Carboxyatractyloside  (Synonyms: CATR)

Carboxyatractyloside (CATR) is a tight-binding inhibitor of adenine nucleotide translocase, and represents the major toxic component of Xanthium sibiricum. Carboxyatractyloside competes with ADP for binding to the translocase, blocks the translocation of ADP/ATP across the inner mitochondrial membrane, and thereby inhibits ADP-stimulated respiration. In the presence of Cyclosporin A (HY-B0579), Carboxyatractyloside still induces permeability transition in liver mitochondria of aged rats, exhibiting significant hepatotoxicity and nephrotoxicity. Carboxyatractyloside is widely used in studies related to hepatotoxicity, nephrotoxicity and Alzheimer's disease^[1][2][3].

Carboxyatractyloside (CATR) (0.07-0.4 μM) potently inhibits ADP-stimulated respiration (a proxy for adenine nucleotide translocation) in Vigna sinensis hypocotyl mitochondria, with maximal inhibition at 0.4 μM, IC₅₀ at 0.16 μM (ADP added first) or 0.21 μM (CATR added first), and an apparent competitive inhibition constant of 0.115 μM under specific concentration ranges^[2].
Carboxyatractyloside (2 μM) induces fast Ca²⁺ efflux from freshly prepared rat liver mitochondria^[3].
Carboxyatractyloside (0.5 μM) induces Ca²⁺ efflux from aged rat liver mitochondria even when they are pre-treated with CSA or BSA to stabilize Ca²⁺ retention^[3].
Carboxyatractyloside (2 μM) does not induce Sr²⁺ efflux from aged rat liver mitochondria pre-loaded with Sr^2+[3].
Carboxyatractyloside (0.5 μM) induces swelling in aged rat liver mitochondria even when they are pre-treated with CSA to reduce basal swelling^[3].
Carboxyatractyloside (0.5 μM) induces fast collapse of transmembrane potential in aged rat liver mitochondria even when they are pre-treated with CSA to stabilize potential^[3].
Carboxyatractyloside (2 μM) induces a slow collapse of transmembrane potential in aged rat liver mitochondria pre-loaded with Sr^2+[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

770.82

C₃₁H₄₆O₁₈S₂

35988-42-2

C[C@]12[C@@]3([H])[C@@]4(CC[C@]1([H])C(C(O)=O)(C[C@H](C2)O[C@@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)OS(=O)(O)=O)OS(=O)(O)=O)OC(CC(C)C)=O)C(O)=O)C[C@@](C([C@@H]4O)=C)([H])CC3

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• [1]. Pan H, et al. Simultaneous quantification of atractyloside and carboxyatractyloside in rat plasma by LC‐MS/MS: Application to a pharmacokinetic study after oral administration of Xanthii Fructus extract[J]. Journal of separation science, 2020, 43(3): 590-597.

  [2]. Lima M S, et al. The effect of atractyloside and carboxyatractyloside on adenine nucleotide translocation in mitochondria of Vigna sinensis (L.) Savi cv. serido[J]. Archives of Biochemistry and Biophysics, 1979, 193(2): 368-372.

  [3]. García N, et al. Cyclosporin A is unable to inhibit carboxyatractyloside-induced permeability transition in aged mitochondria. Comp Biochem Physiol C Toxicol Pharmacol. 2009;149(3):374-381.  [Content Brief]