ATN-161 TFA salt
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MedKoo CAT#: 206976

CAS#: 904763-27-5 (TFA)

Description: ATN-161 is a small peptide antagonist of integrin alpha5beta1 with potential antineoplastic activity. ATN-161 selectively binds to and blocks the receptor for integrin alpha5beta1, thereby preventing integrin alpha5beta1 binding. This receptor blockade may result in inhibition of endothelial cell-cell interactions, endothelial cell-matrix interactions, angiogenesis, and tumor progression. Integrin alpha5beta1 is expressed on endothelial cells and plays a crucial role in endothelial cell adhesion and migration. Note: The Catalog number of ATN-161 TFA salt was changed from 200350B to 206976.

Chemical Structure

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ATN-161 TFA salt
CAS# 904763-27-5 (TFA)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 206976
Name: ATN-161 TFA salt
CAS#: 904763-27-5 (TFA)
Chemical Formula: C25H36F3N9O10S
Exact Mass: 0.00
Molecular Weight: 711.670
Elemental Analysis: C, 42.19; H, 5.10; F, 8.01; N, 17.71; O, 22.48; S, 4.50

Price and Availability

Size Price Availability Quantity
5mg USD 120 Ready to ship
10mg USD 200 Ready to ship
25mg USD 450 Ready to ship
50mg USD 750 Ready to ship
100mg USD 1250 Ready to ship
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Related CAS #: 262438-43-7 (free base)   904763-27-5 (TFA)   904763-42-4 (HCl)   904763-50-4 (mesylate)   904763-58-2 (acetate)   904763-74-2 (sulfate),  

Synonym: ATN-161 TFA; ATN 161 TFA; ATN161 TFA; AcPHSCNNH2 TFA salt.

IUPAC/Chemical Name: (S)-2-((R)-2-((S)-2-((S)-2-((S)-1-acetylpyrrolidine-2-carboxamido)-3-(1H-imidazol-5-yl)propanamido)-3-hydroxypropanamido)-3-mercaptopropanamido)succinamide, trifluoroacetic acid

InChi Key: MCVJOWHOEOLJGI-LQCLSJOXSA-N

InChi Code: InChI=1S/C23H35N9O8S.C2HF3O2/c1-11(34)32-4-2-3-17(32)23(40)29-14(5-12-7-26-10-27-12)20(37)30-15(8-33)21(38)31-16(9-41)22(39)28-13(19(25)36)6-18(24)35;3-2(4,5)1(6)7/h7,10,13-17,33,41H,2-6,8-9H2,1H3,(H2,24,35)(H2,25,36)(H,26,27)(H,28,39)(H,29,40)(H,30,37)(H,31,38);(H,6,7)/t13-,14-,15-,16-,17-;/m0./s1

SMILES Code: O=C(N)[C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H]1N(C(C)=O)CCC1)=O)CC2=CN=CN2)=O)CO)=O)CS)=O)CC(N)=O.O=C(O)C(F)(F)F

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 and water (7 mg/mL).

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: Note: The previous catalog number for this product was 200350b.

Biological target: ATN-161 trifluoroacetate salt is a novel integrin α5β1 antagonist.
In vitro activity: This study performed similar assays to investigate ACE2 binding to α5β1, using a mixture of ATN-161 and hACE2. Clear inhibition of ACE2/α5β1 binding by ATN-161 was apparent and dose-dependent (Figure 1B). Furthermore, application of ATN-161 reduced binding of the trimeric spike protein to hACE2, either alone or in combination with α5β1, the latter of which trended to support greater spike binding than to hACE2 alone (Figure 1C). Application of ATN-161 also reduced binding of the monomeric spike to hACE2 (Supplemental Figure S1). Reference: JACC Basic Transl Sci. 2021 Jan; 6(1): 1–8. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7566794/
In vivo activity: In the present study, 2 mouse models of ocular NV (neurovascularization) were used to investigate the potential role and underlying mechanism of action of ATN-161. The protein levels of integrin α5β1 increased in the CNV (choroidal neovascularization) and OIR (oxygen-induced retinopathy) mice, indicating a close relationship between integrin α5β1 and ocular NV. Next, this study explored the inhibition of integrin α5β1 by ATN-161 and demonstrated that ATN-161 inhibited the protein expression of integrin α5β1 in a dose-dependent manner. The NV areas were reduced in OIR and CNV mice after treatment with ATN-161 compared with PBS groups. Reference: Med Sci Monit. 2018 Aug 22;24:5860-5873. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6116638/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 1.0 1.41
Water 8.3 11.70

Preparing Stock Solutions

The following data is based on the product molecular weight 711.67 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. Beddingfield BJ, Iwanaga N, Chapagain PP, Zheng W, Roy CJ, Hu TY, Kolls JK, Bix GJ. The Integrin Binding Peptide, ATN-161, as a Novel Therapy for SARS-CoV-2 Infection. JACC Basic Transl Sci. 2021 Jan;6(1):1-8. doi: 10.1016/j.jacbts.2020.10.003. Epub 2020 Oct 16. PMID: 33102950; PMCID: PMC7566794. 2. Chen YC, Chuang TY, Liu CW, Liu CW, Lee TL, Lai TC, Chen YL. Particulate matters increase epithelial-mesenchymal transition and lung fibrosis through the ETS-1/NF-κB-dependent pathway in lung epithelial cells. Part Fibre Toxicol. 2020 Aug 14;17(1):41. doi: 10.1186/s12989-020-00373-z. PMID: 32799885; PMCID: PMC7429884. 3. Sui A, Zhong Y, Demetriades AM, Shen J, Su T, Yao Y, Gao Y, Zhu Y, Shen X, Xie B. ATN-161 as an Integrin α5β1 Antagonist Depresses Ocular Neovascularization by Promoting New Vascular Endothelial Cell Apoptosis. Med Sci Monit. 2018 Aug 22;24:5860-5873. doi: 10.12659/MSM.907446. PMID: 30133427; PMCID: PMC6116638. 4. Doñate F, Parry GC, Shaked Y, Hensley H, Guan X, Beck I, Tel-Tsur Z, Plunkett ML, Manuia M, Shaw DE, Kerbel RS, Mazar AP. Pharmacology of the novel antiangiogenic peptide ATN-161 (Ac-PHSCN-NH2): observation of a U-shaped dose-response curve in several preclinical models of angiogenesis and tumor growth. Clin Cancer Res. 2008 Apr 1;14(7):2137-44. doi: 10.1158/1078-0432.CCR-07-4530. PMID: 18381955.
In vitro protocol: 1. Beddingfield BJ, Iwanaga N, Chapagain PP, Zheng W, Roy CJ, Hu TY, Kolls JK, Bix GJ. The Integrin Binding Peptide, ATN-161, as a Novel Therapy for SARS-CoV-2 Infection. JACC Basic Transl Sci. 2021 Jan;6(1):1-8. doi: 10.1016/j.jacbts.2020.10.003. Epub 2020 Oct 16. PMID: 33102950; PMCID: PMC7566794. 2. Chen YC, Chuang TY, Liu CW, Liu CW, Lee TL, Lai TC, Chen YL. Particulate matters increase epithelial-mesenchymal transition and lung fibrosis through the ETS-1/NF-κB-dependent pathway in lung epithelial cells. Part Fibre Toxicol. 2020 Aug 14;17(1):41. doi: 10.1186/s12989-020-00373-z. PMID: 32799885; PMCID: PMC7429884.
In vivo protocol: 1. Sui A, Zhong Y, Demetriades AM, Shen J, Su T, Yao Y, Gao Y, Zhu Y, Shen X, Xie B. ATN-161 as an Integrin α5β1 Antagonist Depresses Ocular Neovascularization by Promoting New Vascular Endothelial Cell Apoptosis. Med Sci Monit. 2018 Aug 22;24:5860-5873. doi: 10.12659/MSM.907446. PMID: 30133427; PMCID: PMC6116638. 2. Doñate F, Parry GC, Shaked Y, Hensley H, Guan X, Beck I, Tel-Tsur Z, Plunkett ML, Manuia M, Shaw DE, Kerbel RS, Mazar AP. Pharmacology of the novel antiangiogenic peptide ATN-161 (Ac-PHSCN-NH2): observation of a U-shaped dose-response curve in several preclinical models of angiogenesis and tumor growth. Clin Cancer Res. 2008 Apr 1;14(7):2137-44. doi: 10.1158/1078-0432.CCR-07-4530. PMID: 18381955.

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1: Dai W, Yang T, Wang X, Wang J, Zhang X, Zhang Q. PHSCNK-Modified and doxorubicin-loaded liposomes as a dual targeting system to integrin-overexpressing tumor neovasculature and tumor cells. J Drug Target. 2010 May;18(4):254-63. PubMed PMID: 19824864.

2: Doñate F, Parry GC, Shaked Y, Hensley H, Guan X, Beck I, Tel-Tsur Z, Plunkett ML, Manuia M, Shaw DE, Kerbel RS, Mazar AP. Pharmacology of the novel antiangiogenic peptide ATN-161 (Ac-PHSCN-NH2): observation of a U-shaped dose-response curve in several preclinical models of angiogenesis and tumor growth. Clin Cancer Res. 2008 Apr 1;14(7):2137-44. PubMed PMID: 18381955.

3: Danese S, Sans M, Spencer DM, Beck I, Doñate F, Plunkett ML, de la Motte C, Redline R, Shaw DE, Levine AD, Mazar AP, Fiocchi C. Angiogenesis blockade as a new therapeutic approach to experimental colitis. Gut. 2007 Jun;56(6):855-62. Epub 2006 Dec 14. PubMed PMID: 17170016.

4: Chidlow JH Jr, Langston W, Greer JJ, Ostanin D, Abdelbaqi M, Houghton J, Senthilkumar A, Shukla D, Mazar AP, Grisham MB, Kevil CG. Differential angiogenic regulation of experimental colitis. Am J Pathol. 2006 Dec;169(6):2014-30. PubMed PMID: 17148665; PubMed Central PMCID: PMC1762465.

5: Khalili P, Arakelian A, Chen G, Plunkett ML, Beck I, Parry GC, Doñate F, Shaw DE, Mazar AP, Rabbani SA. A non-RGD-based integrin binding peptide (ATN-161) blocks breast cancer growth and metastasis in vivo. Mol Cancer Ther. 2006 Sep;5(9):2271-80. PubMed PMID: 16985061.

6: Cianfrocca ME, Kimmel KA, Gallo J, Cardoso T, Brown MM, Hudes G, Lewis N, Weiner L, Lam GN, Brown SC, Shaw DE, Mazar AP, Cohen RB. Phase 1 trial of the antiangiogenic peptide ATN-161 (Ac-PHSCN-NH(2)), a beta integrin antagonist, in patients with solid tumours. Br J Cancer. 2006 Jun 5;94(11):1621-6. PubMed PMID: 16705310; PubMed Central PMCID: PMC2361324.

7: Stoeltzing O, Liu W, Reinmuth N, Fan F, Parry GC, Parikh AA, McCarty MF, Bucana CD, Mazar AP, Ellis LM. Inhibition of integrin alpha5beta1 function with a small peptide (ATN-161) plus continuous 5-FU infusion reduces colorectal liver metastases and improves survival in mice. Int J Cancer. 2003 Apr 20;104(4):496-503. PubMed PMID: 12584749.

1. Amruta N, Bix G. ATN-161 Ameliorates Ischemia/Reperfusion-induced Oxidative Stress, Fibro-inflammation, Mitochondrial damage, and Apoptosis-mediated Tight Junction Disruption in bEnd.3 Cells. Inflammation. 2021 Aug 22:1–18. doi: 10.1007/s10753-021-01509-9. Epub ahead of print. PMID: 34420157; PMCID: PMC8380192.

2. Amruta N, Engler-Chiurazzi EB, Murray-Brown IC, Gressett TE, Biose IJ, Chastain WH, Befeler JB, Bix G. In Vivo protection from SARS-CoV-2 infection by ATN-161 in k18-hACE2 transgenic mice. Life Sci. 2021 Aug 10;284:119881. doi: 10.1016/j.lfs.2021.119881. Epub ahead of print. PMID: 34389403; PMCID: PMC8352850.

3. Hamblin MH, Murad R, Yin J, Vallim G, Lee JP. Modulation of gene expression on a transcriptome-wide level following human neural stem cell transplantation in aged mouse stroke brains. Exp Neurol. 2022 Jan;347:113913. doi: 10.1016/j.expneurol.2021.113913. Epub 2021 Nov 6. PMID: 34752785; PMCID: PMC8647207.

4. Edwards DN, Salmeron K, Lukins DE, Trout AL, Fraser JF, Bix GJ. Integrin α5β1 inhibition by ATN-161 reduces neuroinflammation and is neuroprotective in ischemic stroke. J Cereb Blood Flow Metab. 2020 Aug;40(8):1695-1708. doi: 10.1177/0271678X19880161. Epub 2019 Oct 1. PMID: 31575337; PMCID: PMC7370357.

5. Kawamura T, Yamamoto M, Suzuki K, Suzuki Y, Kamishima M, Sakata M, Kurachi K, Setoh M, Konno H, Takeuchi H. Tenascin-C Produced by Intestinal Myofibroblasts Promotes Colitis-associated Cancer Development Through Angiogenesis. Inflamm Bowel Dis. 2019 Mar 14;25(4):732-741. doi: 10.1093/ibd/izy368. PMID: 30517646.

6. Roberts J, de Hoog L, Bix GJ. Mice deficient in endothelial α5 integrin are profoundly resistant to experimental ischemic stroke. J Cereb Blood Flow Metab. 2017 Jan;37(1):85-96. doi: 10.1177/0271678X15616979. Epub 2015 Nov 13. PMID: 26661237; PMCID: PMC5363730.

7. Sundaram A, Chen C, Khalifeh-Soltani A, Atakilit A, Ren X, Qiu W, Jo H, DeGrado W, Huang X, Sheppard D. Targeting integrin α5β1 ameliorates severe airway hyperresponsiveness in experimental asthma. J Clin Invest. 2017 Jan 3;127(1):365-374. doi: 10.1172/JCI88555. Epub 2016 Dec 5. PMID: 27918306; PMCID: PMC5199700.

8. Leitner L, Schuch K, Jürets A, Itariu BK, Keck M, Grablowitz V, Aszmann OC, Prager G, Staffler G, Zeyda M, Stulnig TM. Immunological blockade of adipocyte inflammation caused by increased matrix metalloproteinase-cleaved osteopontin in obesity. Obesity (Silver Spring). 2015 Apr;23(4):779-85. doi: 10.1002/oby.21024. Epub 2015 Mar 16. PMID: 25776538.

9. Magdaleno C, Dixon L, Rajasekaran N, Varadaraj A. HIFα independent mechanisms in renal carcinoma cells modulate divergent outcomes in fibronectin assembly mediated by hypoxia and CoCl2. Sci Rep. 2020 Oct 29;10(1):18560. doi: 10.1038/s41598-020-75756-5. PMID: 33122751; PMCID: PMC7596723.

10. Liu H, Lee MJ, Solis NV, Phan QT, Swidergall M, Ralph B, Ibrahim AS, Sheppard DC, Filler SG. Aspergillus fumigatus CalA binds to integrin α5β1 and mediates host cell invasion. Nat Microbiol. 2016 Nov 14;2:16211. doi: 10.1038/nmicrobiol.2016.211. PMID: 27841851; PMCID: PMC5495140.

11. Lukas Leitner,. Effects of matrix metalloproteinase cleavage of osteopontin on human adipocyte function and their blockade with a monoclonal antibody. Doctoral thesis at the Medical University of Vienna. https://repositorium.meduniwien.ac.at/obvumwhs/content/titleinfo/2241469/full.pdf

12. Hamblin MH, Murad R, Yin J, Vallim G, Lee JP. Modulation of gene expression on a transcriptome-wide level following human neural stem cell transplantation in aged mouse stroke brains. Exp Neurol. 2022 Jan;347:113913. doi: 10.1016/j.expneurol.2021.113913. Epub 2021 Nov 6. PMID: 34752785; PMCID: PMC8647207.