| Identification | Back Directory | [Name]
LEUKOTRIENE D4 | [CAS]
73836-78-9 | [Synonyms]
LTD4
leukotriened
LEUKOTRIENE D4
leukotriened(sub4)
LTD4 (Leukotriene D4)
(r-(r*,s*-(e,e,z,z)))-inyl)
YEESKJGWJFYOOK-IJHYULJSSA-N
LEUKOTRIENE D4 (ETHANOL SOLUTION)
5S-HYDROXY-6R-(S-CYSTEINYLGLYCINYL)-7E,9E,11Z,14Z-EICOSATETRAENOIC ACID
glycine,n-(s-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-l-cyste
5(S)-HYDROXY-6(R)-S-CYSTEINYLGLYCINYL-7-TRANS-9-TRANS-11-CIS-14-CIS-EICOSATETRAENOIC ACID
S-[(1R,2E,4E,6Z,9Z)-1-[(S)-4-Carboxy-1-hydroxybutyl]-2,4,6,9-pentadecatetren-1-yl]-L-Cys-Gly-OH
N-[S-[(1R,2E,4E,6Z,9Z)-1-[(S)-4-Carboxy-1-hydroxybutyl]-2,4,6,9-pentadecatetren-1-yl]-L-cysteinyl]glycine
N-[S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-1-Hydroxy-4-carboxybutyl]-2,4,6,9-pentadecatetren-1-yl]-L-cysteinyl]glycine
Glycine, S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]-2,4,6,9-pentadecatetraen-1-yl]-L-cysteinyl-
N-[S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-1-Hydroxy-4-carboxybutyl]-2,4,6,9-pentadecatetraene-1-yl]-L-cysteinyl]glycine
(5S,6R,7E,9E,11E,14E)-6-[2-amino-2-(carboxymethylcarbamoyl)ethyl]sulfanyl-5-hydroxy-icosa-7,9,11,14-tetraenoic acid | [Molecular Formula]
C25H40N2O6S | [MDL Number]
MFCD00036839 | [MOL File]
73836-78-9.mol | [Molecular Weight]
496.66 |
| Chemical Properties | Back Directory | [Boiling point ]
785.8±60.0 °C(Predicted) | [density ]
1.162±0.06 g/cm3(Predicted) | [Fp ]
9℃ | [storage temp. ]
-70°C | [solubility ]
A solution in ethanol | [form ]
Liquid. | [pka]
3.03±0.10(Predicted) | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [Description]
Leukotriene D4 (LTD4) is an active metabolite of LTC4 (Item Nos. 20210 | 10007241) and a constituent of slow-reacting substance of anaphylaxis (SRS-A). It is formed via metabolism of LTC4 by γ-glutamyl transpeptidase. Like LTC4, LTD4 (0.01-0.1 pM) induces contractions in isolated guinea pig parenchymal strips and tracheal spirals. In vivo, LTD4 increases insufflation pressure, a marker of bronchoconstriction, in anesthetized guinea pigs by 100% when administered at a dose of 89 pmol per animal. It also increases vascular permeability in guinea pig skin when administered intradermally at a dose of 0.1 pmol per animal. | [Uses]
LTD4 (Leukotriene D4) is a member of the leukotriene family shown to be a potent contractor of smooth muscle. | [Definition]
ChEBI: A leukotriene that is (7E,9E,11Z,14Z)-icosa-7,9,11,14-tetraenoic acid substituted by a hydroxy group at position 5 (5S) and a L-cysteinylglycinyl group at
position 6 (6R). | [Biochem/physiol Actions]
Slow reacting substance of anaphylaxis (SRS-A). Potent bronchoconstrictor and mediator of asthmatic and inflammatory processes. Increases cytosolic free Ca2+ in epithelial cells. | [in vivo]
Leukotriene D4 (1.5, 3, 6, 12, 24 μg/paw; injected intradermally) causes edema and increases capillary permeability in a dose-related manner in mouse[2]. | Animal Model: | 21-24 g, Balb/c male mice[2] | | Dosage: | 1.5, 3, 6, 12, 24 μg/paw | | Administration: | Injected intradermally (10 μL was injected into the left hind paw) | | Result: | Caused significant edematous response and dye extravasation at doses of 1.5-6 ~g/paw. |
| [IC 50]
Human Endogenous Metabolite | [storage]
Store at -80°C | [References]
[1] L ORNING B S S Hammarstr?m. Leukotriene D: a slow reacting substance from rat basophilic leukemia cells.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1980, 77 4: 2014-2017. DOI: 10.1073/pnas.77.4.2014
[2] S HAMMARSTR?M K B L Orning. Metabolism of leukotrienes.[J]. Molecular and Cellular Biochemistry, 1985, 69 1: 7-16. DOI: 10.1007/bf00225922
[3] PER HEDQVIST. Biological profile of Ieukotrienes C4 and D4[J]. Acta Physiologica, 1980, 110 3: 331-333. DOI: 10.1111/j.1748-1716.1980.tb06676.x
[4] EMILIE CERAUDO. Direct evidence that the GPCR CysLTR2 mutant causative of uveal melanoma is constitutively active with highly biased signaling.[J]. The Journal of Biological Chemistry, 2021: 100163. DOI: 10.1074/jbc.ra120.015352
[5] ERICK LU. S-Geranylgeranyl-l-glutathione is a ligand for human B cell-confinement receptor P2RY8[J]. Nature, 2019, 567 7747: 244-248. DOI: 10.1038/s41586-019-1003-z
[6] NATHAN C NI. A selective cysteinyl leukotriene receptor 2 antagonist blocks myocardial ischemia/reperfusion injury and vascular permeability in mice.[J]. Journal of Pharmacology and Experimental Therapeutics, 2011, 339 3: 768-778. DOI: 10.1124/jpet.111.186031
[7] HAI-YAN QI. A cytosolic phospholipase A2-initiated lipid mediator pathway induces autophagy in macrophages.[J]. Journal of immunology, 2011, 187 10: 5286-5292. DOI: 10.4049/jimmunol.1004004
[8] E. ONO. Concentration of 14,15-leukotriene C4 (eoxin C4) in bronchoalveolar lavage fluid[J]. Clinical and Experimental Allergy, 2009, 39 9: 1348-1352. DOI: 10.1111/j.1365-2222.2009.03261.x
[9] PEDRO P MEDINA Montse S C Montse Sanchez Cespedes. Involvement of the chromatin-remodeling factor BRG1/SMARCA4 in human cancer.[J]. Epigenetics, 2008, 3 2: 64-68. DOI: 10.4161/epi.3.2.6153
[10] KARSTEN GRONERT. Selectivity of Recombinant Human Leukotriene D4, Leukotriene B4, and Lipoxin A4 Receptors with Aspirin-Triggered 15-epi-LXA4 and Regulation of Vascular and Inflammatory Responses[J]. American Journal of Pathology, 2001, 158 1: Pages 3-9. DOI: 10.1016/s0002-9440(10)63937-5 |
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