d-penicillamine: Chemistry and clinical use in rheumatic disease

Howard-Lock, H. E.; Lock, C. J. L.; Mewa, Amirudin; Kean, Walter F.

doi:10.1016/0049-0172(86)90022-3

Cited by 72 publications

(31 citation statements)

References 127 publications

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“…Pretreatment of BAPN, a specific inhibitor of LOX (Tang et al, 1983), significantly decreased the covalent binding of [ 14 C]rofecoxib, probably via the prevention of allysine production from lysine. The covalent binding of [ 14 C]rofecoxib was also significantly decreased by pretreatment with D-penicillamine and hydralazine, which have been reported to react with protein aldehydes in connective tissues and to form thiazolidine or hydrazone analog (hydralazine can also inhibit LOX activity) Deshmukh and Nimni, 1969;Gallop and Paz, 1975;Numata et al, 1981;Howard-Lock et al, 1986). These results strongly suggested that the aldehydic functional …”

Section: After Incubation With [supporting

confidence: 56%

Covalent Binding of Rofecoxib, but Not Other Cyclooxygenase-2 Inhibitors, to Allysine Aldehyde in Elastin of Human Aorta

Oitate¹,

Hirota²,

Murai³

et al. 2007

Drug Metab Dispos

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ABSTRACT:In rats, it has been reported that rofecoxib, a cyclooxygenase-2 (COX-2) inhibitor, reacts with the aldehyde group of allysine in elastin to give a condensation covalent adduct, thereby preventing the formation of cross-linkages in the elastin and causing degradation of the elastic fibers in aortas in vivo. Acid, organic solvent, and proteolytic enzyme treatments of human aortic homogenate after incubation with

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Section: After Incubation With [supporting

confidence: 56%

Covalent Binding of Rofecoxib, but Not Other Cyclooxygenase-2 Inhibitors, to Allysine Aldehyde in Elastin of Human Aorta

Oitate¹,

Hirota²,

Murai³

et al. 2007

Drug Metab Dispos

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“…In addition, D-(-)-penicillamine has an older, well-established use in the treatment of patients suffering from Wilson's disease, as well as uses in the treatment of heavy metal poisoning, cystinuria, multiple sclerosis, -and chronic aggressive hepatitis (1).…”

Section: Introductionmentioning

confidence: 99%

2R,4S-2-(2′-Methyl-3′-hydroxy-5′-hydroxymethylenepyridine-C4′)-5,5-dimethylthiazolidine-4-carboxylic acid, the product of the reaction of D-penicillamine and vitamin B6

Faggiani¹,

Howard-Lock²,

Lock³

et al. 1991

Can. J. Chem.

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R. FAGGIANI, H. E. HOWARD-LOCK, C. J. L. LOCK, and R. ORGIAS. Can. J. Chem. 69, 1 (1991).We have studied the reaction of both D-and L-penicillamine with pyridoxal hydrochloride and examined the products by single crystal X-ray diffraction. The structure of the title compound, A, formed by the reaction of D-penicillamine and pyridoxal was determined. Crystals are orthorhombic, P212121, with cell dimensions a = 9.507(5), b = 19.185(5), c = 7.766(2) a and Z = 4. The structure was solved by standard methods and refined to R = 0.088, R,, = 0.079 for 2433 independent reflections. A exists as a zwitterion, and bond lengths and angles are normal. In the solid state, A and the corresponding product obtained from L-penicillamine, B, have identical geometrical structure but are of opposite chirality; that is, D-penicillamine produces the 2R,4S diastereomer and L-penicillamine produces the 2S,4R diastereomer (with no S , S and R,R components). In solution, however, NMR spectra show the presence of both pairs of diastereomers (2R,4S and 2S,4S; 2S,4R and 2R,4R). In neutral or alkaline solution there appears to be a rapid epimerization at the thiazolidine carbon atom attached to the pyridoxal moiety. Features of the mass, 'H NMR, vibrational, and electronic spectra are also discussed. On a CtudiC la reaction des D-et L-~Cnicillamines avec le chlorhydrate du pyridoxal et on a examink la nature des produits obtenu: par diffraction des rayons-X par un cristal unique. On a dtterminC la structure du composC A mentionnC dans le titre et form6 par la rtaction de la D-ptnicillamine avec le pyridoxal. Les cristaux sont orthorhombiques, P212121, avec a = 9,507(5), identiques, mais de chiralitts oppostes; c'est-a-dire que la D-pCnicillamine conduit au diastCrCoisomkre 2R,4S alors que la L-~Cnicillamine conduit au diasttrCoisomkre 2S,4R (sans contamination par les composantes S,S ou R,R). Toutefois, en solution, les spectres RMN montrent qu'il existe deux paires de diastCrCoisomkres (2R,4S et 2S,4S; 2S,4R et 2R,4R). I1 semble que, en solutions neutres ou alcalines, il se produit une tpimkrisation rapide de I'atome de carbone de la thiazolidine qui est attache a la portion pyridoxal. On discute aussi des caracttristiques spectrales (masse, RMN du 'H, vibrationnels et Clectroniques) de ces produits.

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“…Interference with collagen synthesis may be responsible for reported cases of hyperextensibility of young children treated with D-penicillamine, and for a similar reason D-penicillamine has been suggested as a possible teratogen (4). Formation of thiazolidine rings is also the probable mode of action of D-penicillamine as a vitamin B6 antagonist (4,6).…”

mentioning

confidence: 99%

(S)-2,2,5,5-Tetramethylthiazolidine-4-carboxylic acid: a compound which exists in the amino acid rather than the zwitterion form

Howard-Lock¹,

Lock²,

Smalley³

1985

Can. J. Chem.

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The X-ray crystal structure of (S)-2,2,5,5-tetramethylthiazolidine-4-caboxyic acid, b, has been determined. Crystals are monoclinic, P 2 , , with cell dimensions a = 11.351(4) b = 8.303(2), c = 11.969(3) A, P = 116.69(2)", and Z = 4. The structure was solved by standard methods and refined to RI = 0.0774, R2 = 0.0670 for 2388 independent reflections.Compound 1 exists in the amino-acid form as shown by two distinctly different C-0 bond lengths, 1.209 and 1.309 A, typical of the COOH group, and by the positions of the hydrogen atoms. The amino-acid form of 1 found in the solid also exists in solution as shown by infrared and Raman spectra. ' The mass spectra, and 'H and "C nmr spectra are reported, as well as detailed infrared and Raman spectra for the title compound and several deuterated species. [Traduit par le journal]

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d-penicillamine: Chemistry and clinical use in rheumatic disease

Cited by 72 publications

References 127 publications

Covalent Binding of Rofecoxib, but Not Other Cyclooxygenase-2 Inhibitors, to Allysine Aldehyde in Elastin of Human Aorta

Covalent Binding of Rofecoxib, but Not Other Cyclooxygenase-2 Inhibitors, to Allysine Aldehyde in Elastin of Human Aorta

2R,4S-2-(2′-Methyl-3′-hydroxy-5′-hydroxymethylenepyridine-C4′)-5,5-dimethylthiazolidine-4-carboxylic acid, the product of the reaction of D-penicillamine and vitamin B6

(S)-2,2,5,5-Tetramethylthiazolidine-4-carboxylic acid: a compound which exists in the amino acid rather than the zwitterion form

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