Penicillamine

• CAT Number: A000761
• CAS Number: 52-67-5
• Molecular Formula: C5H11NO2S
• Molecular Weight: 149.21
• Purity: ≥95%
• Synonyms: D-Penicillamine; Penicillamine; 52-67-5; Cuprimine; D-(-)-Penicillamine; Depen
• Target: Metabolic Enzyme/Protease
• Storage: -20°C
• IUPAC Name: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
• InChI: 1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
• InChIKey: VVNCNSJFMMFHPL-VKHMYHEASA-N
• SMILES: CC(C)(C(C(=O)O)N)S

Penicillamine (CAS 52-67-5) is an exogenous NOS modulator, found to inhibit urease activity and an antirheumatic and chelating agent used for Wilson/'s disease. It is D-penicillamine, as L-penicillamine is toxic (it inhibits the action of pyridoxine). It is an α-amino acid metabolite of penicillin, although it has no antibiotic properties.

Reference

1: Božić B, Korać J, Stanković DM, Stanić M, Popović-Bijelić A, Bogdanović Pristov J, Spasojević I, Bajčetić M. Mechanisms of redox interactions of bilirubin with copper and the effects of penicillamine. Chem Biol Interact. 2017 Dec 25;278:129-134. doi: 10.1016/j.cbi.2017.10.022. Epub 2017 Oct 26. PubMed PMID: 29079291.
2: Hachmöller O, Zibert A, Zischka H, Sperling M, Groba SR, Grünewald I, Wardelmann E, Schmidt HH, Karst U. Spatial investigation of the elemental distribution in Wilson/'s disease liver after d-penicillamine treatment by LA-ICP-MS. J Trace Elem Med Biol. 2017 Dec;44:26-31. doi: 10.1016/j.jtemb.2017.05.008. Epub 2017 May 29. PubMed PMID: 28965585.
3: Grenács á, Lihi N, Sóvágó I, Várnagy K. The influence of penicillamine/cysteine mutation on the metal complexes of peptides. Dalton Trans. 2017 Oct 10;46(39):13472-13481. doi: 10.1039/c7dt02703f. PubMed PMID: 28951904.
4: Yao XY, Wen GD, Zhou C, Liu BY, Du J, Chen Z, Zhang JZ. D-penicillamine-induced Elastosis Perforans Serpiginosa. Chin Med J (Engl). 2017 Aug 20;130(16):2013-2014. doi: 10.4103/0366-6999.211899. PubMed PMID: 28776563; PubMed Central PMCID: PMC5555145.
5: Beitollahi H, Gholami A, Ganjali MR. First Report for Determination of d-Penicillamine in the Presence of Tryptophan Using a 2-Chlorobenzoyl Ferrocene/Ag-Supported ZnO Nanoplate-Modified Carbon Paste Electrode. J AOAC Int. 2017 Aug 1. doi: 10.5740/jaoacint.16-0361. [Epub ahead of print] PubMed PMID: 28762329.
6: Feli A, Jazayeri S, Bitaraf MA, Solaymani Dodaran M, Parastouei K, Hosseinzadeh-Attar MJ. Combination Therapy with Low Copper Diet, Penicillamine and Gamma Knife Radiosurgery Reduces VEGF and IL-8 In Patients with Recurrent Glioblastoma. Asian Pac J Cancer Prev. 2017 Jul 27;18(7):1999-2003. PubMed PMID: 28749642; PubMed Central PMCID: PMC5648411.
7: Sun D, Zhang W, Yu Q, Chen X, Xu M, Zhou Y, Liu J. Chiral penicillamine-modified selenium nanoparticles enantioselectively inhibit metal-induced amyloid β aggregation for treating Alzheimer/'s disease. J Colloid Interface Sci. 2017 Nov 1;505:1001-1010. doi: 10.1016/j.jcis.2017.06.083. Epub 2017 Jun 27. PubMed PMID: 28693096.
8: Avan A, de Bie RMA, Hoogenraad TU. Wilson/'s Disease Should Be Treated with Zinc rather than Trientine or Penicillamine. Neuropediatrics. 2017 Oct;48(5):394-395. doi: 10.1055/s-0037-1603975. Epub 2017 Jun 30. PubMed PMID: 28666288.
9: Mendes J, de Almeida KJ, Neto JL, Ramalho TC, Duarte HA. Theoretical spectroscopic insights of tautomers and enantiomers of penicillamine. Spectrochim Acta A Mol Biomol Spectrosc. 2017 Sep 5;184:308-317. doi: 10.1016/j.saa.2017.05.025. Epub 2017 May 11. PubMed PMID: 28525866.
10: Sciegienka SJ, Solst SR, Falls KC, Schoenfeld JD, Klinger AR, Ross NL, Rodman SN, Spitz DR, Fath MA. D-penicillamine combined with inhibitors of hydroperoxide metabolism enhances lung and breast cancer cell responses to radiation and carboplatin via H(2)O(2)-mediated oxidative stress. Free Radic Biol Med. 2017 Jul;108:354-361. doi: 10.1016/j.freeradbiomed.2017.04.001. Epub 2017 Apr 5. PubMed PMID: 28389407; PubMed Central PMCID: PMC5495544.