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N3386

Sigma-Aldrich

D-(+)-Neopterin

≥97.5% (sum of enantiomers, HPLC)

Synonym(s):

D-erythro-Neopterin

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About This Item

Empirical Formula (Hill Notation):
C9H11N5O4
CAS Number:
2009-64-5
Molecular Weight:
253.21
Beilstein:
89070
EC Number:
217-924-7
MDL number:
MFCD00042801
UNSPSC Code:
12352005
PubChem Substance ID:
57654449
NACRES:
NA.22

Assay

≥97.5% (sum of enantiomers, HPLC)

form

powder

storage temp.

2-8°C

SMILES string

Nc1nc(O)c2nc(cnc2n1)[C@H](O)[C@H](O)CO

InChI

1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6+/m1/s1

InChI key

BMQYVXCPAOLZOK-XINAWCOVSA-N

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General description

D-(+)-Neopterin is a pteridine derivative, naturally found in Dictyostelium discoideum. It is found in significant amounts in the urine of cancer patients.

Application

D-(+)-Neopterin has been used as a NADPH oxidase inhibitor while assessing the ability of NADPH oxidases in breast cancer cells to produce reactive oxygen species (ROS). [NADPH= nicotinamide adenine dinucleotide phosphate]

Biochem/physiol Actions

Pterin cofactor; precursor of BH4 (tetrahydrobiopterin).

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dictyopterin, 6-(d-threo-1,2-dihydroxypropyl)-pterin, a new natural isomer of L-biopterin.
Klein R, et al.
European Journal of Biochemistry, 187(3), 665-669 (1990)
Pteridine analysis in urine by capillary electrophoresis using laser-induced fluorescence detection.
Han F, et al.
Analytical Chemistry, 71(7), 1265-1269 (1999)
R Caruso et al.
Clinical biochemistry, 46(1-2), 94-98 (2012-10-30)
Neopterin, a marker of inflammation and monocyte activation, is found increased in patients with heart failure (HF). This study investigates whether neopterin levels correlate with left ventricular (LV) remodeling and brain natriuretic peptide (BNP), a marker of cardiac stress, in
Nisreen Husain et al.
Journal of clinical gastroenterology, 47(3), 246-251 (2012-12-28)
Neopterin, a pyrazino-[2,3-d]-pyrimidine compound, is a metabolite of cyclic guanosine monophosphate that is released by activated T lymphocytes and macrophages after induction by γ interferon. We sought to determine whether neopterin concentration in stool, serum, or urine is a useful
Petra Holečková et al.
International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition, 82(2), 77-84 (2012-10-16)
High serum or urinary neopterin concentrations are associated with poor prognosis in patients with tumors of different primary locations, but reports on neopterin in patients with head and neck carcinoma are relatively less numerous. It has been established that decreased
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