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M7391

Sigma-Aldrich

Melittin from honey bee venom

≥65% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C131H229N39O31
CAS Number:
20449-79-0
Molecular Weight:
2846.46
MDL number:
MFCD00076868
UNSPSC Code:
12352200
PubChem Substance ID:
329817905
NACRES:
NA.32

form

lyophilized powder

Quality Level

200

mol wt

~_2.8 kDa

concentration

≥65% (HPLC)

solubility

water: 5.00-5.20 mg/mL, clear, colorless to faintly yellow

foreign activity

Phospholipase A2 ≤2%

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

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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

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 contains 26 amino acids. Monomeric form of melittin has a molecular weight of 2,840Da and tetrameric form has molecular weight of approximately 12,500Da.

Application

Melittin from honey bee venom has been used to study the role of melittin in allergic reactions.

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. Melittin retard cathepsin S-induced invasion, proliferation and angiogenesis via inhibition of the vascular endothelial growth factor A (VEGF-A) /VEGF receptor 2 (VEGFR-2)/ mitogen-activated protein kinase 1 (MEK1)/ extracellular signal-regulated kinase 1/2 (ERK1/2) pathway in human MHCC97-H cells (liver cancer cells). Melittin has therapeutic application in various inflammatory diseases such as skin inflammation, neuroinflammation, atherosclerosis, arthritis and liver inflammation. Accumulated melittin degrades phospholipid packing in the cell membrane and causes cell lysis and cell death.
Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.

Other Notes

The principle hemolytic component of honeybee venom.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Structural and Dynamic Insights into S100B Protein Activity Inhibition by Melittin for the Treatment of Epilepsy
Verma N
International Journal of Computer Applications, 55-60 (2013)
The peptide components of bee venom.
Gauldie J
European Journal of Biochemistry, 61(2), 369-376 (1976)
Application of bee venom and its main constituent melittin for cancer treatment.
Application of bee venom and its main constituent melittin for cancer treatment.
Liu CC
Cancer Chemotherapy and Pharmacology, 78(6), 1113-1130 (2016)
Honey Bee Venom (Apis mellifera) Contains Anticoagulation Factors and Increases the Blood-clotting Time.
Zolfagharian H
Journal of pharmacopuncture, 18(4), 7-11 (2015)
C E Dempsey
Biochimica et biophysica acta, 1031(2), 143-161 (1990-05-07)
The molecular mechanisms underlying the various effects of melittin on membranes have not been completely defined and much of the evidence described indicates that different molecular mechanisms may underlie different actions of the peptide. Ideas about the formation of transbilayer
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