U-73343 | CAS#142878-12-4 | TxA2 Formation Inhibitor

MedKoo Cat#: 510296 | Name: U-73343

Description:

WARNING: This product is for research use only, not for human or veterinary use.

U-73343 is a negative control (or inactive analogue) of U73122, which is a putative phospholipase C inhibitor. U73343 was found to inhibit TxA2 formation; it therefore partially inhibited the rise in [Ca2+]i evoked by low concentrations of thrombin, by thapsigargin or by collagen. U73343 had a greater effect than aspirin on the action of collagen, indicating an action on the TxA2-independent component of the signal, via PLC gamma-U73343 lowered TxA2 production by inhibiting the activation of cPLA2, probably at a tyrosine phosphorylation step. U73343 seems to inhibit only the tyrosine kinases involved in the activation of PLC gamma and the generation of TxA2.

Chemical Structure

U-73343

CAS#142878-12-4

Theoretical Analysis

MedKoo Cat#: 510296

Name: U-73343

CAS#: 142878-12-4

Chemical Formula: C29H42N2O3

Exact Mass: 466.3195

Molecular Weight: 466.65

Elemental Analysis: C, 74.64; H, 9.07; N, 6.00; O, 10.29

Price and Availability

Size	Price	Availability
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 750.00	Ready to ship
500mg	USD 1,650.00	Ready to ship
1g	USD 2,950.00	Ready to ship
2g	USD 5,250.00	Ready to ship

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Related CAS #

No Data

Synonym

U73343, U-73343, U 73343

IUPAC/Chemical Name

1-(6-(((8R,9S,13S,14S,17S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)amino)hexyl)pyrrolidine-2,5-dione

InChi Key

CJHWFIUASFBCKN-ZRJUGLEFSA-N

InChi Code

InChI=1S/C29H42N2O3/c1-29-16-15-23-22-10-8-21(34-2)19-20(22)7-9-24(23)25(29)11-12-26(29)30-17-5-3-4-6-18-31-27(32)13-14-28(31)33/h8,10,19,23-26,30H,3-7,9,11-18H2,1-2H3/t23-,24-,25+,26+,29+/m1/s1

SMILES Code

O=C(CC1)N(CCCCCCN[C@H]2CC[C@@]3([H])[C@]4([H])CCC5=CC(OC)=CC=C5[C@@]4([H])CC[C@]23C)C1=O

Appearance

White to off-white solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#S9S08C16

QC Data

View QC data: current batch, Lot#S9S08C16

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

U-73343, works as a protonophore, is an inactive analog of U-73122 and can be used as a negative control.

In vitro activity:

As shown in Fig. 2A and D, U-73122 prevented the effect of BDNF (97.3 ± 5.7% of baseline, n = 6; baseline, 814.1 ± 148.6 pA; BDNF, 825.8 ± 191.4 pA). In contrast, the inactive analog U-73343 (5 μM) did not block the BDNF effect (Fig. 2B and D). Reference: J Neurophysiol. 2014 Mar 1; 111(5): 1008–1015. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3949235/

In vivo activity:

The application of 1 μM U73122, a phospholipase C (PLC) inhibitor, to the basolateral membrane side significantly decreased the Ca2+ response to 0.31 ± 0.22 times the magnitude of the control response (n = 5, p < 0.008, one-tailed paired t test; Fig. 4b). Washing the mouse taste bud with the control bathing solution failed to recover the magnitude of the response. The application of 1 μM U73343, a negative control, had no effects (0.90 ± 0.21, n = 5, p > 0.14 one-tailed paired t test; Fig. 4c). Reference: Pflugers Arch. 2016; 468(11): 2053–2059. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5138268/

	Solvent	mg/mL	mM
Solubility
	DMSO	3.9	8.34
	DMF	2.0	4.29
	Ethanol	1.3	2.76

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 466.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Zhao L, Levine ES. BDNF-endocannabinoid interactions at neocortical inhibitory synapses require phospholipase C signaling. J Neurophysiol. 2014 Mar;111(5):1008-15. doi: 10.1152/jn.00554.2013. Epub 2013 Dec 11. PMID: 24335212; PMCID: PMC3949235. 2. Dai Y, Dudek NL, Li Q, Muma NA. Phospholipase C, Ca2+, and calmodulin signaling are required for 5-HT2A receptor-mediated transamidation of Rac1 by transglutaminase. Psychopharmacology (Berl). 2011 Feb;213(2-3):403-12. doi: 10.1007/s00213-010-1984-7. Epub 2010 Aug 18. PMID: 20717650; PMCID: PMC3033764. 3. Mori Y, Eguchi K, Yoshii K, Ohtubo Y. Selective expression of muscarinic acetylcholine receptor subtype M3 by mouse type III taste bud cells. Pflugers Arch. 2016 Nov;468(11-12):2053-2059. doi: 10.1007/s00424-016-1879-5. Epub 2016 Sep 14. PMID: 27628900; PMCID: PMC5138268. 4. Kim JC, Woo SH. Shear stress induces a longitudinal Ca(2+) wave via autocrine activation of P2Y1 purinergic signalling in rat atrial myocytes. J Physiol. 2015 Dec 1;593(23):5091-109. doi: 10.1113/JP271016. Epub 2015 Nov 4. PMID: 26377030; PMCID: PMC4666989.

In vitro protocol:

In vivo protocol:

1. Mori Y, Eguchi K, Yoshii K, Ohtubo Y. Selective expression of muscarinic acetylcholine receptor subtype M3 by mouse type III taste bud cells. Pflugers Arch. 2016 Nov;468(11-12):2053-2059. doi: 10.1007/s00424-016-1879-5. Epub 2016 Sep 14. PMID: 27628900; PMCID: PMC5138268. 2. Kim JC, Woo SH. Shear stress induces a longitudinal Ca(2+) wave via autocrine activation of P2Y1 purinergic signalling in rat atrial myocytes. J Physiol. 2015 Dec 1;593(23):5091-109. doi: 10.1113/JP271016. Epub 2015 Nov 4. PMID: 26377030; PMCID: PMC4666989.

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Detachment of surface membrane invagination systems by cationic amphiphilic drugs. Sci Rep. 2016 Jan 4;6:18536. doi: 10.1038/srep18536. PMID: 26725955; PMCID: PMC4698757. 5: Montalbano A, Corradetti R, Mlinar B. Pharmacological Characterization of 5-HT1A Autoreceptor-Coupled GIRK Channels in Rat Dorsal Raphe 5-HT Neurons. PLoS One. 2015 Oct 13;10(10):e0140369. doi: 10.1371/journal.pone.0140369. PMID: 26460748; PMCID: PMC4603796. 6: Zhao L, Levine ES. BDNF-endocannabinoid interactions at neocortical inhibitory synapses require phospholipase C signaling. J Neurophysiol. 2014 Mar;111(5):1008-15. doi: 10.1152/jn.00554.2013. Epub 2013 Dec 11. PMID: 24335212; PMCID: PMC3949235. 7: Hwang MW, Lee HJ, Song HJ, Kim BJ. Involvement of MAPKs and PLC pathways in modulation of pacemaking activity by So-Cheong-Ryong-Tang in interstitial cells of Cajal from murine small intestine. ScientificWorldJournal. 2013 Oct 30;2013:536350. doi: 10.1155/2013/536350. PMID: 24288491; PMCID: PMC3833007. 8: Kato K, Okamura K, Hatta M, Morita H, Kajioka S, Naito S, Yamazaki J. Involvement of IP3-receptor activation in endothelin-1-induced Ca(2+) influx in rat pulmonary small artery. Eur J Pharmacol. 2013 Nov 15;720(1-3):255-63. doi: 10.1016/j.ejphar.2013.09.076. Epub 2013 Oct 22. PMID: 24157978. 9: Hörnig M, Markoutsa S, Häfner AK, George S, Wisniewska JM, Rödl CB, Hofmann B, Maier T, Karas M, Werz O, Steinhilber D. Inhibition of 5-lipoxygenase by U73122 is due to covalent binding to cysteine 416. Biochim Biophys Acta. 2012 Feb;1821(2):279-86. doi: 10.1016/j.bbalip.2011.11.001. Epub 2011 Nov 23. PMID: 22137889. 10: Seo J, Kim K, Jang S, Han S, Choi SY, Kim E. Regulation of hippocampal long- term potentiation and long-term depression by diacylglycerol kinase ζ. Hippocampus. 2012 May;22(5):1018-26. doi: 10.1002/hipo.20889. Epub 2010 Nov 10. PMID: 21069783. 11: Chávez JC, de Blas GA, de la Vega-Beltrán JL, Nishigaki T, Chirinos M, González-González ME, Larrea F, Solís A, Darszon A, Treviño CL. The opening of maitotoxin-sensitive calcium channels induces the acrosome reaction in human spermatozoa: differences from the zona pellucida. Asian J Androl. 2011 Jan;13(1):159-65. doi: 10.1038/aja.2010.80. Epub 2010 Sep 13. PMID: 20835262; PMCID: PMC3739404. 12: Macmillan D, McCarron JG. The phospholipase C inhibitor U-73122 inhibits Ca(2+) release from the intracellular sarcoplasmic reticulum Ca(2+) store by inhibiting Ca(2+) pumps in smooth muscle. Br J Pharmacol. 2010 Jul;160(6):1295-301. doi: 10.1111/j.1476-5381.2010.00771.x. PMID: 20590621; PMCID: PMC2938802. 13: Szatkowski C, Parys JB, Ouadid-Ahidouch H, Matifat F. Inositol 1,4,5-trisphosphate-induced Ca2+ signalling is involved in estradiol-induced breast cancer epithelial cell growth. Mol Cancer. 2010 Jun 21;9:156. doi: 10.1186/1476-4598-9-156. PMID: 20565939; PMCID: PMC2906470. 14: Ouyang Q, Sato H, Murata Y, Nakamura A, Ozaki M, Nakamura T. Contribution of the inositol 1,4,5-trisphosphate transduction cascade to the detection of "bitter" compounds in blowflies. Comp Biochem Physiol A Mol Integr Physiol. 2009 Jul;153(3):309-16. doi: 10.1016/j.cbpa.2009.03.004. Epub 2009 Mar 9. PMID: 19275942. 15: Kataoka A, Tozaki-Saitoh H, Koga Y, Tsuda M, Inoue K. Activation of P2X7 receptors induces CCL3 production in microglial cells through transcription factor NFAT. J Neurochem. 2009 Jan;108(1):115-25. doi: 10.1111/j.1471-4159.2008.05744.x. Epub 2008 Nov 10. PMID: 19014371. 16: Yin X, Eckberg WR. Characterization of phospholipases C beta and gamma and their possible roles in Chaetopterus egg activation. Mol Reprod Dev. 2009 May;76(5):460-70. doi: 10.1002/mrd.20961. PMID: 18951372. 17: Perez-Burgos A, Perez-Rosello T, Salgado H, Flores-Barrera E, Prieto GA, Figueroa A, Galarraga E, Bargas J. Muscarinic M(1) modulation of N and L types of calcium channels is mediated by protein kinase C in neostriatal neurons. Neuroscience. 2008 Sep 9;155(4):1079-97. doi: 10.1016/j.neuroscience.2008.06.047. Epub 2008 Jul 1. PMID: 18644425. 18: Zhou YD, Fang XF, Cui ZJ. UVA-induced calcium oscillations in rat mast cells. Cell Calcium. 2009 Jan;45(1):18-28. doi: 10.1016/j.ceca.2008.05.003. Epub 2008 Jul 3. PMID: 18602157. 19: Clarke CJ, Forman S, Pritchett J, Ohanian V, Ohanian J. Phospholipase C-delta1 modulates sustained contraction of rat mesenteric small arteries in response to noradrenaline, but not endothelin-1. Am J Physiol Heart Circ Physiol. 2008 Aug;295(2):H826-34. doi: 10.1152/ajpheart.01396.2007. Epub 2008 Jun 20. PMID: 18567701; PMCID: PMC2519204. 20: Karashima Y, Prenen J, Meseguer V, Owsianik G, Voets T, Nilius B. Modulation of the transient receptor potential channel TRPA1 by phosphatidylinositol 4,5-biphosphate manipulators. 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