Page last updated: 2024-12-11

latrunculin b

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

latrunculin B: 14-membered macrolide attached to 2-thiazolidinone moiety; from Red Sea sponge Latrunculia magnifica; see also latrunculin A; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

latrunculin B : A macrolide consisting of a 14-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge Latrunculia magnifica. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID6436219
CHEMBL ID411879
CHEBI ID49703
SCHEMBL ID2531366
MeSH IDM0112418

Synonyms (44)

Synonym
BRD-K30455030-001-03-3
IDI1_002180
SMP2_000317
(4r)-4-[(1r,4s,5z,9z,13r,15r)-15-hydroxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo[11.3.1]heptadeca-5,9-dien-15-yl]thiazolidin-2-one
2-thiazolidinone, 4-[(1r,4z,8z,10s,13r,15r)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-, (4r)-
BSPBIO_001189
nsc339663 ,
nsc-339663
latrunculin b
76343-94-7
BCBCMAP01_000226
NCGC00163459-03
2-thiazolidinone, 4-(15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo(11.3.1)heptadeca-4,8-dien-15-yl)-, (1r*,4z,8z,10s*,13r*,15r*(r*))-(+)-
lat-b
HMS1990K11
CHEMBL411879
chebi:49703 ,
DB08080
(+)-latrunculin b
HMS1792K11
HMS1362K11
lat b
(4r)-4-[(1r,4z,8z,10s,13r,15r)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one
nsc 339663
unii-lw7u308u7u
lw7u308u7u ,
latrunculin b from latruncula magnifica
ins-115644
latrunculin b [mi]
2-thiazolidinone, 4-((1r,4z,8z,10s,13r,15r)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo(11.3.1)heptadeca-4,8-dien-15-yl)-, (4r)-
2-thiazolidinone, 4-(15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo(11.3.1)heptadeca-4,8-dien-15-yl)-, (1r-(1r*,4z,8z,10s*,13r*,15r*(r*)))-
ins115644
SCHEMBL2531366
HMS3403K11
(4r)-[(1r,4z,8z,10s,13r,15r)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-2-thiazolidinone
bdbm50508923
latrunculin b from latruncula magnifica, >=80% (hplc), solid
AKOS032947159
Q4255012
latrunculin-b
HY-101848
BDA34394
AS-83262
CS-0022006

Research Excerpts

Treatment

Latrunculin B treatment strongly inhibited the formation of TSWV local lesions in Nicotiana tabacum cv Samsun NN and delayed systemic infection in N.benthamiana. LatrunculIn B treatment, imaging of F-actin in living cells using Lifeact-red fluorescent protein (RFP), and analysis of mutants defective in the Arp2/3 complex demonstrated that actin plays important roles in CAT fusion.

ExcerptReferenceRelevance
"Latrunculin B treatment strongly inhibited the formation of TSWV local lesions in Nicotiana tabacum cv Samsun NN and delayed systemic infection in N. benthamiana."( Nucleocapsid of Tomato spotted wilt tospovirus forms mobile particles that traffic on an actin/endoplasmic reticulum network driven by myosin XI-K.
Bao, Y; Chen, X; Dong, J; Feng, Z; Tao, X; Zhang, Z, 2013
)
1.11
"Latrunculin B treatment, imaging of F-actin in living cells using Lifeact-red fluorescent protein (RFP), and analysis of mutants defective in the Arp2/3 complex demonstrated that actin plays important roles in CAT fusion."( Nuclear dynamics, mitosis, and the cytoskeleton during the early stages of colony initiation in Neurospora crassa.
Freitag, M; Kuo, HC; Lichius, A; Read, ND; Roca, MG, 2010
)
1.08
"Latrunculin B treatment in whole-cell patch-clamped cells inhibited Ca(2+)-dependent Cl(-) current spikes evoked by inositol (2,4,5)-trisphosphate; this is due to an inhibition of the underlying local Ca(2+) signal."( Inositol (1,4,5)-trisphosphate receptor links to filamentous actin are important for generating local Ca2+ signals in pancreatic acinar cells.
Fogarty, KE; Thorn, P; Turvey, MR, 2005
)
1.05
"Latrunculin B-treated cells returned to a quasi-normal state within 3-4 days."( Effects of rhizopodin and latrunculin B on the morphology and on the actin cytoskeleton of mammalian cells.
Gronewold, TM; Lünsdorf, H; Reichenbach, H; Sasse, F, 1999
)
1.32
"Latrunculin B treatment results in rapid relocalization of GFP-neurabin-II to the cytosol, whereas cytochalasin D treatment causes the collapse of GFP-neurabin-II fluorescence to intensely fluorescent foci of F-actin within the cell body."( In vivo dynamics of the F-actin-binding protein neurabin-II.
Banting, G; Stephens, DJ, 2000
)
1.03
"In latrunculin B-pretreated cells inhibition of both, bombesin-stimulated IP(3)- production and Ca(2+)release was partly suspended in the presence of aluminum fluoride, an activator of G-proteins."( Hormone-stimulated calcium release is inhibited by cytoskeleton-disrupting toxins in AR4-2J cells.
Blum, R; Bozem, M; Feick, P; Kuhlmann, S; Schulz, I, 2000
)
0.82
"Latrunculin B (Lat-B) treatment of hypocotyls caused depolymerization of actin MFs in endodermal cells and a significant reduction of hypocotyl growth rates."( Disruption of the actin cytoskeleton results in the promotion of gravitropism in inflorescence stems and hypocotyls of Arabidopsis.
Kiss, JZ; Yamamoto, K, 2002
)
1.04
"Pretreatment with latrunculin B, an inhibitor of actin polymerization, or Y-27632, a Rho kinase inhibitor, attenuated cell spreading and the rapid increase in electrical resistance induced by S1P."( Sphingosine 1-phosphate rapidly increases endothelial barrier function independently of VE-cadherin but requires cell spreading and Rho kinase.
Hu, C; Minnear, FL; Vincent, PA; Waters, CL; Wysolmerski, RB; Xu, M, 2007
)
0.66

Dosage Studied

ExcerptRelevanceReference
" Dose-response studies show a good correlation between inhibition of actin polymerization and increased degranulation."( The role of actin microfilaments in the down-regulation of the degranulation response in RBL-2H3 mast cells.
Apgar, JR; Frigeri, L, 1999
)
0.3
" Whereas supraoptimal FcepsilonRI engagement decreased degranulation, which is known as a bell-shaped dose-response curve, such inhibitory effect was not observed with FcalphaR engagement."( Functionality of the IgA Fc receptor (FcalphaR, CD89) is down-regulated by extensive engagement of FcepsilonRI.
Matsui, T; Nunomura, S; Ra, C; Shimokawa, T; Yoshimaru, T, 2008
)
0.35
" Accurate dose-response curves could be generated, and we found that mild oxidative stress delayed multiple stages of virus production, but eventually infection processes occurred with approximately the same amplitudes."( Kinetics of Mimivirus Infection Stages Quantified Using Image Flow Cytometry.
Dadosh, T; Minsky, A; Mutsafi, Y; Porat, Z; Yaakov, LB, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
actin polymerisation inhibitorAny substance that inhibits the polymerisation of the protein actin.
toxinPoisonous substance produced by a biological organism such as a microbe, animal or plant.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
macrolideA macrocyclic lactone with a ring of twelve or more members derived from a polyketide.
cyclic hemiketalA hemiacetal having the structure R2C(OH)OR (R =/= H), derived from a ketone by formal addition of an alcohol to the carbonyl group. The term 'cyclic hemiketals', once abandoned by IUPAC, has been reinstated as a subclass of hemiacetals.
oxabicycloalkane
thiazolidinone
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Actin, alpha skeletal muscleOryctolagus cuniculus (rabbit)IC50 (µMol)8.47008.47008.47008.4700AID1538798
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID502923Inhibition of actin polymerization in N-WASP VCA-stimulated Xenopus laevis egg extract at 10 uM after 1.5 mins by fluorescence assay2006Nature chemical biology, Jan, Volume: 2, Issue:1
Secramine inhibits Cdc42-dependent functions in cells and Cdc42 activation in vitro.
AID1538807Inhibition of immobilized rabbit skeletal muscle alpha-actin interaction with gelsolin at 12.5 uM pretreated for 30 mins followed by gelsolin addition measured after 1 hr by pull-down assay2019Journal of natural products, 07-26, Volume: 82, Issue:7
Chivosazole A Modulates Protein-Protein Interactions of Actin.
AID1538811Inhibition of immobilized rabbit skeletal muscle alpha-actin interaction with thymosin-beta4 assessed as decrease in cross-linked complex formation at 40 uM pretreated for 30 mins followed by thymosin-beta4 addition measured after 45 mins by cross-linking2019Journal of natural products, 07-26, Volume: 82, Issue:7
Chivosazole A Modulates Protein-Protein Interactions of Actin.
AID454044Antimicrobial activity against Saccharomyces cerevisiae NRRL Y2034 by twofold dilution method2009Bioorganic & medicinal chemistry, Nov-01, Volume: 17, Issue:21
Semisynthetic latrunculin B analogs: studies of actin docking support a proposed mechanism for latrunculin bioactivity.
AID324495Increase in light chain 3-GFP+ autophagosome vesicle area per cell in human H4 cells at 6.3 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID1538800Inhibition of cell migration in human HUVEC cells assessed as decrease in cell velocity measured after 16 hrs by crystal violet staining based scratch assay2019Journal of natural products, 07-26, Volume: 82, Issue:7
Chivosazole A Modulates Protein-Protein Interactions of Actin.
AID344907Cytotoxicity against human MDA-MB-435 cells 48 hrs by SRB assay2008Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22
Interrogating the bioactive pharmacophore of the latrunculin chemotype by investigating the metabolites of two taxonomically unrelated sponges.
AID379715Inhibition of mouse B16B15b cell migration assessed as wound closure rate at 1 uM after 14 hrs by wound healing assay relative to control2006Journal of natural products, Feb, Volume: 69, Issue:2
Bioactive natural and semisynthetic latrunculins.
AID1679213Inhibition of KMEI-induced pyrene-labelled G-actin polymerization (unknown origin) at 100 uM preincubated for 1 min followed by KMEI addition and measured at 15 secs interval for 90 mins by spectrofluorimetric analysis relative to control2016Journal of medicinal chemistry, 12-22, Volume: 59, Issue:24
Truncated Latrunculins as Actin Inhibitors Targeting Plasmodium falciparum Motility and Host Cell Invasion.
AID324443Increase in light chain 3-GFP+ autophagosome vesicle number per cell in human H4 cells at 6.3 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID379716Antiproliferative activity against mouse B16B15b cells at 1 uM after 18 hrs by alamar blue assay relative to control2006Journal of natural products, Feb, Volume: 69, Issue:2
Bioactive natural and semisynthetic latrunculins.
AID379711Antifungal activity against Saccharomyces cerevisiae by modified microtiter plate assay2006Journal of natural products, Feb, Volume: 69, Issue:2
Bioactive natural and semisynthetic latrunculins.
AID344906Cytotoxicity against human HCT116 cells after 3 days by trypan blue assay2008Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22
Interrogating the bioactive pharmacophore of the latrunculin chemotype by investigating the metabolites of two taxonomically unrelated sponges.
AID454046Antimicrobial activity against Aspergillus flavus NRRL 501 by twofold dilution method2009Bioorganic & medicinal chemistry, Nov-01, Volume: 17, Issue:21
Semisynthetic latrunculin B analogs: studies of actin docking support a proposed mechanism for latrunculin bioactivity.
AID344909Disruption of microfilament in rat A10 cells at 9 uM after 18 hrs using DAPI staining by fluorescence microscopy2008Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22
Interrogating the bioactive pharmacophore of the latrunculin chemotype by investigating the metabolites of two taxonomically unrelated sponges.
AID1679214Inhibition of KMEI-induced pyrene-labelled G-actin polymerization (unknown origin) at 10 uM preincubated for 1 min followed by KMEI addition and measured at 15 secs interval for 90 mins by spectrofluorimetric analysis relative to control2016Journal of medicinal chemistry, 12-22, Volume: 59, Issue:24
Truncated Latrunculins as Actin Inhibitors Targeting Plasmodium falciparum Motility and Host Cell Invasion.
AID1538798Inhibition of rabbit skeletal muscle alpha-actin polymerization measured after 24 hrs in presence of ATP and fluorescent pyrene-labelled actin by fluorescence based assay2019Journal of natural products, 07-26, Volume: 82, Issue:7
Chivosazole A Modulates Protein-Protein Interactions of Actin.
AID1679216Inhibition of actin polymerisation in trophozoite-stage of plasmodium falciparum infected in human erythrocytes assessed as parasite growth inhibition measured after 72 hrs by SYBR dye based FACSort flow cytometry analysis2016Journal of medicinal chemistry, 12-22, Volume: 59, Issue:24
Truncated Latrunculins as Actin Inhibitors Targeting Plasmodium falciparum Motility and Host Cell Invasion.
AID379708Antifungal activity against Candida albicans ATCC 10231 by modified microtiter plate assay2006Journal of natural products, Feb, Volume: 69, Issue:2
Bioactive natural and semisynthetic latrunculins.
AID1538809Inhibition of immobilized rabbit skeletal muscle alpha-actin interaction with thymosin-beta4 at 40 uM pretreated for 30 mins followed by thymosin-beta4 addition measured after 45 mins by cross-linking assay2019Journal of natural products, 07-26, Volume: 82, Issue:7
Chivosazole A Modulates Protein-Protein Interactions of Actin.
AID1538799Antiproliferative activity against human HUVEC measured after 72 hrs2019Journal of natural products, 07-26, Volume: 82, Issue:7
Chivosazole A Modulates Protein-Protein Interactions of Actin.
AID1538806Inhibition of immobilized rabbit skeletal muscle alpha-actin interaction with cofilin at 56 uM pretreated for 30 mins followed by cofilin addition measured after 1 hr by pull-down assay2019Journal of natural products, 07-26, Volume: 82, Issue:7
Chivosazole A Modulates Protein-Protein Interactions of Actin.
AID324391Induction of light chain 3-GFP level in human H4 cells at 6.3 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID454045Antimicrobial activity against Candida albicans by twofold dilution method2009Bioorganic & medicinal chemistry, Nov-01, Volume: 17, Issue:21
Semisynthetic latrunculin B analogs: studies of actin docking support a proposed mechanism for latrunculin bioactivity.
AID1538810Binding affinity to immobilized rabbit skeletal muscle alpha-actin assessed as formation of G-actin dimers at 40 uM and pH 6.8 to 8 treated for 30 mins in absence of thymosin-beta4 by size-exclusion chromatography2019Journal of natural products, 07-26, Volume: 82, Issue:7
Chivosazole A Modulates Protein-Protein Interactions of Actin.
AID344911Cytotoxicity against mouse Colon 38 cells at 5.1 uM by disk diffusion soft agar colony formation assay2008Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22
Interrogating the bioactive pharmacophore of the latrunculin chemotype by investigating the metabolites of two taxonomically unrelated sponges.
AID1538808Inhibition of immobilized rabbit skeletal muscle alpha-actin interaction with profilin at 66.7 uM pretreated for 30 mins followed by profilin addition measured after 1 hr by pull-down assay2019Journal of natural products, 07-26, Volume: 82, Issue:7
Chivosazole A Modulates Protein-Protein Interactions of Actin.
AID1895019Anticancer activity against human HepG2 cells assessed as inhibition of cell growth2021European journal of medicinal chemistry, Aug-05, Volume: 220Discovery of cytotoxic natural products from Red Sea sponges: Structure and synthesis.
AID344908Ratio of IC50 for human MDA-MB-435 cells to IC50 for human HCT116 cells2008Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22
Interrogating the bioactive pharmacophore of the latrunculin chemotype by investigating the metabolites of two taxonomically unrelated sponges.
AID511779Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay2010European journal of medicinal chemistry, Sep, Volume: 45, Issue:9
3D-QSAR studies of latrunculin-based actin polymerization inhibitors using CoMFA and CoMSIA approaches.
AID402935Disruption of actin cytoskeleton in rat A10 cells upto 10 ug/ml by rhodamine-phalloidin assay2004Journal of natural products, Jun, Volume: 67, Issue:6
A new dimension to the biosynthetic products isolated from the sponge Negombata magnifica.
AID324547Increase in light chain 3-GFP+ autophagosome vesicle intensity per cell in human H4 cells at 6.3 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (520)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (0.38)18.7374
1990's26 (5.00)18.2507
2000's298 (57.31)29.6817
2010's182 (35.00)24.3611
2020's12 (2.31)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 42.83

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index42.83 (24.57)
Research Supply Index6.27 (2.92)
Research Growth Index6.22 (4.65)
Search Engine Demand Index63.20 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (42.83)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (0.76%)6.00%
Case Studies1 (0.19%)4.05%
Observational0 (0.00%)0.25%
Other521 (99.05%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]