Synonym
Cgp 31362; Cgp31362; Cgp-31362
IUPAC/Chemical Name
sodium (8R,11S,14R,18R)-8-(3-amino-3-oxopropyl)-18-(dodecanoyloxy)-11-methyl-5,7,10,13,21-pentaoxo-14-palmitamido-20-oxa-16-thia-3,6,9,12-tetraazadotriacontane-1-sulfonate
InChi Key
KMXBCAPLZGEGBW-APLTXDPFSA-M
InChi Code
InChI=1S/C58H108N6O13S2.Na/c1-5-8-11-14-17-20-21-22-23-26-27-30-33-36-52(66)62-50(58(72)61-47(4)56(70)63-49(39-40-51(59)65)57(71)64-53(67)43-60-41-42-79(73,74)75)46-78-45-48(77-55(69)38-35-32-29-25-19-16-13-10-7-3)44-76-54(68)37-34-31-28-24-18-15-12-9-6-2;/h47-50,60H,5-46H2,1-4H3,(H2,59,65)(H,61,72)(H,62,66)(H,63,70)(H,64,67,71)(H,73,74,75);/q;+1/p-1/t47-,48+,49+,50-;/m0./s1
SMILES Code
CCCCCCCCCCCCCCCC(N[C@H](C(N[C@H](C(N[C@@H](C(NC(CNCCS(=O)([O-])=O)=O)=O)CCC(N)=O)=O)C)=O)CSC[C@H](OC(CCCCCCCCCCC)=O)COC(CCCCCCCCCCC)=O)=O.[Na+]
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
1,183.63
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Dinney CP, Bucana CD, Utsugi T, Fidler IJ, von Eschenbach AC, Killion JJ. Therapy of spontaneous lung metastasis of murine renal adenocarcinoma by systemic administration of liposomes containing the macrophage activator CGP 31362. Cancer Res. 1991 Jul 15;51(14):3741-7. PMID: 1905975.
2: Dinney CP, Utsugi T, Fidler IJ, von Eschenbach AC, Killion JJ. Immunotherapy of murine renal adenocarcinoma by systemic administration of liposomes containing the synthetic macrophage activator CGP 31362 or CGP 19835A in combination with interleukin 2 or gamma-interferon. Cancer Res. 1992 Mar 1;52(5):1155-61. PMID: 1531322.
3: Utsugi T, Dinney CP, Killion JJ, Fidler IJ. In situ activation of mouse macrophages and therapy of spontaneous renal cell cancer metastasis by liposomes containing the lipopeptide CGP 31362. Cancer Immunol Immunother. 1991;33(6):375-81. doi: 10.1007/BF01741597. PMID: 1878891.
4: Xie K, Huang S, Dong Z, Gutman M, Fidler IJ. Direct correlation between expression of endogenous inducible nitric oxide synthase and regression of M5076 reticulum cell sarcoma hepatic metastases in mice treated with liposomes containing lipopeptide CGP 31362. Cancer Res. 1995 Jul 15;55(14):3123-31. PMID: 7541713.
5: Nii A, Fidler IJ. The incubation of human blood monocytes with tumor necrosis factor-alpha leads to lysis of tumor necrosis factor-sensitive but not resistant tumor cells. Lymphokine Res. 1990 Summer;9(2):113-24. PMID: 2338840.
6: Nii A, Utsugi T, Fan D, Denkins Y, Pak C, Brown D, van Hoogevest P, Fidler IJ. Optimization of the liposomes encapsulating a new lipopeptide CGP 31362 for efficient activation of tumoricidal properties in monocytes and macrophages. J Immunother (1991). 1991 Aug;10(4):236-46. doi: 10.1097/00002371-199108000-00002. PMID: 1931862.
7: Utsugi T, Dinney CP, Killion JJ, Brown D, Fidler IJ. In situ activation of mouse lung macrophages by coadministration of liposomes containing the lipopeptide CGP 31362 and interleukin 2 involves interaction with T lymphocytes and natural killer cells. Lymphokine Cytokine Res. 1991 Dec;10(6):487-93. PMID: 1804312.
8: Dong Z, Qi X, Fidler IJ. Tyrosine phosphorylation of mitogen-activated protein kinases is necessary for activation of murine macrophages by natural and synthetic bacterial products. J Exp Med. 1993 Apr 1;177(4):1071-7. doi: 10.1084/jem.177.4.1071. PMID: 8384652; PMCID: PMC2190980.
9: Utsugi T, Nii A, Fan D, Pak CC, Denkins Y, van Hoogevest P, Fidler IJ. Comparative efficacy of liposomes containing synthetic bacterial cell wall analogues for tumoricidal activation of monocytes and macrophages. Cancer Immunol Immunother. 1991;33(5):285-92. doi: 10.1007/BF01756592. PMID: 1868486.
10: Fidler IJ, Nii A, Utsugi T, Brown D, Bakouche O, Kleinerman ES. Differential release of TNF-alpha, IL 1, and PGE2 by human blood monocytes subsequent to interaction with different bacterial derived agents. Lymphokine Res. 1990 Winter;9(4):449-63. PMID: 2090873.