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Logo of procrsmedFormerly medchtJournal of the Royal Society of MedicineProceedings of the Royal Society of Medicine
 
Proc R Soc Med. 1977; 70(Suppl 3): 50–60.
PMCID: PMC1543571

Chemical basis for pharmacological and therapeutic actions of penicillamine.

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Selected References

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  • Abbott EH, Martell AE. Pyridoxine and pyridoxal analogs. 13. A nuclear magnetic resonance study of the condensation of polyfunctional amino acids with pyridoxal. J Am Chem Soc. 1970 Mar 25;92(6):1754–1759. [PubMed]
  • Augusti KT. Lipid lowering effect of allyl propyl disulphide isolated from Allium cepa Linn. on long term feeding to normal rats. Indian J Biochem Biophys. 1974 Sep;11(3):264–265. [PubMed]
  • Augusti KT, Mathew PT. Lipid lowering effect of allicin (diallyl disulphide-oxide) on long term feeding to normal rats. Experientia. 1974 May 15;30(5):468–470. [PubMed]
  • Baker DH. Nutritional and metabolic interrelationships among sulfur compounds in avian nutrition. Fed Proc. 1976 Jun;35(8):1917–1922. [PubMed]
  • Blois MS. Melanocytic neoplasms. Clin Pharmacol Ther. 1974 Nov;16(5 Pt 2):925–930. [PubMed]
  • Budzinski EE, Box HC. The oxidation and reduction of organic compounds by ionizing radiation: L-penicillamine hydrochloride. J Phys Chem. 1971 Aug 19;75(18):2564–2570. [PubMed]
  • Cavins JF, Friedman M. Specific modification of protein sulfhydryl groups with alpha,beta-unsaturated compounds. J Biol Chem. 1968 Jun 25;243(12):3357–3360. [PubMed]
  • Chauffe L, Windle JJ, Friedman M. Electron spin resonance study of melanin treated with reducing agents. Biophys J. 1975 Jun;15(6):565–572. [PubMed]
  • Copeland ES. Production of free radicals in reduced glutathione and penicillamine by thermal hydrogen atoms and X-radiation. Int J Radiat Biol Relat Stud Phys Chem Med. 1969;16(2):113–120. [PubMed]
  • Cothern CR, Moddeman WE, Albridge RG, Sanders WJ, Kelly PL, Hanley WS, Field L. Some bonding properties of D-penicillamine and related compounds measured by X-ray photoelectron spectroscopy. Anal Chem. 1976 Jan;48(1):162–166. [PubMed]
  • CRAWHALL JC, THOMPSON CJ. CYSTINURIA: EFFECT OF D-PENICILLAMINE ON PLASMA AND URINARY CYSTINE CONCENTRATIONS. Science. 1965 Mar 19;147(3664):1459–1460. [PubMed]
  • Darrow DK, Schroeder HA. Childhood exposure to environmental lead. Adv Exp Med Biol. 1974;48(0):425–445. [PubMed]
  • Datko AH, Giovanelli J, Mudd SH. Preparation of cystathionine sulfoxide and sulfone and some properties relating to their differentiation. Anal Biochem. 1975 Mar;64(1):80–84. [PubMed]
  • Doornbos DA, Feitsma MT. The acid strength of the sulfhydryl and ammonium groups in L-cysteine and D-penicillamine; the determination of the micro acid stability constants. Pharm Weekbl. 1967 Jun 23;102(25):587–598. [PubMed]
  • Ekberg M, Jeppsson JO, Denneberg T. Penicillamine treatment of cystinuria. Acta Med Scand. 1974 May;195(5):415–419. [PubMed]
  • Ercoli N. Chemotherapeutic and toxicological properties of antimonyl tartrate-dimethylcysteine chelates. Proc Soc Exp Biol Med. 1968 Oct;129(1):284–290. [PubMed]
  • Field L, Hanley WS, Kelly PL, Sanders WJ, White JE, Jaffe IA, Merryman P. Biologically oriented organic sulfur chemistry. 12. Further principles of structure-activity relationships for penicillamine analogs and derivatives. J Med Chem. 1973 Oct;16(10):1152–1157. [PubMed]
  • Friedman M, Krull LH, Cavins JF. The chromatographic determination of cystine and cysteine residues in proteins as s-beta-(4-pyridylethyl)cysteine. J Biol Chem. 1970 Aug 10;245(15):3868–3871. [PubMed]
  • Friedman M, Masri MS. Interactions of mercury compounds with wool and related biopolymers. Adv Exp Med Biol. 1974;48(0):505–550. [PubMed]
  • Friedman M, Noma AT, Masri MS. New internal standards for basic amino acid analyses. Anal Biochem. 1973 Jan;51(1):280–287. [PubMed]
  • Friedman M, Sigel CW. A kinetic study of the ninhydrin reaction. Biochemistry. 1966 Feb;5(2):478–485. [PubMed]
  • Hasenbank G, Körber F, Siegmund P. Uber die Reaktioen von D- und L-Penicillamin mit Alanintransaminase und mit einigen Aldiminen des Pyridoxalphosphats. Hoppe Seylers Z Physiol Chem. 1968 Mar;349(3):310–316. [PubMed]
  • Hayes KC. A review on the biological function of taurine. Nutr Rev. 1976 Jun;34(6):161–165. [PubMed]
  • Ishikawa Y, Israel SE, Melville DB. Participation of an intermediate sulfoxide in the enzymatic thiolation of the imidazole ring of hercynine to form ergothioneine. J Biol Chem. 1974 Jul 25;249(14):4420–4427. [PubMed]
  • Kochakian CD, Marcais J. The free amino acids, hypotaurine and other ninhydrin reacting substances of the prostate and seminal vesicles of the guinea pig: regulation by testosterone. Ala J Med Sci. 1974 Jul;11(3):240–251. [PubMed]
  • Kroll W, Lichte KH. Cystinosis: a review of the different forms and of recent advances. Humangenetik. 1973;20(2):75–87. [PubMed]
  • Krull LH, Gibbs DE, Friedman M. 2-Vinylquinoline, a reagent to determine protein sulfhydryl groups spectrophotometrically. Anal Biochem. 1971 Mar;40(1):80–85. [PubMed]
  • DU VIGNEAUD V, KUCHINSKAS EJ. An increased vitamin B6 requirement in the rat on a diet containing L-penicillamine. Arch Biochem Biophys. 1957 Jan;66(1):1–9. [PubMed]
  • Lal M, Lin WS, Gaucher GM, Armstrong DA. The repair, protection and sensitization of papain with respect to inactivation by H2O2 and OH: effects of dithiothreitol, penicillamine, cystine and penicillamine disulphide. Int J Radiat Biol Relat Stud Phys Chem Med. 1975 Dec;28(6):549–564. [PubMed]
  • Letter JE, Jr, Jordan RB. Complexing of nickel(II) by cysteine, tyrosine, and related ligands and evidence for Zwitterion reactivity. J Am Chem Soc. 1975 Apr 30;97(9):2381–2390. [PubMed]
  • Lilis R, Fischbein A. Chelation therapy in workers exposed to lead. A critical review. JAMA. 1976 Jun 28;235(26):2823–2824. [PubMed]
  • Lovstad RA. Effect of penicillamine on the conversion of dopa to dopachrome in the presence of tyrosinase or ceruloplasmin. Biochem Pharmacol. 1976 Mar 1;25(5):533–535. [PubMed]
  • MacGregor JT, Clarkson TW. Distribution, tissue binding and toxicity of mercurials. Adv Exp Med Biol. 1974;48(0):463–503. [PubMed]
  • Masri MS, Windle JJ, Friedman M. p-Nitrostyrene: new alkylating agent for sulfhydryl groups in reduced soluble proteins and keratins. Biochem Biophys Res Commun. 1972 Jun 28;47(6):1408–1413. [PubMed]
  • Matoltsy AG. Keratinization. J Invest Dermatol. 1976 Jul;67(1):20–25. [PubMed]
  • Misuraca G, Nicolaus RA, Prota G, Ghiara G. A cytochemical study of phaeomelanin formation in feather papillae of New Hampshire chick embryos. Experientia. 1969 Sep 15;25(9):920–922. [PubMed]
  • Nagasawa HT, Goon DJ, Constantino NV, Alexander CS. Diversion of ethanol metabolism by sulfhydryl amino acids. D-penicillamine-directed excretion of 2,5,5-trimethyl-D-thiazolidine-4-carboxylic acid in the urine of rats after ethanol administration. Life Sci. 1975 Sep 1;17(5):707–713. [PubMed]
  • Okamura S, Toshioka N, Asakura S, Oya M, Nagamori S. [Studies on the oxidation-reduction potentials of 2-mercaptopropionylglycine and penicillamine using thiol-disulfide exchange reactions with cysteine and glutathione (author's transl)]. Yakugaku Zasshi. 1974 Jun;94(6):655–659. [PubMed]
  • Otsuka K, Mori Y. Inhibitory effect of D-penicillamine on degradation of hexosamine-containing substances in the involution of carrageenin granuloma induced by calcium chelate ethylenediaminetetraacetate. Chem Pharm Bull (Tokyo) 1976 Feb;24(2):215–219. [PubMed]
  • PATRICK AD. The degradative metabolism of L-cysteine and L-cystine in vitro by liver in cystinosis. Biochem J. 1962 May;83:248–256. [PubMed]
  • Perings E, Junge U. Wirkungen und Nebenwirkungen von D-Penicillamin. Med Klin. 1975 Aug 1;70(31):1265–1274. [PubMed]
  • Planas-Bohne F. Untersuchungen zur Bildung gemischter Disulfide zwischen D-Penicillamin und Serumproteinen. Res Exp Med (Berl) 1973 Nov 23;161(4):289–297. [PubMed]
  • Raab W, Mörth C. Inhibition of alkaline phosphatase activity by D-penicillamine. Z Klin Chem Klin Biochem. 1974 Jun;12(6):309–310. [PubMed]
  • Rabenstein DL, Fairhurst MT. Nuclear magnetic resonance studies of the solution chemistry of metal complexes. XI. The binding of methylmercury by sulfhydryl-containing amino acids and by glutathione. J Am Chem Soc. 1975 Apr 16;97(8):2086–2092. [PubMed]
  • Rorsman H, Rosengren AM, Rosengren E. Determination of 5-S-cysteinyldopa in melanomas with a fluorimetric method. Yale J Biol Med. 1973 Dec;46(5):516–522. [PMC free article] [PubMed]
  • Rucker RB, Murray J, Riggins RS. Nutritional copper deficiency and penicillamine administration: some effects on bone collagen and arterial elastin crosslinking. Adv Exp Med Biol. 1977;86B:619–648. [PubMed]
  • Ruiz-Torres A. Zur Frage der Penicillaminwirkung auf die Kollagensynthese. Arzneimittelforschung. 1974 Jan;24(1):43–45. [PubMed]
  • Schneider W. Die Wirkung von Penicillamin auf pathologische Makroglobuline. Munch Med Wochenschr. 1967 Mar 10;109(10):531–535. [PubMed]
  • Schonbeck ND, Skalski M, Shafer JA. Reactions of pyrzdoxal 5'-phosphate, 6-aminocaproic acid, cysteine, and penicilamine. Models for reactions of Schiff base linkages in pyridoxal 5'-phosphate-requiring enymes. J Biol Chem. 1975 Jul 25;250(14):5343–5351. [PubMed]
  • Schulman JD, Bradley KH. Cystinosis: selective induction of vacuolation in fibroblasts by L-cysteine-D-penicillamine disulfide. Science. 1970 Aug 7;169(3945):595–597. [PubMed]
  • Snow JT, Finley JW, Friedman M. Oxidation of sulfhydryl groups to disulfides by sulfoxides. Biochem Biophys Res Commun. 1975 May 5;64(1):441–447. [PubMed]
  • Sweetman BJ, Vestling MM, Ticaric ST, Kelly PL, Field L, Merryman P, Jaffe IA. Biologically oriented organic sulfur chemistry. 8. Structure-activity relationships of penicillamine analogs and derivatives. J Med Chem. 1971 Sep;14(9):868–872. [PubMed]
  • Thich JA, Mastropaolo D, Potenza J, Schugar HJ. Crystal and molecular structure of bis(copper(II) D-penicillamine disulfide) nonahydrate, a derivative of copper(II) cystinate. J Am Chem Soc. 1974 Feb 6;96(3):726–731. [PubMed]
  • Tomono I, Abe M, Matsuda M. Effect of penicillamine (a vitamin B6 antagonist) on pyridoxal enzymes. J Biochem. 1973 Sep;74(3):587–592. [PubMed]
  • van Rensburg NJ, Swanepoel OA. Reactions of unsymmetrical disulfides. I. Sulfitolysis of sulfur derivatives of cysteamine and cysteine. Arch Biochem Biophys. 1967 Mar 20;118(3):531–535. [PubMed]
  • Vsail'ev VI, Korobkin VN, Korchagin VB, Fedorets TM, Kaverkina TD. Differentsirovannoe opredelenie funktsional'nykh grupp v khlorgidrate penitsillamina. Antibiotiki. 1974 Feb;19(2):146–150. [PubMed]
  • Vasiliev V, Usviatsov AA, Korchagin VB, Fedorets TM, Korobkin VN. Amperometricheskoe titrovanie khlorgidrata d-penitsillamina. Antibiotiki. 1973 May;18(5):402–406. [PubMed]
  • Walshe JM. Copper chelation in patients with Wilson's disease. A comparison of penicillamine and triethylene tetramine dihydrochloride. Q J Med. 1973 Jul;42(167):441–452. [PubMed]
  • Weigert WM, Offermanns H, Scherberich P. D-Penicillamine--production and properties. Angew Chem Int Ed Engl. 1975 May;14(5):330–336. [PubMed]
  • Wu JT, Kuntz RR. Letter: The reactions of hydrogens atoms in aqueous solutions: effect of pH on reactions with cysteine and penicillamine. Radiat Res. 1975 Dec;64(3):662–666. [PubMed]
  • Wu YV, Cluskey JE, Krull LH, Friedman M. Some optical properties of S- -(4-pyridylethyl)-L-cysteine and its wheat gluten and serum albumin derivatives. Can J Biochem. 1971 Sep;49(9):1042–1049. [PubMed]

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