DNP PEG

• Small-molecule DNP PEG

2,4-Dinitrophenol PEG (DNP PEG) is a polyethylene glycol derivative that has attracted widespread attention in the fields of chemistry, pharmacology, and biochemistry due to its unique properties and potential applications. The addition of PEG to dinitrophenol improves the solubility and stability of the compound. The chemical structure of DNP PEG consists of a dinitrophenol core linked to a PEG polymer chain, giving the compound water solubility and biocompatibility. Furthermore, the unique properties of DNP PEG result from the combination of the uncoupling effect of dinitrophenol and the biocompatibility of PEG. DNP PEG has been shown to disrupt the proton gradient across the mitochondrial membrane, leading to increased energy expenditure and heat production. This property has sparked interest in the potential use of DNP PEG as an anti-obesity agent and metabolic modulator.

Fig. 1. Structure of DNP-PEG4-acid.

What is 2,4-Dinitrophenol (DNP)?

2,4-Dinitrophenol was first synthesized in the late 19th century and was initially used to make dyes and wood preservatives. Its biological effects were discovered in the early 20th century when weight loss was observed in workers exposed to DNP in industrial settings. This serendipitous discovery sparked the exploration of DNP as a potential weight loss agent. DNP exerts its effect by uncoupling oxidative phosphorylation in mitochondria. Typically, the oxidative phosphorylation process couples electron transport and ATP synthesis to produce energy in the form of ATP. However, DNP disrupts this coupling by dissipating the proton gradient across the inner mitochondrial membrane, resulting in the production of heat instead of ATP. This uncoupling effect increases metabolic rate and energy expenditure, making it a potentially attractive target for weight loss interventions. Currently, DNP is used in drug development for weight loss drug research, mitochondrial dysfunction and cancer treatment.

Synthesis of DNP PEG

The synthesis of DNP PEG involves several steps of functionalizing the dinitrophenol core with PEG chains. A common approach is to first prepare dinitrophenol derivatives that can be readily conjugated to PEG molecules. The PEG chains are then attached to the dinitrophenol core using coupling reagents or click chemistry. PEG chain length and selection of functional groups (carboxylic acid, hydroxyl, azide, NHS ester) can be customized to optimize the solubility, stability, and bioactivity of DNP PEG. Purification methods such as chromatography and filtration are used to isolate the desired DNP PEG product from the reaction mixture.

DNP PEG Derivatives

BOC Sciences is committed to providing 2,4-dinitrophenol PEG (DNP PEG) reagents with various reactive groups, including carboxylic acid, hydroxyl, azide, NHS ester, etc. Our DNP PEG has been widely used in various research fields such as bioconjugation, drug delivery and molecular biology. In addition, a variety of PEG reagents are also available at BOC Sciences via custom synthesis.

DNP-PEG4-COOH

DNP-PEG4-COOH is a compound composed of a dinitrophenyl (DNP) group, a polyethylene glycol (PEG) spacer, and a carboxylic acid functional group. The DNP group is commonly used as a hapten in immunoassays and can be recognized by antibodies. PEG spacers help improve solubility and biocompatibility, while carboxylic acid groups enable further functionalization.

• Characteristic:

- DNP-PEG4-COOH is water-soluble due to the PEG content.

- Carboxylic acid groups can participate in chemical reactions such as amidation or esterification.

- The DNP group can be recognized by anti-DNP antibodies.

• Application:

- Immunoassays: DNP-PEG4-COOH can be used as a hapten to study antibody-antigen interactions.

- Drug delivery: PEG components help improve the pharmacokinetics of drugs.

- Surface functionalization: Carboxylic acid groups allow other molecules to attach to the surface.

DNP-PEG4 NHS ester

DNP-PEG4 NHS ester is a derivative of DNP-PEG4-COOH in which the carboxylic acid group has been activated to N-hydroxysuccinimide (NHS) ester. This activation allows efficient coupling of compounds to primary amines on proteins or other molecules.

• Characteristic:

- NHS ester groups react specifically with primary amines to form stable amide bonds.

- PEG spacer helps maintain solubility and flexibility.

- The DNP group retains its antigenic properties.

• Application:

- Protein labeling: DNP-PEG4 NHS ester can be used to label proteins with DNP groups for various assays.

- Drug conjugation: NHS ester groups allow conjugation of DNP-PEG4 to drug molecules for targeted delivery.

- Biomaterial functionalization: DNP-PEG4 NHS ester can be used to modify the surface of biomaterials to suit specific applications.

DNP PEG DSPE

DNP PEG DSPE is a lipid derivative combining a DNP group, a PEG spacer and a phospholipid component (DSPE). This compound is commonly used in liposome formulations for drug delivery applications.

• Characteristic:

- DSPE assembly allows the incorporation of DNP-PEG4 into lipid bilayers.

- PEG spacer improves liposome stability and circulation time in the body.

- DNP groups can be used for targeting and imaging purposes.

• Application:

- Liposome drug delivery: DNP PEG DSPE can be used to formulate liposomes for targeted drug delivery.

-Imaging agents: DNP groups can be used as contrast agents in imaging studies.

- Theranostics: DNP PEG DSPE can be used in combination therapeutic and diagnostic applications.

Case Study

BOC Sciences once provided a high-quality DNP PEG DSPE product to a cancer research team. The research team needs to encapsulate its small molecule anti-cancer drugs in liposomes coated with DNP PEG DSPE, so it has strict requirements on the molecular weight and product stability of the product. Through close communication with customers, our scientists decided to challenge a new synthesis route. They comprehensively considered starting materials, reaction conditions, purification methods and other factors, and benefited from BOC Sciences' rich accumulation of synthesis technology. In the end, the scientists successfully synthesized 10g of qualified products in the laboratory. During the production process, our team pays special attention to sampling inspection and testing, and examines the key parameters of the product in detail, such as purity, molecular weight, particle size, etc.

Through validation studies and rigorous testing, the team created a DNP PEG-based targeted drug delivery system that can selectively deliver targeted small molecules to cancer cells while minimizing off-target effects. The superior efficacy of its drug delivery system has been demonstrated in preclinical models.