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MedKoo Cat#: 598318 | Name: Stichoposide

Description:

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

Stichoposide is a triterpene glycoside.

Chemical Structure

Stichoposide
Stichoposide
CAS#37341-37-0

Theoretical Analysis

MedKoo Cat#: 598318

Name: Stichoposide

CAS#: 37341-37-0

Chemical Formula: C43H69O14

Exact Mass: 809.4687

Molecular Weight: 810.01

Elemental Analysis: C, 63.76; H, 8.59; O, 27.65

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.
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Related CAS #
No Data
Synonym
Stichoposide; Stichoposide A; Holotoxins;
IUPAC/Chemical Name
(2S)-2-((3S,5R,9R,10S,13S,17S)-3-(((2S,3R,4S,5R)-4,5-dihydroxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-4,4,10,14-tetramethyl-19-oxo-1,2,3,4,5,6,9,10,11,12,14,15,16,17-tetradecahydro-14l5-14,13-(epoxymethano)cyclopenta[a]phenanthren-17-yl)-2-hydroxy-6-methylheptan-4-yl acetate
InChi Key
KTMADCBJGDJBHH-OOYIRBOKSA-N
InChi Code
InChI=1S/C43H69O14/c1-21(2)18-24(54-23(4)44)19-41(8,51)29-14-17-43(9)26-10-11-28-39(5,6)30(13-15-40(28,7)25(26)12-16-42(29,43)38(50)57-43)55-37-35(32(47)27(45)20-52-37)56-36-34(49)33(48)31(46)22(3)53-36/h10,21-22,24-25,27-37,45-49,51H,11-20H2,1-9H3/t22-,24?,25+,27-,28+,29-,30+,31-,32+,33+,34-,35-,36+,37+,40-,41+,42-/m1/s1
SMILES Code
CC1(C)[C@@H](O[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C)O3)O)O)O)CC[C@]4(C)[C@@]5([H])CC[C@]6(C(O7)=O)[C@@H]([C@@](C)(O)CC(OC(C)=O)CC(C)C)CCC67(C)C5=CC[C@@]14[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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 810.01 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
1: Yun SH, Park ES, Shin SW, Ju MH, Han JY, Jeong JS, Kim SH, Stonik VA, Kwak JY, Park JI. By activating Fas/ceramide synthase 6/p38 kinase in lipid rafts, stichoposide D inhibits growth of leukemia xenografts. Oncotarget. 2015 Sep 29;6(29):27596-612. doi: 10.18632/oncotarget.4820. PubMed PMID: 26318294; PubMed Central PMCID: PMC4695011. 2: Yun SH, Park ES, Shin SW, Na YW, Han JY, Jeong JS, Shastina VV, Stonik VA, Park JI, Kwak JY. Stichoposide C induces apoptosis through the generation of ceramide in leukemia and colorectal cancer cells and shows in vivo antitumor activity. Clin Cancer Res. 2012 Nov 1;18(21):5934-48. doi: 10.1158/1078-0432.CCR-12-0655. PubMed PMID: 23132899. 3: Aminin DL, Shentsova EB, Anisimov MM, Kuznetsova TA. [Spectrophotometric determination of the stichoposide A from the holothurian Stichopus japonicus S]. Antibiotiki. 1981 Aug;26(8):585-9. Russian. PubMed PMID: 7294749. 4: Park JI, Bae HR, Kim CG, Stonik VA, Kwak JY. Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers. Front Chem. 2014 Sep 9;2:77. doi: 10.3389/fchem.2014.00077. eCollection 2014. Review. Erratum in: Front Chem. 2014;2:103. PubMed PMID: 25250309; PubMed Central PMCID: PMC4159031. 5: Sabo T, Kronman C, Mazor O. Ricin-Holotoxin-Based Vaccines: Induction of Potent Ricin-Neutralizing Antibodies. Methods Mol Biol. 2016;1403:683-94. doi: 10.1007/978-1-4939-3387-7_38. PubMed PMID: 27076160. 6: Li S, Wang Y, Jiang T, Wang H, Yang S, Lv Z. Absorption and Transport of Sea Cucumber Saponins from Apostichopus japonicus. Mar Drugs. 2016 Jun 17;14(6). pii: E114. doi: 10.3390/md14060114. PubMed PMID: 27322290; PubMed Central PMCID: PMC4926073. 7: Elyakov GB, Anisimov MM, Prokofyeva NG, Kuznetsova TA, Fronert EB. Sensitivity of rat marrow cells in culture to the toxic effect of stichoposide A 1 from Stichopus Japonicus Selenka. Toxicon. 1972 May;10(3):299-300. PubMed PMID: 5072095. 8: Noy-Porat T, Rosenfeld R, Ariel N, Epstein E, Alcalay R, Zvi A, Kronman C, Ordentlich A, Mazor O. Isolation of Anti-Ricin Protective Antibodies Exhibiting High Affinity from Immunized Non-Human Primates. Toxins (Basel). 2016 Mar 3;8(3). pii: E64. doi: 10.3390/toxins8030064. PubMed PMID: 26950154; PubMed Central PMCID: PMC4810209. 9: Popov AM, Rovin IuG, Anisimov MM, Likhatskaia GN, Strigina LI. [Effect of triterpene glycosides on the stability of bilayer lipid membranes, containing different sterols]. Biofizika. 1982 Sep-Oct;27(5):827-31. Russian. PubMed PMID: 7138933. 10: Cohen O, Mechaly A, Sabo T, Alcalay R, Aloni-Grinstein R, Seliger N, Kronman C, Mazor O. Characterization and epitope mapping of the polyclonal antibody repertoire elicited by ricin holotoxin-based vaccination. Clin Vaccine Immunol. 2014 Nov;21(11):1534-40. doi: 10.1128/CVI.00510-14. Epub 2014 Sep 10. PubMed PMID: 25209559; PubMed Central PMCID: PMC4248767. 11: Bradshaw M, Tepp WH, Whitemarsh RC, Pellett S, Johnson EA. Holotoxin Activity of Botulinum Neurotoxin Subtype A4 Originating from a Nontoxigenic Clostridium botulinum Expression System. Appl Environ Microbiol. 2014 Dec;80(23):7415-22. doi: 10.1128/AEM.01795-14. Epub 2014 Sep 19. PubMed PMID: 25239905; PubMed Central PMCID: PMC4249187. 12: Anisimov MM, Kuznetsova TA, Shirokov VP, Prokofyeva NG, Elyakov GB. The toxic effect of stichoposide A 1 from Stichopus japonicus selenka on early embryogenesis of the sea urchin. Toxicon. 1972 Mar;10(2):187-8. PubMed PMID: 4673049. 13: Popov AA, Kalinovskaia NI, Kuznetsova TA, Agafonova IG, Anisimov MM. [Role of sterols in the membranotropic activity of triterpene glycosides]. Antibiotiki. 1983 Sep;28(9):656-9. Russian. PubMed PMID: 6638979. 14: Mudrak B, Kuehn MJ. Heat-labile enterotoxin: beyond G(m1) binding. Toxins (Basel). 2010 Jun;2(6):1445-70. doi: 10.3390/toxins2061445. Epub 2010 Jun 14. Review. PubMed PMID: 22069646; PubMed Central PMCID: PMC3153253. 15: Taylor M, Banerjee T, Ray S, Tatulian SA, Teter K. Protein-disulfide isomerase displaces the cholera toxin A1 subunit from the holotoxin without unfolding the A1 subunit. J Biol Chem. 2011 Jun 24;286(25):22090-100. doi: 10.1074/jbc.M111.237966. Epub 2011 May 4. PubMed PMID: 21543321; PubMed Central PMCID: PMC3121353. 16: Shcheglov VV, Anisimov MM, Popov AM, Sebko IG. [Effect of triterpene glycosides on plasma membrane permeability for UV-absorbing substances in Saccharomyces carlsbergensis yeast cells]. Antibiotiki. 1979 Jan;24(1):49-55. Russian. PubMed PMID: 34359. 17: Popov AM, Anisimov MM, Ivanov AS, Korepanova EA, Antonov VF. [Characteristics of membrane activity of triterpene glycosides]. Antibiotiki. 1982 Apr;27(4):276-80. Russian. PubMed PMID: 7092199. 18: Mats MN, Korkhov VV, Stepanov VR, Kupera EV, Oleĭnikova GK, Anisimov MM. [The contraceptive activity of triterpene glycosides--the total sum of holotoxins A1 and B1 and holothurin A in an experiment]. Farmakol Toksikol. 1990 Mar-Apr;53(2):45-7. Russian. PubMed PMID: 2369955. 19: Anisimov MM, Baranova SI, Strigina LI, Chetyrina NS, Sokol'skiĭ IN. [Effect of triterpene glycosides on RNA biosynthesis in a yeast cell culture of Saccharomyces carlsbergensis]. Antibiotiki. 1977 Sep;22(9):837-41. Russian. PubMed PMID: 911157. 20: Wang HH, Riding S, Lindo P, Singh BR. Endopeptidase activities of botulinum neurotoxin type B complex, holotoxin, and light chain. Appl Environ Microbiol. 2010 Oct;76(19):6658-63. doi: 10.1128/AEM.00731-10. Epub 2010 Aug 6. PubMed PMID: 20693440; PubMed Central PMCID: PMC2950459.

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