Iseganan

Iseganan is a synthetic analog of a peptide, and with broad-spectrum antimicrobial activity. It is under development for the prevention of oral mucositis from chemotherapy and radiation therapy.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: 10-101-184

CAS No:257277-05-7

Synonyms/Alias:Iseganan;257277-05-7;Antimicrobial peptide IB-367;Iseganan [INN];IB-367;UNII-Q9SAI36COS;IB 367;DTXSID80180415;IB-367-03;L-Argininamide, L-arginylglycylglycyl-L-leucyl-L-cysteinyl-L-tyrosyl-L-cysteinyl-L-arginylglycyl-L-arginyl-L-phenylalanyl-L-cysteinyl-L-valyl-L-cysteinyl-L-valylglycyl-, cyclic (5-14),(7-12)-;isegananum;ISEGANAN [MI];Q9SAI36COS;ISEGANAN [WHO-DD];CHEMBL2110753;GTPL10822;DTXCID90102906;EX-A7465;DA-64513;NS00121746;ARG-GLY-GLY-LEU-CYS-TYR-CYS-ARG-GLY-ARG-PHE-CYS-VAL-CYS-VAL-GLY-ARG-NH2, CYCLIC (5-14, 7-12) DISULFIDE;L-ARGININAMIDE, L-ARGINYLGLYCYLGLYCYL-L-LEUCYL-L-CYSTEINYL-L-TYROSYL-L-CYSTEINYL-L-ARGINYLGLYCYL-L-ARGINYL-L-PHENYLALANYL-L-CYSTEINYL-L-VALYL-L-CYSTEINYL-L-VALYLGLYCYL-, CYCLIC (5->14), (7->12)-BIS(DISULFIDE);

Custom Peptide Synthesis
cGMP Peptide
  • Registration of APIs
  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C78H126N30O18S4
M.W/Mr.
1900.3
Sequence
One Letter Code:RGGLCYCRGRFCVCVGR
Three Letter Code:H-Arg-Gly-Gly-Leu-Cys(1)-Tyr-Cys(2)-Arg-Gly-Arg-Phe-Cys(2)-Val-Cys(1)-Val-Gly-Arg-NH2
Application
Antibacterial.
Biological Activity
Iseganan, an antimicrobial peptide, is active against aerobic and anaerobic gram-positive and gram-negative bacteria as well as fungi and yeasts.

Iseganan is a synthetic peptide compound belonging to the class of antimicrobial peptides, specifically designed to mimic the innate immune system's natural defense mechanisms. Structurally, it is a cationic peptide derivative of protegrin, characterized by its ability to interact with microbial membranes and disrupt their integrity. Due to its broad-spectrum antimicrobial activity and unique mode of action, iseganan has attracted significant attention in the fields of microbiology, peptide therapeutics research, and membrane biochemistry. Its stability, ease of synthesis, and well-characterized mechanism make it a valuable tool for exploring host-pathogen interactions and developing new antimicrobial strategies in a laboratory setting.

Antimicrobial mechanism studies: Iseganan serves as an important model for investigating the mechanisms underlying peptide-mediated microbial killing. Researchers utilize it to dissect how cationic peptides interact with bacterial, fungal, or viral membranes, leading to membrane permeabilization and cell death. These studies provide critical insights into the molecular determinants of antimicrobial selectivity and potency, informing the rational design of next-generation peptide antibiotics and advancing the understanding of innate immune defense systems.

Peptide-membrane interaction assays: Due to its well-defined amphipathic structure, iseganan is frequently employed in biophysical studies examining peptide-lipid interactions. Using techniques such as circular dichroism spectroscopy, fluorescence assays, and electron microscopy, scientists can elucidate how iseganan binds to and perturbs model lipid bilayers. These experiments contribute to the broader understanding of membrane-active peptides, supporting both fundamental membrane biochemistry research and the development of synthetic analogs with tailored properties.

Biofilm inhibition research: Iseganan is widely investigated for its ability to prevent or disrupt biofilm formation by pathogenic microorganisms. In vitro assays utilize this peptide to measure its effects on biofilm biomass, cell viability within biofilms, and the modulation of biofilm-associated gene expression. Such studies are crucial for identifying strategies to combat persistent infections and for screening new peptide-based agents capable of targeting microbial communities that are resistant to conventional antimicrobials.

Peptide engineering and structure-activity relationship analysis: The defined sequence and activity profile of iseganan make it a valuable template for peptide engineering efforts. Researchers modify its amino acid composition, charge distribution, or secondary structure to generate analogs with improved specificity, reduced cytotoxicity, or enhanced stability. Systematic structure-activity relationship (SAR) studies using iseganan derivatives enable the identification of key residues and motifs responsible for antimicrobial activity, guiding the rational optimization of peptide-based antimicrobial agents.

Analytical method development: Iseganan is also utilized as a reference standard or positive control in the development and validation of analytical methods for peptide quantification and characterization. Techniques such as high-performance liquid chromatography (HPLC), mass spectrometry, and capillary electrophoresis rely on well-characterized peptides like iseganan to establish assay sensitivity, reproducibility, and specificity. This application supports the broader field of peptide analytics, ensuring the reliability of experimental results and facilitating quality control in peptide research and manufacturing workflows.

Source#
Synthetic
InChI
InChI=1S/C78H126N30O18S4/c1-39(2)28-49(99-57(111)32-93-56(110)31-94-63(115)45(79)16-10-24-89-75(81)82)66(118)103-53-36-128-130-38-55(72(124)107-60(40(3)4)73(125)96-34-58(112)97-46(62(80)114)17-11-25-90-76(83)84)106-74(126)61(41(5)6)108-71(123)54-37-129-127-35-52(104-68(120)51(102-70(53)122)30-43-20-22-44(109)23-21-43)69(121)100-47(18-12-26-91-77(85)86)64(116)95-33-59(113)98-48(19-13-27-92-78(87)88)65(117)101-50(67(119)105-54)29-42-14-8-7-9-15-42/h7-9,14-15,20-23,39-41,45-55,60-61,109H,10-13,16-19,24-38,79H2,1-6H3,(H2,80,114)(H,93,110)(H,94,115)(H,95,116)(H,96,125)(H,97,112)(H,98,113)(H,99,111)(H,100,121)(H,101,117)(H,102,122)(H,103,118)(H,104,120)(H,105,119)(H,106,126)(H,107,124)(H,108,123)(H4,81,82,89)(H4,83,84,90)(H4,85,86,91)(H4,87,88,92)/t45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,60-,61-/m0/s1
InChI Key
GUCYBPFJNGVFEB-XELKFLSISA-N

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