OSMI-1 | CAS#1681056-61-0 | OGT inhibitor

MedKoo Cat#: 562300 | Name: OSMI-1

Description:

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

OSMI-1 is an inhibitor of O-GlcNAc transferase (OGT). Pharmacological inhibition of OGT with OSMI-1 disrupted the wake-sleep patterns of zebrafish without affecting expression of circadian rhythm-regulating genes.

Chemical Structure

OSMI-1

CAS#1681056-61-0

Theoretical Analysis

MedKoo Cat#: 562300

Name: OSMI-1

CAS#: 1681056-61-0

Chemical Formula: C28H25N3O6S2

Exact Mass: 563.1185

Molecular Weight: 563.64

Elemental Analysis: C, 59.67; H, 4.47; N, 7.46; O, 17.03; S, 11.38

Price and Availability

Size	Price	Availability
25mg	USD 750.00	2 Weeks
100mg	USD 1,950.00	2 Weeks
1g	USD 4,650.00	2 Weeks

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Synonym

OSMI-1; OSMI 1; OSMI1;

IUPAC/Chemical Name

(R)-N-(Furan-2-ylmethyl)-2-(2-methoxyphenyl)-2-(2-oxo-1,2-dihydroquinoline-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamide

InChi Key

IYIGLWQQAMROOF-HHHXNRCGSA-N

InChi Code

InChI=1S/C28H25N3O6S2/c1-36-25-9-3-2-8-23(25)27(28(33)31(17-20-6-4-14-37-20)18-21-7-5-15-38-21)30-39(34,35)22-11-12-24-19(16-22)10-13-26(32)29-24/h2-16,27,30H,17-18H2,1H3,(H,29,32)/t27-/m1/s1

SMILES Code

O=C(N(CC1=CC=CO1)CC2=CC=CS2)[C@@H](C3=CC=CC=C3OC)NS(=O)(C4=CC5=C(NC(C=C5)=O)C=C4)=O

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:

OSMI-1 is an inhibitor of O-GlcNAc transferase (OGT).

In vitro activity:

This study reports a small molecule OGT inhibitor, OSMI-1, developed from a high-throughput screening hit. It is cell-permeable and inhibits protein O-GlcNAcylation in several mammalian cell lines without qualitatively altering cell surface N- or O-linked glycans. The development of this molecule validates high-throughput screening approaches for the discovery of glycosyltransferase inhibitors, and further optimization of this scaffold may lead to yet more potent OGT inhibitors useful for studying OGT in animal models. Reference: ACS Chem Biol. 2015 Jun 19;10(6):1392-7. https://pubmed.ncbi.nlm.nih.gov/25751766/

In vivo activity:

This study demonstrated that the combination of DOX and OSMI-1 stimulated cell death, dramatically reducing cell proliferation and tumor growth in vivo using a HepG2 xenograft mouse model. These findings indicate that OSMI-1 acts as a potential chemosensitizer by enhancing DOX-induced cell death. Reference: Cancers (Basel). 2020 Oct 27;12(11):3154. https://pubmed.ncbi.nlm.nih.gov/33121131/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	44.35
	DMF:PBS (pH 7.2) (1:5)	0.2	0.28
	DMSO	73.3	130.11

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 563.64 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. Papanicolaou KN, Jung J, Ashok D, Zhang W, Modaressanavi A, Avila E, Foster DB, Zachara NE, O'Rourke B. Inhibiting O-GlcNAcylation impacts p38 and Erk1/2 signaling and perturbs cardiomyocyte hypertrophy. J Biol Chem. 2023 Mar;299(3):102907. doi: 10.1016/j.jbc.2023.102907. Epub 2023 Jan 13. PMID: 36642184; PMCID: PMC9988579. 2.Ortiz-Meoz RF, Jiang J, Lazarus MB, Orman M, Janetzko J, Fan C, Duveau DY, Tan ZW, Thomas CJ, Walker S. A small molecule that inhibits OGT activity in cells. ACS Chem Biol. 2015 Jun 19;10(6):1392-7. doi: 10.1021/acschembio.5b00004. Epub 2015 Mar 18. PMID: 25751766; PMCID: PMC4475500. 3. Lee SJ, Kwon OS. O-GlcNAc Transferase Inhibitor Synergistically Enhances Doxorubicin-Induced Apoptosis in HepG2 Cells. Cancers (Basel). 2020 Oct 27;12(11):3154. doi: 10.3390/cancers12113154. PMID: 33121131; PMCID: PMC7693581.

In vitro protocol:

In vivo protocol:

1. Lee SJ, Kwon OS. O-GlcNAc Transferase Inhibitor Synergistically Enhances Doxorubicin-Induced Apoptosis in HepG2 Cells. Cancers (Basel). 2020 Oct 27;12(11):3154. doi: 10.3390/cancers12113154. PMID: 33121131; PMCID: PMC7693581.

1: Gholkar AA, Gimeno TV, Edgemon JE, Sim MS, Torres JZ. MI-181 Modulates Cilia Length and Restores Cilia Length in Cells with Defective Shortened Cilia. ACS Chem Biol. 2024 Aug 6. doi: 10.1021/acschembio.4c00186. Epub ahead of print. PMID: 39106364. 2: Park J, Kim DY, Oh ES, Han IO. Light-Dependent Circadian Rhythm Governs O-GlcNAc Cycling to Influence Cognitive Function in Adult Zebrafish. J Pineal Res. 2024 Aug;76(5):e13001. doi: 10.1111/jpi.13001. PMID: 39092800. 3: Loaeza-Reyes KJ, Zenteno E, Ramírez-Hernández E, Salinas-Marin R, Moreno- Rodríguez A, Torres-Rosas R, Argueta-Figueroa L, Fernández-Rojas B, Pina-Canseco S, Acevedo-Mascarúa AE, Hernández-Antonio A, Pérez-Cervera Y. The modulation of the hexosamine biosynthetic pathway impacts the localization of CD36 in macrophages. Acta Biochim Pol. 2024 Jul 8;71:13004. doi: 10.3389/abp.2024.13004. PMID: 39041003; PMCID: PMC11261345. 4: Ayodele AO, Udosen B, Oluwagbemi OO, Oladipo EK, Omotuyi I, Isewon I, Nash O, Soremekun O, Fatumo S. An in-silico analysis of OGT gene association with diabetes mellitus. BMC Res Notes. 2024 Mar 27;17(1):89. doi: 10.1186/s13104-024-06744-5. PMID: 38539217; PMCID: PMC10976716. 5: Wu QP, Vang S, Zhou JQ, Krick S, Barnes JW, Sanders YY. O-GlcNAc regulates anti-fibrotic genes in lung fibroblasts through EZH2. J Cell Mol Med. 2024 Apr;28(7):e18191. doi: 10.1111/jcmm.18191. PMID: 38494860; PMCID: PMC10945079. 6: Yaqin Z, Kehan W, Yi Z, Naijian W, Wei Q, Fei M. Resveratrol alleviates inflammatory bowel disease by inhibiting JAK2/STAT3 pathway activity via the reduction of O-GlcNAcylation of STAT3 in intestinal epithelial cells. Toxicol Appl Pharmacol. 2024 Mar;484:116882. doi: 10.1016/j.taap.2024.116882. Epub 2024 Mar 2. PMID: 38437956. 7: Zhang CC, Li Y, Jiang CY, Le QM, Liu X, Ma L, Wang FF. O-GlcNAcylation mediates H2O2-induced apoptosis through regulation of STAT3 and FOXO1. Acta Pharmacol Sin. 2024 Apr;45(4):714-727. doi: 10.1038/s41401-023-01218-z. Epub 2024 Jan 8. PMID: 38191912; PMCID: PMC10943090. 8: Wang J, Xin Lv, Aniwan A, Liu H, Lin Y, Shao X, Zhou S, Yu P. O-GlcNAcylation regulates HIF-1α and induces mesothelial-mesenchymal transition and fibrosis of human peritoneal mesothelial cells. Heliyon. 2023 Dec 1;9(12):e22916. doi: 10.1016/j.heliyon.2023.e22916. PMID: 38144265; PMCID: PMC10746441. 9: Lin B, Chai S, Zhang Q, Lu Y, Hu J, Zhang J, Du YZ, Wu L. Sialic Acid- Modified O-GlcNAc Transferase Inhibitor Liposome Presents Antitumor Effect in Hepatocellular Carcinoma. Mol Pharm. 2024 Jan 1;21(1):102-112. doi: 10.1021/acs.molpharmaceut.3c00451. Epub 2023 Nov 23. PMID: 37994899. 10: Fernández-Rojas B, Gómez-Sierra T, Medina-Campos ON, Hernández-Juárez J, Hernández-Cruz PA, Gallegos-Velasco IB, Pérez-Cervera Y, Pedraza-Chaverri J. Antioxidant activity of glucosamine and its effects on ROS production, Nrf2, and O-GlcNAc expression in HMEC-1 cells. Curr Res Toxicol. 2023 Sep 22;5:100128. doi: 10.1016/j.crtox.2023.100128. PMID: 37808439; PMCID: PMC10558709. 11: Lee DE, Lee GY, Lee HM, Choi SY, Lee SJ, Kwon OS. Synergistic apoptosis by combination of metformin and an O-GlcNAcylation inhibitor in colon cancer cells. Cancer Cell Int. 2023 Jun 2;23(1):108. doi: 10.1186/s12935-023-02954-2. PMID: 37268905; PMCID: PMC10239094. 12: Pokharel E, Aryal YP, Kim TY, Kim A, Jung JK, An SY, Kwon TY, Min BK, Yamamoto H, Cho SW, Sohn WJ, An CH, Lee Y, Kim DY, Ha JH, Kim JY. The role of O-GlcNAcylation mediated by OGT during tooth development. J Cell Physiol. 2023 Jul;238(7):1520-1529. doi: 10.1002/jcp.31024. Epub 2023 Apr 26. PMID: 37098720. 13: Yang Y, Yan Y, Yin J, Tang N, Wang K, Huang L, Hu J, Feng Z, Gao Q, Huang A. O-GlcNAcylation of YTHDF2 promotes HBV-related hepatocellular carcinoma progression in an N6-methyladenosine-dependent manner. Signal Transduct Target Ther. 2023 Feb 10;8(1):63. doi: 10.1038/s41392-023-01316-8. PMID: 36765030; PMCID: PMC9918532. 14: Taira TM, Ramos-Junior ES, Melo PH, Costa-Silva CC, Alteen MG, Vocadlo DJ, Dias WB, Cunha FQ, Alves-Filho JC, Søe K, Fukada SY. HBP/O-GlcNAcylation Metabolic Axis Regulates Bone Resorption Outcome. J Dent Res. 2023 Apr;102(4):440-449. doi: 10.1177/00220345221141043. Epub 2023 Feb 7. PMID: 36749069. 15: Xuefei Y, Dongyan L, Tianming L, Hejuan Z, Jianhua F. O-linked N-acetylglucosamine affects mitochondrial homeostasis by regulating Parkin- dependent mitophagy in hyperoxia-injured alveolar type II cells injury. Respir Res. 2023 Jan 16;24(1):16. doi: 10.1186/s12931-022-02287-0. PMID: 36647045; PMCID: PMC9841680. 16: Papanicolaou KN, Jung J, Ashok D, Zhang W, Modaressanavi A, Avila E, Foster DB, Zachara NE, O'Rourke B. Inhibiting O-GlcNAcylation impacts p38 and Erk1/2 signaling and perturbs cardiomyocyte hypertrophy. J Biol Chem. 2023 Mar;299(3):102907. doi: 10.1016/j.jbc.2023.102907. Epub 2023 Jan 13. PMID: 36642184; PMCID: PMC9988579. 17: Chen L, Li Y, Zeng S, Duan S, Huang Z, Liang Y. The interaction of O-GlcNAc- modified NLRX1 and IKK-α modulates IL-1β expression in M1 macrophages. In Vitro Cell Dev Biol Anim. 2022 May;58(5):408-418. doi: 10.1007/s11626-022-00654-1. Epub 2022 May 5. PMID: 35513753. 18: Feinberg D, Ramakrishnan P, Wong DP, Asthana A, Parameswaran R. Inhibition of O-GlcNAcylation Decreases the Cytotoxic Function of Natural Killer Cells. Front Immunol. 2022 Apr 11;13:841299. doi: 10.3389/fimmu.2022.841299. PMID: 35479087; PMCID: PMC9036377. 19: Weiss M, Anderluh M, Gobec M. Inhibition of O-GlcNAc Transferase Alters the Differentiation and Maturation Process of Human Monocyte Derived Dendritic Cells. Cells. 2021 Nov 26;10(12):3312. doi: 10.3390/cells10123312. PMID: 34943826; PMCID: PMC8699345. 20: Bova RA, Melton-Celsa A. Shiga toxin (Stx) type 2-induced increase in O-linked N-acetyl glucosamine protein modification: a new therapeutic target? EMBO Mol Med. 2022 Jan 11;14(1):e15389. doi: 10.15252/emmm.202115389. Epub 2021 Dec 22. PMID: 34935281; PMCID: PMC8749490.