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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. |
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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. |
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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,
A highly efficient method for chemical m...
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
N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine
Fmoc-L-Arg-OH
melittin from honey bee venom
| Conditions | Yield |
|---|---|
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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;
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melittin from honey bee venom
2,3,5,6-tetrafluorophenyl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate
ethyl 4-(4-(formyloxy)phenoxy)butanoate
7-mercapto-4-methyl-2H-chromen-2-one
C132H230N40O32
4-(4-ethoxy-4-oxobutoxy)benzoic acid
4-(4-hydroxy-phenoxy)-butyric acid ethyl ester
| Conditions | Yield |
|---|---|
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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;
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N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Val-OH
Fmoc-Leu-OH
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
4-(4-ethoxy-4-oxobutoxy)benzoic acid
4-(4-hydroxy-phenoxy)-butyric acid ethyl ester