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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

Quality Level

200

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)
Ferroptosis is induced following siramesine and lapatinib treatment of breast cancer cells.
Ma S, et al.
Cell Death & Disease, 7(7), e2307-e2307 (2016)
Ashok Kumar Yadav et al.
Mediators of inflammation, 2012, 476979-476979 (2012-09-13)
The serum levels of neopterin, a marker associated with cell-mediated immunity are elevated in chronic kidney disease (CKD). We evaluated serum neopterin levels and investigated its association with markers of inflammation in a cross-section of CKD subjects without known cardiovascular
Mahmoud Sadeghi et al.
Transplantation, 95(8), 1021-1029 (2013-04-18)
Plasmapheresis (PP) has been used in the treatment of various immunologic disorders, and its efficacy has mainly been attributed to the removal of humoral factors and autoantibodies. Besides these effects, PP may induce modifications of the cellular immunologic status, contributing
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