8-METHOXY-6-NITROPHENANTHROL(3,4-D)-1,3-DIOXIDE-5-CARBOXYLIC ACID - CAS 313-67-7
Catalog number: 313-67-7
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C17H10NO7
COA:
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Chemical Family:
Phenols
Description:
Aristolochic acids occur in Aristolochiaceae and in butterflies feeding on these plants. One of a group of fourteen known, substituted 1-phenanthrenecarboxylic acids.
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Purity:
>98%
Appearance:
Powder
Synonyms:
8-Methoxy-6-nitro-phenanthro[3,4-d]-1,3-dioxole-5-carboxylic Acid; Aristolochine; Aristolochia A; Aristolochic Acid; Aristolochic Acid 1; Aristolochic Acid I; NSC 11926; NSC 50413; TR 1736; Tardolyt;
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Quality Standard:
Enterprise Standard
Quantity:
Milligrams-Grams
1.Aristolactam I a metabolite of aristolochic acid I upon activation forms an adduct found in DNA of patients with Chinese herbs nephropathy.
Stiborová M;Frei E;Breuer A;Bieler CA;Schmeiser HH Exp Toxicol Pathol. 1999 Jul;51(4-5):421-7.
Aristolochic acid (AA) a naturally occuring nephrotoxin and carcinogen is implicated in a unique type of renal fibrosis, designated Chinese herbs nephropathy (CHN). We identified AA-specific DNA adducts in kidneys and in a ureter obtained from CHN patients after renal transplantation. AA is a plant extract of aristolochia species containing AA I as the major component. Aristolactams are the principal detoxication metabolites of AA, which were detected in urine and faeces from animals and humans. They are activated by cytochrome P450 (P450) and peroxidase to form DNA adducts. Using the 32P-postlabelling assay we investigated the formation of DNA adducts by aristolactam I in these two activation systems. A combination of two independent chromatographic systems (ion-exchange chromatography TLC and reversed-phase HPLC) with reference compounds was used for the identification of adducts. Aristolactam I activated by peroxidase led to the formation of several adducts. Two major adducts were identical to adducts previously observed in vivo. 7-(deoxyguanosin-N2-yl)aristolactam I (dG-AAI) and 7-(deoxyadenosin-N6-yl)aristolactam I (dA-AAI) were formed in DNA during the peroxidase-mediated one-electron oxidation of aristolactam I.
2.Human liver-kidney model elucidates the mechanisms of aristolochic acid nephrotoxicity.
Chang SY;Weber EJ;Sidorenko VS;Chapron A;Yeung CK;Gao C;Mao Q;Shen D;Wang J;Rosenquist TA;Dickman KG;Neumann T;Grollman AP;Kelly EJ;Himmelfarb J;Eaton DL JCI Insight. 2017 Nov 16;2(22). pii: 95978. doi: 10.1172/jci.insight.95978. [Epub ahead of print]
Environmental exposures pose a significant threat to human health. However, it is often difficult to study toxicological mechanisms in human subjects due to ethical concerns. Plant-derived aristolochic acids are among the most potent nephrotoxins and carcinogens discovered to date, yet the mechanism of bioactivation in humans remains poorly understood. Microphysiological systems (organs-on-chips) provide an approach to examining the complex, species-specific toxicological effects of pharmaceutical and environmental chemicals using human cells. We microfluidically linked a kidney-on-a-chip with a liver-on-a-chip to determine the mechanisms of bioactivation and transport of aristolochic acid I (AA-I), an established nephrotoxin and human carcinogen. We demonstrate that human hepatocyte-specific metabolism of AA-I substantially increases its cytotoxicity toward human kidney proximal tubular epithelial cells, including formation of aristolactam adducts and release of kidney injury biomarkers. Hepatic biotransformation of AA-I to a nephrotoxic metabolite involves nitroreduction, followed by sulfate conjugation. Here, we identify, in a human tissue-based system, that the sulfate conjugate of the hepatic NQO1-generated aristolactam product of AA-I (AL-I-NOSO3) is the nephrotoxic form of AA-I.
3.Arachidonic acid released by phospholipase A(2) activation triggers Ca(2+)-dependent apoptosis through the mitochondrial pathway.
Penzo D;Petronilli V;Angelin A;Cusan C;Colonna R;Scorrano L;Pagano F;Prato M;Di Lisa F;Bernardi P J Biol Chem. 2004 Jun 11;279(24):25219-25. Epub 2004 Apr 7.
We studied the effects of the divalent cation ionophore A23187 on apoptotic signaling in MH1C1 cells. Addition of A23187 caused a fast rise of cytosolic Ca(2+) ([Ca(2+)](c)), which returned close to the resting level within about 40 s. The [Ca(2+)](c) rise was immediately followed by phospholipid hydrolysis, which could be inhibited by aristolochic acid or by pretreatment with thapsigargin in Ca(2+)-free medium, indicating that the Ca(2+)-dependent cytosolic phospholipase A(2) (cPLA(2)) was involved. These early events were followed by opening of the mitochondrial permeability transition pore (PTP) and by apoptosis in about 30% of the cell population. In keeping with a cause-effect relationship between addition of A23187, activation of cPLA(2), PTP opening, and cell death, all events but the [Ca(2+)](c) rise were prevented by aristolochic acid. The number of cells killed by A23187 was doubled by treatment with 0.5 microm MK886 and 5 microm indomethacin, which inhibit arachidonic acid metabolism through the 5-lipoxygenase and cyclooxygenase pathway, respectively. Consistent with the key role of free arachidonic acid, its levels increased within minutes of treatment with A23187; the increase being more pronounced in the presence of MK886 plus indomethacin.
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Chemical Structure

CAS 313-67-7 8-METHOXY-6-NITROPHENANTHROL(3,4-D)-1,3-DIOXIDE-5-CARBOXYLIC ACID

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