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Melittin

  • CasNo: 20449-79-0
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  • Molecular Formula:C131H229N39O31
  • Molecular Weight:2846.5
  • PSA:1152.34000 
  • Density:1.39 
  • LogP:7.51980 

Melittin(Cas 20449-79-0) Usage

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.

Definition

ChEBI: A 26-membered polypeptide consisting of 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 and Gln-NH2 residues joined in sequence. It is the principal active com onent of bee venom.

General Description

Chemical structure: peptide

InChI:InChI=1/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,

20449-79-0 Relevant articles

Impact of chain length on antibacterial activity and hemocompatibility of quaternary N-alkyl and N, N-dialkyl chitosan derivatives

Sahariah, Priyanka,Benediktssdóttir, Berglind E.,Hjálmarsdóttir, Martha á.,Sigurjonsson, Olafur E.,S?rensen, Kasper K.,Thygesen, Mikkel B.,Jensen, Knud J.,Másson, Már

, p. 1449 - 1460 (2015)

A highly efficient method for chemical m...

20449-79-0 Process route

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3,136132-75-7

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

Fmoc-Ile-OH
71989-23-6,251316-98-0

Fmoc-Ile-OH

Fmoc-Trp-OH
35737-15-6

Fmoc-Trp-OH

Fmoc-Thr-OH
73731-37-0

Fmoc-Thr-OH

Fmoc-Lys-OH
105047-45-8

Fmoc-Lys-OH

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine
73724-45-5

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

N<sub>2</sub>-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine
71989-20-3

N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine

Fmoc-L-Arg-OH
91000-69-0,130752-32-8

Fmoc-L-Arg-OH

melittin from honey bee venom
20449-79-0

melittin from honey bee venom

Conditions
Conditions Yield
N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine; With 1-hydroxy-7-aza-benzotriazole; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide;
With piperidine; In N,N-dimethyl-formamide; for 0.55h;
N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Pro-OH; Fmoc-Ile-OH; Fmoc-Trp-OH; Fmoc-Thr-OH; Fmoc-Lys-OH; N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine; Fmoc-L-Arg-OH; Further stages;
melittin from honey bee venom
20449-79-0

melittin from honey bee venom

2,3,5,6-tetrafluorophenyl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate

2,3,5,6-tetrafluorophenyl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate

ethyl 4-(4-(formyloxy)phenoxy)butanoate

ethyl 4-(4-(formyloxy)phenoxy)butanoate

7-mercapto-4-methyl-2H-chromen-2-one
137215-27-1

7-mercapto-4-methyl-2H-chromen-2-one

C<sub>132</sub>H<sub>230</sub>N<sub>40</sub>O<sub>32</sub>

C132H230N40O32

4-(4-ethoxy-4-oxobutoxy)benzoic acid
143216-03-9

4-(4-ethoxy-4-oxobutoxy)benzoic acid

4-(4-hydroxy-phenoxy)-butyric acid ethyl ester
166954-96-7

4-(4-hydroxy-phenoxy)-butyric acid ethyl ester

Conditions
Conditions Yield
melittin from honey bee venom; ethyl 4-(4-(formyloxy)phenoxy)butanoate; In aq. phosphate buffer; dimethyl sulfoxide; at 25 ℃; for 3h; pH=7.0;
2,3,5,6-tetrafluorophenyl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate; In aq. phosphate buffer; dimethyl sulfoxide; for 0.25h; pH=7.0;
7-mercapto-4-methyl-2H-chromen-2-one; In aq. phosphate buffer; dimethyl sulfoxide;

20449-79-0 Upstream products

  • 29022-11-5
    29022-11-5

    N-(fluoren-9-ylmethoxycarbonyl)glycine

  • 68858-20-8
    68858-20-8

    Fmoc-Val-OH

  • 35661-60-0
    35661-60-0

    Fmoc-Leu-OH

  • 35661-39-3
    35661-39-3

    N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

20449-79-0 Downstream products

  • 143216-03-9
    143216-03-9

    4-(4-ethoxy-4-oxobutoxy)benzoic acid

  • 166954-96-7
    166954-96-7

    4-(4-hydroxy-phenoxy)-butyric acid ethyl ester

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