Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H31NO5S |
Molecular Weight | 421.55 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]1(CSC(=O)N1)[C@@]2(O)C[C@@]3([H])C[C@@H](CC[C@H](C)C=C\C=C\CCC(C)=CC(=O)O3)O2
InChI
InChIKey=DDVBPZROPPMBLW-IZGXTMSKSA-N
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
Latrunculin A is a naturally occurring toxin that can be purified from the red sea sponge Latrunculia magnifica. It disrupts actin polymerization and prevents mitotic spindle formation; therefore preventing proper cellular replication. It was discovered that latrunculin A has strong anticancer effects, and it was investigated as a treatment candidate for peritoneal dissemination of gastric cancer.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P68133 Gene ID: 58.0 Gene Symbol: ACTA1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3556584 |
0.2 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Microtubules, but not actin filaments, drive daughter cell budding and cell division in Toxoplasma gondii. | 2000 Apr |
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Seizures induced by in vivo latrunculin a and jasplakinolide microperfusion in the rat hippocampus. | 2006 |
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Cocaine increases actin cycling: effects in the reinstatement model of drug seeking. | 2006 Feb 1 |
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A mutation of beta -actin that alters depolymerization dynamics is associated with autosomal dominant developmental malformations, deafness, and dystonia. | 2006 Jun |
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Myosin light chain kinase plays a role in the regulation of epithelial cell survival. | 2006 Jun 1 |
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Azaspiracid-1 inhibits endocytosis of plasma membrane proteins in epithelial cells. | 2010 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19528469
in mice: Mice bearing peritoneally disseminated MKN45 or NUGC-4 (gastric cancer cells) tumors were prepared by an i.p. inoculation of 1×107 cells in 5% DMSO/0.7 mL PBS. On day 3, 10 and 17 after tumor inoculation, each mouse was given an i.p.injection of latrunculin A. The i.p. injection group were treated with latrunculin A (0.05 mg/kg, 5% DMSO in 0.7 mL PBS, n=14, MKN45; and n=10, NUGC-4), and the control group was treated with 5% DMSO in 0.7 mL PBS (n=19, MKN45; and n=9, NUGC-4). Negative (n=10) group was given latrunculin A without tumor inoculation.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28833824
It was reported that 25 µM Latrunculin A (LatA) blocked actin polymerization in the capacitated sperm head, resulting in a marked decrease in sperm with relocated IZUMO1 during the A23187-induced acrosome reaction and cumulus layer penetration. Treated sperm also exhibited reduced zona pellucida penetration and fertilizing capacity. Interestingly, LatA-treated sperm present in the perivitelline space of eggs did not show impaired IZUMO1 relocation.
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Latrunculin
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DB02621
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C037067
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DTXSID90893488
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76343-93-6
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69136
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m6703
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613011
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445420
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SRQ9WWM084
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SUBSTANCE RECORD