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DMRIE
DMRIE is a quaternary ammonium compound with surfactant properties. It features a hydrophilic head with dimethyl and hydroxyethyl groups, and two hydrophobic tetradecyl (C14) alkyl chains, making it effective in forming micelles and emulsifying agents. The bromide counterion balances the charge of the ammonium group. This compound is commonly used in formulations requiring surfactants, such as in detergents, personal care products, and possibly in drug delivery systems due to its amphiphilic nature.
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Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BRP-02117 | 1 mg | $298 | In stock |
Catalog
BRP-02117
Synonyms
N-(2-Hydroxyethyl)-N,N-dimethyl-2,3-bis(tetradecyloxy)-1-propaniminium Bromide; 1-Propanaminium, N-(2-hydroxyethyl)-N,N-dimethyl-2,3-bis(tetradecyloxy)-, bromide (1:1); Dimethyl-2-hydroxyethyl-2,3-ditetradecyloxypropylammonium bromide; Dimyristyloxypropyl-3-dimethyl-hydroxyethyl ammonium; N-[1-(2,3-Ditetradecyloxy)propyl]-N,N-dimethyl-N-hydroxyethylammonium bromide; N-(2-Hydroxyethyl)-N,N-dimethyl-2,3-bis(tetradecyloxy)propan-1-aminium bromide
CAS
153312-64-2
IUPAC Name
2,3-di(tetradecoxy)propyl-(2-hydroxyethyl)-dimethylazanium;bromide
Molecular Weight
636.87
Molecular Formula
C35H74BrNO3
Canonical SMILES
CCCCCCCCCCCCCCOCC(C[N+](C)(C)CCO)OCCCCCCCCCCCCCC.[Br-]
InChI
InChI=1S/C35H74NO3.BrH/c1-5-7-9-11-13-15-17-19-21-23-25-27-31-38-34-35(33-36(3,4)29-30-37)39-32-28-26-24-22-20-18-16-14-12-10-8-6-2;/h35,37H,5-34H2,1-4H3;1H/q+1;/p-1
InChIKey
WALUVDCNGPQPOD-UHFFFAOYSA-M
Purity
≥95%
Related CAS
191980-81-1 (free base)
Chemical Structure:
Reference Reading
1. Leuvectin Vical Inc
A Kaushik. Curr Opin Investig Drugs. 2001 Jul;2(7):976-81.
Vical's Leuvectin, a plasmid DNA expression vector encoding interleukin-2 (IL-2) complexed with a lipid delivery vehicle (DMRIE/DOPE)for intratumoral injection, is under development as a potential gene therapy for cancer. In 1997, it was in phase II trials for kidney and prostate cancer [249445], [270243]. In April 2001, the phase II trial in kidney cancer was discontinued, with a new phase II trial planned for this indication [406405]. In May 2001, prostate cancer trials were ongoing [409071]. By March 1999, testing for other indications had been suspended, with the company's priority being to work toward the most promising indications [316709]. In November 2000, it was announced that Vical has been issued US-06147055 for the use of gene-based, non-viral delivery of IL-2 for the treatment of cancer. The company was also issued US-05641665 covering the Leuvectin construct in 1997 [389677].
2. Immunotherapy of renal cell carcinoma by intratumoral administration of an IL-2 cDNA/DMRIE/DOPE lipid complex
G A Daniels, E Galanis. Curr Opin Mol Ther. 2001 Feb;3(1):70-6.
Intratumoral administration of cytokine genes in order to achieve paracrine secretion of immunostimulatory cytokines and to create tumor vaccines in situ can avoid difficulties associated with the production of autologous and allogeneic vaccines, and toxicity related to systemic administration of cytokines. In this review, we summarize our experience with intratumoral administration of IL-2 cDNA/DMRIE/DOPE lipid complex in patients with metastatic renal cell carcinoma. An objective response rate of 14% was achieved in a phase I/II clinical trial and was confirmed in the low-risk subgroup of a phase II study. The achieved objective clinical responses (PR/CR) were long lasting. Application of PCR and immunohistochemistry in post-treatment tumor biopsies detected the IL-2 plasmid in addition to increased IL-2 expression in tumor cells and CD8 infiltration. Clinical trials employing higher doses of the plasmid in renal cell carcinoma patients with limited disease are ongoing.
3. Allovectin-7 therapy in metastatic melanoma
Agop Y Bedikian, Michele Del Vecchio. Expert Opin Biol Ther. 2008 Jun;8(6):839-44. doi: 10.1517/14712598.8.6.839.
Patients with metastatic melanoma are immunosuppressed by the growing tumor. Allovectin-7 therapy is a form of active immunotherapy that aims at immunization of the host with substances designed to elicit an immune reaction that will eliminate or slow down the growth and spread of the cancer. To describe the rationale for immunotherapy with Allovectin-7 and assess its safety profile and efficacy based on the results of completed melanoma clinical trials. We reviewed both the published medical literature and the results of trials pending publication. Allovectin-7 is a safe and active immunotherapeutic agent. It induces local and systemic durable responses in patients with metastatic melanoma.
