Synonym
Tylocrebrine DL-form;
IUPAC/Chemical Name
2,3,5,6-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline
InChi Key
YFEPHJVWLFGWKH-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H27NO4/c1-26-20-8-7-15-19-13-25-9-5-6-14(25)10-16(19)17-11-21(27-2)22(28-3)12-18(17)23(15)24(20)29-4/h7-8,11-12,14H,5-6,9-10,13H2,1-4H3
SMILES Code
COc(cc1)c(OC)c2c1c(CN3CCCC3C4)c4c5c2cc(OC)c(OC)c5
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
393.48
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: Kirtane AR, Wong HL, Guru BR, Lis LG, Georg GI, Gurvich VJ, Panyam J. Reformulating Tylocrebrine in Epidermal Growth Factor Receptor Targeted Polymeric Nanoparticles Improves Its Therapeutic Index. Mol Pharm. 2015 Aug 3;12(8):2912-23. doi: 10.1021/acs.molpharmaceut.5b00173. Epub 2015 Jul 3. PMID: 26065924; PMCID: PMC4525301.
2: Zheng Y, Liu Y, Wang Q. Collective asymmetric synthesis of (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert- butanesulfinamide as a chiral auxiliary. J Org Chem. 2014 Apr 18;79(8):3348-57. doi: 10.1021/jo500013e. Epub 2014 Mar 28. PMID: 24679059.
3: Gupta RS, Siminovitch L. Mutants of CHO cells resistant to the protein synthesis inhibitors, cryptopleurine and tylocrebrine: genetic and biochemical evidence for common site of action of emetine, cryptopleurine, tylocrebine, and tubulosine. Biochemistry. 1977 Jul 12;16(14):3209-14. doi: 10.1021/bi00633a026. PMID: 560858.
4: Niphakis MJ, Georg GI. Synthesis of tylocrebrine and related phenanthroindolizidines by VOF3-mediated oxidative aryl-alkene coupling. Org Lett. 2011 Jan 21;13(2):196-9. doi: 10.1021/ol1023954. Epub 2010 Dec 14. PMID: 21142214.
5: Damu AG, Kuo PC, Shi LS, Li CY, Kuoh CS, Wu PL, Wu TS. Phenanthroindolizidine alkaloids from the stems of Ficus septica. J Nat Prod. 2005 Jul;68(7):1071-5. doi: 10.1021/np050095o. PMID: 16038551.
6: Donaldson GR, Atkinson MR, Murray AW. Inhibition of protein synthesis in Ehrlich ascites-tumour cells by the phenanthrene alkaloids tylophorine, tylocrebrine and cryptopleurine. Biochem Biophys Res Commun. 1968 Apr 5;31(1):104-9. doi: 10.1016/0006-291x(68)90037-5. PMID: 4869942.
7: Gupta RS, Krepinsky JJ, Siminovitch L. Structural determinants responsible for the biological activity of (-)-emetine, (-)-cryptopleurine, and (-)-tylocrebrine: structure-activity relationship among related compounds. Mol Pharmacol. 1980 Jul;18(1):136-43. PMID: 7412757.
8: GELLERT E, RUDZATS R. THE ANTILEUKEMIA ACTIVITY OF TYLOCREBRINE. J Med Chem. 1964 May;7:361-2. doi: 10.1021/jm00333a029. PMID: 14204981.
9: Huang MT, Grollman AP. Mode of action of tylocrebrine: effects on protein and nucleic acid synthesis. Mol Pharmacol. 1972 Sep;8(5):538-50. PMID: 4343427.
10: Grant P, Sánchez L, Jiménez A. Cryptopleurine resistance: genetic locus for a 40S ribosomal component in Saccharomyces cerevisiae. J Bacteriol. 1974 Dec;120(3):1308-14. doi: 10.1128/JB.120.3.1308-1314.1974. PMID: 4612014; PMCID: PMC245916.
