WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H584282
CAS#: 41451-75-6
Description: 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.
Hodoodo Cat#: H584282
Name: Bruceantin
CAS#: 41451-75-6
Chemical Formula: C28H36O11
Exact Mass: 548.23
Molecular Weight: 548.585
Elemental Analysis: C, 61.30; H, 6.61; O, 32.08
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:
| 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 | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 100.0 | 182.29 |
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: | 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. |
| 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. |
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