Duramycin

• CAS: 1391-36-2
• Catalog Number: ACM1391362
• Category: Main Products
• Molecular Weight: 2013.28
• Molecular Formula: C₈₉H₁₂₅N₂₃O₂₅S₃
• Synonyms: Ancovenin,2-L-lysine-6-(3-aminoalanine)-10-L-phenylalanine-12-L-phenylalanine-13-L-valine-15-(erythro-3-hydroxy-L-aspartic acid)-,cyclic 6-19)-imine; LANCOVUTIDE; Leucopeptin; UNII-BPR0F3X56H; Lancovutide [INN]
• IUPAC Name: Duramycin
• Canonical SMILES: CC1C2C(=O)NC(C(=O)NC(C(=O)NC3CSCC4C(=O)NC(CS1)C(=O)NC(CNCCCCC(NC(=O)C(CSCC(C(=O)NC(C(=O)NC(C(=O)N4)CCC(=O)N)CCCCN)N)NC(=O)C(NC(=O)CNC(=O)C(NC3=O)C(C(=O)O)O)CC(=O)N)C(=O)O)C(=O)NC(C(=O)NCC(=O)N5CCCC5C(=O)NC(C(=O)N2)CC6=CC=CC=C6)CC7=CC=CC=C7)C(C)C)CC8=CC=CC=C8
• InChI Key: BPIFGBWRBGTMHX-CREJVHTASA-N
• Melting Point: 271-273ºC
• Exact Mass: 1997.82000

Case Study

Duramycin Used to Detect Lipids Containing Phosphoethanolamine in Membranes

Hullin-Matsuda, Françoise, et al. Biochimie, 2016, 130, 81-90.

Duramycin and cinnamycin specifically bind to a variety of phosphatidylethanolamine species (PEs). These lantibiotics promote their binding to PE-containing membranes by altering membrane curvature and inducing transbilayer lipid movement.
Biological use of PE-specific lantibiotic probes
Cinnamycin and duramycin derivatives are significant for detecting phosphatidylethanolamine (PE) on cell surfaces, and they can also be utilized to examine PE within the inner leaflet of the plasma membrane through a method known as immunoelectron microscopy, which combines sodium dodecyl sulfate freeze-fracture replicas with immunochemical labeling (SDS-FRL). This approach involves physically separating the outer and inner leaflets of the bilayer, followed by gentle SDS digestion.
Afterward, a probe is introduced and identified using a colloidal gold-conjugated secondary antibody. Notably, this method allows for a quantitative comparison of lipid density across the two leaflets. Employing biotinylated duramycin revealed that in human red blood cells, PE was predominantly found on the inner leaflet of the plasma membrane (99.8%). In contrast, among nucleated cells, such as human skin fibroblasts and neutrophils, a portion of PE was located on the outer leaflet, while 97.7% remained in the inner leaflet.

[99mTc]Duramycin as a SPECT Imaging Agent for Evaluating Tumor Cell Apoptosis

Elvas, Filipe, et al. Molecular imaging and biology, 2015, 17, 838-847.

Duramycin is a tetracyclic peptide that binds to phosphatidylethanolamine (PE) with excellent affinity and specificity. This work developed a [99mTc]Duramycin-based single-photon emission computed tomography (SPECT) cell death imaging agent and evaluated its utility in monitoring early responses to cancer therapy in mice.
Evaluation methods and results
· Healthy CD1-/- mice were administered [99mTc]Duramycin to evaluate the radiation dose of human [99mTc]duramycin. The SPECT imaging of apoptosis with [99mTc]Duramycin in a mouse model of colorectal cancer undergoing irinotecan treatment was assessed and further validated through ex vivo techniques, including autoradiography, cleaved caspase-3 analysis, and TdT-mediated dUTP nick-end labeling (TUNEL) histology of the tumors.
· The average effective dose was calculated to be 3.74 × 10-3 ± 3.43 × 10-4 mSv/MBq for non-purified [99mTc]duramycin and 3.19 × 10-3 ± 2.16 × 10-4 mSv/MBq for the purified variant. Following treatment, the uptake of [99mTc]Duramycin in vivo was significantly higher in apoptotic tumors that had been treated with irinotecan (p = 0.008). Moreover, radioactivity in the tumors showed a strong positive correlation with both cleaved caspase-3 (r = 0.85, p < 0.001) and TUNEL (r = 0.92, p < 0.001) staining.
· [99mTc]Duramycin proves to be effective in identifying early chemotherapy-induced tumor cell death, making it a promising candidate for clinical SPECT imaging to assess tumor responses to therapy.

Custom Q&A

What is the molecular formula of Duramycin?

The molecular formula of Duramycin is C89H125N23O25S3.

What is the molecular weight of Duramycin?

The molecular weight of Duramycin is 2013.3 g/mol.

Is Duramycin a peptide antibiotic or a bacteriocin?

Duramycin is a peptide antibiotic.

What is the clinical development purpose of Lancovutide?

Lancovutide is being developed for the treatment of cystic fibrosis.

What is the relationship between Lancovutide and cinnamycin?

Lancovutide is closely related to cinnamycin (Ro09-0198).

What are lantibiotics?

Lantibiotics are bacteriocins that are characterized by the presence of a high proportion of unusual amino acids.

What are the synonyms of Duramycin?

The synonyms of Duramycin are Leucopeptin, Moli1901, and BPR0F3X56H.

When was Duramycin created and modified?

Duramycin was created on November 19, 2019, and modified on October 21, 2023.

What is the IUPAC name of Duramycin?

The IUPAC name of Duramycin is (1S,4S,13S,16S,19S,22S,25S,28R,31S,37S,40S,41S,44R,47S,50S,53S,56R,65S,70S)-44-amino-47-(4-aminobutyl)-37-(2-amino-2-oxoethyl)-50-(3-amino-3-oxopropyl)-4,16,22-tribenzyl-31-[(R)-carboxy(hydroxy)methyl]-41,70-dimethyl-2,5,8,14,17,20,23,26,29,32,35,38,45,48,51,54,57,67-octadecaoxo-25-propan-2-yl-42,69,72-trithia-3,6,9,15,18,21,24,27,30,33,36,39,46,49,52,55,58,60,66-nonadecazapentacyclo[38.18.9.319,56.328,53.09,13]triheptacontane-65-carboxylic acid.

What is the InChIKey of Duramycin?

The InChIKey of Duramycin is SFWLDKQAUHFCBS-AOEYGKNYSA-N.