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MedKoo Cat#: 462297 | Name: TAPI 1
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Description:

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

TAPI 1 is a ADAM-17 (TACE) and MMP inhibitor. TAPI-1 Exhibits Anti-tumor Efficacy in Human Esophageal Squamous Cell Carcinoma Cells via Suppression of NF-kappaB Signaling Pathway.

Chemical Structure

TAPI 1
TAPI 1
CAS#163847-77-6

Theoretical Analysis

MedKoo Cat#: 462297

Name: TAPI 1

CAS#: 163847-77-6

Chemical Formula: C26H37N5O5

Exact Mass: 499.2795

Molecular Weight: 499.61

Elemental Analysis: C, 62.51; H, 7.46; N, 14.02; O, 16.01

Price and Availability

Size Price Availability Quantity
1mg USD 550.00 2 Weeks
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Related CAS #
No Data
Synonym
TAPI 1; TAPI1; TAPI-1
IUPAC/Chemical Name
(R)-N1-((S)-1-(((S)-1-((2-aminoethyl)amino)-1-oxopropan-2-yl)amino)-3-(naphthalen-2-yl)-1-oxopropan-2-yl)-N4-hydroxy-2-isobutylsuccinamide
InChi Key
AWNBSWDIOCXWJW-WTOYTKOKSA-N
InChi Code
InChI=1S/C26H37N5O5/c1-16(2)12-21(15-23(32)31-36)25(34)30-22(26(35)29-17(3)24(33)28-11-10-27)14-18-8-9-19-6-4-5-7-20(19)13-18/h4-9,13,16-17,21-22,36H,10-12,14-15,27H2,1-3H3,(H,28,33)(H,29,35)(H,30,34)(H,31,32)/t17-,21+,22-/m0/s1
SMILES Code
ONC(C[C@@H](CC(C)C)C(N[C@@H](CC1=CC(C=CC=C2)=C2C=C1)C(N[C@@H](C)C(NCCN)=O)=O)=O)=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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 499.61 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
1: Gao L, Li L, Zhang D, Qiu J, Qian J, Liu H. TAPI-1 Exhibits Anti-tumor Efficacy in Human Esophageal Squamous Cell Carcinoma Cells via Suppression of NF-κB Signaling Pathway. Dig Dis Sci. 2024 Jan;69(1):81-94. doi: 10.1007/s10620-023-08181-z. Epub 2023 Nov 26. PMID: 38007701; PMCID: PMC10787672. 2: Nango H, Ohtani M. S-1-propenyl-L-cysteine suppresses lipopolysaccharide- induced expression of matrix metalloproteinase-1 through inhibition of tumor necrosis factor-α converting enzyme-epidermal growth factor receptor axis in human gingival fibroblasts. PLoS One. 2023 Apr 21;18(4):e0284713. doi: 10.1371/journal.pone.0284713. PMID: 37083725; PMCID: PMC10121056. 3: Bienstein M, Minond D, Schwaneberg U, Davari MD, Yildiz D. In Silico and Experimental ADAM17 Kinetic Modeling as Basis for Future Screening System for Modulators. Int J Mol Sci. 2022 Jan 25;23(3):1368. doi: 10.3390/ijms23031368. PMID: 35163294; PMCID: PMC8835787. 4: Bai H, Zhang L, Sun P, Wu H, Li M, Gu Y, Zhang C, Lou C, Li J. ADAM17: A novel treatment target for aneurysms. Biomed Pharmacother. 2022 Apr;148:112712. doi: 10.1016/j.biopha.2022.112712. Epub 2022 Feb 11. PMID: 35158143. 5: Liao K, Lv DY, Yu HL, Chen H, Luo SX. iNOS regulates activation of the NLRP3 inflammasome through the sGC/cGMP/PKG/TACE/TNF-α axis in response to cigarette smoke resulting in aortic endothelial pyroptosis and vascular dysfunction. Int Immunopharmacol. 2021 Dec;101(Pt B):108334. doi: 10.1016/j.intimp.2021.108334. Epub 2021 Nov 9. PMID: 34768128. 6: Minamidate A, Onizawa M, Saito C, Hikichi R, Mochimaru T, Murakami M, Sakuma C, Asakawa T, Hiraoka Y, Oshima S, Nagaishi T, Tsuchiya K, Ohira H, Okamoto R, Watanabe M. A potent endocytosis inhibitor Ikarugamycin up-regulates TNF production. Biochem Biophys Rep. 2021 Jul 8;27:101065. doi: 10.1016/j.bbrep.2021.101065. PMID: 34286109; PMCID: PMC8274290. 7: Miao K, Zhou L, Ba H, Li C, Gu H, Yin B, Wang J, Yang XP, Li Z, Wang DW. Transmembrane tumor necrosis factor alpha attenuates pressure-overload cardiac hypertrophy via tumor necrosis factor receptor 2. PLoS Biol. 2020 Dec 3;18(12):e3000967. doi: 10.1371/journal.pbio.3000967. PMID: 33270628; PMCID: PMC7714153. 8: Sultana S, Bishayi B. Potential anti-arthritic and anti-inflammatory effects of TNF-α processing inhibitor-1 (TAPI-1): A new approach to the treatment of S. aureus arthritis. Immunobiology. 2020 Mar;225(2):151887. doi: 10.1016/j.imbio.2019.11.022. Epub 2019 Nov 30. PMID: 31822434. 9: Dutta P, Sultana S, Dey R, Bishayi B. Regulation of Staphylococcus aureus- induced CXCR1 expression via inhibition of receptor mobilization and receptor shedding during dual receptor (TNFR1 and IL-1R) neutralization. Immunol Res. 2019 Jun;67(2-3):241-260. doi: 10.1007/s12026-019-09083-x. PMID: 31290001. 10: Laber A, Gadermaier E, Wallwitz J, Berg G, Himmler G. A high-sensitivity enzyme immunoassay for the quantification of soluble human semaphorin 4D in plasma. Anal Biochem. 2019 Jun 1;574:15-22. doi: 10.1016/j.ab.2019.03.004. Epub 2019 Mar 14. PMID: 30879960. 11: Kelly FL, Weinberg KE, Nagler AE, Nixon AB, Star MD, Todd JL, Brass DM, Palmer SM. EGFR-Dependent IL8 Production by Airway Epithelial Cells After Exposure to the Food Flavoring Chemical 2,3-Butanedione. Toxicol Sci. 2019 Jun 1;169(2):534-542. doi: 10.1093/toxsci/kfz066. PMID: 30851105. 12: Tajbakhsh A, Gheibi Hayat SM, Butler AE, Sahebkar A. Effect of soluble cleavage products of important receptors/ligands on efferocytosis: Their role in inflammatory, autoimmune and cardiovascular disease. Ageing Res Rev. 2019 Mar;50:43-57. doi: 10.1016/j.arr.2019.01.007. Epub 2019 Jan 9. PMID: 30639340. 13: Kaye R, Botten N, Lippestad M, Li D, Hodges RR, Utheim TP, Serhan CN, Dartt DA. Resolvin D1, but not resolvin E1, transactivates the epidermal growth factor receptor to increase intracellular calcium and glycoconjugate secretion in rat and human conjunctival goblet cells. Exp Eye Res. 2019 Mar;180:53-62. doi: 10.1016/j.exer.2018.11.018. Epub 2018 Dec 1. PMID: 30513286; PMCID: PMC6389367. 14: He M, Lippestad M, Li D, Hodges RR, Utheim TP, Dartt DA. Activation of the EGF Receptor by Histamine Receptor Subtypes Stimulates Mucin Secretion in Conjunctival Goblet Cells. Invest Ophthalmol Vis Sci. 2018 Jul 2;59(8):3543-3553. doi: 10.1167/iovs.18-2476. PMID: 30025103; PMCID: PMC6049985. 15: Taylor RR, Filia A, Paredes U, Asai Y, Holt JR, Lovett M, Forge A. Regenerating hair cells in vestibular sensory epithelia from humans. Elife. 2018 Jul 18;7:e34817. doi: 10.7554/eLife.34817. PMID: 30019672; PMCID: PMC6078492. 16: Yu T, Ma Y, Wang H. EpCAM Intracellular Domain Promotes Porcine Cell Reprogramming by Upregulation of Pluripotent Gene Expression via Beta-catenin Signaling. Sci Rep. 2017 Apr 10;7:46315. doi: 10.1038/srep46315. PMID: 28393933; PMCID: PMC5385527. 17: Uchibori T, Matsuda K, Shimodaira T, Sugano M, Uehara T, Honda T. IL-6 trans-signaling is another pathway to upregulate Osteopontin. Cytokine. 2017 Feb;90:88-95. doi: 10.1016/j.cyto.2016.11.006. Epub 2016 Nov 15. PMID: 27863335. 18: Chen Q, Takahashi Y, Oka K, Ma JX. Functional Differences of Very-Low- Density Lipoprotein Receptor Splice Variants in Regulating Wnt Signaling. Mol Cell Biol. 2016 Sep 26;36(20):2645-54. doi: 10.1128/MCB.00235-16. PMID: 27528615; PMCID: PMC5038150. 19: Luo Q, Zhang Z, Liu D, Feng K, Jin X, Zhang J. Human neutrophil elastase induces MUC5AC overexpression in chronic rhinosinusitis through tumour necrosis factor-α converting enzyme. Acta Otolaryngol. 2016 Jun;136(6):641-8. doi: 10.3109/00016489.2016.1144145. Epub 2016 Feb 16. PMID: 26881964. 20: Sun X, Liang J, Yao X, Lu C, Zhong T, Hong X, Wang X, Xu W, Gu M, Tang J. The activation of EGFR promotes myocardial tumor necrosis factor-α production and cardiac failure in endotoxemia. Oncotarget. 2015 Nov 3;6(34):35478-95. doi: 10.18632/oncotarget.6071. PMID: 26486084; PMCID: PMC4742119.

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