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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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Pteridine analysis in urine by capillary electrophoresis using laser-induced fluorescence detection.
Han F, et al.
Analytical Chemistry, 71(7), 1265-1269 (1999)
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)
Ferroptosis is induced following siramesine and lapatinib treatment of breast cancer cells.
Ma S, et al.
Cell Death & Disease, 7(7), e2307-e2307 (2016)
N Iu Kon'kova
Eksperimental'naia i klinicheskaia gastroenterologiia = Experimental & clinical gastroenterology, (6)(6), 123-126 (2013-02-14)
The study included 71 children with chronic gastroduodenitis aged 5-17 years. PCR DNA was determined by the presence of Helicobacter pylori, human papilloma virus high cancer risk 16, 18 types (HPV), herpes simplex 1 and type 2 (HSV), cytomegalovirus (CMV)
Bohuslav Melichar et al.
Anticancer research, 32(9), 4077-4084 (2012-09-21)
To investigate the relation between intima-media thickness (IMT) and laboratory parameters of atherosclerosis risk in patients with breast carcinoma. IMT and a panel of laboratory parameters associated with the risk of atherosclerosis were studied in 192 patients with histologically-verified breast
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