Latrunculin A

AdipoGen Life Sciences
Product Code: AG-CN2-0027
CodeSizePrice
AG-CN2-0027-C100100 ug£115.00
Quantity:
AG-CN2-0027-C500500 ug£430.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
LAT-A; NSC 613011
Appearance:
Colorless viscous film
CAS:
76343-93-6
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Protect from light.
Hazards:
H302, H312, H332
InChi:
InChI=1S/C22H31NO5S/c1-15-7-5-3-4-6-8-16(2)11-20(24)27-18-12-17(10-9-15)28-22(26,13-18)19-14-29-21(25)23-19/h3-5,7,11,15,17-19,26H,6,8-10,12-14H2,1-2H3,(H,23,25)/b4-3+,7-5-,16-11-/t15-,17-,18-,19+,22-/m1/s1
InChiKey:
DDVBPZROPPMBLW-IZGXTMSKSA-N
Long Description:
Chemical. CAS: 76343-93-6. Formula: C22H31NO5S. MW: 421.6. Isolated from Latrunculia magnifica. Cell permeable marine toxin. Disrupts microfilament-mediated processes. Actin polymerization inhibitor in vitro and in vivo by the formation of a 1:1 complex with monomeric G-actin. Depolymerizes actin filaments (F-actin). Potent phagocytosis inhibitor. Anticancer compound. Suppresses hypoxia-induced HIF-1 activation in tumor cells. Inhibits tumor cell invasion. Acts via a different mechanism than cytochalasins.
MDL:
MFCD27977552
Molecular Formula:
C22H31NO5S
Molecular Weight:
421.6
Package Type:
Vial
Precautions:
P261, P280, P301, P312, P302, P352, P304, P340
Product Description:
Cell permeable marine toxin [1]. Disrupts microfilament-mediated processes [2]. Actin polymerization inhibitor in vitro and in vivo by the formation of a 1:1 complex with monomeric G-actin [1, 2, 3, 6]. Depolymerizes actin filaments (F-actin) [3]. Potent phagocytosis inhibitor [4]. Anticancer compound [7, 8]. Suppresses hypoxia-induced HIF-1 activation in tumor cells [7]. Inhibits tumor cell invasion [7]. Acts via a different mechanism than cytochalasins.
Purity:
>97% (HPLC)
Signal word:
Warning
SMILES:
O=C(SC1)N[C@]1([H])[C@](C2)(O)O[C@@H](C[C@H]2O3)CC[C@H](C)/C=CC=CCC/C(C)=CC3=O
Solubility Chemicals:
Soluble in DMSO (25mg/ml) or ethanol (25mg/ml).
Source / Host:
Isolated from Latrunculia magnifica.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C. Store solutions at -20°C in the dark.

References

Latrunculins: novel marine toxins that disrupt microfilament organization in cultured cells: I. Spector, et al.; Science 219, 493 (1983) | Latrunculin inhibits the microfilament-mediated processes during fertilization, cleavage and early development in sea urchins and mice: G. Schatten, et al.; Exp. Cell Res. 166, 191 (1986) | Inhibition of actin polymerization by latrunculin: A: M. Coue, et al.; FEBS Lett. 213, 316 (1987) | Latrunculin A is a potent inhibitor of phagocytosis by macrophages: C.A. de Oliveira & B. Mantovani; Life Sci. 43, 1825 (1988) | Latrunculins-novel marine macrolides that disrupt microfilament organization and affect cell growth: I. Comparison with cytochalasin D: I. Spector, et al.; Cell Motil. Cytoskeleton 13, 127 (1989) | Actin-latrunculin A structure and function. Differential modulation of actin-binding protein function by latrunculin A: E.G. Yarmola, et al.; J. Biol. Chem. 275, 28120 (2000) | Latrunculin A and its C-17-O-carbamates inhibit prostate tumor cell invasion and HIF-1 activation in breast tumor cells: K.A. Sayed, et al.; J. Nat. Prod. 71, 396 (2008) | Latrunculin a has a strong anticancer effect in a peritoneal dissemination model of human gastric cancer in mice: H. Konishi, et al.; Anticancer Res. 29, 2091 (2009) | Nucleolar asymmetry and the importance of septin integrity upon cell cycle arrest: U. Rai, et al.; PLoS ONE 12, e0174306 (2017) | Trogocytosis of ligand-receptor complex and its intracellular transport in CD30 signaling: M. Nakashima, et al.; Biol Cell. 110, 109 (2018) | Integrating chemical and mechanical signals through dynamic coupling between cellular protrusions and pulsed ERK activation: J.M. Yang, et al.; Nat. Comm. 9, 4673 (2018)

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