PABA/NO | CAS#875769-11-2 | Nitric oxide donor

MedKoo Cat#: 464090 | Name: PABA/NO

Description:

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

PABA/NO is a novel glutathione-S-transferase-p-activated nitric oxide donor, inhibiting proliferation and inducing apoptosis by targeting PI3K/AKT/mTOR and MEK/ERK pathways in hepatocellular carcinoma cells.

Chemical Structure

PABA/NO

CAS#875769-11-2

Theoretical Analysis

MedKoo Cat#: 464090

Name: PABA/NO

CAS#: 875769-11-2

Chemical Formula: C16H16N6O8

Exact Mass: 420.1030

Molecular Weight: 420.34

Elemental Analysis: C, 45.72; H, 3.84; N, 19.99; O, 30.45

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

PABA/NO;

IUPAC/Chemical Name

(Z)-3,3-dimethyl-1-(5-((4-(methylamino)benzoyl)oxy)-2,4-dinitrophenoxy)triaz-1-ene 2-oxide

InChi Key

DZJYJYAXGBNEMK-PYCFMQQDSA-N

InChi Code

InChI=1S/C16H16N6O8/c1-17-11-6-4-10(5-7-11)16(23)29-14-9-15(30-18-22(28)19(2)3)13(21(26)27)8-12(14)20(24)25/h4-9,17H,1-3H3/b22-18-

SMILES Code

O=C(OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(O/N=[N+]([O-])/N(C)C)=C1)C2=CC=C(NC)C=C2

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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

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 420.34 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

1: Kim Y, Maciag AE, Cao Z, Deschamps JR, Saavedra JE, Keefer LK, Holland RJ. PABA/NO lead optimization: Improved targeting of cytotoxicity to glutathione S-transferase P1-overexpressing cancer cells. Bioorg Med Chem. 2015 Aug 1;23(15):4980-4988. doi: 10.1016/j.bmc.2015.05.020. Epub 2015 May 19. PMID: 26043946. 2: Liu L, Chen J, Cao M, Wang J, Wang S. NO donor inhibits proliferation and induces apoptosis by targeting PI3K/AKT/mTOR and MEK/ERK pathways in hepatocellular carcinoma cells. Cancer Chemother Pharmacol. 2019 Dec;84(6):1303-1314. doi: 10.1007/s00280-019-03965-5. Epub 2019 Sep 25. PMID: 31555866. 3: Saavedra JE, Srinivasan A, Buzard GS, Davies KM, Waterhouse DJ, Inami K, Wilde TC, Citro ML, Cuellar M, Deschamps JR, Parrish D, Shami PJ, Findlay VJ, Townsend DM, Tew KD, Singh S, Jia L, Ji X, Keefer LK. PABA/NO as an anticancer lead: analogue synthesis, structure revision, solution chemistry, reactivity toward glutathione, and in vitro activity. J Med Chem. 2006 Feb 9;49(3):1157-64. doi: 10.1021/jm050700k. PMID: 16451080; PMCID: PMC6522251. 4: Hutchens S, Manevich Y, He L, Tew KD, Townsend DM. Cellular resistance to a nitric oxide releasing glutathione S-transferase P-activated prodrug, PABA/NO. Invest New Drugs. 2011 Oct;29(5):719-29. doi: 10.1007/s10637-010-9407-5. Epub 2010 Mar 16. PMID: 20232108; PMCID: PMC2912140. 5: Kogias E, Osterberg N, Baumer B, Psarras N, Koentges C, Papazoglou A, Saavedra JE, Keefer LK, Weyerbrock A. Growth-inhibitory and chemosensitizing effects of the glutathione-S-transferase-π-activated nitric oxide donor PABA/NO in malignant gliomas. Int J Cancer. 2012 Mar 1;130(5):1184-94. doi: 10.1002/ijc.26106. Epub 2011 Jul 21. PMID: 21455987; PMCID: PMC3161158. 6: Kumar V, Hong SY, Maciag AE, Saavedra JE, Adamson DH, Prud'homme RK, Keefer LK, Chakrapani H. Stabilization of the nitric oxide (NO) prodrugs and anticancer leads, PABA/NO and Double JS-K, through incorporation into PEG-protected nanoparticles. Mol Pharm. 2010 Feb 1;7(1):291-8. doi: 10.1021/mp900245h. PMID: 20000791; PMCID: PMC2815019. 7: Liu L, Fu J, Li T, Cui R, Ling J, Yu X, Ji H, Zhang Y. NG, a novel PABA/NO- based oleanolic acid derivative, induces human hepatoma cell apoptosis via a ROS/MAPK-dependent mitochondrial pathway. Eur J Pharmacol. 2012 Sep 15;691(1-3):61-8. doi: 10.1016/j.ejphar.2012.07.031. Epub 2012 Jul 20. PMID: 22824464. 8: Ji X, Pal A, Kalathur R, Hu X, Gu Y, Saavedra JE, Buzard GS, Srinivasan A, Keefer LK, Singh SV. Structure-Based Design of Anticancer Prodrug PABA/NO. Drug Des Devel Ther. 2008;2:123-130. doi: 10.2147/dddt.s3931. PMID: 19662104; PMCID: PMC2721280. 9: Findlay VJ, Townsend DM, Saavedra JE, Buzard GS, Citro ML, Keefer LK, Ji X, Tew KD. Tumor cell responses to a novel glutathione S-transferase-activated nitric oxide-releasing prodrug. Mol Pharmacol. 2004 May;65(5):1070-9. doi: 10.1124/mol.65.5.1070. PMID: 15102935. 10: Chakrapani H, Wilde TC, Citro ML, Goodblatt MM, Keefer LK, Saavedra JE. Synthesis, nitric oxide release, and anti-leukemic activity of glutathione- activated nitric oxide prodrugs: Structural analogues of PABA/NO, an anti-cancer lead compound. Bioorg Med Chem. 2008 Mar 1;16(5):2657-64. doi: 10.1016/j.bmc.2007.11.035. Epub 2007 Nov 17. PMID: 18060792; PMCID: PMC2631658. 11: Townsend DM, Findlay VJ, Fazilev F, Ogle M, Fraser J, Saavedra JE, Ji X, Keefer LK, Tew KD. A glutathione S-transferase pi-activated prodrug causes kinase activation concurrent with S-glutathionylation of proteins. Mol Pharmacol. 2006 Feb;69(2):501-8. doi: 10.1124/mol.105.018523. Epub 2005 Nov 15. PMID: 16288082; PMCID: PMC6522256. 12: Manevich Y, Townsend DM, Hutchens S, Tew KD. Diazeniumdiolate mediated nitrosative stress alters nitric oxide homeostasis through intracellular calcium and S-glutathionylation of nitric oxide synthetase. PLoS One. 2010 Nov 30;5(11):e14151. doi: 10.1371/journal.pone.0014151. PMID: 21152397; PMCID: PMC2994766. 13: Keefer LK; behalf of the JS-K Consortium. Broad-Spectrum Anti-Cancer Activity of O-Arylated Diazeniumdiolates. For Immunopathol Dis Therap. 2010 Jul 1;1(3):205-218. doi: 10.1615/ForumImmunDisTher.v1.i3.30. PMID: 21949595; PMCID: PMC3179376. 14: El-Sehemy A, Postovit LM, Fu Y. Nitric oxide signaling in human ovarian cancer: A potential therapeutic target. Nitric Oxide. 2016 Apr 1;54:30-7. doi: 10.1016/j.niox.2016.02.002. Epub 2016 Feb 15. PMID: 26891890. 15: Townsend DM, Findlay VL, Tew KD. Glutathione S-transferases as regulators of kinase pathways and anticancer drug targets. Methods Enzymol. 2005;401:287-307. doi: 10.1016/S0076-6879(05)01019-0. PMID: 16399394; PMCID: PMC6522258. 16: Townsend DM, Manevich Y, He L, Xiong Y, Bowers RR Jr, Hutchens S, Tew KD. Nitrosative stress-induced s-glutathionylation of protein disulfide isomerase leads to activation of the unfolded protein response. Cancer Res. 2009 Oct 1;69(19):7626-34. doi: 10.1158/0008-5472.CAN-09-0493. Epub 2009 Sep 22. PMID: 19773442; PMCID: PMC2756322. 17: Xiong Y, Manevich Y, Tew KD, Townsend DM. S-Glutathionylation of Protein Disulfide Isomerase Regulates Estrogen Receptor α Stability and Function. Int J Cell Biol. 2012;2012:273549. doi: 10.1155/2012/273549. Epub 2012 May 13. PMID: 22654912; PMCID: PMC3359683. 18: Fu J, Liu L, Huang Z, Lai Y, Ji H, Peng S, Tian J, Zhang Y. Hybrid molecule from O2-(2,4-dinitrophenyl)diazeniumdiolate and oleanolic acid: a glutathione S-transferase π-activated nitric oxide prodrug with selective anti-human hepatocellular carcinoma activity and improved stability. J Med Chem. 2013 Jun 13;56(11):4641-55. doi: 10.1021/jm400393u. Epub 2013 May 16. Erratum in: J Med Chem. 2019 Nov 27;62(22):10473. PMID: 23617697. 19: Andrei D, Maciag AE, Chakrapani H, Citro ML, Keefer LK, Saavedra JE. Aryl bis(diazeniumdiolates): potent inducers of S-glutathionylation of cellular proteins and their in vitro antiproliferative activities. J Med Chem. 2008 Dec 25;51(24):7944-52. doi: 10.1021/jm800831y. PMID: 19053760; PMCID: PMC2629944. 20: Findlay VJ, Townsend DM, Morris TE, Fraser JP, He L, Tew KD. A novel role for human sulfiredoxin in the reversal of glutathionylation. Cancer Res. 2006 Jul 1;66(13):6800-6. doi: 10.1158/0008-5472.CAN-06-0484. PMID: 16818657; PMCID: PMC6361143.