Synonym
Phosphonoacetic Acid
IUPAC/Chemical Name
2-(2-imino-3-phosphonoimidazolidin-1-yl)acetic acid
InChi Key
CUPWIVAPVWUAHI-UHFFFAOYSA-N
InChi Code
InChI=1S/C5H10N3O5P/c6-5-7(3-4(9)10)1-2-8(5)14(11,12)13/h6H,1-3H2,(H,9,10)(H2,11,12,13)
SMILES Code
N=C1N(P(O)(O)=O)CCN1CC(O)=O
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
Biological target:
Phosphonoacetic acid is an endogenous metabolite. Phosphonoacetic acid also has anti-orthopoxvirus activity.
In vitro activity:
This study compares expression of 67 viral genes induced by ZEBRA versus expression induced by AP-1(A/S) proteins. This study shows that AP-1(A/S) proteins are defective at stimulating viral lytic DNA replication. The impairment of expression of many late genes compared to that of ZEBRA is likely due to the inability of AP-1(A/S) proteins to promote viral DNA replication. However, even in the absence of detectable viral DNA replication, AP-1(A/S) proteins stimulated expression of a subgroup of late genes that encode viral structural proteins and immune modulators. In response to ZEBRA, expression of this subgroup of late genes was inhibited by phosphonoacetic acid (PAA), which is a potent viral replication inhibitor.
Reference: J Virol. 2018 Sep 12;92(19):e01062-18. https://pubmed.ncbi.nlm.nih.gov/30021895/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
28.0 |
125.49 |
|
| Ethanol |
28.0 |
125.49 |
|
| Water |
144.0 |
645.38 |
|
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
223.12
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 |
Formulation protocol:
1. Lyons DE, Yu KP, Vander Heiden JA, Heston L, Dittmer DP, El-Guindy A, Miller G. Mutant Cellular AP-1 Proteins Promote Expression of a Subset of Epstein-Barr Virus Late Genes in the Absence of Lytic Viral DNA Replication. J Virol. 2018 Sep 12;92(19):e01062-18. doi: 10.1128/JVI.01062-18. PMID: 30021895; PMCID: PMC6146812.
2. Pisano G, Roy A, Ahmed Ansari M, Kumar B, Chikoti L, Chandran B. Interferon-γ-inducible protein 16 (IFI16) is required for the maintenance of Epstein-Barr virus latency. Virol J. 2017 Nov 13;14(1):221. doi: 10.1186/s12985-017-0891-5. PMID: 29132393; PMCID: PMC5683537.
In vitro protocol:
1. Lyons DE, Yu KP, Vander Heiden JA, Heston L, Dittmer DP, El-Guindy A, Miller G. Mutant Cellular AP-1 Proteins Promote Expression of a Subset of Epstein-Barr Virus Late Genes in the Absence of Lytic Viral DNA Replication. J Virol. 2018 Sep 12;92(19):e01062-18. doi: 10.1128/JVI.01062-18. PMID: 30021895; PMCID: PMC6146812.
2. Pisano G, Roy A, Ahmed Ansari M, Kumar B, Chikoti L, Chandran B. Interferon-γ-inducible protein 16 (IFI16) is required for the maintenance of Epstein-Barr virus latency. Virol J. 2017 Nov 13;14(1):221. doi: 10.1186/s12985-017-0891-5. PMID: 29132393; PMCID: PMC5683537.
1: Mikalkėnas A, Ravoitytė B, Tauraitė D, Servienė E, Meškys R, Serva S. Conjugation of phosphonoacetic acid to nucleobase promotes a mechanism-based inhibition. J Enzyme Inhib Med Chem. 2018 Dec;33(1):384-389. doi: 10.1080/14756366.2017.1417275. PMID: 29372656; PMCID: PMC6010136.
2: Felsenfeld AD, Abee CR, Gerone PJ, Soike KF, Williams SR. Phosphonoacetic acid in the treatment of simian varicella. Antimicrob Agents Chemother. 1978 Sep;14(3):331-5. doi: 10.1128/AAC.14.3.331. PMID: 213014; PMCID: PMC352460.
3: Gordon YJ, Lahav M, Photiou S, Becker Y. Effect of phosphonoacetic acid in the treatment of experimental herpes simplex keratitis. Br J Ophthalmol. 1977 Aug;61(8):506-9. doi: 10.1136/bjo.61.8.506. PMID: 199232; PMCID: PMC1043027.
4: Davini E, Di Leo C, Norelli F, Zappelli P. Synthesis and applications of phosphonoacetic derivatives. J Biotechnol. 1993 Apr;28(2-3):321-38. doi: 10.1016/0168-1656(93)90180-u. PMID: 7764051.
5: Martuza RL, Malick A, Markert JM, Ruffner KL, Coen DM. Experimental therapy of human glioma by means of a genetically engineered virus mutant. Science. 1991 May 10;252(5007):854-6. doi: 10.1126/science.1851332. PMID: 1851332.
6: Kern ER, Richards JT, Overall JC Jr, Glasgow LA. A comparison of phosphonoacetic acid and phosphonoformic acid activity in genital herpes simplex virus type 1 and type 2 infections of mice. Antiviral Res. 1981 Nov;1(4):225-35. doi: 10.1016/0166-3542(81)90013-9. PMID: 6280607.
7: Chen Y, Morera S, Pasti C, Angusti A, Solaroli N, Véron M, Janin J, Manfredini S, Deville-Bonne D. Adenosine phosphonoacetic acid is slowly metabolized by NDP kinase. Med Chem. 2005 Nov;1(6):529-36. doi: 10.2174/157340605774598162. PMID: 16787337.
8: Goodrich JM, Lee KW, Hinze HC. In vitro and in vivo inhibition of myxoma virus by treatment with phosphonoacetic acid. Arch Virol. 1981;70(2):157-64. doi: 10.1007/BF01315009. PMID: 7332492.
9: Nishibe Y, Inoue YK. Effects of phosphonoacetic acid on subacute myeloopticoneuropathy virus in vitro and in vivo. J Med Virol. 1978;2(3):225-9. doi: 10.1002/jmv.1890020306. PMID: 212527.
10: Foscarnet. Med Lett Drugs Ther. 1992 Jan 10;34(861):3-4. PMID: 1309469.
