Swainsonine

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

MedKoo CAT#: 585188

CAS#: 72741-87-8

Description: Swainsonine is an anticancer drug from three endophytic fungi.


Chemical Structure

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Swainsonine
CAS# 72741-87-8

Theoretical Analysis

MedKoo Cat#: 585188
Name: Swainsonine
CAS#: 72741-87-8
Chemical Formula: C8H15NO3
Exact Mass: 173.1052
Molecular Weight: 173.212
Elemental Analysis: C, 55.47; H, 8.73; N, 8.09; O, 27.71

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Swainsonine; Tridolgosir

IUPAC/Chemical Name: 1,2,8-Indolizinetriol, octahydro-, (1S-(1alpha,2alpha,8beta,8abeta))-

InChi Key: FXUAIOOAOAVCGD-WCTZXXKLSA-N

InChi Code: InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1

SMILES Code: O[C@@H]1[C@H](O)CN2CCC[C@@H](O)[C@]12[H]

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

Preparing Stock Solutions

The following data is based on the product molecular weight 173.212 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.

Recalculate based on batch purity %
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

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Reconstitution Calculator

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1: Cook D, Gardner DR, Pfister JA, Lee ST, Welch KD, Welsh SL. A Screen for Swainsonine in Select North American Astragalus Species. Chem Biodivers. 2017 Apr;14(4). doi: 10.1002/cbdv.201600364. Epub 2017 Mar 23. PubMed PMID: 28155255.

2: Cook D, Gardner DR, Roper JM, Ransom CV, Pfister JA, Panter KE. Fungicide treatment and clipping of Oxytropis sericea does not disrupt swainsonine concentrations. Toxicon. 2016 Nov;122:26-30. doi: 10.1016/j.toxicon.2016.09.012. Epub 2016 Sep 16. PubMed PMID: 27644899.

3: Wu C, Han T, Lu H, Zhao B. The toxicology mechanism of endophytic fungus and swainsonine in locoweed. Environ Toxicol Pharmacol. 2016 Oct;47:38-46. doi: 10.1016/j.etap.2016.08.018. Epub 2016 Aug 31. Review. PubMed PMID: 27606974.

4: Ren Z, Song R, Wang S, Quan H, Yang L, Sun L, Zhao B, Lu H. The Biosynthesis Pathway of Swainsonine, a New Anticancer Drug from Three Endophytic Fungi. J Microbiol Biotechnol. 2017 Nov 28;27(11):1897-1906. doi: 10.4014/jmb.1709.09003. Review. PubMed PMID: 29092390.

5: Cook D, Gardner DR, Pfister JA. Swainsonine-containing plants and their relationship to endophytic fungi. J Agric Food Chem. 2014 Jul 30;62(30):7326-34. doi: 10.1021/jf501674r. Epub 2014 May 6. Review. PubMed PMID: 24758700.

6: Cook D, Gardner DR, Martinez A, Robles CA, Pfister JA. Screening for swainsonine among South American Astragalus species. Toxicon. 2017 Dec 1;139:54-57. doi: 10.1016/j.toxicon.2017.09.014. Epub 2017 Sep 28. PubMed PMID: 28964750.

7: Lindsay KB, Pyne SG. Asymmetric synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, and (+)-1,2,8-tri-epi-swainsonine. J Org Chem. 2002 Nov 1;67(22):7774-80. PubMed PMID: 12398502.

8: Louvel J, Chemla F, Demont E, Ferreira F, Pérez-Luna A. Synthesis of (-)-swainsonine and (-)-8-epi-swainsonine by the addition of allenylmetals to chiral α,β-alkoxy sulfinylimines. Org Lett. 2011 Dec 16;13(24):6452-5. doi: 10.1021/ol202747p. Epub 2011 Nov 14. PubMed PMID: 22082237.

9: Grum DS, Cook D, Baucom D, Mott IW, Gardner DR, Creamer R, Allen JG. Production of the alkaloid swainsonine by a fungal endophyte in the host Swainsona canescens. J Nat Prod. 2013 Oct 25;76(10):1984-8. doi: 10.1021/np400274n. Epub 2013 Sep 20. PubMed PMID: 24053110.

10: Wu C, Feng K, Lu D, Yan D, Han T, Zhao B. Reproductive Toxicities Caused by Swainsonine from Locoweed in Mice. Biomed Res Int. 2016;2016:6824374. doi: 10.1155/2016/6824374. Epub 2016 Nov 24. PubMed PMID: 27999809; PubMed Central PMCID: PMC5143690.

11: Si CM, Mao ZY, Dong HQ, Du ZT, Wei BG, Lin GQ. Divergent Method to trans-5-Hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-Epiquinamide and (+)-Swainsonine. J Org Chem. 2015 Jun 5;80(11):5824-33. doi: 10.1021/acs.joc.5b00803. Epub 2015 May 20. PubMed PMID: 25973892.

12: Cook D, Oliveira CA, Gardner DR, Pfister JA, Riet-Correa G, Riet-Correa F. Changes in swainsonine, calystegine, and nitrogen concentrations on an annual basis in Ipomoea carnea. Toxicon. 2015 Mar;95:62-6. doi: 10.1016/j.toxicon.2015.01.002. Epub 2015 Jan 5. PubMed PMID: 25572338.

13: Qian BC, Kamori A, Kinami K, Kato A, Li YX, Fleet GW, Yu CY. Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars. Org Biomol Chem. 2016 May 11;14(19):4488-98. doi: 10.1039/c6ob00531d. PubMed PMID: 27093691.

14: Wu L, Chen P, Liu G. Pd(II)-Catalyzed Aminofluorination of Alkenes in Total Synthesis 6-(R)-Fluoroswainsonine and 5-(R)-Fluorofebrifugine. Org Lett. 2016 Mar 4;18(5):960-3. doi: 10.1021/acs.orglett.6b00030. Epub 2016 Feb 16. PubMed PMID: 26881909.

15: Wu C, Liu X, Ma F, Zhao B. Hematological and histopathological effects of swainsonine in mouse. BMC Vet Res. 2015 Feb 3;11:16. doi: 10.1186/s12917-015-0336-6. PubMed PMID: 25644684; PubMed Central PMCID: PMC4335725.

16: Dhand V, Draper JA, Moore J, Britton R. A short, organocatalytic formal synthesis of (-)-swainsonine and related alkaloids. Org Lett. 2013 Apr 19;15(8):1914-7. doi: 10.1021/ol400566j. Epub 2013 Apr 3. PubMed PMID: 23550817.

17: Cook D, Gardner DR, Grum D, Pfister JA, Ralphs MH, Welch KD, Green BT. Swainsonine and endophyte relationships in Astragalus mollissimus and Astragalus lentiginosus. J Agric Food Chem. 2011 Feb 23;59(4):1281-7. doi: 10.1021/jf103551t. Epub 2011 Jan 7. PubMed PMID: 21214242.

18: Cook D, Gardner DR, Pfister JA, Stonecipher CA, Robins JG, Morgan JA. Effects of Elevated CO(2) on the Swainsonine Chemotypes of Astragalus lentiginosus and Astragalus mollissimus. J Chem Ecol. 2017 Mar;43(3):307-316. doi: 10.1007/s10886-017-0820-5. Epub 2017 Feb 11. PubMed PMID: 28190150.

19: Cook D, Beaulieu WT, Mott IW, Riet-Correa F, Gardner DR, Grum D, Pfister JA, Clay K, Marcolongo-Pereira C. Production of the alkaloid swainsonine by a fungal endosymbiont of the Ascomycete order Chaetothyriales in the host Ipomoea carnea. J Agric Food Chem. 2013 Apr 24;61(16):3797-803. doi: 10.1021/jf4008423. Epub 2013 Apr 12. PubMed PMID: 23547913.

20: Oelschlegel AM, Weissmann C. Acquisition of drug resistance and dependence by prions. PLoS Pathog. 2013 Feb;9(2):e1003158. doi: 10.1371/journal.ppat.1003158. Epub 2013 Feb 7. PubMed PMID: 23408888; PubMed Central PMCID: PMC3567182.