Puwainaphycin F - CAS 1379577-47-5 Catalog number: BADC-00815

Description

Puwainaphycin F, a cyanobacterial cyclic lipopeptide, is a moderate cytotoxin isolated from the soil cyanobacterium Cylindrospermum alatosporum C24/89. Puwainaphycin F causes necrotic cell death to mammalian cells via cell membrane permeabilization and subsequent unusual actin relocalization.

Synonyms

Taltobulin

IUPAC Name

2-[(3S,6R,9S,12S,15E,18S,21E,24S,31S)-3,18-bis(2-amino-2-oxoethyl)-28-dodecan-2-yl-15,21-di(ethylidene)-27-hydroxy-6-[(1S)-1-hydroxyethyl]-4,9-dimethyl-2,5,8,11,14,17,20,23,26,30-decaoxo-24-propan-2-yl-1,4,7,10,13,16,19,22,25,29-decazabicyclo[29.3.0]tetratriacontan-12-yl]acetamide

Canonical SMILES

O=C(N1CCC[C@]1(C(NC(C(CCCCCCCCCC)C)C(O)C(N[C@@H](C(C)C)C(N/C(C(N[C@H]2CC(N)=O)=O)=C/C)=O)=O)=O)[H])[C@H](CC(N)=O)N(C)C([C@]([H])([C@@H](C)O)NC(C(C)NC([C@H](CC(N)=O)NC(/C(NC2=O)=C\C)=O)=O)=O)=O

InChI

InChI=1S/C53H87N13O15/c1-10-13-14-15-16-17-18-19-21-28(6)41-43(71)51(79)62-40(27(4)5)50(78)59-32(12-3)46(74)61-34(25-38(55)69)48(76)58-31(11-2)45(73)60-33(24-37(54)68)47(75)57-29(7)44(72)64-42(30(8)67)53(81)65(9)36(26-39(56)70)52(80)66-23-20-22-35(66)49(77)63-41/h11-12,27-30,33-36,40-43,67,71H,10,13-26H2,1-9H3,(H2,54,68)(H2,55,69)(H2,56,70)(H,57,75)(H,58,76)(H,59,78)(H,60,73)(H,61,74)(H,62,79)(H,63,77)(H,64,72)/b31-11+,32-12+/t28?,29-,30-,33-,34-,35-,36-,40-,41?,42+,43?/m0/s1

Solubility

10 mm in DMSO

In Vitro

Puwainaphycin F has an IC50 of 2.19 μM in HeLa cells.

Purity

≥95%

Shelf Life

-20℃ 3 years powder; -80℃ 2 years in solvent

Shipping

Room temperature, or blue ice upon request.

Storage

Store at -5°C,keep in dry and avoid sunlight.