MedKoo Cat#: 145927 | Name: Penao

Description:

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

Penao (also known as 3-(2-Pyridyl)-5-ethenyl-1,2,4-oxadiazole) is a small molecule that has been studied for its potential applications in cancer therapy. It works by inhibiting the protein, NADPH oxidase, which is involved in the production of reactive oxygen species (ROS) within cells. By reducing the oxidative stress caused by ROS, PENAO can interfere with cancer cell survival and proliferation, ultimately leading to tumor cell death. Its selective action on cancer cells makes it a promising candidate for targeted cancer treatments with potentially fewer side effects compared to conventional therapies.

Chemical Structure

Penao
Penao
CAS#1192411-43-0

Theoretical Analysis

MedKoo Cat#: 145927

Name: Penao

CAS#: 1192411-43-0

Chemical Formula: C13H19AsN2O5S

Exact Mass: 390.0200

Molecular Weight: 390.29

Elemental Analysis: C, 40.01; H, 4.91; As, 19.20; N, 7.18; O, 20.50; S, 8.21

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Penao;
IUPAC/Chemical Name
(S)-2-amino-3-((2-((4-(dihydroxyarsanyl)phenyl)amino)-2-oxoethyl)thio)-3-methylbutanoic acid
InChi Key
BTIKNFALDXFWCX-NSHDSACASA-N
InChi Code
1S/C13H19AsN2O5S/c1-13(2,11(15)12(18)19)22-7-10(17)16-9-5-3-8(4-6-9)14(20)21/h3-6,11,20-21H,7,15H2,1-2H3,(H,16,17)(H,18,19)/t11-/m0/s1
SMILES Code
CC(C)(SCC(=O)NC1=CC=C(C=C1)[As](O)O)[C@@H](N)C(O)=O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 390.29 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: Hogg PJ. Toxicokinetics of the tumour cell mitochondrial toxin, PENAO, in rodents. Invest New Drugs. 2021 Jun;39(3):756-763. doi: 10.1007/s10637-021-01065-x. Epub 2021 Jan 19. PMID: 33469723. 2: Shen H, Decollogne S, Dilda PJ, Hau E, Chung SA, Luk PP, Hogg PJ, McDonald KL. Dual-targeting of aberrant glucose metabolism in glioblastoma. J Exp Clin Cancer Res. 2015 Feb 5;34(1):14. doi: 10.1186/s13046-015-0130-0. PMID: 25652202; PMCID: PMC4324653. 3: Decollogne S, Joshi S, Chung SA, Luk PP, Yeo RX, Nixdorf S, Fedier A, Heinzelmann-Schwarz V, Hogg PJ, Dilda PJ. Alterations in the mitochondrial responses to PENAO as a mechanism of resistance in ovarian cancer cells. Gynecol Oncol. 2015 Aug;138(2):363-71. doi: 10.1016/j.ygyno.2015.06.018. Epub 2015 Jun 14. PMID: 26080289. 4: Sarkar S, Tran B, Horvath L, Lam M, Savas P, Grimison P, Whittle JR, Kuo JC, Signal N, Edmonds D, Hogg P, Rischin D, Desai J, Hamilton A. A phase 1 trial of 4-(N-(S-penicillaminylacetyl)amino)-phenylarsonous acid (PENAO) in patients with advanced solid tumours. Cancer Chemother Pharmacol. 2021 May;87(5):613-620. doi: 10.1007/s00280-020-04225-7. Epub 2021 Jan 26. PMID: 33496801. 5: Wang X, Yeo RX, Hogg PJ, Goldstein D, Crowe P, Dilda PJ, Yang JL. The synergistic inhibitory effect of combining therapies targeting EGFR and mitochondria in sarcomas. Oncotarget. 2020 Jan 7;11(1):46-61. doi: 10.18632/oncotarget.27416. PMID: 32002123; PMCID: PMC6967775. 6: Seneviratne JA, Carter DR, Mittra R, Gifford A, Kim PY, Luo JS, Mayoh C, Salib A, Rahmanto AS, Murray J, Cheng NC, Nagy Z, Wang Q, Kleynhans A, Tan O, Sutton SK, Xue C, Chung SA, Zhang Y, Sun C, Zhang L, Haber M, Norris MD, Fletcher JI, Liu T, Dilda PJ, Hogg PJ, Cheung BB, Marshall GM. Inhibition of mitochondrial translocase SLC25A5 and histone deacetylation is an effective combination therapy in neuroblastoma. Int J Cancer. 2023 Apr 1;152(7):1399-1413. doi: 10.1002/ijc.34349. Epub 2022 Nov 17. PMID: 36346110; PMCID: PMC10953412. 7: Gang BP, Dilda PJ, Hogg PJ, Blackburn AC. Targeting of two aspects of metabolism in breast cancer treatment. Cancer Biol Ther. 2014;15(11):1533-41. doi: 10.4161/15384047.2014.955992. PMID: 25482950; PMCID: PMC4622508. 8: Noy JM, Chen F, Akhter DT, Houston ZH, Fletcher NL, Thurecht KJ, Stenzel MH. Direct Comparison of Poly(ethylene glycol) and Phosphorylcholine Drug-Loaded Nanoparticles In Vitro and In Vivo. Biomacromolecules. 2020 Jun 8;21(6):2320-2333. doi: 10.1021/acs.biomac.0c00257. Epub 2020 May 12. PMID: 32343128. 9: Peña-Otero D. COVID-19 Vaccination. Where Are We and Where Should We Go? Arch Bronconeumol. 2022 Apr;58 Suppl 1:11-12. doi: 10.1016/j.arbres.2022.03.009. Epub 2022 Apr 15. PMID: 35489982; PMCID: PMC9012507. 10: Noy JM, Lu H, Hogg PJ, Yang JL, Stenzel M. Direct Polymerization of the Arsenic Drug PENAO to Obtain Nanoparticles with High Thiol-Reactivity and Anti- Cancer Efficiency. Bioconjug Chem. 2018 Feb 21;29(2):546-558. doi: 10.1021/acs.bioconjchem.8b00032. Epub 2018 Feb 7. PMID: 29346731. 11: Park D, Chiu J, Perrone GG, Dilda PJ, Hogg PJ. The tumour metabolism inhibitors GSAO and PENAO react with cysteines 57 and 257 of mitochondrial adenine nucleotide translocase. Cancer Cell Int. 2012 Mar 26;12(1):11. doi: 10.1186/1475-2867-12-11. PMID: 22448968; PMCID: PMC3349534. 12: Noy JM, Chen F, Stenzel M. Post-functionalization of drug-loaded nanoparticles prepared by polymerization-induced self-assembly (PISA) with mitochondria targeting ligands. Beilstein J Org Chem. 2021 Sep 3;17:2302-2314. doi: 10.3762/bjoc.17.148. PMID: 34621393; PMCID: PMC8450966. 13: Tsoli M, Liu J, Franshaw L, Shen H, Cheng C, Jung M, Joshi S, Ehteda A, Khan A, Montero-Carcabosso A, Dilda PJ, Hogg P, Ziegler DS. Dual targeting of mitochondrial function and mTOR pathway as a therapeutic strategy for diffuse intrinsic pontine glioma. Oncotarget. 2018 Jan 8;9(7):7541-7556. doi: 10.18632/oncotarget.24045. PMID: 29484131; PMCID: PMC5800923. 14: Noy JM, Cao C, Stenzel M. Length of the Stabilizing Zwitterionic Poly(2-methacryloyloxyethyl phosphorycholine) Block Influences the Activity of the Conjugated Arsenic Drug in Drug-Directed Polymerization-Induced Self- Assembly Particles. ACS Macro Lett. 2019 Jan 15;8(1):57-63. doi: 10.1021/acsmacrolett.8b00853. Epub 2018 Dec 21. PMID: 35619410. 15: Dilda PJ, Decollogne S, Weerakoon L, Norris MD, Haber M, Allen JD, Hogg PJ. Optimization of the antitumor efficacy of a synthetic mitochondrial toxin by increasing the residence time in the cytosol. J Med Chem. 2009 Oct 22;52(20):6209-16. doi: 10.1021/jm9008339. PMID: 19788237.