OSW-1| CAS#145075-81-6| Enterovirus replication inhibitor

MedKoo Cat#: 565452 | Name: OSW-1

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Description:

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

OSW-1, also known as Orsaponin, is a natural broad-range inhibitor of enterovirus replication. OSW-1 was shown to trigger necroptosis via activation of the RIPK1/RIPK3/MLKL pathway.

Chemical Structure

OSW-1

CAS#145075-81-6

Theoretical Analysis

MedKoo Cat#: 565452

Name: OSW-1

CAS#: 145075-81-6

Chemical Formula: C47H68O15

Exact Mass: 872.4558

Molecular Weight: 873.05

Elemental Analysis: C, 64.66; H, 7.85; O, 27.49

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 750.00	2 Weeks
5mg	USD 1,650.00	2 Weeks

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Related CAS #

No Data

Synonym

OSW-1; OSW 1; OSW1; Orsaponin

IUPAC/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

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

SMILES Code

O=C(O[C@H]1[C@H](O[C@@H]2[C@@H](OC(C)=O)[C@H](O[C@H]3C[C@@]4([H])[C@]5([H])CC=C6C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@@]3(O)[C@@H](C(CCC(C)C)=O)C)OC[C@@H]2O)OC[C@@H](O)[C@@H]1O)C7=CC=C(OC)C=C7

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

OSW-1, isolated from Ornithogalum caudatum, 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.

In vitro activity:

The cholestane saponin OSW-1 is isolated from plant OCA and has recently been shown to have potent cytotoxic effects against different types of cancers. The therapeutic efficacy of OSW-1 on prostate cancer and its underlying mechanism are yet to be established. OSW-1 inhibited the growth of prostate cancer cells by interrupting the interaction between mTOR and Rictor/mTORC2. Reference: J Asian Nat Prod Res. 2022 Jul;24(7):663-672. https://pubmed.ncbi.nlm.nih.gov/34292111/

In vivo activity:

The nude mouse xenograft model was used to detect the effect of OSW-1 on inhibiting the proliferation of glioma cells in vivo. OSW-1 significantly inhibited the viability and proliferation of glioma cells in a dose- and time-dependent manner. Furthermore, the mouse xenograft model confirmed the suppressive effect of OSW-1 on tumor growth in vivo. Reference: Front Pharmacol. 2022 Sep 5;13:967141. https://pubmed.ncbi.nlm.nih.gov/36133816/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	114.54

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 873.05 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

Formulation protocol:

1. Wu M, Huang Q, Liao M, Wu X, Xi H, Ma H, Li S, Zhang Y, Xia Y. OSW-1 induces apoptosis and cyto-protective autophagy, and synergizes with chemotherapy on triple negative breast cancer metastasis. Cell Oncol (Dordr). 2022 Dec;45(6):1255-1275. doi: 10.1007/s13402-022-00716-2. Epub 2022 Sep 26. PMID: 36155886. 2. Elgehama A. Selective obstruction of the mTORC2 complex by a naturally occurring cholestane saponin (OSW-1) for inhibiting prostate cancer cell growth. J Asian Nat Prod Res. 2022 Jul;24(7):663-672. doi: 10.1080/10286020.2021.1951255. Epub 2021 Jul 22. PMID: 34292111. 3. Zhan Z, Liu Z, Zhang C, Gao H, Lai J, Chen Y, Huang H. Anticancer effects of OSW-1 on glioma cells via regulation of the PI3K/AKT signal pathway: A network pharmacology approach and experimental validation in vitro and in vivo. Front Pharmacol. 2022 Sep 5;13:967141. doi: 10.3389/fphar.2022.967141. PMID: 36133816; PMCID: PMC9483153. 4. Zhang Y, Fang F, Fan K, Zhang Y, Zhang J, Guo H, Yu P, Ma J. 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. doi: 10.3892/or.2017.5582. Epub 2017 Apr 19. PMID: 28440433.

In vitro protocol:

In vivo protocol:

1. Zhan Z, Liu Z, Zhang C, Gao H, Lai J, Chen Y, Huang H. Anticancer effects of OSW-1 on glioma cells via regulation of the PI3K/AKT signal pathway: A network pharmacology approach and experimental validation in vitro and in vivo. Front Pharmacol. 2022 Sep 5;13:967141. doi: 10.3389/fphar.2022.967141. PMID: 36133816; PMCID: PMC9483153. 2. Zhang Y, Fang F, Fan K, Zhang Y, Zhang J, Guo H, Yu P, Ma J. 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. doi: 10.3892/or.2017.5582. Epub 2017 Apr 19. PMID: 28440433.

1: Iguchi T, Kuroda M, Naito R, Watanabe T, Matsuo Y, Yokosuka A, Mimaki Y. Cholestane glycosides from Ornithogalum saundersiae bulbs and the induction of apoptosis in HL-60 cells by OSW-1 through a mitochondrial-independent signaling pathway. J Nat Med. 2019 Jan;73(1):131-145. doi: 10.1007/s11418-018-1252-4. Epub 2018 Oct 16. PubMed PMID: 30327993. 2: Mesmin B, Bigay J, Polidori J, Jamecna D, Lacas-Gervais S, Antonny B. Sterol transfer, PI4P consumption, and control of membrane lipid order by endogenous OSBP. EMBO J. 2017 Nov 2;36(21):3156-3174. doi: 10.15252/embj.201796687. Epub 2017 Oct 4. PubMed PMID: 28978670; PubMed Central PMCID: PMC5666618. 3: Malabed R, Hanashima S, Murata M, Sakurai K. Sterol-recognition ability and membrane-disrupting activity of Ornithogalum saponin OSW-1 and usual 3-O-glycosyl saponins. Biochim Biophys Acta Biomembr. 2017 Dec;1859(12):2516-2525. doi: 10.1016/j.bbamem.2017.09.019. Epub 2017 Sep 22. PubMed PMID: 28947142. 4: Zhang Y, Fang F, Fan K, Zhang Y, Zhang J, Guo H, Yu P, Ma J. 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. doi: 10.3892/or.2017.5582. Epub 2017 Apr 19. PubMed PMID: 28440433. 5: Hiraizumi M, Komatsu R, Shibata T, Ohta Y, Sakurai K. Dissecting the structural basis for the intracellular delivery of OSW-1 by fluorescent probes. Org Biomol Chem. 2017 May 3;15(17):3568-3570. doi: 10.1039/c7ob00486a. PubMed PMID: 28345721. 6: Albulescu L, Bigay J, Biswas B, Weber-Boyvat M, Dorobantu CM, Delang L, van der Schaar HM, Jung YS, Neyts J, Olkkonen VM, van Kuppeveld FJM, Strating JRPM. Uncovering oxysterol-binding protein (OSBP) as a target of the anti-enteroviral compound TTP-8307. Antiviral Res. 2017 Apr;140:37-44. doi: 10.1016/j.antiviral.2017.01.008. Epub 2017 Jan 11. PubMed PMID: 28088354. 7: Sakurai K, Hiraizumi M, Isogai N, Komatsu R, Shibata T, Ohta Y. Synthesis of a fluorescent photoaffinity probe of OSW-1 by site-selective acylation of an inactive congener and biological evaluation. Chem Commun (Camb). 2017 Jan 3;53(3):517-520. doi: 10.1039/c6cc08955k. Erratum in: Chem Commun (Camb). 2016 Dec 22;53(2):462. PubMed PMID: 27909709. 8: Albulescu L, Strating JR, Thibaut HJ, van der Linden L, Shair MD, Neyts J, van Kuppeveld FJ. Broad-range inhibition of enterovirus replication by OSW-1, a natural compound targeting OSBP. Antiviral Res. 2015 May;117:110-4. doi: 10.1016/j.antiviral.2015.02.013. Epub 2015 Mar 6. PubMed PMID: 25752737. 9: Sakurai K, Takeshita T, Hiraizumi M, Yamada R. Synthesis of OSW-1 derivatives by site-selective acylation and their biological evaluation. Org Lett. 2014 Dec 19;16(24):6318-21. doi: 10.1021/ol503044j. Epub 2014 Dec 9. PubMed PMID: 25490062. 10: Pan N, Rao W, Kothapalli NR, Liu R, Burgett AW, Yang Z. The single-probe: a miniaturized multifunctional device for single cell mass spectrometry analysis. Anal Chem. 2014 Oct 7;86(19):9376-80. doi: 10.1021/ac5029038. Epub 2014 Sep 19. PubMed PMID: 25222919. 11: Yamada R, Takeshita T, Hiraizumi M, Shinohe D, Ohta Y, Sakurai K. Fluorescent analog of OSW-1 and its cellular localization. Bioorg Med Chem Lett. 2014 Apr 1;24(7):1839-42. doi: 10.1016/j.bmcl.2014.02.009. Epub 2014 Feb 14. PubMed PMID: 24613377. 12: Kong JQ, Lu D, Wang ZB. Molecular cloning and yeast expression of cinnamate 4-hydroxylase from Ornithogalum saundersiae baker. Molecules. 2014 Jan 28;19(2):1608-21. doi: 10.3390/molecules19021608. PubMed PMID: 24476601; PubMed Central PMCID: PMC6270737. 13: Guan YY, Song C, Lei PS. Synthesis of three OSW-1 analogs with maltose side chains bearing different protection groups. J Asian Nat Prod Res. 2014 Jan;16(1):43-52. doi: 10.1080/10286020.2013.863185. Epub 2013 Dec 6. PubMed PMID: 24313263. 14: Jin JC, Jin XL, Zhang X, Piao YS, Liu SP. Effect of OSW-1 on microRNA expression profiles of hepatoma cells and functions of novel microRNAs. Mol Med Rep. 2013 Jun;7(6):1831-7. doi: 10.3892/mmr.2013.1428. Epub 2013 Apr 11. PubMed PMID: 23588479. 15: Tang Y, Li N, Duan JA, Tao W. Structure, bioactivity, and chemical synthesis of OSW-1 and other steroidal glycosides in the genus Ornithogalum. Chem Rev. 2013 Jul 10;113(7):5480-514. doi: 10.1021/cr300072s. Epub 2013 Mar 26. Review. PubMed PMID: 23530990. 16: Jin J, Jin X, Qian C, Ruan Y, Jiang H. Signaling network of OSW 1 induced apoptosis and necroptosis in hepatocellular carcinoma. Mol Med Rep. 2013 May;7(5):1646-50. doi: 10.3892/mmr.2013.1366. Epub 2013 Mar 13. PubMed PMID: 23503804. 17: Garcia-Prieto C, Riaz Ahmed KB, Chen Z, Zhou Y, Hammoudi N, Kang Y, Lou C, Mei Y, Jin Z, Huang P. Effective killing of leukemia cells by the natural product OSW-1 through disruption of cellular calcium homeostasis. J Biol Chem. 2013 Feb 1;288(5):3240-50. doi: 10.1074/jbc.M112.384776. Epub 2012 Dec 17. PubMed PMID: 23250754; PubMed Central PMCID: PMC3561545. 18: Burgett AW, Poulsen TB, Wangkanont K, Anderson DR, Kikuchi C, Shimada K, Okubo S, Fortner KC, Mimaki Y, Kuroda M, Murphy JP, Schwalb DJ, Petrella EC, Cornella-Taracido I, Schirle M, Tallarico JA, Shair MD. Natural products reveal cancer cell dependence on oxysterol-binding proteins. Nat Chem Biol. 2011 Aug 7;7(9):639-47. doi: 10.1038/nchembio.625. PubMed PMID: 21822274; PubMed Central PMCID: PMC3158287. 19: Zheng D, Guan Y, Chen X, Xu Y, Chen X, Lei P. Synthesis of cholestane saponins as mimics of OSW-1 and their cytotoxic activities. Bioorg Med Chem Lett. 2011 Jun 1;21(11):3257-60. doi: 10.1016/j.bmcl.2011.04.030. Epub 2011 Apr 13. PubMed PMID: 21530251. 20: Wang N, Li CY, Yao TF, Kang XD, Guo HS. OSW-1 triggers necroptosis in colorectal cancer cells through the RIPK1/RIPK3/MLKL signaling pathway facilitated by the RIPK1-p62/SQSTM1 complex. World J Gastroenterol. 2024 Apr 21;30(15):2155-2174. doi: 10.3748/wjg.v30.i15.2155. PMID: 38681991; PMCID: PMC11045482.