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M2272 Sigma-Aldrich

Melittin from honey bee venom

≥85% (HPLC)

  • CAS Number 20449-79-0

  • Empirical Formula (Hill Notation) C131H229N39O31

  • Molecular Weight 2846.46

  •  MDL number MFCD00076868

  •  PubChem Substance ID 24896718

  •  NACRES NA.32

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Properties

Related Categories Antibiotics, Biochemicals and Reagents, Calcium Antagonists, Cell Biology, Cell Signaling and Neuroscience,
Quality Level   200
biological source   animal (Apis mellifera)
assay   ≥85% (HPLC)
form   lyophilized powder
mol wt   ~_2.8 kDa
solubility   water: 5.00-5.20 mg/mL, clear, colorless to faintly yellow
Mode of action   cell membrane | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
foreign activity   Phospholipase A2 ≤0.5%
storage temp.   −20°C
SMILES string   CC[C@H](C)[C@H](NC(=O)CN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(N)=O
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)/t71-,72-,73-,74-,75-,76+,77+,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,100-,101-,102-,103-,104-,105-,106-/m0/s1
InChI key   VDXZNPDIRNWWCW-JFTDCZMZSA-N

Description

Amino Acid Sequence

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

General description

Chemical structure: peptide

Melittin is hydrophobic in nature except for a region with Lys-Arg-Lys-Arg sequence near C-terminal end. This structural characteristic makes melittin a highly surface-active and a powerful, direct haemolytic agent.† The encoded protein containins 26 amino acids. Monomeric form of melittin has a molecular weight of 2,840 Daltons and tetrameric form has molecular weight of approximately 12,500 Daltons.

Application

Melittin from honey bee venom has been used:
• In 3-(4, 5-dimethyl thiazol-2-yl)-2,5diphenyl tetrazolium bromide (MTT) assay to determine its cytotoxicity effect on the growth of human cell lines.
• To study the anti-microbial activity of melittin on the growth of Borrelia burgdorferi in in vitro conditions.
• As a positive control in hemolysis assay and as a cytotoxic agent against HeLa cells.

Packaging

1, 5, 25 mg in glass bottle

Biochem/physiol Actions

Melittin acts as an anti-coagulating protein by increasing the time of blood clotting in vitro. Melittin inhibits the activity of S100 calcium-binding protein B (S100B) and plays a vital role in Epilepsy treatment.

Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.

Other Notes

The principle hemolytic component of honeybee venom.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3462 6.1 / PGI
WGK Germany 
WGK 3
RTECS 
OS3960000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Antimicrobial Peptides

With bacterial resistance and emerging infectious diseases becoming potential threats to humans, ribosomally synthesized antimicrobial peptides have become a promising focus area in antibiotic resear...
Chloe McClanahan
BioFiles 2009, 4.3, 4.
Keywords: Antibiotics, Antimicrobials, Antiparasitics, Antivirals, Apoptosis, Cancer, Clinical, Diseases, Environmental, Fermentation, Food Safety, Gene expression, Genetic, Genetics, Infectious Diseases, Microbiology, Peptide synthesis, Pesticides, Respiratory

Peer-Reviewed Papers
15

References

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