polybia-MP1   Click here for help

GtoPdb Ligand ID: 8861

Abbreviated name: MP1
Synonyms: MP-1
Compound class: Peptide or derivative
Comment: This is a mastoparan (PubChem CID 6324633) type peptide toxin isolated from the venom of the Brazilian wasp, Polybia paulista, with reported antimicrobial [1] and anti-cancer effects [3,5-6]. The N-terminal aspartic acid residue at position 2 of this peptide is important for the peptide's interaction with anionic vesicles in vitro [4].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES NCCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)CC(C)C)C(CC)C)CCC(=O)N)CCCCN)C)C)CC(=O)O)CC(C)C)CC(C)C)NC(=O)C(NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(NC(=O)C(C(CC)C)N)CC(=O)O)CCCCN
Isomeric SMILES CC[C@H](C)[C@H](N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(N)=O)[C@@H](C)CC
InChI InChI=1S/C78H132N20O19/c1-13-43(9)63(83)77(116)97-59(38-62(102)103)76(115)95-57(36-47-39-85-49-24-16-15-23-48(47)49)75(114)90-51(26-18-21-31-80)69(108)89-52(27-19-22-32-81)70(109)93-55(34-41(5)6)73(112)94-56(35-42(7)8)74(113)96-58(37-61(100)101)72(111)87-45(11)66(105)86-46(12)67(106)88-50(25-17-20-30-79)68(107)91-53(28-29-60(82)99)71(110)98-64(44(10)14-2)78(117)92-54(65(84)104)33-40(3)4/h15-16,23-24,39-46,50-59,63-64,85H,13-14,17-22,25-38,79-81,83H2,1-12H3,(H2,82,99)(H2,84,104)(H,86,105)(H,87,111)(H,88,106)(H,89,108)(H,90,114)(H,91,107)(H,92,117)(H,93,109)(H,94,112)(H,95,115)(H,96,113)(H,97,116)(H,98,110)(H,100,101)(H,102,103)/t43-,44-,45-,46-,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,63-,64-/m0/s1
InChI Key WQWSKHPVGKVCQT-KXOXSZQSSA-N
References
1. de Souza BM, da Silva AV, Resende VM, Arcuri HA, Dos Santos Cabrera MP, Ruggiero Neto J, Palma MS. (2009)
Characterization of two novel polyfunctional mastoparan peptides from the venom of the social wasp Polybia paulista.
Peptides, 30 (8): 1387-95. [PMID:19463874]
2. dos Santos Cabrera MP, Arcisio-Miranda M, Gorjão R, Leite NB, de Souza BM, Curi R, Procopio J, Ruggiero Neto J, Palma MS. (2012)
Influence of the bilayer composition on the binding and membrane disrupting effect of Polybia-MP1, an antimicrobial mastoparan peptide with leukemic T-lymphocyte cell selectivity.
Biochemistry, 51 (24): 4898-908. [PMID:22630563]
3. Leite NB, Aufderhorst-Roberts A, Palma MS, Connell SD, Neto JR, Beales PA. (2015)
PE and PS Lipids Synergistically Enhance Membrane Poration by a Peptide with Anticancer Properties.
Biophys J, 109 (5): 936-47. [PMID:26331251]
4. Leite NB, Dos Santos Alvares D, de Souza BM, Palma MS, Ruggiero Neto J. (2014)
Effect of the aspartic acid D2 on the affinity of Polybia-MP1 to anionic lipid vesicles.
Eur Biophys J, 43 (4-5): 121-30. [PMID:24595375]
5. Wang KR, Yan JX, Zhang BZ, Song JJ, Jia PF, Wang R. (2009)
Novel mode of action of polybia-MPI, a novel antimicrobial peptide, in multi-drug resistant leukemic cells.
Cancer Lett, 278 (1): 65-72. [PMID:19233550]
6. Wang KR, Zhang BZ, Zhang W, Yan JX, Li J, Wang R. (2008)
Antitumor effects, cell selectivity and structure-activity relationship of a novel antimicrobial peptide polybia-MPI.
Peptides, 29 (6): 963-8. [PMID:18328599]