JSH-23
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MedKoo CAT#: 406426

CAS#: 749886-87-1

Description: JSH-23 is a nuclear factor-kappa B (NF-κB) nuclear translocation inhibitor. JSH-23 inhibits LPS and cytokine-induced nuclear translocation of the p65 subunit of NF-kB as analyzed by EMSA and western blot. JSH-23 treatment significantly reversed the nerve conduction and nerve blood flow deficits seen in diabetic animals. Reduction in mechanical pain threshold was also partially corrected by the treatment. Protein expression studies showed that nuclear translocation of p65/p50 subunit was inhibited by JSH-23 treatment in the sciatic nerve. The treatment also lowered the elevated IL-6, TNF-α, cyclo-oxygenase (COX-2) and inducible nitric oxide synthase (iNOS) levels/expression, indicating reduction in the inflammatory damage of the sciatic nerve. Apart from these effects, JSH-23 also increased Nrf2 and hemeoxygenase-1 (HO-1) levels which could imply its potential in increasing the strength of antioxidant defence.


Chemical Structure

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JSH-23
CAS# 749886-87-1

Theoretical Analysis

MedKoo Cat#: 406426
Name: JSH-23
CAS#: 749886-87-1
Chemical Formula: C16H20N2
Exact Mass: 240.16265
Molecular Weight: 240.3434
Elemental Analysis: C, 79.96; H, 8.39; N, 11.66

Price and Availability

Size Price Availability Quantity
10.0mg USD 90.0 Same day
25.0mg USD 150.0 Same day
50.0mg USD 250.0 Same day
100.0mg USD 450.0 Same day
200.0mg USD 750.0 Same day
500.0mg USD 1650.0 Same day
1.0g USD 2950.0 Same day
2.0g USD 5250.0 2 Weeks
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Synonym: JSH23; JSH 23; JSH-23.

IUPAC/Chemical Name: 4-methyl-N1-(3-phenylpropyl)benzene-1,2-diamine

InChi Key: YMFNPBSZFWXMAD-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H20N2/c1-13-9-10-16(15(17)12-13)18-11-5-8-14-6-3-2-4-7-14/h2-4,6-7,9-10,12,18H,5,8,11,17H2,1H3

SMILES Code: NC1=CC(C)=CC=C1NCCCC2=CC=CC=C2

Appearance: white 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, not in water

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

Biological target: JSH-23 inhibits NF-κB transcriptional activity with an IC50 of 7.1 μM in RAW 264.7 cells.
In vitro activity: JSH‑23, an inhibitor of the NF‑κB pathway, impaired the migration of liver cancer cells, and was found to act synergistically with cordycepin. Furthermore, cordycepin treatment reduced the chemotactic migration ability of liver cancer cells to stromal cell‑derived factor 1 (SDF1), which was significantly enhanced following treatment with JSH‑23. Reference: Int J Mol Med. 2020 Jan;45(1):141-150. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6889938/
In vivo activity: The antidepressant-like effects of JSH-23 were investigated in the chronic mild stress (CMS) mouse model. Administration of JSH-23 significantly prevented the decreased sucrose preference in the SPT (sucrose preference test) and prevented the increased immobility time in the FST (forced swimming test) caused by CMS, but had no effect on locomotor activity. Expression of NF-κB p65 protein in the hippocampus was decreased, and elevated levels of IL-6 and TNF-α were reduced, after JSH-23 administration. In addition to its anti-inflammatory effect, JSH-23 treatment increased the expression of SOD and Nrf 2 in the hippocampus, suggesting that it strengthens antioxidant defense. Reference: Pharmacol Biochem Behav. 2018 Jun;169:59-66. https://www.sciencedirect.com/science/article/abs/pii/S0091305718300364?via%3Dihub

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 104.02
DMSO 43.0 178.91
DMSO:PBS (pH 7.2) (1:2) 0.3 1.25
Ethanol 15.0 62.41

Preparing Stock Solutions

The following data is based on the product molecular weight 240.3434 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.

Recalculate based on batch purity %
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. Guo Z, Chen W, Dai G, Huang Y. Cordycepin suppresses the migration and invasion of human liver cancer cells by downregulating the expression of CXCR4. Int J Mol Med. 2020 Jan;45(1):141-150. doi: 10.3892/ijmm.2019.4391. Epub 2019 Oct 31. PMID: 31746344; PMCID: PMC6889938. 2. Kumar A, Negi G, Sharma SS. JSH-23 targets nuclear factor-kappa B and reverses various deficits in experimental diabetic neuropathy: effect on neuroinflammation and antioxidant defence. Diabetes Obes Metab. 2011 Aug;13(8):750-8. doi: 10.1111/j.1463-1326.2011.01402.x. PMID: 21447040. 3. Wang Q, Dong X, Li N, Wang Y, Guan X, Lin Y, Kang J, Zhang X, Zhang Y, Li X, Xu T. JSH-23 prevents depressive-like behaviors in mice subjected to chronic mild stress: Effects on inflammation and antioxidant defense in the hippocampus. Pharmacol Biochem Behav. 2018 Jun;169:59-66. doi: 10.1016/j.pbb.2018.04.005. Epub 2018 Apr 21. PMID: 29684396.
In vitro protocol: 1. Guo Z, Chen W, Dai G, Huang Y. Cordycepin suppresses the migration and invasion of human liver cancer cells by downregulating the expression of CXCR4. Int J Mol Med. 2020 Jan;45(1):141-150. doi: 10.3892/ijmm.2019.4391. Epub 2019 Oct 31. PMID: 31746344; PMCID: PMC6889938.
In vivo protocol: 1. Kumar A, Negi G, Sharma SS. JSH-23 targets nuclear factor-kappa B and reverses various deficits in experimental diabetic neuropathy: effect on neuroinflammation and antioxidant defence. Diabetes Obes Metab. 2011 Aug;13(8):750-8. doi: 10.1111/j.1463-1326.2011.01402.x. PMID: 21447040. 2. Wang Q, Dong X, Li N, Wang Y, Guan X, Lin Y, Kang J, Zhang X, Zhang Y, Li X, Xu T. JSH-23 prevents depressive-like behaviors in mice subjected to chronic mild stress: Effects on inflammation and antioxidant defense in the hippocampus. Pharmacol Biochem Behav. 2018 Jun;169:59-66. doi: 10.1016/j.pbb.2018.04.005. Epub 2018 Apr 21. PMID: 29684396.

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1: Almeida PE, Roque NR, Magalhães KG, Mattos KA, Teixeira L, Maya-Monteiro C, Almeida CJ, Castro-Faria-Neto HC, Ryffel B, Quesniaux VF, Bozza PT. Differential TLR2 downstream signaling regulates lipid metabolism and cytokine production triggered by Mycobacterium bovis BCG infection. Biochim Biophys Acta. 2014 Jan;1841(1):97-107. doi: 10.1016/j.bbalip.2013.10.008. Epub 2013 Oct 10. PubMed PMID: 24120921.

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3: Staudt ND, Jo M, Hu J, Bristow JM, Pizzo DP, Gaultier A, VandenBerg SR, Gonias SL. Myeloid cell receptor LRP1/CD91 regulates monocyte recruitment and angiogenesis in tumors. Cancer Res. 2013 Jul 1;73(13):3902-12. doi: 10.1158/0008-5472.CAN-12-4233. Epub 2013 Apr 30. PubMed PMID: 23633492; PubMed Central PMCID: PMC3702673.

4: Ahmed KM, Zhang H, Park CC. NF-κB regulates radioresistance mediated by β1-integrin in three-dimensional culture of breast cancer cells. Cancer Res. 2013 Jun 15;73(12):3737-48. doi: 10.1158/0008-5472.CAN-12-3537. Epub 2013 Apr 10. PubMed PMID: 23576567; PubMed Central PMCID: PMC3698967.

5: Ren S, Zhang S, Li M, Huang C, Liang R, Jiang A, Guo Y, Pu Y, Huang N, Yang J, Li Z. NF-κB p65 and c-Rel subunits promote phagocytosis and cytokine secretion by splenic macrophages in cirrhotic patients with hypersplenism. Int J Biochem Cell Biol. 2013 Feb;45(2):335-43. doi: 10.1016/j.biocel.2012.11.012. Epub 2012 Nov 26. PubMed PMID: 23195252.

6: Kesanakurti D, Chetty C, Rajasekhar Maddirela D, Gujrati M, Rao JS. Essential role of cooperative NF-κB and Stat3 recruitment to ICAM-1 intronic consensus elements in the regulation of radiation-induced invasion and migration in glioma. Oncogene. 2013 Oct 24;32(43):5144-55. doi: 10.1038/onc.2012.546. Epub 2012 Nov 26. PubMed PMID: 23178493; PubMed Central PMCID: PMC3664652.

7: Katula KS, Joyner-Powell NB, Hsu CC, Kuk A. Differential regulation of the mouse and human Wnt5a alternative promoters A and B. DNA Cell Biol. 2012 Nov;31(11):1585-97. doi: 10.1089/dna.2012.1698. Epub 2012 Oct 9. PubMed PMID: 23046419; PubMed Central PMCID: PMC3482380.

8: Kumar A, Negi G, Sharma SS. JSH-23 targets nuclear factor-kappa B and reverses various deficits in experimental diabetic neuropathy: effect on neuroinflammation and antioxidant defence. Diabetes Obes Metab. 2011 Aug;13(8):750-8. doi: 10.1111/j.1463-1326.2011.01402.x. PubMed PMID: 21447040.

9: Wu X, Li L. Rosiglitazone suppresses lipopolysaccharide-induced matrix metalloproteinase-2 activity in rat aortic endothelial cells via Ras-MEK1/2 signaling. Int J Cardiol. 2012 Jun 28;158(1):54-8. doi: 10.1016/j.ijcard.2010.12.105. Epub 2011 Jan 17. PubMed PMID: 21247645.

10: Liu Q, Kou JP, Yu BY. Ginsenoside Rg1 protects against hydrogen peroxide-induced cell death in PC12 cells via inhibiting NF-κB activation. Neurochem Int. 2011 Jan;58(1):119-25. doi: 10.1016/j.neuint.2010.11.004. Epub 2010 Nov 13. PubMed PMID: 21078355.

11: Arias-Salvatierra D, Silbergeld EK, Acosta-Saavedra LC, Calderon-Aranda ES. Role of nitric oxide produced by iNOS through NF-κB pathway in migration of cerebellar granule neurons induced by Lipopolysaccharide. Cell Signal. 2011 Feb;23(2):425-35. doi: 10.1016/j.cellsig.2010.10.017. Epub 2010 Oct 15. PubMed PMID: 20955790.

12: Hu C, Sun L, Hu Y, Lu D, Wang H, Tang S. Functional characterization of the NF-kappaB binding site in the human NOD2 promoter. Cell Mol Immunol. 2010 Jul;7(4):288-95. doi: 10.1038/cmi.2010.16. Epub 2010 May 3. PubMed PMID: 20436512.

13: Koo JW, Russo SJ, Ferguson D, Nestler EJ, Duman RS. Nuclear factor-kappaB is a critical mediator of stress-impaired neurogenesis and depressive behavior. Proc Natl Acad Sci U S A. 2010 Feb 9;107(6):2669-74. doi: 10.1073/pnas.0910658107. Epub 2010 Jan 26. PubMed PMID: 20133768; PubMed Central PMCID: PMC2823860.

14: Shin HM, Kim MH, Kim BH, Jung SH, Kim YS, Park HJ, Hong JT, Min KR, Kim Y. Inhibitory action of novel aromatic diamine compound on lipopolysaccharide-induced nuclear translocation of NF-kappaB without affecting IkappaB degradation. FEBS Lett. 2004 Jul 30;571(1-3):50-4. PubMed PMID: 15280016.

JSH-23

10.0mg / USD 90.0


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