Glaucarubin | CAS#1448-23-3 | antiamebic

MedKoo Cat#: 585207 | Name: Glaucarubin

Description:

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

Glaucarubin is a quassinoid (Simaroubolide) from Simaruba glauca, a tropical shrub, that has been used as an antiamebic agent found to be cytotoxic, and may be of use in cancer chemotherapy.

Chemical Structure

Glaucarubin

CAS#1448-23-3

Theoretical Analysis

MedKoo Cat#: 585207

Name: Glaucarubin

CAS#: 1448-23-3

Chemical Formula: C25H36O10

Exact Mass: 496.2308

Molecular Weight: 496.55

Elemental Analysis: C, 60.47; H, 7.31; O, 32.22

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Glaucarubin; Glaumeba; MK-53; MK53; MK 53

IUPAC/Chemical Name

Picras-3-en-16-one, 11,20-epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)-, (1beta,2alpha,11beta,12alpha,15beta(S))-

InChi Key

LZKVXMYVBSNXER-PGGNBUIBSA-N

InChi Code

InChI=1S/C25H36O10/c1-6-22(4,31)21(30)35-16-15-11(3)17(27)25(32)20-23(5)12(10(2)7-13(26)18(23)28)8-14(34-19(16)29)24(15,20)9-33-25/h7,11-18,20,26-28,31-32H,6,8-9H2,1-5H3/t11-,12+,13+,14-,15-,16-,17-,18-,20-,22?,23-,24+,25+/m1/s1

SMILES Code

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

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 496.55 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

1: Yeo D, Huynh N, Beutler JA, Baldwin GS, He H, Nikfarjam M. Glaucarubinone Combined with Gemcitabine Improves Pancreatic Cancer Survival in an Immunocompetent Orthotopic Murine Model. J Invest Surg. 2016 Dec;29(6):366-372. Epub 2016 Mar 30. PubMed PMID: 27027695. 2: Cragg G, Suffness M. Metabolism of plant-derived anticancer agents. Pharmacol Ther. 1988;37(3):425-61. Review. PubMed PMID: 3290912. 3: VAN ASSENDELFT F, MILLER JW, MINTZ DT, SCHACK JA, OTTOLENGHI P, MOST H. The use of glaucarubin (a crystalline glycoside isolated from Simarouba glauca) in the treatment of human colonic amebiasis. Am J Trop Med Hyg. 1956 May;5(3):501-3. PubMed PMID: 13327185. 4: WOODRUFF AW, BELL S, SCHOFIELD FD. Symposium on the treatment of human amoebiasis. II. The treatment of intestinal amoebiasis with emetine bismuth iodide, glaucarubin, dichloroacet-hydroxy-methylanilide, camoform and various antibiotics. Trans R Soc Trop Med Hyg. 1956 Mar;50(2):114-27; discussion, 127-38. PubMed PMID: 13324920. 5: DEL POZO EC, ALCARAZ M. Clinical trial of glaucarubin in treatment of amebiasis. Am J Med. 1956 Mar;20(3):412-7. PubMed PMID: 13292450. 6: Yeo D, Huynh N, Beutler JA, Christophi C, Shulkes A, Baldwin GS, Nikfarjam M, He H. Glaucarubinone and gemcitabine synergistically reduce pancreatic cancer growth via down-regulation of P21-activated kinases. Cancer Lett. 2014 May 1;346(2):264-72. doi: 10.1016/j.canlet.2014.01.001. Epub 2014 Jan 31. PubMed PMID: 24491405. 7: Ohno N, Fukamiya N, Okano M, Tagahara K, Lee KH. Synthesis of cytotoxic fluorinated quassinoids. Bioorg Med Chem. 1997 Aug;5(8):1489-95. PubMed PMID: 9313855. 8: Huynh N, Beutler JA, Shulkes A, Baldwin GS, He H. Glaucarubinone inhibits colorectal cancer growth by suppression of hypoxia-inducible factor 1α and β-catenin via a p-21 activated kinase 1-dependent pathway. Biochim Biophys Acta. 2015 Jan;1853(1):157-65. doi: 10.1016/j.bbamcr.2014.10.013. Epub 2014 Oct 22. PubMed PMID: 25409929. 9: Shing TK, Jiang Q. Total synthesis of (+)-quassin. J Org Chem. 2000 Oct 20;65(21):7059-69. PubMed PMID: 11031029. 10: Darwish FA, Evans FJ, Phillipson JD. Cytotoxic bruceolides from Brucea javanica [proceedings]. J Pharm Pharmacol. 1979 Dec;31 Suppl:10P. PubMed PMID: 42672. 11: KARTHA G, HAAS DJ, SCHAFFER HM, KAISTRA KK. CRYSTAL AND MOLECULAR STRUCTURE OF GLAUCARUBIN. Nature. 1964 Apr 25;202:389-90. PubMed PMID: 14152823. 12: Polonsky J. Quassinoid bitter principles. II. Fortschr Chem Org Naturst. 1985;47:221-64. Review. PubMed PMID: 3896993. 13: Badal SAM, Asuncion Valenzuela MM, Zylstra D, Huang G, Vendantam P, Francis S, Quitugua A, Amis LH, Davis W, Tzeng TJ, Jacobs H, Gangemi DJ, Raner G, Rowland L, Wooten J, Campbell P, Brantley E, Delgoda R. Glaucarubulone glucoside from Castela macrophylla suppresses MCF-7 breast cancer cell growth and attenuates benzo[a]pyrene-mediated CYP1A gene induction. J Appl Toxicol. 2017 Jul;37(7):873-883. doi: 10.1002/jat.3436. Epub 2017 Jan 31. PubMed PMID: 28138972; PubMed Central PMCID: PMC5435539. 14: PEDOYA C, CHARLET R, SAVELLI A, ENJALBERT M, BENSAUDE A. [The treatment of intestinal amebiasis by glaucarubin]. Presse Med. 1959 Aug 8;67:1481-3. French. PubMed PMID: 14431343. 15: Gillin FD, Reiner DS, Suffness M. Bruceantin, a potent amoebicide from a plant, Brucea antidysenterica. Antimicrob Agents Chemother. 1982 Aug;22(2):342-5. PubMed PMID: 6100431; PubMed Central PMCID: PMC183739. 16: Hall IH, Lee KH, Imakura Y, Okano M, Johnson A. Anti-inflammatory agents III: Structure-activity relationships of brusatol and related quassinoids. J Pharm Sci. 1983 Nov;72(11):1282-4. PubMed PMID: 6417321. 17: Wright CW, Anderson MM, Allen D, Phillipson JD, Kirby GC, Warhurst DC, Chang HR. Quassinoids exhibit greater selectivity against Plasmodium falciparum than against Entamoeba histolytica, Giardia intestinalis or Toxoplasma gondii in vitro. J Eukaryot Microbiol. 1993 May-Jun;40(3):244-6. PubMed PMID: 8508162. 18: Apers S, Cimanga K, Vanden Berghe D, Van Meenen E, Longanga AO, Foriers A, Vlietinck A, Pieters L. Antiviral activity of simalikalactone D, a quassinoid from Quassia africana. Planta Med. 2002 Jan;68(1):20-4. PubMed PMID: 11842321. 19: François G, Diakanamwa C, Timperman G, Bringmann G, Steenackers T, Atassi G, Van Looveren M, Holenz J, Tassin JP, Assi LA, Vanhaelen-Fastre R, Vanhaelen M. Antimalarial and cytotoxic potential of four quassinoids from Hannoa chlorantha and Hannoa klaineana, and their structure-activity relationships. Int J Parasitol. 1998 Apr;28(4):635-40. PubMed PMID: 9602388. 20: Willingham W 3rd, Considine RT, Chaney SG, Lee KH, Hall IH. Reversibility of protein synthesis inhibition by quassinoid antineoplastic agents in a rabbit reticulocyte system. Biochem Pharmacol. 1984 Jan 15;33(2):330-3. PubMed PMID: 6704156.