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Bruceantin

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Bruceantin
Names
IUPAC name Methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclononadec-9-ene-17-carboxylate
Other names Bruceantine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
InChI
  • 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/s1Key: IRQXZTBHNKVIRL-GOTQHHPNSA-N
SMILES
  • CC1=C(C(=O)C2(1C3452(((4(C(=O)O3)OC(=O)/C=C(\C)/C(C)C)(OC5)C(=O)OC)O)O)C)O
Properties
Chemical formula C28H36O11
Molar mass 548.585 g·mol
Melting point 225–226 °C (437–439 °F; 498–499 K)
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose) mouse (male, IV) 1.95 mg/kg
mouse (female, IV) 2.58 mg/kg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Bruceantin is a chemical compound that was first isolated from the plant Brucea antidysenterica in 1973. Chemically, it is classified as a secotriterpenoid and a quassinoid.

Bucreantin has attracted interest as a potential antitumor drug because of its antineoplastic activity. It inhibits the peptidyl transferase elongation reaction, resulting in decreased protein and DNA synthesis. Bruceantin also has antibiotic, antiamoebic, and antimalarial activity.

Phase I and II clinical trials were conducted for the treatment of metastatic breast cancer and malignant melanoma, but tumor regression was not observed and clinical development was terminated.

References

  1. ^ Merck Index, 12th Edition, 1475
  2. Kupchan, S. Morris; Britton, Ronald W.; Ziegler, Myra F.; Sigel, Carl W. (1973). "Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica". J. Org. Chem. 38 (1): 178–179. doi:10.1021/jo00941a049. PMID 4682660.
  3. ^ "Bruceantin". NCI Cancer Dictionary. National Institutes of Health.
  4. Gillin, F. D.; Reiner, D. S.; Suffness, M. (2021). "Bruceantin, a potent amoebicide from a plant, Brucea antidysenterica". Antimicrobial Agents and Chemotherapy. 22 (2): 342–345. doi:10.1128/AAC.22.2.342. PMC 183739. PMID 6100431.
  5. Cuendet, Muriel; Pezzuto, John M. (2004). "Antitumor activity of bruceantin: an old drug with new promise". J Nat Prod. 67 (2): 269–272. doi:10.1021/np030304+. PMID 14987068.
  6. "Bruceantin". Inxsight Drugs.


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