Synonym
Leurosidine N'b-oxide;
IUPAC/Chemical Name
(5S,7R,9S)-9-((3aS,3a1R,4R,5R,5aS,10bS)-4-acetoxy-3a-ethyl-5-hydroxy-8-methoxy-5-(methoxycarbonyl)-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazol-9-yl)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-3,7-methano[1]azacycloundecino[5,4-b]indole 3(2H)-oxide
InChi Key
JJNRGDILJOBAEK-UHFFFAOYSA-N
InChi Code
1S/C46H58N4O10/c1-8-42(54)23-28-24-45(40(52)58-6,36-30(15-20-50(56,25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)57-5)48(4)38-44(31)17-19-49-18-12-16-43(9-2,37(44)49)39(60-27(3)51)46(38,55)41(53)59-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3
SMILES Code
COc1cc(N(C)[C@@H]2[C@@](C(OC)=O)(O)[C@H](OC(C)=O)[C@]3(CC)[C@@H]4N(CC[C@@]524)CC=C3)c5cc1[C@]6(C(OC)=O)c7[nH]c8ccccc8c7CCN9(C[C@@](CC)(O)C[C@H](C9)C6)=O
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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
826.98
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: Mukhopadhyay S, Cordell GA. Catharanthus alkaloids. XXXV. Isolation of leurosidine N'b-oxide from Catharanthus roseus. J Nat Prod. 1981 Sep-Oct;44(5):611-3. PubMed PMID: 7320741.
2: Kuehne ME, Qin Y, Huot AE, Bane SL. The syntheses of 16a'-homo-leurosidine and 16a'-homo-vinblastine. Generation of atropisomers. J Org Chem. 2001 Aug 10;66(16):5317-28. PubMed PMID: 11485450.
3: Ishikawa H, Colby DA, Seto S, Va P, Tam A, Kakei H, Rayl TJ, Hwang I, Boger DL. Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues. J Am Chem Soc. 2009 Apr 8;131(13):4904-16. doi: 10.1021/ja809842b. PubMed PMID: 19292450; PubMed Central PMCID: PMC2727944.
4: Ishikawa H, Colby DA, Boger DL. Direct coupling of catharanthine and vindoline to provide vinblastine: total synthesis of (+)- and ent-(-)-vinblastine. J Am Chem Soc. 2008 Jan 16;130(2):420-1. PubMed PMID: 18081297; PubMed Central PMCID: PMC2570212.
5: FARNSWORTH NR, HILINSKI IM. STUDIES ON CATHARANTHUS ALKALOIDS. 3. SEPARATION OF VINCALEUKOBLASTINE, LEUROCRISTINE, LEUROSINE AND LEUROSIDINE BY THIN-LAYER CHROMATOGRAPHY. J Chromatogr. 1965 Apr;18:184-8. PubMed PMID: 14334202.
