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M4171

Sigma-Aldrich

Melittin

≥97% (HPLC), synthetic

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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:
24896910
NACRES:
NA.32

Quality Level

200

Assay

≥97% (HPLC)

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

Gene Information

human ... ATP1A1(476) , CALM1(801)
mouse ... ATP1A1(11928) , CALM1(12313)
rat ... ATP1A1(24211) , CALM1(24242)

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 hemolytic agent.The encoed 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 has been used in standard bacterium-killing assay to determine bactericidal activity and 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.
Lyophilized from 0.1% TFA in H2O

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Mohammed Ghalib Enayathullah et al.
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The COVID19 pandemic has led to multipronged approaches for treatment of the disease. Since de novo discovery of drugs is time consuming, repurposing of molecules is now considered as one of the alternative strategies to treat COVID19. Antibacterial peptides are
Anti-Inflammatory Applications of Melittin, a Major Component of Bee Venom: Detailed Mechanism of Action and Adverse Effects.
Lee G and Bae H
Molecules (Basel), 21(5), E616-E616 (2016)
Alexey I Kuzmenkov et al.
Frontiers in pharmacology, 13, 977440-977440 (2022-10-04)
Apamin is often cited as one of the few substances selectively acting on small-conductance Ca2+-activated potassium channels (KCa2). However, published pharmacological and structural data remain controversial. Here, we investigated the molecular pharmacology of apamin by two-electrode voltage-clamp in Xenopus laevis
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)
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