Need Assistance?

US & Canada:
+
UK: +

Our Highlights

GMP Grade Efficient workshop for GMP production.
Optimal Prices Buying products on this site guarantees the best price!
Commercial Batches Independent GMP manufacturing suites that handle commercial batches
Prompt Delivery Warehouses in multiple cities to ensure timely delivery
Flexible Quantity Quantities available from milligrams to ton

Cathelicidin-PY

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

Cathelicidin-PY has been identified from the skin secretions of the frog Paa yunnanensis. The action of antimicrobial activity of Cathelicidin-PY is through the destruction of the cell membrane.

Category

Functional Peptides

Catalog number

BAT-013502

Molecular Formula

C151H261N47O39S2

Molecular Weight

3423.10

Specification
Reference Reading

IUPAC Name

(4S)-4-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(4R,7S,10S,13S,16R)-16-[[(2S)-6-amino-2-[[(2S)-2-amino-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]-13-(2-amino-2-oxoethyl)-10-benzyl-7-(2-methylpropyl)-6,9,12,15-tetraoxo-1,2-dithia-5,8,11,14-tetrazacycloheptadecane-4-carbonyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]amino]-5-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-5-amino-1-(carboxymethylamino)-1,5-dioxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-oxopentanoic acid

Sequence

RKCNFLCKLKEKLRTVITSHIDKVLRPQG

InChI

InChI=1S/C151H261N47O39S2/c1-19-82(15)117(144(233)188-105(69-113(206)207)136(225)175-93(45-28-33-57-156)128(217)192-115(80(11)12)142(231)187-101(65-79(9)10)132(221)180-97(47-36-60-169-151(164)165)148(237)198-61-37-48-109(198)141(230)179-95(49-51-110(158)202)122(211)170-71-114(208)209)194-137(226)103(67-87-70-166-75-171-87)185-138(227)106(72-199)189-146(235)119(84(17)200)197-145(234)118(83(16)20-2)195-143(232)116(81(13)14)193-147(236)120(85(18)201)196-129(218)94(46-35-59-168-150(162)163)176-131(220)99(63-77(5)6)181-124(213)91(43-26-31-55-154)173-127(216)96(50-52-112(204)205)178-123(212)90(42-25-30-54-153)174-130(219)98(62-76(3)4)182-125(214)92(44-27-32-56-155)177-139(228)107-73-238-239-74-108(190-126(215)89(41-24-29-53-152)172-121(210)88(157)40-34-58-167-149(160)161)140(229)186-104(68-111(159)203)135(224)184-102(66-86-38-22-21-23-39-86)134(223)183-100(64-78(7)8)133(222)191-107/h21-23,38-39,70,75-85,88-109,115-120,199-201H,19-20,24-37,40-69,71-74,152-157H2,1-18H3,(H2,158,202)(H2,159,203)(H,166,171)(H,170,211)(H,172,210)(H,173,216)(H,174,219)(H,175,225)(H,176,220)(H,177,228)(H,178,212)(H,179,230)(H,180,221)(H,181,213)(H,182,214)(H,183,223)(H,184,224)(H,185,227)(H,186,229)(H,187,231)(H,188,233)(H,189,235)(H,190,215)(H,191,222)(H,192,217)(H,193,236)(H,194,226)(H,195,232)(H,196,218)(H,197,234)(H,204,205)(H,206,207)(H,208,209)(H4,160,161,167)(H4,162,163,168)(H4,164,165,169)/t82-,83-,84+,85+,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,115-,116-,117-,118-,119-,120-/m0/s1

InChI Key

YFYXVASEOIOKIC-RKCSMFMJSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CC(=O)O)C(=O)NC(CCCCN)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(CCCNC(=N)N)C(=O)N1CCCC1C(=O)NC(CCC(=O)N)C(=O)NCC(=O)O)NC(=O)C(CC2=CN=CN2)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(C(C)CC)NC(=O)C(C(C)C)NC(=O)C(C(C)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)O)NC(=O)C(CCCCN)NC(=O)C(CC(C)C)NC(=O)C(CCCCN)NC(=O)C3CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N3)CC(C)C)CC4=CC=CC=C4)CC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CCCNC(=N)N)N

1. Flow-Based Fmoc-SPPS Preparation and SAR Study of Cathelicidin-PY Reveals Selective Antimicrobial Activity

Shama Dissanayake, Junming He, Sung H Yang, Margaret A Brimble, Paul W R Harris, Alan J Cameron Molecules. 2023 Feb 20;28(4):1993. doi: 10.3390/molecules28041993.

Antimicrobial peptides (AMPs) hold promise as novel therapeutics in the fight against multi-drug-resistant pathogens. Cathelicidin-PY (NH2-RKCNFLCKLKEKLRTVITSHIDKVLRPQG-COOH) is a 29-residue disulfide-cyclised antimicrobial peptide secreted as an innate host defence mechanism by the frog Paa yunnanensis (PY) and reported to possess broad-spectrum antibacterial and antifungal properties, exhibiting low cytotoxic and low hemolytic activity. Herein, we detail the total synthesis of cathelicidin-PY using an entirely on-resin synthesis, including assembly of the linear sequence by rapid flow Fmoc-SPPS and iodine-mediated disulfide bridge formation. By optimising a synthetic strategy to prepare cathelicidin-PY, this strategy was subsequently adapted to prepare a bicyclic head-to-tail cyclised derivative of cathelicidin-PY. The structure-activity relationship (SAR) of cathelicidin-PY with respect to the N-terminally positioned disulfide was further probed by preparing an alanine-substituted linear analogue and a series of lactam-bridged peptidomimetics implementing side chain to side chain cyclisation. The analogues were investigated for antimicrobial activity, secondary structure by circular dichroism (CD), and stability in human serum. Surprisingly, the disulfide bridge emerged as non-essential to antimicrobial activity and secondary structure but was amenable to synthetic modification. Furthermore, the synthetic AMP and multiple analogues demonstrated selective activity towards Gram-negative pathogen E. coli in physiologically relevant concentrations of divalent cations.

2. Structure and function of a potent lipopolysaccharide-binding antimicrobial and anti-inflammatory peptide

Lin Wei, Juanjuan Yang, Xiaoqin He, Guoxiang Mo, Jing Hong, Xiuwen Yan, Donghai Lin, Ren Lai J Med Chem. 2013 May 9;56(9):3546-56. doi: 10.1021/jm4004158. Epub 2013 Apr 29.

Antimicrobial peptides (AMPs) play pivotal roles in the innate defense of vertebrates. A novel AMP (cathelicidin-PY) has been identified from the skin secretions of the frog Paa yunnanensis . Cathelicidin-PY has an amino acid sequence of RKCNFLCKLKEKLRTVITSHIDKVLRPQG. Nuclear magnetic resonance (NMR) spectroscopy analysis revealed that cathelicidin-PY adopts a tertiary structure with a mostly positively charged surface containing a helix (Thr15-Ser19). It possesses strong antimicrobial activity, low hemolytic activity, low cytotoxicity against RAW 264.7 cells, and strong anti-inflammatory activity. The action of antimicrobial activity of cathelicidin-PY is through the destruction of the cell membrane. Moreover, cathelicidin-PY exerts anti-inflammatory activity by inhibiting the production of nitric oxide (NO) and inflammatory cytokines such as tumor necrosis factor (TNF-α), interleukin-6 (IL-6), and monocyte chemoattractant protein-1 (MCP-1). Cathelicidin-PY inhibits the activation of Toll-like receptor 4 (TLR4) inflammatory response pathways induced by lipopolysaccharide (LPS). The NMR titration experiments indicated that cathelicidin-PY can bind to LPS. In conclusion, we have identified a novel potent peptide antibiotic with both antimicrobial and anti-inflammatory activities and laid the groundwork for future research and development.

3. [Preliminary study of antimicrobial peptide cathelicidin-PY therapy in mice with acute liver failure]

Y Wang, X P Huang, J H Gan Zhonghua Gan Zang Bing Za Zhi. 2020 Mar 20;28(3):254-258. doi: 10.3760/cma.j.cn501113-20190301-00061.

Objective: To investigate the feasibility of cationic antimicrobial peptide cathelicidin-PY(PY) therapy through a mouse model of acute liver failure. Methods: The ability of different concentrations of antimicrobial peptide PY to neutralize endotoxin / lipopolysaccharide (LPS) in vitro was detected by Limulus Amebocyte Lysate (LAL) assay. Cell counting kit-8 (CCK-8) was used to detect the toxic effect of different concentrations of antimicrobial peptide PY on mouse monocyte macrophages (RAW264.7). An in vitro hemolysis experiment was used to evaluate the activity of antimicrobial peptide PY on healthy human erythrocytes. D-galactosamine combined with LPS- induced mouse model of acute liver failure was constructed. The antimicrobial peptide PY effect on survival rate of mouse model was observed. HE staining was used to observe the pathological changes of liver tissue. Immunohistochemistry and Western blotting were used to detect the expression of apoptosis-associated protein caspase-3. Intra-group comparisons were performed using t-test and analysis of variance. χ (2) test was used for the comparison of rates. Results: An in vitro experiment showed that the endotoxin neutralization rate was higher at very low dose (0.01 μmol/L), and exceeded 70% at medium-dose (10-40 μmol/L), and the difference between groups with different concentration was statistically significant (F = 569.22, P < 0.05). Medium-dose antimicrobial peptide PY had strong endotoxin neutralizing effect, low cytotoxicity and hemolytic activity. Moreover, in vivo experiments showed that the degree of liver injury and survival rate of mouse model was significantly improved with the medium-dose of antimicrobial peptide PY. Immunohistochemistry results showed that the expression of caspase-3 in the liver tissue was significantly depleted in the medium-dose group than that of the liver failure group, and the results were consistent with protein immunoblotting testing. Conclusion: Antimicrobial peptide PY possesses a strong ability to neutralize endotoxin and few toxic side effects. A specific dose of antimicrobial peptide PY can attenuate hepatocyte apoptosis and significantly improve the survival rate of animal model, and thus provides a new idea for the liver failure treatment.