Bruceantin

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Bruceantin
Bruceantin.svg
Names
IUPAC name
Methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
Other names
Bruceantine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • 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
    Key: IRQXZTBHNKVIRL-GOTQHHPNSA-N
  • CC1=C(C(=O)C[C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)C)(OC5)C(=O)OC)O)O)C)O
Properties
C28H36O11
Molar mass 548.585 g·mol−1
Melting point 225–226 °C (437–439 °F; 498–499 K) [1]
Hazards
Lethal dose or concentration (LD, LC):
mouse (male, IV) 1.95 mg/kg
mouse (female, IV) 2.58 mg/kg [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bruceantin is a chemical compound that was first isolated from the plant Brucea antidysenterica in 1973. [2] Chemically, it is classified as a secotriterpenoid and a quassinoid.

Bucreantin has attracted interest as a potential antitumor drug because of its antineoplastic activity. [3] It inhibits the peptidyl transferase elongation reaction, resulting in decreased protein and DNA synthesis. [3] Bruceantin also has antibiotic, antiamoebic, [4] and antimalarial activity. [3]

Phase I and II clinical trials were conducted for the treatment of metastatic breast cancer and melanoma, but tumor regression was not observed and clinical development was terminated. [5] [6]

References

  1. 1 2 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. 1 2 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. Bibcode:2004JNAtP..67..269C. doi:10.1021/np030304+. PMID   14987068.
  6. ↑ "Bruceantin". Inxsight Drugs.


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