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Melittin

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

Melittin is an oligopeptide constituent discovered within the venom of bees, showcasing remarkable characteristics encompassing its effectiveness against microbes, viruses and cancer cells. Its capacity to assail cellular membranes renders Melittin a prospective tool in studying an array of ailments such as cancer, HIV and drug-resistant infections.

Category

Functional Peptides

Catalog number

BAT-016463

CAS number

37231-28-0

Molecular Formula

C131H229N39O31

Molecular Weight

2846.46

Specification
Reference Reading

IUPAC Name

2-[[5-amino-2-[[2-[[6-amino-2-[[2-[[6-amino-2-[[2-[[2-[[2-[[2-[[2-[2-[[1-[2-[[2-[[2-[[2-[[2-[[2-[[6-amino-2-[[2-[[2-[2-[[2-[[2-[(2-aminoacetyl)amino]-3-methylpentanoyl]amino]acetyl]amino]propanoylamino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]acetyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]amino]propanoylamino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-methylpentanoyl]amino]hexanoyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]pentanediamide

Synonyms

melittinfrombeevenomsequencing*grade; melittinhoneybeevenom; melittin-t; H-GLY-ILE-GLY-ALA-VAL-LEU-LYS-VAL-LEU-THR-THR-GLY-LEU-PRO-ALA-LEU-ILE-SER-TRP-ILE-LYS-ARG-LYS-ARG-GLN-GLN-NH2

Appearance

solid

Sequence

GXGAVLKVLXXGLPALXSWXKRKRQQ

InChI

InChI=1S/C131H229N39O31/c1-23-71(16)102(163-97(176)60-135)122(194)146-62-98(177)148-74(19)109(181)164-100(69(12)13)124(196)160-88(55-65(4)5)116(188)155-84(41-30-33-51-134)115(187)165-101(70(14)15)125(197)161-90(57-67(8)9)118(190)168-106(77(22)173)128(200)169-105(76(21)172)123(195)147-63-99(178)150-92(58-68(10)11)129(201)170-54-36-44-94(170)121(193)149-75(20)108(180)158-89(56-66(6)7)117(189)166-104(73(18)25-3)127(199)162-93(64-171)120(192)159-91(59-78-61-145-80-38-27-26-37-79(78)80)119(191)167-103(72(17)24-2)126(198)157-83(40-29-32-50-133)111(183)154-85(42-34-52-143-130(139)140)112(184)152-82(39-28-31-49-132)110(182)153-86(43-35-53-144-131(141)142)113(185)156-87(46-48-96(137)175)114(186)151-81(107(138)179)45-47-95(136)174/h26-27,37-38,61,65-77,81-94,100-106,145,171-173H,23-25,28-36,39-60,62-64,132-135H2,1-22H3,(H2,136,174)(H2,137,175)(H2,138,179)(H,146,194)(H,147,195)(H,148,177)(H,149,193)(H,150,178)(H,151,186)(H,152,184)(H,153,182)(H,154,183)(H,155,188)(H,156,185)(H,157,198)(H,158,180)(H,159,192)(H,160,196)(H,161,197)(H,162,199)(H,163,176)(H,164,181)(H,165,187)(H,166,189)(H,167,191)(H,168,190)(H,169,200)(H4,139,140,143)(H4,141,142,144)

InChI Key

VDXZNPDIRNWWCW-UHFFFAOYSA-N

Canonical SMILES

CCC(C)C(C(=O)NCC(=O)NC(C)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(CCCCN)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(C(C)O)C(=O)NC(C(C)O)C(=O)NCC(=O)NC(CC(C)C)C(=O)N1CCCC1C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(C(C)CC)C(=O)NC(CO)C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)NC(C(C)CC)C(=O)NC(CCCCN)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)N)C(=O)N)NC(=O)CN

1. Melittin: from honeybees to superbugs

Hamed Memariani, Mojtaba Memariani, Soheila Nasiri, Mohammad Shahidi-Dadras, Hamideh Moravvej, Maziar Mohammad Akhavan Appl Microbiol Biotechnol . 2019 Apr;103(8):3265-3276. doi: 10.1007/s00253-019-09698-y.

The emergence of antibiotic-resistant bacteria, dubbed superbugs, together with relative stagnation in developing efficient antibiotics has led to enormous health and economic problems, necessitating the need for discovering and developing novel antimicrobial agents. In this respect, animal venoms represent a rich repertoire of pharmacologically active components. As a major component in the venom of European honeybee Apis mellifera, melittin has a great potential in medical applications. In this mini-review, we summarize a multitude of studies on anti-bacterial effects of melittin against planktonic and biofilm-embedded bacteria. Several investigations regarding synergistic effects between melittin and antibiotics were also described. On the whole, the properties of melittin can open up new horizons in a range of biomedical areas, from agriculture to veterinary and clinical microbiology.

2. Delivery Strategies for Melittin-Based Cancer Therapy

Hao Huang, Chao Wan, Jie Zhou, Jonathan F Lovell, Jing Cheng, Honglin Jin ACS Appl Mater Interfaces . 2021 Apr 21;13(15):17158-17173. doi: 10.1021/acsami.1c03640.

Melittin (MLT) has been studied preclinically as an anticancer agent based on its broad lytic effects in multiple tumor types. However, unsatisfactory tissue distribution, hemolysis, rapid metabolism, and limited specificity are critical obstacles that limit the translation of MLT. Emerging drug delivery strategies hold promise for targeting, controlled drug release, reduced side effects, and ultimately improved treatment efficiency. In this review, we discuss recent advances in the use of diverse carriers to deliver MLT, with an emphasis on the design and mechanisms of action. We further outline the opportunities for MLT-based cancer immunotherapy.

3. Applications and evolution of melittin, the quintessential membrane active peptide

Shantanu Guha, Sarah Y Kim, Ryan P Ferrie, Leisheng Sun, Gregory R Wiedman, Eric Wu, Jenisha Ghimire, Cristina R Ventura, Kalina Hristova, Wimley C Wimley Biochem Pharmacol . 2021 Nov;193:114769. doi: 10.1016/j.bcp.2021.114769.

Melittin, the main venom component of the European Honeybee, is a cationic linear peptide-amide of 26 amino acid residues with the sequence: GIGAVLKVLTTGLPALISWIKRKRQQ-NH2. Melittin binds to lipid bilayer membranes, folds into amphipathic α-helical secondary structure and disrupts the permeability barrier. Since melittin was first described, a remarkable array of activities and potential applications in biology and medicine have been described. Melittin is also a favorite model system for biophysicists to study the structure, folding and function of peptides and proteins in membranes. Melittin has also been used as a template for the evolution of new activities in membranes. Here we overview the rich history of scientific research into the many activities of melittin and outline exciting future applications.