D-(+)-NEOPTERIN Property

Melting point:

>232°C (dec.)

alpha 

D25 +45 ± 3° (c = 0.3 in 0.1N HCl)

Boiling point:

396.41°C (rough estimate)

Density 

1.3957 (rough estimate)

refractive index 

1.7610 (estimate)

storage temp. 

2-8°C

solubility 

Aqueous Acid (Slightly, Sonicated), Aqueous Base (Slightly)

form 

Off-white to yellow solid.

pka

12.60±0.20(Predicted)

color 

Light Orange to Light Brown

Merck 

13,6490

BRN 

89070

Stability:

Hygroscopic

InChIKey

BMQYVXCPAOLZOK-XINAWCOVSA-N

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

F 

23

HS Code 

29335990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

D-(+)-NEOPTERIN Chemical Properties,Usage,Production

Description

Neopterin is a pyrazino-pyrimidine compound derived from GTP that represents an intermediate product in the synthetic pathway of biopterin and is an essential cofactor in neurotransmitter synthesis. Neopterin is released from macrophages upon immune stimulation with interferon-γ from activated T cells. It is routinely used as a biochemical tool to screen for and monitor the progression of certain diseases accompanied by hyperimmune stimulation.

Chemical Properties

off-white to yellow solid

Uses

Precursor in the biosynthesis of Biopterin. First isolated from the pupae of bees.

Uses

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]

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.

Biochem/physiol Actions

Pterin cofactor; precursor of BH4 (tetrahydrobiopterin).

storage

Store at -20°C

Purification Methods

Purification is as for biopterin. Also purify it on a Dowex-1 x 8 (formate form) column and elute with 0.03M ammonium formate buffer pH 8.0 then pH 7.2. The fluorescent neopterin fraction is evaporated under reduced pressure, leaving neopterin and ammonium formate (the latter sublimes out at high vacuum) behind. Stir the residue for 24hours with EtOH, collect the solid and recrystallise it from H2O. [Viscontini et al. Helv Chim Acta 53 1202 1970, cf Wachter et al. Eds Neopterin W de Gruyter, Berlin 1992, ISBN 9783110117905, Beilstein 26 IV 4038.]