OGT2115 | OGT-2115 | CAS#853929-59-6 | heparanase inhibitor

MedKoo Cat#: 406968 | Name: OGT2115

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Description:

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

OGT-2115 is a heparanase inhibitor (IC50 = 0.4 μM). Heparanase inhibitors suppress breast cancer cell invasion and migration induced by ER stress, and provide a strong rationale for the development of heparanase-based therapeutics for the prevention of metastasis induced by chemotherapeutic reagents.

Chemical Structure

OGT2115

CAS#853929-59-6

Theoretical Analysis

MedKoo Cat#: 406968

Name: OGT2115

CAS#: 853929-59-6

Chemical Formula: C24H16BrFN2O4

Exact Mass: 494.0277

Molecular Weight: 495.30

Elemental Analysis: C, 58.20; H, 3.26; Br, 16.13; F, 3.84; N, 5.66; O, 12.92

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 550.00	2 Weeks

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Related CAS #

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Synonym

OGT -115; OGT2115; OGT2115.

IUPAC/Chemical Name

2-[4-[[3-(4-Bromophenyl)-1-oxo-2-propenyl]amino]-3-fluorophenyl]-5-benzoxazoleacetic acid

InChi Key

LKBXWNYXDMSFQU-ONNFQVAWSA-N

InChi Code

InChI=1S/C24H16BrFN2O4/c25-17-6-1-14(2-7-17)4-10-22(29)27-19-8-5-16(13-18(19)26)24-28-20-11-15(12-23(30)31)3-9-21(20)32-24/h1-11,13H,12H2,(H,27,29)(H,30,31)/b10-4+

SMILES Code

O=C(O)CC1=CC=C(OC(C2=CC=C(NC(/C=C/C3=CC=C(Br)C=C3)=O)C(F)=C2)=N4)C4=C1

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

>2 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:

OGT 2115 is a potent, cell-permeable and orally active heparanase inhibitor with an IC50 of 0.4 μM.

In vitro activity:

This study observed a decrease in HSV-2 infection as measured by green fluorescent protein (GFP) reporter activity in the presence of OGT 2115 at 10 μM (Fig. 5C and D). These data combined with observations showing higher levels of virus in lysates of OGT 2115-treated cells (Fig. 6F) suggest that pharmacological inhibition of HPSE using OGT 2115 significantly increases HS expression on the cell surface while reducing the overall viral egress and spread. Reference: J Virol. 2018 Nov 12;92(23):e01179-18. https://pubmed.ncbi.nlm.nih.gov/30232188/

In vivo activity:

The HPSE inhibitor OGT2115 and specific siRNAs were used to study the role of HPSE during HS degradation caused by Cl2 exposure or histone H4 challenge. Cl2 exposure or histone H4 challenge caused obvious acute lung injury in mice, and the pulmonary glycocalyx was degraded evidently as observed from endothelial HS staining and measurement of plasma HS fragments. Pretreatment with OGT2115, an HPSE inhibitor, relieved the acute lung injury and HS degradation caused by Cl2 exposure or histone H4 challenge. Reference: Respir Res. 2022 Jan 24;23(1):14. https://pubmed.ncbi.nlm.nih.gov/35073921/

	Solvent	mg/mL	mM
Solubility
	DMSO	8.2	16.46

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 495.30 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. Hopkins J, Yadavalli T, Agelidis AM, Shukla D. Host Enzymes Heparanase and Cathepsin L Promote Herpes Simplex Virus 2 Release from Cells. J Virol. 2018 Nov 12;92(23):e01179-18. doi: 10.1128/JVI.01179-18. PMID: 30232188; PMCID: PMC6232460. 2. Zhang Y, Xu F, Guan L, Chen M, Zhao Y, Guo L, Li X, Zheng Y, Gao A, Li S. Histone H4 induces heparan sulfate degradation by activating heparanase in chlorine gas-induced acute respiratory distress syndrome. Respir Res. 2022 Jan 24;23(1):14. doi: 10.1186/s12931-022-01932-y. PMID: 35073921; PMCID: PMC8785471. 3. Changyaleket B, Chong ZZ, Dull RO, Nanegrungsunk D, Xu H. Heparanase promotes neuroinflammatory response during subarachnoid hemorrhage in rats. J Neuroinflammation. 2017 Jul 18;14(1):137. doi: 10.1186/s12974-017-0912-8. PMID: 28720149; PMCID: PMC5516362.

In vitro protocol:

In vivo protocol:

1. Zhang Y, Xu F, Guan L, Chen M, Zhao Y, Guo L, Li X, Zheng Y, Gao A, Li S. Histone H4 induces heparan sulfate degradation by activating heparanase in chlorine gas-induced acute respiratory distress syndrome. Respir Res. 2022 Jan 24;23(1):14. doi: 10.1186/s12931-022-01932-y. PMID: 35073921; PMCID: PMC8785471. 2. Changyaleket B, Chong ZZ, Dull RO, Nanegrungsunk D, Xu H. Heparanase promotes neuroinflammatory response during subarachnoid hemorrhage in rats. J Neuroinflammation. 2017 Jul 18;14(1):137. doi: 10.1186/s12974-017-0912-8. PMID: 28720149; PMCID: PMC5516362.

1: Zhang Y, Xu F, Guan L, Chen M, Zhao Y, Guo L, Li X, Zheng Y, Gao A, Li S. Histone H4 induces heparan sulfate degradation by activating heparanase in chlorine gas-induced acute respiratory distress syndrome. Respir Res. 2022 Jan 24;23(1):14. doi: 10.1186/s12931-022-01932-y. PMID: 35073921; PMCID: PMC8785471. 2: Song WY, Jiang XH, Ding Y, Wang Y, Zhou MX, Xia Y, Zhang CY, Yin CC, Qiu C, Li K, Sun P, Han X. Inhibition of heparanase protects against pancreatic beta cell death in streptozotocin-induced diabetic mice via reducing intra-islet inflammatory cell infiltration. Br J Pharmacol. 2020 Oct;177(19):4433-4447. doi: 10.1111/bph.15183. Epub 2020 Aug 19. PMID: 32608014; PMCID: PMC7484558. 3: Giannini G, Battistuzzi G, Rivara S. The Control of Heparanase Through the Use of Small Molecules. Adv Exp Med Biol. 2020;1221:567-603. doi: 10.1007/978-3-030-34521-1_23. PMID: 32274727. 4: Eddy AC, Chapman H, George EM. Heparanase regulation of sFLT-1 release in trophoblasts in vitro. Placenta. 2019 Sep 15;85:63-68. doi: 10.1016/j.placenta.2019.07.004. Epub 2019 Jul 9. PMID: 31327483; PMCID: PMC7099653. 5: Shen S, Tang JX. Mechanisms of OGT2115 inhibition of invasion and migration in KB oral cancer cells. Eur Rev Med Pharmacol Sci. 2017 Oct;21(17):3744. PMID: 28975997. 6: Changyaleket B, Chong ZZ, Dull RO, Nanegrungsunk D, Xu H. Heparanase promotes neuroinflammatory response during subarachnoid hemorrhage in rats. J Neuroinflammation. 2017 Jul 18;14(1):137. doi: 10.1186/s12974-017-0912-8. PMID: 28720149; PMCID: PMC5516362. 7: Shen S, Tang JX. Mechanisms of OGT2115 inhibition of invasion and migration in KB oral cancer cells. Retracted. Eur Rev Med Pharmacol Sci. 2017 Jan;21(1):55-60. Retraction in: Eur Rev Med Pharmacol Sci. 2017 Oct;21(17):3744. PMID: 28121356. 8: Shimada K, Anai S, Fujii T, Tanaka N, Fujimoto K, Konishi N. Syndecan-1 (CD138) contributes to prostate cancer progression by stabilizing tumour- initiating cells. J Pathol. 2013 Dec;231(4):495-504. doi: 10.1002/path.4271. PMID: 24549646. 9: Li Y, Liu H, Huang YY, Pu LJ, Zhang XD, Jiang ZW, Jiang CC. [Effects of cisplatin combined with heparanase inhibitor on proliferation and invasion of human nasopharyngeal carcinoma cells]. Yao Xue Xue Bao. 2013 Apr;48(4):609-14. Chinese. PMID: 23833953. 10: Li Y, Liu H, Huang YY, Pu LJ, Zhang XD, Jiang CC, Jiang ZW. Suppression of endoplasmic reticulum stress-induced invasion and migration of breast cancer cells through the downregulation of heparanase. Int J Mol Med. 2013 May;31(5):1234-42. doi: 10.3892/ijmm.2013.1292. Epub 2013 Mar 5. Retraction in: Int J Mol Med. 2021 Oct;48(4):188. doi: 10.3892/ijmm.2021.5021. PMID: 23467544.