D-(-)-Penicillamine

SKU: orb1224795

Description

(2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid is the most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease. Target: Others (2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid (Cuprimine, Depen) is used as an antirheumatic and as a chelating agent in Wilson's disease and is a chelating agent recommended for the removal of excess copper in patients with Wilson's disease. From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine. \n(In Vitro):Penicillamine (D-(-)-Penicillamine) (5 mg; 7 d; CD4+ and CD+ splenocytes) promotes cellular immune responses.(In Vivo):Penicillamine (D-(-)-Penicillamine) (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) increases serum free copper concentration.Penicillamine (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) increases ATP7A and CTR1 mRNA expression in the brain of tx mice.Penicillamine (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) induces oxidative-stress in the central nervous system.Penicillamine (0.1-250 mg/kg; i.p.; once, for 90 min; male NMRI mice) has binaural phase effect on seizure.Penicillamine (5 mg/kg; i.v.; daily, for 8 weeks; male BN rats) prevents the onset of autoimmunity at a low dose.

Key Properties

• CAS Number: 52-67-5
• MW: 149.21
• Purity: >98% (HPLC)
• Formula: C₅H₁₁NO₂S
• SMILES: CC(C)([C@H](C(=O)O)N)S
• Target: Copper
• Solubility: Water: 30 mg/mL (201.05 mM)

Bioactivity

• In Vivo:
  Penicillamine (D-(-)-Penicillamine) (200 mg/kg; i. g. ; daily, for 3, 10 and 14 d; tx mice and DL mice) increases serum free copper concentration. Penicillamine (200 mg/kg; i. g. ; daily, for 3, 10 and 14 d; tx mice and DL mice) increases ATP7A and CTR1 mRNA expression in the brain of tx mice. Penicillamine (200 mg/kg; i. g. ; daily, for 3, 10 and 14 d; tx mice and DL mice) induces oxidative-stress in the central nervous system. Penicillamine (0.1-250 mg/kg; i.p.; once, for 90 min; male NMRI mice) has binaural phase effect on seizure. Penicillamine (5 mg/kg; i. v. ; daily, for 8 weeks; male BN rats) prevents the onset of autoimmunity at a low dose. Animal model: Toxic milk mutant mice (tx mice) and DL mice. Dosage: 200 mg/kg. Administration: Oral gavage; daily, for 3, 10 and 14 days. Result: Increased the free copper concentrations in the tx mice serum on the 3rd day. Animal model: Toxic milk mutant mice (tx mice) and DL mice. Dosage: 200 mg/kg. Administration: Oral gavage; daily, for 3, 10 and 14 days. Result: Increased the mRNA expression of ATP7A by 4-fold. Increased CTR1 mRNA expression by 6.9-fold in the cortex and 9.1-fold in the basal ganglia of tx mice. Animal model: Toxic milk mutant mice (tx mice) and DL mice. Dosage: 200 mg/kg. Administration: Oral gavage; daily, for 3, 10 and 14 days. Result: Increased the concentration of MDA and decreased GSH/GSSG ratios through nitric oxide/NMDA pathways. Animal model: Male NMRI mice. Dosage: 0.1, 0.5, 1, 10, 100, 150 and 250 mg/kg. Administration: Intraperitoneal injection; once, for 90 minutes. Result: Had anticonvulsant effects at a low dose (0.5 mg/kg) and had anticonvulsant effects at a high dose (250 mg/kg). Reversed the anti-and proconvulsant effects by acute pretreatment of L-NAME (a nonselective nitric oxide synthase inhibitor) and 7-NI (a selective neuronal nitric oxide synthase inhibitor). Animal model: Male BN rats. Dosage: 5 mg/kg. Administration: Intravenous injection; daily, for 8 weeks. Result: Inhibited IgE upregulation and prevented the onset of autoimmunity.
• In Vitro:
  Penicillamine (D-(-)-Penicillamine) (5 mg; 7 d; CD4+ and CD+ splenocytes) promotes cellular immune responses. Western blot analysis. Cell line: CD4+ and CD+ splenocytes. Concentration: 5 mg. Incubation time: 7 days. Result: Increased IL-4 and IFN-γ mRNA expression in response to high dose treatment and remained high in both CD4+ and CD+ splenocytes.

Storage & Handling

• Storage: Storage temperature: -20°C. Stability: ≥ 2 years
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

NSC 81549 | D-Penicillamine | β-Thiovaline

Quick Database Links

Gene Symbol

Copper