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Ixosin-B

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Ixosin-B is an antibacterial peptide isolated from Ixodes sinensis (Hard tick). It has activity against gram-positive bacteria, gram-negative bacteria and fungi.

Category

Functional Peptides

Catalog number

BAT-012498

Molecular Formula

C165H263N57O48

Molecular Weight

3813.2

Specification
Reference Reading

IUPAC Name

(4S)-5-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-[[(2S)-1-[(2S)-5-amino-2-[[(2S,3S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]amino]-3-methylbutanoyl]amino]-3-carboxypropanoyl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxypropanoyl]amino]acetyl]amino]-3-methylpentanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoic acid

Synonyms

Ixosin-B-amide; Gln-Leu-Lys-Val-Asp-Leu-Trp-Gly-Thr-Arg-Ser-Gly-Ile-Gln-Pro-Glu-Gln-His-Ser-Ser-Gly-Lys-Ser-Asp-Val-Arg-Arg-Trp-Arg-Ser-Arg-Tyr-NH2

Purity

97.2%

Sequence

QLKVDLWGTRSGIQPEQHSSGKSDVRRWRSRY-NH2

Storage

Store at -20°C

InChI

InChI=1S/C165H263N57O48/c1-12-83(10)130(218-123(234)71-193-135(245)113(73-223)213-142(252)101(37-25-57-188-165(181)182)203-159(269)131(84(11)228)219-124(235)72-191-134(244)108(62-86-67-189-93-29-15-13-27-90(86)93)208-147(257)107(60-80(4)5)207-150(260)111(65-126(238)239)212-157(267)129(82(8)9)220-145(255)96(32-18-20-52-167)197-146(256)106(59-79(2)3)206-133(243)92(168)43-47-119(169)230)158(268)204-104(45-49-121(171)232)160(270)222-58-26-38-118(222)155(265)201-103(46-50-125(236)237)143(253)200-102(44-48-120(170)231)144(254)210-110(64-88-69-183-78-194-88)149(259)217-117(77-227)154(264)214-114(74-224)136(246)192-70-122(233)195-95(31-17-19-51-166)137(247)215-116(76-226)153(263)211-112(66-127(240)241)151(261)221-128(81(6)7)156(266)202-100(36-24-56-187-164(179)180)138(248)196-98(34-22-54-185-162(175)176)140(250)209-109(63-87-68-190-94-30-16-14-28-91(87)94)148(258)198-99(35-23-55-186-163(177)178)141(251)216-115(75-225)152(262)199-97(33-21-53-184-161(173)174)139(249)205-105(132(172)242)61-85-39-41-89(229)42-40-85/h13-16,27-30,39-42,67-69,78-84,92,95-118,128-131,189-190,223-229H,12,17-26,31-38,43-66,70-77,166-168H2,1-11H3,(H2,169,230)(H2,170,231)(H2,171,232)(H2,172,242)(H,183,194)(H,191,244)(H,192,246)(H,193,245)(H,195,233)(H,196,248)(H,197,256)(H,198,258)(H,199,262)(H,200,253)(H,201,265)(H,202,266)(H,203,269)(H,204,268)(H,205,249)(H,206,243)(H,207,260)(H,208,257)(H,209,250)(H,210,254)(H,211,263)(H,212,267)(H,213,252)(H,214,264)(H,215,247)(H,216,251)(H,217,259)(H,218,234)(H,219,235)(H,220,255)(H,221,261)(H,236,237)(H,238,239)(H,240,241)(H4,173,174,184)(H4,175,176,185)(H4,177,178,186)(H4,179,180,187)(H4,181,182,188)/t83-,84+,92-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,128-,129-,130-,131-/m0/s1

InChI Key

OAIRJZDFDFGABD-ZYAMVHPISA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CCC(=O)N)C(=O)N1CCCC1C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)N)C(=O)NC(CC2=CN=CN2)C(=O)NC(CO)C(=O)NC(CO)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CO)C(=O)NC(CC(=O)O)C(=O)NC(C(C)C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NC(CCCNC(=N)N)C(=O)NC(CO)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC5=CC=C(C=C5)O)C(=O)N)NC(=O)CNC(=O)C(CO)NC(=O)C(CCCNC(=N)N)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(CC6=CNC7=CC=CC=C76)NC(=O)C(CC(C)C)NC(=O)C(CC(=O)O)NC(=O)C(C(C)C)NC(=O)C(CCCCN)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)N)N

1. Structure-activity relationship of potent antimicrobial peptide analogs of Ixosin-B amide

Yu-Shan Wu, Zih-Jie Liao, Kai-Shiuan Wang, Feng-Di T Lung Bioorg Med Chem Lett. 2013 May 15;23(10):2929-32. doi: 10.1016/j.bmcl.2013.03.053. Epub 2013 Mar 25.

There is a great urgency in developing a new generation of antibiotics and antimicrobial agents since the bacterial resistance to antibiotics have increased dramatically. A series of overlapped peptide fragments of Ixosin-B, an antimicrobial peptide with amino acid sequence of QLKVDLWGTRSGIQPEQHSSGKSDVRRWRSRY, was designed, synthesized and examined for their antimicrobial activities against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa. A potent 11-mer peptide TSG-8-1, WWSYVRRWRSR-amide, was developed, which exhibited antimicrobial activity against E. coli and S. aureus while very little hemolytic activity in human erythrocytes was observed at high dose level. This peptide could be further modified for the development of a potent antimicrobial agent in the future.

2. Central Role of the Copper-Binding Motif in the Complex Mechanism of Action of Ixosin: Enhancing Oxidative Damage and Promoting Synergy with Ixosin B

M Daben J Libardo, Vitaliy Y Gorbatyuk, Alfredo M Angeles-Boza ACS Infect Dis. 2016 Jan 8;2(1):71-81. doi: 10.1021/acsinfecdis.5b00140. Epub 2015 Dec 14.

Ticks transmit multiple pathogens to different hosts without compromising their health. Their ability to evade microbial infections is largely a result of their effective innate immune response including various antimicrobial peptides. Therefore, a deep understanding of how ticks (and other arthropod vectors) control microbial loads could lead to the design of broad-spectrum antimicrobial agents. In this paper we study the role of the amino-terminal copper and nickel (ATCUN)-binding sequence in the peptide ixosin, isolated from the salivary glands of the hard tick Ixodes sinensis. Our results indicate that the ATCUN motif is not essential to the potency of ixosin, but is indispensable to its oxidative mechanism of action. Specifically, the ATCUN motif promotes dioxygen- and copper-dependent lipid (per)oxidation of bacterial membranes in a temporal fashion coinciding with the onset of bacterial death. Microscopy and studies on model membranes indicate that the oxidized phospholipids are utilized as potential targets of ixosin B (another tick salivary gland peptide) involving its delocalization to the bacterial membrane, thus resulting in a synergistic effect. Our proposed mechanism of action highlights the centrality of the ATCUN motif to ixosin's mechanism of action and demonstrates a novel way in which (tick) antimicrobial peptides (AMPs) utilize metal ions in its activity. This study suggests that ticks employ a variety of effectors to generate an amplified immune response, possibly justifying its vector competence.

3. Anticancer activities of an antimicrobial peptide derivative of Ixosin-B amide

Yu-Cheng Hsiao, Kai-Shiuan Wang, Shu-Huai Tsai, Wei-Ting Chao, Feng-Di T Lung Bioorg Med Chem Lett. 2013 Oct 15;23(20):5744-7. doi: 10.1016/j.bmcl.2013.07.063. Epub 2013 Aug 9.

In nature, antimicrobial peptides (AMPs) represent the first line of defense against infection by pathogens; thus, they are generally good candidates for the development of antimicrobial agents. Recently, we reported two potent antimicrobial peptides, KWLRRVWRWWR-amide (MAP-04-03) and KRLRRVWRRWR-amide (MAP-04-04), which were derived from a fragment of Ixosin-B-amide (KSDVRRWRSRY). Since some cationic AMPs exhibited cytotoxic activity against cancer cells, in the current study, we further investigated the anticancer activity of these potent antimicrobial peptides by antiproliferative assays and wound-healing assays, and the effect of peptide on the cytoskeleton alteration and cell morphology were analyzed by confocal microscopy. Results indicated that MAP-04-03 not only exhibited inhibitory effects on the proliferation (IC50=61.5 μM) and on the cell migration of MCF-7 breast cancer cells (at a concentration of 5 μM), but also affected the cytoskeleton at the concentration of 25 μM. These results demonstrated that MAP-04-03 can serve as a lead peptide analog for developing potent anticancer agents.