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P1101

Sigma-Aldrich

D-Penicillamine disulfide

97%, cell analysis

Synonym(s):

3,3′-Dithiobis(2-amino-3-methylbutanoic acid), 3,3′-Dithiobis(2-amino-3-methylbutyric acid), 3,3′-Dithiobis-D-valine, S,S′-Bi(D-penicillamine), NSC 87505

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About This Item

Linear Formula:
[-SC(CH3)2CH(NH2)CO2H]2
CAS Number:
20902-45-8
Molecular Weight:
296.41
Beilstein:
4461521
EC Number:
244-107-2
MDL number:
MFCD00004264
UNSPSC Code:
12352116
PubChem Substance ID:
24898153
NACRES:
NA.22

product name

D-Penicillamine disulfide, 97%

Assay

97%

form

powder or crystals

optical activity

[α]25/D −75°, c = 1 in 1 M NaOH

reaction suitability

reaction type: solution phase peptide synthesis

color

white

mp

204 °C (dec.) (lit.)

application(s)

cell analysis

SMILES string

CC(C)(SSC(C)(C)[C@@H](N)C(O)=O)[C@@H](N)C(O)=O

InChI

1S/C10H20N2O4S2/c1-9(2,5(11)7(13)14)17-18-10(3,4)6(12)8(15)16/h5-6H,11-12H2,1-4H3,(H,13,14)(H,15,16)/t5-,6-/m0/s1

InChI key

POYPKGFSZHXASD-WDSKDSINSA-N

Application

Used in pharmacological studies of:
  • Molecules dermatomyositis activity
  • Antimelanoma activity of apoptogenic carbonyl scavengers

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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P Unak et al.
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 49(7), 805-809 (1998-05-07)
Complex forming conditions of Penicillamine di sulfide with 99mTc have been specified. Labeling of penicillamine di sulfide with 99mTc by direct reduction with SnCl2 did not give favorable good results while the 99mTc complex of penicillamine can be easily obtained.
J C Crawhall
Clinical and investigative medicine. Medecine clinique et experimentale, 7(1), 31-34 (1984-01-01)
Penicillamine disulfides have been analysed by automatic amino acid analysis. Because the free thiol reacts poorly with ninhydrin, other detection methods are preferred, particularly high pressure liquid chromatography using an electrochemical detector or gas chromatography with a flame ionization detector.
T F Yu et al.
The Journal of rheumatology, 11(4), 467-470 (1984-08-01)
Four patients with recurrent cystine stones and 5 with rheumatoid arthritis (RA) were studied. After a single dose of D-penicillamine to cystinuric patients, cystine excretion decreased considerably. Cysteine-penicillamine mixed disulfide (CSSP) and penicillamine disulfide (PSSP) metabolites appeared within 1-2 h
J K Nicholson et al.
Drug metabolism and drug interactions, 6(3-4), 439-446 (1988-01-01)
Preliminary studies on the use of high resolution 1H-NMR spectroscopy for the detection of the thiol drug penicillamine and its metabolites in human urine are described. The technique is rapid, simple and requires minimal sample pretreatment. Application of NMR to
K K Millis et al.
Biochimica et biophysica acta, 1055(1), 10-18 (1990-10-15)
The oxidation/reduction chemistry of penicillamine in human erythrocytes was characterized directly in intact erythrocytes by 1H-NMR spectroscopy. Spectra were measured by the Carr-Purcell-Meiboom-Gill pulse sequence to selectively eliminate interfering resonances from hemoglobin and membrane protons and from the intracellular water.
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