Indolicidin (BioDeep_00000180017)

   

human metabolite blood metabolite


代谢物信息卡片


6-amino-2-[2-({1-[2-(2-amino-3-methylpentanamido)-4-methylpentanoyl]pyrrolidin-2-yl}formamido)-3-(1H-indol-3-yl)propanamido]-N-(1-{2-[(1-{[1-(2-{[1-({4-carbamimidamido-1-[(4-carbamimidamido-1-carbamoylbutyl)carbamoyl]butyl}carbamoyl)-2-(1H-indol-3-yl)ethyl]carbamoyl}pyrrolidin-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamoyl}-2-(1H-indol-3-yl)ethyl)carbamoyl]pyrrolidin-1-yl}-3-(1H-indol-3-yl)-1-oxopropan-2-yl)hexanamide

化学式: C100H132N26O13 (1905.0466662000003)
中文名称: Indolicidin
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCC(C)C(C(=O)NC(CC(C)C)C(=O)N1CCCC1C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)NC(CCCCN)C(=O)NC(CC4=CNC5=CC=CC=C54)C(=O)N6CCCC6C(=O)NC(CC7=CNC8=CC=CC=C87)C(=O)NC(CC9=CNC1=CC=CC=C19)C(=O)N1CCCC1C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)N)N
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)

描述信息

D000890 - Anti-Infective Agents > D023181 - Antimicrobial Cationic Peptides

同义名列表

2 个代谢物同义名

6-amino-2-[2-({1-[2-(2-amino-3-methylpentanamido)-4-methylpentanoyl]pyrrolidin-2-yl}formamido)-3-(1H-indol-3-yl)propanamido]-N-(1-{2-[(1-{[1-(2-{[1-({4-carbamimidamido-1-[(4-carbamimidamido-1-carbamoylbutyl)carbamoyl]butyl}carbamoyl)-2-(1H-indol-3-yl)ethyl]carbamoyl}pyrrolidin-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamoyl}-2-(1H-indol-3-yl)ethyl)carbamoyl]pyrrolidin-1-yl}-3-(1H-indol-3-yl)-1-oxopropan-2-yl)hexanamide; Indolicidin



数据库引用编号

5 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Lawrence R Walker, Michael T Marty. Lipid tails modulate antimicrobial peptide membrane incorporation and activity. Biochimica et biophysica acta. Biomembranes. 2022 04; 1864(4):183870. doi: 10.1016/j.bbamem.2022.183870. [PMID: 35077676]
  • Mark A McLean, Ilia G Denisov, Yelena V Grinkova, Stephen G Sligar. Dark, Ultra-Dark and Ultra-Bright Nanodiscs for membrane protein investigations. Analytical biochemistry. 2020 10; 607(?):113860. doi: 10.1016/j.ab.2020.113860. [PMID: 32750355]
  • Annarita Falanga, Antonietta Siciliano, Mariateresa Vitiello, Gianluigi Franci, Valentina Del Genio, Stefania Galdiero, Marco Guida, Federica Carraturo, Amir Fahmi, Emilia Galdiero. Ecotoxicity Evaluation of Pristine and Indolicidin-coated Silver Nanoparticles in Aquatic and Terrestrial Ecosystem. International journal of nanomedicine. 2020; 15(?):8097-8108. doi: 10.2147/ijn.s260396. [PMID: 33116520]
  • Josefine Eilsø Nielsen, Tania Kjellerup Lind, Abdullah Lone, Yuri Gerelli, Paul Robert Hansen, Håvard Jenssen, Marité Cárdenas, Reidar Lund. A biophysical study of the interactions between the antimicrobial peptide indolicidin and lipid model systems. Biochimica et biophysica acta. Biomembranes. 2019 07; 1861(7):1355-1364. doi: 10.1016/j.bbamem.2019.04.003. [PMID: 30978313]
  • Josefine Eilsø Nielsen, Victoria Ariel Bjørnestad, Reidar Lund. Resolving the structural interactions between antimicrobial peptides and lipid membranes using small-angle scattering methods: the case of indolicidin. Soft matter. 2018 Nov; 14(43):8750-8763. doi: 10.1039/c8sm01888j. [PMID: 30358793]
  • Ching-Wei Tsai, Ze-Wei Lin, Wen-Fang Chang, Yi-Fan Chen, Wei-Wen Hu. Development of an indolicidin-derived peptide by reducing membrane perturbation to decrease cytotoxicity and maintain gene delivery ability. Colloids and surfaces. B, Biointerfaces. 2018 May; 165(?):18-27. doi: 10.1016/j.colsurfb.2018.02.007. [PMID: 29448216]
  • Karen Luna-Ramirez, Marisa Skaljac, Jens Grotmann, Phillipp Kirfel, Andreas Vilcinskas. Orally Delivered Scorpion Antimicrobial Peptides Exhibit Activity against Pea Aphid (Acyrthosiphon pisum) and Its Bacterial Symbionts. Toxins. 2017 08; 9(9):. doi: 10.3390/toxins9090261. [PMID: 28837113]
  • Peter Fojan, Leonid Gurevich. Atomic Force Microscopy Study of the Interactions of Indolicidin with Model Membranes and DNA. Methods in molecular biology (Clifton, N.J.). 2017; 1548(?):201-215. doi: 10.1007/978-1-4939-6737-7_14. [PMID: 28013506]
  • Sapir Ron-Doitch, Beate Sawodny, Andreas Kühbacher, Mirjam M Nordling David, Ayan Samanta, Jaywant Phopase, Anke Burger-Kentischer, May Griffith, Gershon Golomb, Steffen Rupp. Reduced cytotoxicity and enhanced bioactivity of cationic antimicrobial peptides liposomes in cell cultures and 3D epidermis model against HSV. Journal of controlled release : official journal of the Controlled Release Society. 2016 05; 229(?):163-171. doi: 10.1016/j.jconrel.2016.03.025. [PMID: 27012977]
  • Rajat Gupta, Prasanta Kalita, Omkar Patil, Sanat Mohanty. An investigation of folic acid-protein association sites and the effect of this association on folic acid self-assembly. Journal of molecular modeling. 2015 Dec; 21(12):308. doi: 10.1007/s00894-015-2847-2. [PMID: 26560480]
  • Kathleen F Wang, Ramanathan Nagarajan, Terri A Camesano. Differentiating antimicrobial peptides interacting with lipid bilayer: Molecular signatures derived from quartz crystal microbalance with dissipation monitoring. Biophysical chemistry. 2015 Jan; 196(?):53-67. doi: 10.1016/j.bpc.2014.09.003. [PMID: 25307196]
  • V A Lazarenko, Yu D Lyashev, N I Shevchenko. Effect of a synthetic indolicidin analogue on lipid peroxidation in thermal burns. Bulletin of experimental biology and medicine. 2014 Aug; 157(4):447-9. doi: 10.1007/s10517-014-2587-9. [PMID: 25110080]
  • Chris Neale, Jenny C Y Hsu, Christopher M Yip, Régis Pomès. Indolicidin binding induces thinning of a lipid bilayer. Biophysical journal. 2014 Apr; 106(8):L29-31. doi: 10.1016/j.bpj.2014.02.031. [PMID: 24739184]
  • Tod D Romo, Alan Grossfield. Unknown unknowns: the challenge of systematic and statistical error in molecular dynamics simulations. Biophysical journal. 2014 Apr; 106(8):1553-4. doi: 10.1016/j.bpj.2014.03.007. [PMID: 24739152]
  • Ching-Wei Tsai, Ruoh-Chyu Ruaan, Chih-I Liu. Adsorption of antimicrobial indolicidin-derived peptides on hydrophobic surfaces. Langmuir : the ACS journal of surfaces and colloids. 2012 Jul; 28(28):10446-52. doi: 10.1021/la301401v. [PMID: 22721449]
  • In-Chul Yeh, Daniel R Ripoll, Anders Wallqvist. Free energy difference in indolicidin attraction to eukaryotic and prokaryotic model cell membranes. The journal of physical chemistry. B. 2012 Mar; 116(10):3387-96. doi: 10.1021/jp211883u. [PMID: 22376120]
  • Tatyana I Rokitskaya, Nikolay I Kolodkin, Elena A Kotova, Yuri N Antonenko. Indolicidin action on membrane permeability: carrier mechanism versus pore formation. Biochimica et biophysica acta. 2011 Jan; 1808(1):91-7. doi: 10.1016/j.bbamem.2010.09.005. [PMID: 20851098]
  • Attila Gergely Végh, Krisztina Nagy, Zoltán Bálint, Adám Kerényi, Gábor Rákhely, György Váró, Zsolt Szegletes. Effect of antimicrobial peptide-amide: indolicidin on biological membranes. Journal of biomedicine & biotechnology. 2011; 2011(?):670589. doi: 10.1155/2011/670589. [PMID: 21765635]
  • Seema Joshi, Gopal Singh Bisht, Diwan S Rawat, Anil Kumar, Rita Kumar, Souvik Maiti, Santosh Pasha. Interaction studies of novel cell selective antimicrobial peptides with model membranes and E. coli ATCC 11775. Biochimica et biophysica acta. 2010 Oct; 1798(10):1864-75. doi: 10.1016/j.bbamem.2010.06.016. [PMID: 20599694]
  • John Oreopoulos, Christopher M Yip. 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. 2009 Oct; 168(1):21-36. doi: 10.1016/j.jsb.2009.02.011. [PMID: 19268707]
  • Ching-Wei Tsai, Ning-Yi Hsu, Chang-Hsu Wang, Chia-Yu Lu, Yung Chang, Hui-Hsu Gavin Tsai, Rouh-Chyu Ruaan. Coupling molecular dynamics simulations with experiments for the rational design of indolicidin-analogous antimicrobial peptides. Journal of molecular biology. 2009 Sep; 392(3):837-54. doi: 10.1016/j.jmb.2009.06.071. [PMID: 19576903]
  • J Kovacs-Nolan, J W Mapletoft, Z Lawman, L A Babiuk, S van Drunen Littel-van den Hurk. Formulation of bovine respiratory syncytial virus fusion protein with CpG oligodeoxynucleotide, cationic host defence peptide and polyphosphazene enhances humoral and cellular responses and induces a protective type 1 immune response in mice. The Journal of general virology. 2009 Aug; 90(Pt 8):1892-1905. doi: 10.1099/vir.0.011684-0. [PMID: 19386785]
  • C A Fuzo, J R M Castro, L Degrève. Study of the antimicrobial peptide indolicidin and a mutant in micelle medium by molecular dynamics simulation. Genetics and molecular research : GMR. 2008 Oct; 7(4):986-99. doi: 10.4238/vol7-4gmr477. [PMID: 19048478]
  • Juha-Pekka Mattila, Karen Sabatini, Paavo K J Kinnunen. Oxidized phospholipids as potential molecular targets for antimicrobial peptides. Biochimica et biophysica acta. 2008 Oct; 1778(10):2041-50. doi: 10.1016/j.bbamem.2008.03.020. [PMID: 18440299]
  • H J Askou, R N Jakobsen, P Fojan. An atomic force microscopy study of the interactions between indolicidin and supported planar bilayers. Journal of nanoscience and nanotechnology. 2008 Sep; 8(9):4360-9. doi: 10.1166/jnn.2008.291. [PMID: 19049026]
  • Valery V Andrushchenko, Mohammed H Aarabi, Leonard T Nguyen, Elmar J Prenner, Hans J Vogel. Thermodynamics of the interactions of tryptophan-rich cathelicidin antimicrobial peptides with model and natural membranes. Biochimica et biophysica acta. 2008 Apr; 1778(4):1004-14. doi: 10.1016/j.bbamem.2007.12.022. [PMID: 18222168]
  • James E Shaw, Raquel F Epand, Jenny C Y Hsu, Gary C H Mo, Richard M Epand, Christopher M Yip. Cationic peptide-induced remodelling of model membranes: direct visualization by in situ atomic force microscopy. Journal of structural biology. 2008 Apr; 162(1):121-38. doi: 10.1016/j.jsb.2007.11.003. [PMID: 18180166]
  • Roberto Ghiselli, Andrea Giacometti, Oscar Cirioni, Federico Mocchegiani, Fiorenza Orlando, Carmela Silvestri, Fabio Di Matteo, Alessandra Abbruzzetti, Giorgio Scalise, Vittorio Saba. Efficacy of the bovine antimicrobial peptide indolicidin combined with piperacillin/tazobactam in experimental rat models of polymicrobial peritonitis. Critical care medicine. 2008 Jan; 36(1):240-5. doi: 10.1097/01.ccm.0000292157.60632.89. [PMID: 18090372]
  • Jenny C Y Hsu, Christopher M Yip. Molecular dynamics simulations of indolicidin association with model lipid bilayers. Biophysical journal. 2007 Jun; 92(12):L100-2. doi: 10.1529/biophysj.107.108050. [PMID: 17416617]
  • James E Shaw, Jean-René Alattia, Jocelyne E Verity, Gilbert G Privé, Christopher M Yip. Mechanisms of antimicrobial peptide action: studies of indolicidin assembly at model membrane interfaces by in situ atomic force microscopy. Journal of structural biology. 2006 Apr; 154(1):42-58. doi: 10.1016/j.jsb.2005.11.016. [PMID: 16459101]
  • Chun-Hua Hsu, Chinpan Chen, Maou-Lin Jou, Alan Yueh-Luen Lee, Yu-Ching Lin, Yi-Ping Yu, Wei-Ting Huang, Shih-Hsiung Wu. Structural and DNA-binding studies on the bovine antimicrobial peptide, indolicidin: evidence for multiple conformations involved in binding to membranes and DNA. Nucleic acids research. 2005; 33(13):4053-64. doi: 10.1093/nar/gki725. [PMID: 16034027]
  • Annett Rozek, Jon-Paul S Powers, Carol L Friedrich, Robert E W Hancock. Structure-based design of an indolicidin peptide analogue with increased protease stability. Biochemistry. 2003 Dec; 42(48):14130-8. doi: 10.1021/bi035643g. [PMID: 14640680]
  • Revital Halevy, Annett Rozek, Sofiya Kolusheva, Robert E W Hancock, Raz Jelinek. Membrane binding and permeation by indolicidin analogs studied by a biomimetic lipid/polydiacetylene vesicle assay. Peptides. 2003 Nov; 24(11):1753-61. doi: 10.1016/j.peptides.2003.08.019. [PMID: 15019207]
  • Dong Gun Lee, Hyung Keun Kim, Sun Am Kim, Yoonkyung Park, Seong-Cheol Park, Seung-Hwan Jang, Kyung-Soo Hahm. Fungicidal effect of indolicidin and its interaction with phospholipid membranes. Biochemical and biophysical research communications. 2003 May; 305(2):305-10. doi: 10.1016/s0006-291x(03)00755-1. [PMID: 12745074]
  • Ananya Bera, Shashi Singh, Ramakrishnan Nagaraj, Tushar Vaidya. Induction of autophagic cell death in Leishmania donovani by antimicrobial peptides. Molecular and biochemical parasitology. 2003 Mar; 127(1):23-35. doi: 10.1016/s0166-6851(02)00300-6. [PMID: 12615333]
  • Andrea Giacometti, Oscar Cirioni, Roberto Ghiselli, Federico Mocchegiani, Maria Simona Del Prete, Claudio Viticchi, Wojciech Kamysz, Elzbieta ŁEmpicka, Vittorio Saba, Giorgio Scalise. Potential therapeutic role of cationic peptides in three experimental models of septic shock. Antimicrobial agents and chemotherapy. 2002 Jul; 46(7):2132-6. doi: 10.1128/aac.46.7.2132-2136.2002. [PMID: 12069965]
  • Qingshun Li, Christopher B Lawrence, H Maelor Davies, Nicholas P Everett. A tridecapeptide possesses both antimicrobial and protease-inhibitory activities. Peptides. 2002 Jan; 23(1):1-6. doi: 10.1016/s0196-9781(01)00572-1. [PMID: 11814611]
  • David J Schibli, Raquel F Epand, Hans J Vogel, Richard M Epand. Tryptophan-rich antimicrobial peptides: comparative properties and membrane interactions. Biochemistry and cell biology = Biochimie et biologie cellulaire. 2002; 80(5):667-77. doi: 10.1139/o02-147. [PMID: 12440706]
  • H Zhao, J P Mattila, J M Holopainen, P K Kinnunen. Comparison of the membrane association of two antimicrobial peptides, magainin 2 and indolicidin. Biophysical journal. 2001 Nov; 81(5):2979-91. doi: 10.1016/s0006-3495(01)75938-3. [PMID: 11606308]
  • P A Luchette, T N Vetman, R S Prosser, R E Hancock, M P Nieh, C J Glinka, S Krueger, J Katsaras. Morphology of fast-tumbling bicelles: a small angle neutron scattering and NMR study. Biochimica et biophysica acta. 2001 Aug; 1513(2):83-94. doi: 10.1016/s0005-2736(01)00358-3. [PMID: 11470082]
  • A S Ladokhin, S H White. Protein chemistry at membrane interfaces: non-additivity of electrostatic and hydrophobic interactions. Journal of molecular biology. 2001 Jun; 309(3):543-52. doi: 10.1006/jmbi.2001.4684. [PMID: 11397078]
  • R S Prosser, P A Luchette, P W Westerman, A Rozek, R E Hancock. Determination of membrane immersion depth with O(2): a high-pressure (19)F NMR study. Biophysical journal. 2001 Mar; 80(3):1406-16. doi: 10.1016/s0006-3495(01)76113-9. [PMID: 11222301]
  • A Rozek, C L Friedrich, R E Hancock. Structure of the bovine antimicrobial peptide indolicidin bound to dodecylphosphocholine and sodium dodecyl sulfate micelles. Biochemistry. 2000 Dec; 39(51):15765-74. doi: ". [PMID: 11123901]
  • N Sitaram, R Nagaraj. Interaction of antimicrobial peptides with biological and model membranes: structural and charge requirements for activity. Biochimica et biophysica acta. 1999 Dec; 1462(1-2):29-54. doi: 10.1016/s0005-2736(99)00199-6. [PMID: 10590301]
  • A Giacometti, O Cirioni, F Barchiesi, M Fortuna, G Scalise. In-vitro activity of cationic peptides alone and in combination with clinically used antimicrobial agents against Pseudomonas aeruginosa. The Journal of antimicrobial chemotherapy. 1999 Nov; 44(5):641-5. doi: 10.1093/jac/44.5.641. [PMID: 10552980]
  • A S Ladokhin, M E Selsted, S H White. Bilayer interactions of indolicidin, a small antimicrobial peptide rich in tryptophan, proline, and basic amino acids. Biophysical journal. 1997 Feb; 72(2 Pt 1):794-805. doi: 10.1016/s0006-3495(97)78713-7. [PMID: 9017204]
  • C Subbalakshmi, V Krishnakumari, R Nagaraj, N Sitaram. Requirements for antibacterial and hemolytic activities in the bovine neutrophil derived 13-residue peptide indolicidin. FEBS letters. 1996 Oct; 395(1):48-52. doi: 10.1016/0014-5793(96)00996-9. [PMID: 8849687]
  • T J Falla, D N Karunaratne, R E Hancock. Mode of action of the antimicrobial peptide indolicidin. The Journal of biological chemistry. 1996 Aug; 271(32):19298-303. doi: 10.1074/jbc.271.32.19298. [PMID: 8702613]
  • I Ahmad, W R Perkins, D M Lupan, M E Selsted, A S Janoff. Liposomal entrapment of the neutrophil-derived peptide indolicidin endows it with in vivo antifungal activity. Biochimica et biophysica acta. 1995 Jul; 1237(2):109-14. doi: 10.1016/0005-2736(95)00087-j. [PMID: 7632702]