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Bombinin-Like Peptide BLP-1

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Bombinin-Like Peptide BLP-1 is an antimicrobial peptide derived from Bombina species.

Category

Peptide Inhibitors

Catalog number

BAT-009194

CAS number

138220-00-5

Molecular Formula

C115H194N34O33

Molecular Weight

2580.98

Specification
Reference Reading

IUPAC Name

(3S)-4-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S,3S)-2-[(2-aminoacetyl)amino]-3-methylpentanoyl]amino]acetyl]amino]propanoyl]amino]-3-hydroxypropanoyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]acetyl]amino]hexanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]hexanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-3-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]-3-(4H-imidazol-4-yl)propanoyl]amino]-3-phenylpropanoyl]amino]propanoyl]amino]-4-oxobutanoic acid

Synonyms

H-Gly-Ile-Gly-Ala-Ser-Ile-Leu-Ser-Ala-Gly-Lys-Ser-Ala-Leu-Lys-Gly-Leu-Ala-Lys-Gly-Leu-Ala-Glu-His-Phe-Ala-Asn-NH2; L-Aspartamide, glycyl-L-isoleucylglycyl-L-alanyl-L-seryl-L-isoleucyl-L-leucyl-L-seryl-L-alanylglycyl-L-lysyl-L-seryl-L-alanyl-L-leucyl-L-lysylglycyl-L-leucyl-L-alanyl-L-lysylglycyl-L-leucyl-L-alanyl-L-alpha-glutamyl-L-

Appearance

White Lyophilized Powder

Purity

≥95%

Density

1.3±0.1 g/cm3

Boiling Point

2546.9±65.0°C at 760 mmHg

Sequence

GIGASILSAGKSALKGLAKGLAEHFAN-NH2

Storage

Store in a cool and dry place and at 2-8°C for short term (days to weeks) or store at -20°C for long term (months to years)

InChI

InChI=1S/C115H194N34O33/c1-19-61(11)92(147-86(154)47-119)114(181)126-49-87(155)128-64(14)95(162)144-84(55-152)113(180)148-93(62(12)20-2)115(182)143-78(43-60(9)10)108(175)146-83(54-151)111(178)129-63(13)94(161)123-50-88(156)134-74(34-26-29-39-118)103(170)145-82(53-150)112(179)133-67(17)97(164)139-77(42-59(7)8)107(174)138-73(33-25-28-38-117)102(169)125-52-90(158)135-75(40-57(3)4)104(171)130-65(15)96(163)137-72(32-24-27-37-116)101(168)124-51-89(157)136-76(41-58(5)6)105(172)132-68(18)99(166)149-110(177)81(46-91(159)160)140-98(165)66(16)131-106(173)79(44-69-30-22-21-23-31-69)142-109(176)80(45-70-48-122-56-127-70)141-100(167)71(120)35-36-85(121)153/h21-23,30-31,48,56-68,70-84,92-93,150-152H,19-20,24-29,32-47,49-55,116-120H2,1-18H3,(H2,121,153)(H,123,161)(H,124,168)(H,125,169)(H,126,181)(H,128,155)(H,129,178)(H,130,171)(H,131,173)(H,132,172)(H,133,179)(H,134,156)(H,135,158)(H,136,157)(H,137,163)(H,138,174)(H,139,164)(H,140,165)(H,141,167)(H,142,176)(H,143,182)(H,144,162)(H,145,170)(H,146,175)(H,147,154)(H,148,180)(H,159,160)(H,149,166,177)/t61-,62-,63-,64-,65-,66-,67-,68-,70?,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,92-,93-/m0/s1

InChI Key

BVYRHZUKPPVMAQ-JGKRARPPSA-N

Canonical SMILES

CCC(C)C(C(=O)NCC(=O)NC(C)C(=O)NC(CO)C(=O)NC(C(C)CC)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(C)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CO)C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(CCCCN)C(=O)NCC(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NC(CCCCN)C(=O)NCC(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NC(=O)C(CC(=O)O)NC(=O)C(C)NC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC2C=NC=N2)NC(=O)C(CCC(=O)N)N)NC(=O)CN

1. The alyteserins: two families of antimicrobial peptides from the skin secretions of the midwife toad Alytes obstetricans (Alytidae)

J Michael Conlon, Anni Demandt, Per F Nielsen, Jérôme Leprince, Hubert Vaudry, Douglas C Woodhams Peptides. 2009 Jun;30(6):1069-73. doi: 10.1016/j.peptides.2009.03.004. Epub 2009 Mar 24.

Two families of structurally related C-terminally alpha-amidated antimicrobial peptides have been identified in norepinephrine-stimulated skin secretions of the midwife toad Alytes obstetricans (Alytidae). The alyteserin-1 peptides (Gly-Leu-Lys-(Asp/Glu)-Ile-Phe-Lys-Ala-Gly-Leu-Gly-Ser-Leu-Val-Lys-(Gly/Asn)-Ile-Ala-Ala-His-Val-Ala-(Asn/Ser).NH(2)) show limited structural similarity to the ascaphins from the skins of frogs of the family Leiopelmatidae. Alyteserin-2a (Ile-Leu-Gly-Lys-Leu-Leu-Ser-Thr-Ala-Ala-Gly-Leu-Leu-Ser-Asn-Leu.NH(2)) and alyteserin-2b and -2c (Ile-Leu-Gly-Ala-Ile-Leu-Pro-Leu-Val-Ser-Gly-Leu-Leu-Ser-(Asn/Ser)-Lys-Leu x NH(2)) show limited sequence identity with bombinin H6, present in the skins of frogs of the family Bombinatoridae. The alyteserin-1 peptides show selective growth inhibitory activity against the Gram-negative bacteria Escherichia coli (MIC=25 microM) whereas alyteserin-2a is more potent against the Gram-positive bacteria Staphylococcus aureus (MIC=50 microM). The hemolytic activity against human erythrocytes of all peptides tested is relatively weak (LC(50)>100 microM). The data demonstrate that the frogs belonging to the family Alytidae are among those producing dermal antimicrobial peptides that may represent a component of the animal's system of innate immunity.

2. Discovery of two bombinin peptides with antimicrobial and anticancer activities from the skin secretion of Oriental fire-bellied toad, Bombina orientalis

Chang Zhou, Zhengming Wang, Xin Peng, Yao Liu, Yangjun Lin, Zhe Zhang, Yuling Qiu, Meihua Jin, Ran Wang, Dexin Kong Chem Biol Drug Des. 2018 Jan;91(1):50-61. doi: 10.1111/cbdd.13055. Epub 2017 Jul 19.

Amphibian skin secretions are known to contain numerous peptides with a large array of biological activities. Bombinins are a group of amphibian-derived peptides with broad spectrum antimicrobial activities that have been only identified from the ancient toad species, Bombina. In this study, we described the identification and characterization of a novel bombinin precursor which encoded a bombinin-like peptide (BLP-7) and a novel bombinin H-type peptide (named as Bombinin H-BO) from the skin secretion of Oriental fire-bellied toad, Bombina orientalis. The primary structures of both mature peptides were determined by combinations of molecular cloning of peptide precursor-encoding cDNAs and mass spectrometry techniques. Secondary structure prediction revealed that both peptides had cationic amphipathic α-helical structural features. The synthetic replicate of BLP-7 displayed more potent antimicrobial activity than Bombinin H-BO against Gram-positive and Gram-negative bacteria and yeast. Also, in vitro antitumour assay showed that both peptides possessed obvious antiproliferative activity on three human hepatoma cells (Hep G2/SK-HEP-1/Huh7) at the non-toxic doses. These results indicate the peptide family of bombinins could be a potential source of drug candidates for anti-infection and anticancer therapy.

3. Molecular characterization and bioactivity evaluation of two novel bombinin peptides from the skin secretion of Oriental fire-bellied toad, Bombina orientalis

Xin Peng, Chang Zhou, Xuan Hou, Yao Liu, Zhengming Wang, Xiaolin Peng, Zhe Zhang, Ran Wang, Dexin Kong Amino Acids. 2018 Feb;50(2):241-253. doi: 10.1007/s00726-017-2509-z. Epub 2017 Nov 2.

Following the exploration of biochemicals in amphibian defensive skin secretion, great attention has been focused on the novel bioactive peptides with unique molecular structures and complicated features and functions. In this study, the skin secretion of Oriental fire-bellied toad, Bombina orientalis, was acquired to search peptides with therapeutic potential. Using "shotgun" cloning technique, a full-length peptide precursor co-encoding two novel bombinin peptides was cloned from the skin secretion-derived cDNA library of B. orientalis. The deduced peptides were identified as one bombinin-like peptide (BLP) (GIGSAILSAGKSIIKGLAKGLAEHF-NH2) and one bombinin H-type peptide (BH) (IIGPVLGLVGKALGGLL-NH2). The primary structures of both peptides were confirmed through reverse-phase HPLC fractionation and mass spectrometry. Secondary structural prediction revealed Bombinin-BO1 and Bombinin H-BO1 adopted α-helical structural features. In addition, the two peptides exhibited broad-spectrum antimicrobial effect against Gram-positive and Gram-negative bacteria and yeast. Meanwhile, the anticancer activity assay indicated both peptides exerted significant anticancer effects against human hepatoma cell lines tested (Hep G2/SK-HEP-1/Huh7). The peptides reported here for the first time may represent novel lead compounds for the design/development of new therapeutics for human infection and neoplastic disease.