Cucumarioside A2-2 | CAS#95499-80-2 | triterpene glycoside

MedKoo Cat#: 598354 | Name: Cucumarioside A2-2

Description:

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

Cucumarioside A2-2 is a triterpene glycoside. Cucumarioside A2-2 is isolated from the Far-Eastern sea cucumber Cucumaria japonica. Cucumarioside A2-2 exhibits antitumor activity.

Chemical Structure

Cucumarioside A2-2

CAS#95499-80-2

Theoretical Analysis

MedKoo Cat#: 598354

Name: Cucumarioside A2-2

CAS#: 95499-80-2

Chemical Formula: C59H91NaO29S

Exact Mass:

Molecular Weight: 1319.39

Elemental Analysis: C, 53.71; H, 6.95; Na, 1.74; O, 35.17; S, 2.43

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

Cucumarioside A2-2;

IUPAC/Chemical Name

sodium (3R,4R,5S,6S)-5-(((2S,3S,4S,5S,6S)-5-(((2R,3S,4S,5S,6R)-4-(((2R,3R,4R,5R,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxytetrahydro-2H-pyran-2-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-methyl-3-(((2R,3R,4R,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-(((3R,3aS,5aS,7aS,9R,11aR,11bS,13aS)-3,5a,8,8,11a-pentamethyl-3-(4-methylpent-4-en-1-yl)-1,4-dioxo-3a,4,5,5a,7,7a,8,9,10,11,11a,11b,12,13-tetradecahydro-1H,3H-naphtho[2',1':4,5]indeno[1,7a-c]furan-9-yl)oxy)tetrahydro-2H-pyran-3-yl sulfate

InChi Key

WULKPPVSMODIMK-NQSPPEQVSA-M

InChi Code

InChI=1S/C59H92O29S.Na/c1-24(2)11-10-16-58(8)48-28(62)19-57(7)27-12-13-33-55(4,5)34(15-17-56(33,6)26(27)14-18-59(48,57)54(72)87-58)82-52-46(38(67)32(23-78-52)88-89(73,74)75)86-53-47(85-49-39(68)35(64)29(63)22-77-49)40(69)43(25(3)79-53)83-51-42(71)45(37(66)31(21-61)81-51)84-50-41(70)44(76-9)36(65)30(20-60)80-50;/h12,25-26,29-53,60-61,63-71H,1,10-11,13-23H2,2-9H3,(H,73,74,75);/q;+1/p-1/t25-,26+,29+,30-,31+,32+,33+,34+,35+,36+,37-,38-,39+,40-,41+,42-,43+,44+,45-,46-,47-,48+,49+,50+,51+,52-,53-,56+,57-,58+,59+;/m0./s1

SMILES Code

O[C@H]1[C@@H](O)[C@@H](O)[C@@H](O[C@@H]2[C@H](O[C@@H]3[C@H](O[C@@H]4CC[C@]5(C)[C@@H]6CC[C@@]78[C@@](C)(CC([C@@H]7[C@@](C)(CCCC(C)=C)OC8=O)=O)C6=CC[C@@H]5C4(C)C)OC[C@H]([C@@H]3O)OS([O-])(=O)=O)O[C@H]([C@H]([C@@H]2O)O[C@@H]9[C@H]([C@H]([C@H]([C@H](O9)CO)O)O[C@@H]%10[C@H](O)[C@H](OC)[C@H](O)[C@H](CO)O%10)O)C)OC1.[Na+]

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,319.39 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: Menchinskaya ES, Pislyagin EA, Kovalchyk SN, Davydova VN, Silchenko AS, Avilov SA, Kalinin VI, Aminin DL. Antitumor activity of cucumarioside A2-2. Chemotherapy. 2013;59(3):181-91. doi: 10.1159/000354156. Epub 2013 Nov 8. PubMed PMID: 24217558. 2: Pislyagin EA, Dmitrenok PS, Gorpenchenko TY, Avilov SA, Silchenko AS, Aminin DL. Determination of cucumarioside A₂-2 in mouse spleen by radiospectroscopy, MALDI-MS and MALDI-IMS. Eur J Pharm Sci. 2013 Jul 16;49(4):461-7. doi: 10.1016/j.ejps.2013.05.017. Epub 2013 May 30. PubMed PMID: 23727465. 3: Menchinskaya ES, Aminin DL, Avilov SA, Silchenko AS, Andryjashchenko PV, Kalinin VI, Stonik VA. Inhibition of tumor cells multidrug resistance by cucumarioside A2-2, frondoside A and their complexes with cholesterol. Nat Prod Commun. 2013 Oct;8(10):1377-80. PubMed PMID: 24354179. 4: Pislyagin EA, Manzhulo IV, Dmitrenok PS, Aminin DL. Cucumarioside A2-2 causes changes in the morphology and proliferative activity in mouse spleen. Acta Histochem. 2016 May;118(4):387-92. doi: 10.1016/j.acthis.2016.03.009. Epub 2016 Apr 11. PubMed PMID: 27079859. 5: Reunov AA, Reunov AV, Pimenova EA, Reunova YA, Menchinskaya ES, Lapshina LA, Aminin DL. Cucumarioside A2-2 stimulates apoptotic necrosis in Ehrlich ascites carcinoma cells. Dokl Biol Sci. 2015;462:161-3. doi: 10.1134/S0012496615020040. Epub 2015 Jul 12. PubMed PMID: 26164340. 6: Kostetsky EY, Sanina NM, Mazeika AN, Tsybulsky AV, Vorobyeva NS, Shnyrov VL. Tubular immunostimulating complex based on cucumarioside A2-2 and monogalactosyldiacylglycerol from marine macrophytes. J Nanobiotechnology. 2011 Sep 2;9:35. doi: 10.1186/1477-3155-9-35. PubMed PMID: 21888630; PubMed Central PMCID: PMC3175152. 7: Jin JO, Shastina VV, Shin SW, Xu Q, Park JI, Rasskazov VA, Avilov SA, Fedorov SN, Stonik VA, Kwak JY. Differential effects of triterpene glycosides, frondoside A and cucumarioside A2-2 isolated from sea cucumbers on caspase activation and apoptosis of human leukemia cells. FEBS Lett. 2009 Feb 18;583(4):697-702. doi: 10.1016/j.febslet.2009.01.010. Epub 2009 Jan 20. PubMed PMID: 19162021. 8: Pislyagin EA, Gladkikh RV, Kapustina II, Kim NY, Shevchenko VP, Nagaev IY, Avilov SA, Aminin DL. Interaction of holothurian triterpene glycoside with biomembranes of mouse immune cells. Int Immunopharmacol. 2012 Sep;14(1):1-8. doi: 10.1016/j.intimp.2012.05.020. Epub 2012 Jun 6. PubMed PMID: 22683181. 9: Aminin D, Pislyagin E, Astashev M, Es'kov A, Kozhemyako V, Avilov S, Zelepuga E, Yurchenko E, Kaluzhskiy L, Kozlovskaya E, Ivanov A, Stonik V. Glycosides from edible sea cucumbers stimulate macrophages via purinergic receptors. Sci Rep. 2016 Dec 22;6:39683. doi: 10.1038/srep39683. PubMed PMID: 28004778; PubMed Central PMCID: PMC5177912. 10: Li IA, Popov AM, Tsybul'skiĭ AV, Sanina NM, Kostetskiĭ EIa, Novikova OD, Portniagina OIu, Mazeĭka AV. [Immunostimulatory characteristics of a novel carrier on the basis of cucumarioside A2-2 and monogalactosyldiacylgycerol]. Prikl Biokhim Mikrobiol. 2008 Nov-Dec;44(6):694-700. Russian. PubMed PMID: 19145978. 11: Tsybul'skiĭ AV, Popov AM, Artiukov AA, Mazeĭka AN, Kostetskiĭ É, Sanina NM, Krivoshapko ON. [Enhancing the immunogenic activity of influvac vaccine in the use of adjuvant TI complexes modified by echinochrome A]. Vopr Virusol. 2012 Mar-Apr;57(2):23-7. Russian. PubMed PMID: 22834143. 12: Belousov MV, Novozheeva TP, Akhmedzhanov RR, Novitskaia LN, Iusubov MS, Aminin DL, Avilov SA, Stonik VA, Kalinin VI. [Toxicological characteristics of cumazid]. Eksp Klin Farmakol. 2010 Feb;73(2):22-4. Russian. PubMed PMID: 20369597. 13: Aminin DL, Chaykina EL, Agafonova IG, Avilov SA, Kalinin VI, Stonik VA. Antitumor activity of the immunomodulatory lead Cumaside. Int Immunopharmacol. 2010 Jun;10(6):648-54. doi: 10.1016/j.intimp.2010.03.003. Epub 2010 Mar 20. PubMed PMID: 20227525. 14: Sanina N, Chopenko N, Mazeika A, Kostetsky E. Nanoparticulate Tubular Immunostimulating Complexes: Novel Formulation of Effective Adjuvants and Antigen Delivery Systems. Biomed Res Int. 2017;2017:4389525. doi: 10.1155/2017/4389525. Epub 2017 Jul 20. Review. PubMed PMID: 28808657; PubMed Central PMCID: PMC5541816.