. PMID: 33289552; PMCID: PMC7812702. 6: Kirubhanand C, Selvaraj J, Rekha UV, Vishnupriya V, Sivabalan V, Manikannan M, Nalini D, Vijayalakshmi P, Rajalakshmi M, Ponnulakshmi R. Molecular docking analysis of Bcl-2 with phyto-compounds. Bioinformation. 2020 Jun 30;16(6):468-473. doi: 10.6026/97320630016468. PMID: 32884211; PMCID: PMC7452744. 7: Hwang D, Ramsey JD, Makita N, Sachse C, Jordan R, Sokolsky-Papkov M, Kabanov AV. Novel poly(2-oxazoline) block copolymer with aromatic heterocyclic side chains as a drug delivery platform. J Control Release. 2019 Aug 10;307:261-271. doi: 10.1016/j.jconrel.2019.06.037. Epub 2019 Jun 28. PMID: 31260756; PMCID: PMC7482421. 8: Lichota A, Gwozdzinski K. Anticancer Activity of Natural Compounds from Plant and Marine Environment. Int J Mol Sci. 2018 Nov 9;19(11):3533. doi: 10.3390/ijms19113533. PMID: 30423952; PMCID: PMC6275022. 9: Ryu SM, Kwon J, Seo YH, Song EG, Hong SS, Kim BS, Hong JS, Ryu KH, Lee D. Quassinoids isolated from Brucea javanica inhibit pepper mottle virus in pepper. Virus Res. 2017 Jan 2;227:49-56. doi: 10.1016/j.virusres.2016.09.013. Epub 2016 Sep 26. PMID: 27686478. 10: Issa ME, Berndt S, Carpentier G, Pezzuto JM, Cuendet M. Bruceantin inhibits multiple myeloma cancer stem cell proliferation. Cancer Biol Ther. 2016 Sep;17(9):966-75. doi: 10.1080/15384047.2016.1210737. Epub 2016 Jul 19. PMID: 27434731; PMCID: PMC5036415. 11: Ravindar K, Caron PY, Deslongchamps P. Anionic polycyclization entry to tricycles related to quassinoids and terpenoids: a stereocontrolled total synthesis of (+)-cassaine. J Org Chem. 2014 Sep 5;79(17):7979-99. doi: 10.1021/jo501122k. Epub 2014 Aug 7. PMID: 25057897. 12: Fiaschetti G, Grotzer MA, Shalaby T, Castelletti D, Arcaro A. Quassinoids: From traditional drugs to new cancer therapeutics. Curr Med Chem. 2011;18(3):316-28. doi: 10.2174/092986711794839205. PMID: 21143123. 13: Kim JA, Lau EK, Pan L, De Blanco EJ. NF-kappaB inhibitors from Brucea javanica exhibiting intracellular effects on reactive oxygen species. Anticancer Res. 2010 Sep;30(9):3295-300. PMID: 20944100; PMCID: PMC3013507. 14: Robert F, Carrier M, Rawe S, Chen S, Lowe S, Pelletier J. Altering chemosensitivity by modulating translation elongation. PLoS One. 2009;4(5):e5428. doi: 10.1371/journal.pone.0005428. Epub 2009 May 1. PMID: 19412536; PMCID: PMC2671598. 15: Gürel G, Blaha G, Moore PB, Steitz TA. U2504 determines the species specificity of the A-site cleft antibiotics: the structures of tiamulin, homoharringtonine, and bruceantin bound to the ribosome. J Mol Biol. 2009 May 29;389(1):146-56. doi: 10.1016/j.jmb.2009.04.005. Epub 2009 Apr 9. PMID: 19362093; PMCID: PMC2682339. 16: Pan L, Chin YW, Chai HB, Ninh TN, Soejarto DD, Kinghorn AD. Bioactivity- guided isolation of cytotoxic constituents of Brucea javanica collected in Vietnam. Bioorg Med Chem. 2009 Mar 15;17(6):2219-24. doi: 10.1016/j.bmc.2008.10.076. Epub 2008 Nov 5. Erratum in: Bioorg Med Chem. 2011 Feb 15;19(4):1562. PMID: 19026551; PMCID: PMC2683946. 17: Guo Z, Vangapandu S, Nimrod A, Walker LA, Sindelar RD. Synthesis of A/B-ring partial analogs of bruceantin as potential antimalarial agents. Med Chem. 2005 Jan;1(1):3-11. doi: 10.2174/1573406053402488. PMID: 16789880. 18: Kinghorn AD, Su BN, Jang DS, Chang LC, Lee D, Gu JQ, Carcache-Blanco EJ, Pawlus AD, Lee SK, Park EJ, Cuendet M, Gills JJ, Bhat K, Park HS, Mata-Greenwood E, Song LL, Jang M, Pezzuto JM. Natural inhibitors of carcinogenesis. Planta Med. 2004 Aug;70(8):691-705. doi: 10.1055/s-2004-827198. PMID: 15326546. 19: Cuendet M, Pezzuto JM. Antitumor activity of bruceantin: an old drug with new promise. J Nat Prod. 2004 Feb;67(2):269-72. doi: 10.1021/np030304+. PMID: 14987068. 20: Cuendet M, Christov K, Lantvit DD, Deng Y, Hedayat S, Helson L, McChesney JD, Pezzuto JM. Multiple myeloma regression mediated by bruceantin. Clin Cancer Res. 2004 Feb 1;10(3):1170-9. doi: 10.1158/1078-0432.ccr-0362-3. PMID: 14871997.