144558-52-1

Basic information

• Product Name: 1,3-dipalmitoyl-2-(4'-(bis(2''-chloroethyl)amino)phenylalaninoyl)glycerol
• Synonyms: 1,3-dipalmitoyl-2-(4'-(bis(2''-chloroethyl)amino)phenylalaninoyl)glycerol
• CAS NO: 144558-52-1
• Molecular Formula: C₄₈H₈₄Cl₂N₂O₆
• Molecular Weight: 856.09636
• Mol File: 144558-52-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 813.7°Cat760mmHg
• Flash Point: 445.9°C
• Appearance: /
• Density: 1.037g/cm³
• CAS DataBase Reference: 1,3-dipalmitoyl-2-(4'-(bis(2''-chloroethyl)amino)phenylalaninoyl)glycerol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dipalmitoyl-2-(4'-(bis(2''-chloroethyl)amino)phenylalaninoyl)glycerol(144558-52-1)
• EPA Substance Registry System: 1,3-dipalmitoyl-2-(4'-(bis(2''-chloroethyl)amino)phenylalaninoyl)glycerol(144558-52-1)

Safety Data

• Hazardous Substances Data: 144558-52-1(Hazardous Substances Data)

Usage

General Description

1,3-dipalmitoyl-2-(4'-(bis(2''-chloroethyl)amino)phenylalaninoyl)glycerol, also known as DPPG-C2, is a synthetic lipid chemical compound with potential antineoplastic and anti-HIV activities. It is a dipalmitoyl glycerol derivative conjugated with N, N-bis(2-chloroethyl)-L-phenylalanine. 1,3-dipalmitoyl-2-(4'-(bis(2''-chloroethyl)amino)phenylalaninoyl)glycerol has been studied for its potential in treating various types of cancers, including leukemia and lymphoma, as well as its antiviral activity against HIV. DPPG-C2 has also been shown to possess immunostimulatory properties and has been investigated as a potential adjuvant for cancer vaccines. Its mechanism of action involves affecting membrane fluidity and stability, as well as inhibiting DNA synthesis in cancer cells. Further research is ongoing to understand its full potential and applications in medical treatment.

Upstream product

• 112-67-4 n-hexadecanoyl chloride 
• 24472-45-5 1,3-dipalmitoyloxy-2-propanone 
• 502-52-3 hexadecanoic acid, 2-hydroxy-1,3-propanediyl ester 
• 144558-51-0 1,3-Dipalmitoyl-2-<3'-<4''-(bis-(2'''-chloroethyl)amino)phenyl>-2'-<(tert-butoxycarbonyl)amino>propanoyl>glycerol 
• 79145-92-9 N-((tert-butoxy)carbonyl)-4-(bis(2-chloroethyl)amino)-L-phenylalanine 
• 148-82-3 L-PAM 

Relevant articles and documents

Synthesis of the orally macrofilaricidal and stable glycerolipidic prodrug of melphalan, 1,3-dipalmitoyl-2-(4'(bis(2''-chloroethyl)amino)phenylalaninoyl)glycer ol

A new strategy is presented to develop macrofilaricidal compounds orally administered and able to concentrate in the lymphatic system. A diglyceride derivative of melphalan, 1,3-dipalmitoyl-2-(4'(bis(2''-chloroethyl]amino) phenylalaninoyl) glycerol, was synthesized. The esterification of melphalan by 1,3-dipalmitin allowed chemical stabilization of the alkylating agent in aqueous dispersion. No degradation of this prodrug was observed after a 3 month storage of an aqueous dispersion at 4°C. The filaricidal activity of the prodrug was compared with those of melphalan in vitro against adults, infective larvae and microfilariae of Molinema dessetae, and evaluated in vivo on Molinema dessetae infected Proechimys oris. In vitro, melphalan and the glycerolipidic prodrug were inactive against microfilariae but active at 1 mmol/l against infective larvae and adults. In vivo studies were performed with rodents subcutaneously inoculated with infective larvae from Aedes aegypti. The number of macrofilariae was significantly reduced following treatment with a single oral dose of the alkylating agent prodrug (0.082 mmol/kg).