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51321-79-0

51321-79-0 structure
51321-79-0 structure
  • Name: Sparfosic acid
  • Chemical Name: (2S)-2-[(2-phosphonoacetyl)amino]butanedioic acid
  • CAS Number: 51321-79-0
  • Molecular Formula: C6H10NO8P
  • Molecular Weight: 255.11900
  • Catalog: Signaling Pathways Apoptosis Apoptosis
  • Create Date: 2017-11-06 00:10:08
  • Modify Date: 2024-01-09 18:12:31
  • Sparfosic acid is a DNA antimetabolite agent and a potent inhibitor of aspartate transcarbamoyl transferase. Sparfosic acid has anti-tumor activity. Aspartate transcarbamoyl transferase catalyzes the second step of de novo pyrimidine biosynthesis[1][2].

Name (2S)-2-[(2-phosphonoacetyl)amino]butanedioic acid
Synonyms Acide sparfosique [INN-French]
n-(phosphonacetyl)-l-aspartic acid
N-(Phosphonoacetyl)-L-aspartic acid
N-(phosphonacetyl)-L-aspartate
Sparfosic acid
Acidum sparfosicum [INN-Latin]
Acido sparfosico [INN-Spanish]
Phosphonacetyl-L-aspartic acid
N-(phosphonoacetyl)-L-aspartate
Description Sparfosic acid is a DNA antimetabolite agent and a potent inhibitor of aspartate transcarbamoyl transferase. Sparfosic acid has anti-tumor activity. Aspartate transcarbamoyl transferase catalyzes the second step of de novo pyrimidine biosynthesis[1][2].
Related Catalog
In Vitro Sparfosic acid (PALA) causes apoptosis in the resistant Br1 cells[1]. Sparfosic acid (300 µM) shows progressive accumulation of cells in S phase and activation of an apoptotic pathway leading to cell death[1]. Cell Viability Assay[1] Cell Line: Br-l and L-2 cell lines established from metastasis in nude mouse injected with the human tumor cell line MDA-MB-435 Concentration: 300 µM Incubation Time: 12, 24 and 48 hours Result: Cells were predominantly in S phase in both the cell lines, although slightly higher proportion of cells in S phase were noted in L-2 than Brl-3prl cells. Western Blot Analysis[1] Cell Line: Br-l and L-2 cell lines Concentration: 300 µM Incubation Time: 4, 10 and 24 hours Result: There was moderate difference in the level of phosphorylated Rb proteins seen in the two cell types.Marked increase in the amount of cyclin A protein was detected in the L-2 cells undergoing apoptosis with the highest level detected at 10 h post-drug treatment.In contrast, there was no increase in the level of cyclin A seen in the Brl-3prl cells.Cyclin E protein was found elevated in the L-2 cells and Brl-3prl cells compared to their respective controls.
References

[1]. Wang J, et al. Elevated cyclin A associated kinase activity promotes sensitivity of metastatic human cancer cells to DNA antimetabolite drug. Int J Oncol. 2015 Aug;47(2):782-90.

[2]. Angela D. Morris, et al. A New, Efficient, Two Step Procedure for the Preparation of the Antineoplastic Agent Sparfosic Acid.

Molecular Formula C6H10NO8P
Molecular Weight 255.11900
Exact Mass 255.01400
PSA 171.04000

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CI9469000
CHEMICAL NAME :
L-Aspartic acid, N-(phosphonoacetyl)-
CAS REGISTRY NUMBER :
51321-79-0
LAST UPDATED :
199604
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C6-H10-N-O8-P
MOLECULAR WEIGHT :
255.14
WISWESSER LINE NOTATION :
QV1YVQMV1PQQO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human
DOSE/DURATION :
862 mg/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - respiratory system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system

MUTATION DATA

TEST SYSTEM :
Mammal - dog
DOSE/DURATION :
20 mg/kg
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 43,2565,1983