U-73343
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MedKoo CAT#: 510296

CAS#: 142878-12-4

Description: 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

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U-73343
CAS# 142878-12-4

Theoretical Analysis

MedKoo Cat#: 510296
Name: U-73343
CAS#: 142878-12-4
Chemical Formula: C29H42N2O3
Exact Mass: 466.31954
Molecular Weight: 466.65
Elemental Analysis: C, 74.64; H, 9.07; N, 6.00; O, 10.29

Price and Availability

Size Price Availability Quantity
25.0mg USD 150.0 Ready to ship
50.0mg USD 250.0 Ready to ship
100.0mg USD 450.0 Ready to ship
200.0mg USD 850.0 Ready to ship
500.0mg USD 1750.0 Ready to ship
1.0g USD 2950.0 Ready to ship
2.0g USD 5350.0 Ready to ship
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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

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 3.89 8.34
DMF 2.0 4.29
Ethanol 1.29 2.76

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.

Recalculate based on batch purity %
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: 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.
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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1: Takenouchi T, Ogihara K, Sato M, Kitani H. Inhibitory effects of U73122 and U73343 on Ca2+ influx and pore formation induced by the activation of P2X7 nucleotide receptors in mouse microglial cell line. Biochim Biophys Acta. 2005 Nov 15;1726(2):177-86. Epub 2005 Aug 15. PubMed PMID: 16122875.

2: Bosch RR, Patel AM, Van Emst-de Vries SE, Smeets RL, De Pont JJ, Willems PH. U73122 and U73343 inhibit receptor-mediated phospholipase D activation downstream of phospholipase C in CHO cells. Eur J Pharmacol. 1998 Apr 10;346(2-3):345-51. PubMed PMID: 9652379.

3: Muto Y, Nagao T, Urushidani T. The putative phospholipase C inhibitor U73122 and its negative control, U73343, elicit unexpected effects on the rabbit parietal cell. J Pharmacol Exp Ther. 1997 Sep;282(3):1379-88. PubMed PMID: 9316850.

4: Heemskerk JW, Feijge MA, Sage SO, Farndale RW. Human platelet activation is inhibited upstream of the activation of phospholipase A2 by U73343. Biochem Pharmacol. 1997 May 9;53(9):1257-62. PubMed PMID: 9214686.

5: Heemskerk JW, Farndale RW, Sage SO. Effects of U73122 and U73343 on human platelet calcium signalling and protein tyrosine phosphorylation. Biochim Biophys Acta. 1997 Jan 10;1355(1):81-8. PubMed PMID: 9030204.

U-73343

25.0mg / USD 150.0