Synonym
Symplostatin 1; Symplostatin-1;
IUPAC/Chemical Name
(2S,3S)-2-(dimethylamino)-N-(N-((3R,4S,5S)-3-methoxy-1-((S)-2-((1R,2R)-1-methoxy-2-methyl-3-oxo-3-(((S)-2-phenyl-1-(thiazol-2-yl)ethyl)amino)propyl)pyrrolidin-1-yl)-5-methyl-1-oxoheptan-4-yl)-N-methyl-L-valyl)-3-methylpentanamide
InChi Key
QUBPPXJLERPMJG-KJTFKGMVSA-N
InChi Code
InChI=1S/C43H70N6O6S/c1-13-28(5)37(48(10)36(27(3)4)41(52)46-42(53)38(47(8)9)29(6)14-2)34(54-11)26-35(50)49-23-18-21-33(49)39(55-12)30(7)40(51)45-32(43-44-22-24-56-43)25-31-19-16-15-17-20-31/h15-17,19-20,22,24,27-30,32-34,36-39H,13-14,18,21,23,25-26H2,1-12H3,(H,45,51)(H,46,52,53)/t28-,29-,30+,32-,33-,34+,36-,37-,38-,39+/m0/s1
SMILES Code
CC(C)[C@@H](C(NC([C@H]([C@@H](C)CC)N(C)C)=O)=O)N([C@@H]([C@@H](C)CC)[C@H](OC)CC(N1[C@H]([C@H](OC)[C@@H](C)C(N[C@H](C2=NC=CS2)CC3=CC=CC=C3)=O)CCC1)=O)C
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
799.12
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: Harrigan GG, Luesch H, Yoshida WY, Moore RE, Nagle DG, Paul VJ, Mooberry SL, Corbett TH, Valeriote FA. Symplostatin 1: A dolastatin 10 analogue from the marine cyanobacterium Symploca hydnoides. J Nat Prod. 1998 Sep;61(9):1075-7. PubMed PMID: 9748368.
2: Salvador-Reyes LA, Engene N, Paul VJ, Luesch H. Targeted natural products discovery from marine cyanobacteria using combined phylogenetic and mass spectrometric evaluation. J Nat Prod. 2015 Mar 27;78(3):486-92. doi: 10.1021/np500931q. Epub 2015 Jan 30. PubMed PMID: 25635943; PubMed Central PMCID: PMC4724867.
3: Salvador LA, Paul VJ, Luesch H. Caylobolide B, a macrolactone from symplostatin 1-producing marine cyanobacteria Phormidium spp. from Florida. J Nat Prod. 2010 Sep 24;73(9):1606-9. doi: 10.1021/np100467d. Erratum in: J Nat Prod. 2016 Feb 26;79(2):452. PubMed PMID: 20806908; PubMed Central PMCID: PMC2965599.
4: Mooberry SL, Leal RM, Tinley TL, Luesch H, Moore RE, Corbett TH. The molecular pharmacology of symplostatin 1: a new antimitotic dolastatin 10 analog. Int J Cancer. 2003 Apr 20;104(4):512-21. PubMed PMID: 12584751.
5: Luesch H, Moore RE, Paul VJ, Mooberry SL, Corbett TH. Isolation of dolastatin 10 from the marine cyanobacterium Symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1. J Nat Prod. 2001 Jul;64(7):907-10. PubMed PMID: 11473421.
6: Horgen FD, Kazmierski EB, Westenburg HE, Yoshida WY, Scheuer PJ. Malevamide D: isolation and structure determination of an isodolastatin H analogue from the marine cyanobacterium Symploca hydnoides. J Nat Prod. 2002 Apr;65(4):487-91. Erratum in: J Nat Prod. 2003 Jan;66(1):155.. PubMed PMID: 11975485.
