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OSW-1 (Orsaponin)

Alias: Orsaponin OSW-1 OSW1OSW 1
Cat No.:V9112 Purity: ≥98%
OSW-1(Orsaponin) is a naturally occuring and broad spectrum inhibitor of enterovirus replicationisolated from Ornithogalum caudatum, it is a specific antagonist of osterol-binding protein (OSBP) and OSBP-related protein 4 (ORP4) with GI50s in the nanomolar range in human cancer lines.
OSW-1 (Orsaponin)
OSW-1 (Orsaponin) Chemical Structure CAS No.: 145075-81-6
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
Other Sizes
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

OSW-1 (Orsaponin) is a naturally occuring and broad spectrum inhibitor of enterovirus replication isolated from Ornithogalum caudatum, it is a specific antagonist of osterol-binding protein (OSBP) and OSBP-related protein 4 (ORP4) with GI50s in the nanomolar range in human cancer lines.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
OSW-1 has an anti-proliferative effect on sandwich circles and is less cytotoxic to normal cells. The antiproliferative activity of OSW-1 on SW480 and LoVo sandwich circles, as evidenced by cell viability determined by the CCK8 assay, placed the results in comparison with other clinical anticancer treatments. SW480 and LoVo cell lines are obtained from Dukes stage B non-lymphoma and lymphoma metastatic nodules and represent metastatic and metastatic malignancy, respectively. OSW-1 not only demonstrates extraordinarily powerful anti-cancer action in SW480 and LoVo cell lines, with IC50 at nanomolar doses, and is 10-100 times more effective than other anti-cancer medicines, it is cytotoxic to normal epithelial cells The effect is minimal. These data demonstrate that OSW-1 has a high anti-cancer effect, but has a low cytotoxic effect on normal cells [2].
ln Vivo
In a nude mouse model implanted with LoVo cells and treated with OSW-1 when tumors became operable, we investigated whether OSW-1 was as effective in vivo. The tumor sizes in the treated mice were, on average, less than those in the control group, according to the results. Significant changes were seen 15–17 days after treatment, and as time went on, the discrepancies grew larger until the animals were killed by the solution. The OSW-1 treated group's tumor weight was considerably lower (P<0.05) than that of the control group. Furthermore, tumors treated with OSW-1 did not show any discernible response. According to these findings, OSW-1 tumors have a noticeable in vivo response and a potent inhibitory effect on blood vessel formation [2].
References

[1]. Natural products reveal cancer cell dependence onoxysterol-binding proteins.Nat Chem Biol. 2011 Aug 7;7(9):639-47.

[2]. Zhang Y, et al, Effective cytotoxic activity of OSW-1 on colon cancer by inducing apoptosis in vitro and in vivo.Oncol Rep. 2017 Jun;37(6):3509-3519.

Additional Infomation
[(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-3,17-dihydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxyoxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl] 4-methoxybenzoate has been reported in Ornithogalum saundersiae with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C47H68O15
Molecular Weight
873.03
Exact Mass
872.456
CAS #
145075-81-6
PubChem CID
9854230
Appearance
White to off-white solid powder
Density
1.31 g/cm3
Boiling Point
932.5ºC at 760 mmHg
Flash Point
267ºC
Vapour Pressure
0mmHg at 25°C
Index of Refraction
1.592
LogP
4.024
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
15
Rotatable Bond Count
15
Heavy Atom Count
62
Complexity
1630
Defined Atom Stereocenter Count
17
SMILES
[C@H]1(CC2=CC[C@]3([H])[C@@]([H])([C@]2(CC1)C)CC[C@@]1([C@](O)([C@H](C[C@]13[H])O[C@@]1([H])[C@@H]([C@@H](O[C@@]2([H])[C@@H]([C@H]([C@@H](CO2)O)O)OC(C2C=CC(OC)=CC=2)=O)[C@H](CO1)O)OC(=O)C)[C@H](C)C(=O)CCC(C)C)C)O
InChi Key
MPXTYZZFIJTPPA-MKQTXCTDSA-N
InChi Code
InChI=1S/C47H68O15/c1-24(2)8-15-34(50)25(3)47(55)37(21-33-31-14-11-28-20-29(49)16-18-45(28,5)32(31)17-19-46(33,47)6)60-44-41(59-26(4)48)39(36(52)23-58-44)62-43-40(38(53)35(51)22-57-43)61-42(54)27-9-12-30(56-7)13-10-27/h9-13,24-25,29,31-33,35-41,43-44,49,51-53,55H,8,14-23H2,1-7H3/t25-,29+,31-,32+,33+,35-,36+,37+,38+,39+,40-,41-,43+,44+,45+,46+,47-/m1/s1
Chemical Name
(2S,3R,4S,5R)-2-(((2S,3R,4S,5S)-3-acetoxy-2-(((3S,8R,9S,10R,13S,14S,16S,17S)-3,17-dihydroxy-10,13-dimethyl-17-((S)-6-methyl-3-oxoheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl)oxy)-5-hydroxytetrahydro-2H-pyran-4-yl)oxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yl 4-methoxybenzoate
Synonyms
Orsaponin OSW-1 OSW1OSW 1
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.  (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~114.54 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.86 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (2.86 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (2.86 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.1454 mL 5.7272 mL 11.4544 mL
5 mM 0.2291 mL 1.1454 mL 2.2909 mL
10 mM 0.1145 mL 0.5727 mL 1.1454 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Chemical structures Natural products cephalostatin 1 (1), OSW-1 (2), ritterazine B (3), schweinfurthin A (4), schweinfurthin B (5) and stellettin E. OSW-1 analogs 6–10 and the OSW-1 affinity reagent (OAR). PMbz, para-methoxy benzoyl.[1].Burgett AW, et al. Natural products reveal cancer cell dependence onoxysterol-binding proteins.Nat Chem Biol. 2011 Aug 7;7(9):639-47.
  • OSBP and ORP4L are high-affinity receptors of ORPphilins (a) Cephalostatin 1 (1), OSW-1 (2), ritterazine B (3), schweinfurthin A (4), stellettin E and OSW-1 analogs 6–10 are selectively growth-inhibitory toward HCT-116 cells lacking p21. GI50 values of the compounds were determined in HCT-116 p21+/+ and p21−/− cells after 48 h using a resazurin redox dye to measure cell viability. Values are mean ± s.d. of three individual experiments. Asterisk denotes value from ref. 5. (b) Affinity chromatography experiment with HeLa S-100 lysate using OSW-1 affinity reagent (OAR) in the absence (left lane) and presence (right lane) of excess OSW-1 (10 μM). The intense band indicated with a red arrow was excised from the gel and identified as oxysterol binding protein (OSBP). (c) Scatter plot depicting 121 proteins identified and quantified by itRAQ-based quantitative proteomics. Competition is plotted on the y axis as log10 fold change for 10 μM OSW-1 over DMSO control, and the P value representing statistical significance is plotted on the x axis. P values are arbitrarily set to 1 for nonsignificant single peptide quantitations. (d,e) Representative competition-binding experiments of [3H]25-OHC (20 nM) with ORPphilins in S100 lysate made from HEK-293t cells overexpressing either OSBP-Myc-His (d) or ORP4L-Myc-His (e). Ki values are mean ± s.d. from at least three independent experiments. An accurate Ki value for ritterazine B with ORP4L could not be determined because of insufficient quantities of compound. 25-OHC, 25-hydroxycholesterol; BFA, brefeldin A; 5-FU, 5-fluorouracil.[1].Burgett AW, et al. Natural products reveal cancer cell dependence onoxysterol-binding proteins.Nat Chem Biol. 2011 Aug 7;7(9):639-47.
  • Suppression of antiproliferative activity by 25-OHC administration and effects of lipoprotein-deficient media on proliferation (a) Effect of 25-OHC coadministration on growth-inhibitory activity (48 h) of cephalostatin 1 or OSW-1 in HCT-116 cells. (b) Removal of lipoproteins from the growth medium sensitizes CHO-7 cells to 25-OHC but not cephalostatin 1, OSW-1 or schweinfurthin A. Graphs represent mean ± s.d. of two individual experiments. CHO-7 is a CHO-K1 subclone that tolerates growth media depleted of lipoproteins.[1].Burgett AW, et al. Natural products reveal cancer cell dependence onoxysterol-binding proteins.Nat Chem Biol. 2011 Aug 7;7(9):639-47.
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