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140896-21-5 | Indolicidin
CAS No: 140896-21-5 Catalog No: AG01CPAF MDL No:MFCD00214306
Product Description
Catalog Number:
AG01CPAF
Chemical Name:
Indolicidin
CAS Number:
140896-21-5
Molecular Formula:
C100H132N26O13
Molecular Weight:
1906.2845
MDL Number:
MFCD00214306
IUPAC Name:
(2S)-1-[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]hexanoyl]amino]-3-(1H-indol-3-yl)propanoyl]-N-[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-5-carbamimidamido-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
InChI:
InChI=1S/C100H132N26O13/c1-5-57(4)85(102)95(136)123-79(45-56(2)3)96(137)124-42-20-36-82(124)92(133)118-76(46-58-51-110-68-28-11-6-23-63(58)68)89(130)116-74(33-16-17-39-101)88(129)121-80(49-61-54-113-71-31-14-9-26-66(61)71)97(138)125-43-21-38-84(125)94(135)120-78(48-60-53-112-70-30-13-8-25-65(60)70)91(132)122-81(50-62-55-114-72-32-15-10-27-67(62)72)98(139)126-44-22-37-83(126)93(134)119-77(47-59-52-111-69-29-12-7-24-64(59)69)90(131)117-75(35-19-41-109-100(106)107)87(128)115-73(86(103)127)34-18-40-108-99(104)105/h6-15,23-32,51-57,73-85,110-114H,5,16-22,33-50,101-102H2,1-4H3,(H2,103,127)(H,115,128)(H,116,130)(H,117,131)(H,118,133)(H,119,134)(H,120,135)(H,121,129)(H,122,132)(H,123,136)(H4,104,105,108)(H4,106,107,109)/t57-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-/m0/s1
InChI Key:
USSYUMHVHQSYNA-SLDJZXPVSA-N
SMILES:
NCCCCC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)CCCNC(=N)N)CCCNC(=N)N)Cc1c[nH]c2c1cccc2)Cc1c[nH]c2c1cccc2)Cc1c[nH]c2c1cccc2)Cc1c[nH]c2c1cccc2)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C1CCCN1C(=O)C(NC(=O)C(C(CC)C)N)CC(C)C
Properties
Complexity:
4190
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
14
Defined Bond Stereocenter Count:
0
Exact Mass:
1906.05g/mol
Formal Charge:
0
Heavy Atom Count:
139
Hydrogen Bond Acceptor Count:
17
Hydrogen Bond Donor Count:
23
Isotope Atom Count:
0
Molecular Weight:
1906.325g/mol
Monoisotopic Mass:
1905.047g/mol
Rotatable Bond Count:
50
Topological Polar Surface Area:
621A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.8
Literature
| Title | Journal |
|---|---|
| In vitro activity of several antimicrobial peptides against colistin-susceptible and colistin-resistant Acinetobacter baumannii. | Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20120401 |
| Antibacterial and anti-biofilm effects of cathelicidin peptides against pathogens isolated from cystic fibrosis patients. | Peptides 20110901 |
| Isopeptide ligation catalyzed by quintessential sortase A: mechanistic cues from cyclic and branched oligomers of indolicidin. | The Journal of biological chemistry 20110708 |
| Indolicidin action on membrane permeability: carrier mechanism versus pore formation. | Biochimica et biophysica acta 20110101 |
| Effect of antimicrobial peptide-amide: indolicidin on biological membranes. | Journal of biomedicine & biotechnology 20110101 |
| Interaction studies of novel cell selective antimicrobial peptides with model membranes and E. coli ATCC 11775. | Biochimica et biophysica acta 20101001 |
| The effects of tryptophan and hydrophobicity on the structure and bioactivity of novel indolicidin derivatives with promising pharmaceutical potential. | Organic & biomolecular chemistry 20100407 |
| Structure-activity relationship of indolicidin, a Trp-rich antibacterial peptide. | Journal of peptide science : an official publication of the European Peptide Society 20100401 |
| High potency and broad-spectrum antimicrobial peptides synthesized via ring-opening polymerization of alpha-aminoacid-N-carboxyanhydrides. | Biomacromolecules 20100111 |
| Differential activity of innate defense antimicrobial peptides against Nocardia species. | BMC microbiology 20100101 |
| Combinatorial microscopy for the study of protein-membrane interactions in supported lipid bilayers: Order parameter measurements by combined polarized TIRFM/AFM. | Journal of structural biology 20091001 |
| Coupling molecular dynamics simulations with experiments for the rational design of indolicidin-analogous antimicrobial peptides. | Journal of molecular biology 20090925 |
| Design of novel indolicidin-derived antimicrobial peptides with enhanced cell specificity and potent anti-inflammatory activity. | Peptides 20090501 |
| The novel adjuvant combination of CpG ODN, indolicidin and polyphosphazene induces potent antibody- and cell-mediated immune responses in mice. | Vaccine 20090323 |
| Study of the antimicrobial peptide indolicidin and a mutant in micelle medium by molecular dynamics simulation. | Genetics and molecular research : GMR 20081007 |
| Oxidized phospholipids as potential molecular targets for antimicrobial peptides. | Biochimica et biophysica acta 20081001 |
| An atomic force microscopy study of the interactions between indolicidin and supported planar bilayers. | Journal of nanoscience and nanotechnology 20080901 |
| Cationic peptide-induced remodelling of model membranes: direct visualization by in situ atomic force microscopy. | Journal of structural biology 20080401 |
| Thermodynamics of the interactions of tryptophan-rich cathelicidin antimicrobial peptides with model and natural membranes. | Biochimica et biophysica acta 20080401 |
| Efficacy of the bovine antimicrobial peptide indolicidin combined with piperacillin/tazobactam in experimental rat models of polymicrobial peritonitis. | Critical care medicine 20080101 |
| [Activity of indolicidin, alone or together with oxacillin, against Staphylococcus aureus and S. epidermidis]. | Medycyna doswiadczalna i mikrobiologia 20080101 |
| Molecular dynamics simulations of indolicidin association with model lipid bilayers. | Biophysical journal 20070615 |
| Cation-pi interactions stabilize the structure of the antimicrobial peptide indolicidin near membranes: molecular dynamics simulations. | The journal of physical chemistry. B 20070111 |
| Fungicidal activity of five cathelicidin peptides against clinically isolated yeasts. | The Journal of antimicrobial chemotherapy 20061101 |
| Solvent-dependent structure of two tryptophan-rich antimicrobial peptides and their analogs studied by FTIR and CD spectroscopy. | Biochimica et biophysica acta 20061001 |
| Recombinant expression of indolicidin concatamers in Escherichia coli. | Applied microbiology and biotechnology 20060501 |
| Mechanisms of antimicrobial peptide action: studies of indolicidin assembly at model membrane interfaces by in situ atomic force microscopy. | Journal of structural biology 20060401 |
| Synthesis and HIV-1 integrase inhibitory activity of dimeric and tetrameric analogs of indolicidin. | Bioorganic & medicinal chemistry letters 20041115 |
| New indolicidin analogues with potent antibacterial activity. | The journal of peptide research : official journal of the American Peptide Society 20041101 |
| Membrane-mediated capillary electrophoresis: interaction of cationic peptides with bicelles. | Electrophoresis 20040501 |
| Antiviral activity of antimicrobial cationic peptides against Junin virus and herpes simplex virus. | International journal of antimicrobial agents 20040401 |
| [Structure-function relationship between analogues of the antibacterial peptide indolicidin. I. Synthesis and biological activity of analogues with increased amphipathicity and elevated net positive charge of the molecule]. | Bioorganicheskaia khimiia 20040101 |
| Structure-based design of an indolicidin peptide analogue with increased protease stability. | Biochemistry 20031209 |
| Membrane binding and permeation by indolicidin analogs studied by a biomimetic lipid/polydiacetylene vesicle assay. | Peptides 20031101 |
| Indolicidin, a 13-residue basic antimicrobial peptide rich in tryptophan and proline, interacts with Ca(2+)-calmodulin. | Biochemical and biophysical research communications 20031003 |
| Fungicidal effect of indolicidin and its interaction with phospholipid membranes. | Biochemical and biophysical research communications 20030530 |
| Induction of autophagic cell death in Leishmania donovani by antimicrobial peptides. | Molecular and biochemical parasitology 20030301 |
| Cathelicidin peptides as candidates for a novel class of antimicrobials. | Current pharmaceutical design 20020101 |
| Tryptophan-rich antimicrobial peptides: comparative properties and membrane interactions. | Biochemistry and cell biology = Biochimie et biologie cellulaire 20020101 |
| Comparison of the membrane association of two antimicrobial peptides, magainin 2 and indolicidin. | Biophysical journal 20011101 |
| Structure-function relationships in the tryptophan-rich, antimicrobial peptide indolicidin. | Journal of peptide science : an official publication of the European Peptide Society 20011001 |
| Morphology of fast-tumbling bicelles: a small angle neutron scattering and NMR study. | Biochimica et biophysica acta 20010806 |
| Protein chemistry at membrane interfaces: non-additivity of electrostatic and hydrophobic interactions. | Journal of molecular biology 20010608 |
| Determination of membrane immersion depth with O(2): a high-pressure (19)F NMR study. | Biophysical journal 20010301 |
| Formation and characterization of a single Trp-Trp cross-link in indolicidin that confers protease stability without altering antimicrobial activity. | The Journal of biological chemistry 20000421 |
| Activity of nitazoxanide alone and in combination with azithromycin and rifabutin against Cryptosporidium parvum in cell culture. | The Journal of antimicrobial chemotherapy 20000401 |
| Structural features and biological activities of the cathelicidin-derived antimicrobial peptides. | Biopolymers 20000101 |
| Antimicrobial activity of polycationic peptides. | Peptides 19991101 |
| In vitro anticryptosporidial activity of ranalexin alone and in combination with other peptides and with hydrophobic antibiotics. | European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 19991101 |
| In-vitro activity of polycationic peptides against Cryptosporidium parvum, Pneumocystis carinii and yeast clinical isolates. | The Journal of antimicrobial chemotherapy 19990901 |
| In-vitro activity of lytic peptides alone and in combination with macrolides and inhibitors of dihydrofolate reductase against Pneumocystis carinii. | The Journal of antimicrobial chemotherapy 19981001 |
| Anti-HIV-1 activity of indolicidin, an antimicrobial peptide from neutrophils. | Journal of leukocyte biology 19980101 |
| Liposomal entrapment of the neutrophil-derived peptide indolicidin endows it with in vivo antifungal activity. | Biochimica et biophysica acta 19950726 |
| Indolicidin, a novel bactericidal tridecapeptide amide from neutrophils. | The Journal of biological chemistry 19920305 |
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