Synonym
L690330; L 690330; L-690330.
IUPAC/Chemical Name
[1-(4-hydroxyphenoxy)-1-phosphonoethyl]phosphonic acid
InChi Key
JKOCAAWWDVHWKB-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H12O8P2/c1-8(17(10,11)12,18(13,14)15)16-7-4-2-6(9)3-5-7/h2-5,9H,1H3,(H2,10,11,12)(H2,13,14,15)
SMILES Code
CC(OC1=CC=C(O)C=C1)(P(O)(O)=O)P(O)(O)=O
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
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:
L-690330 is a competitive inhibitor of inositol monophosphatase (IMPase) with Kis of 0.27 and 0.19 μM for recombinant human and bovine IMPase, 0.30 and 0.42 μM for human and bovine frontal cortex IMPase, respectively.
In vitro activity:
Likewise, the time course and maximum accumulation of [3H] CMP-PA in L-690,488-treated m1 CHO cells was similar to lithium but L-690,488 was again much more potent (EC50 values = 3.5 +/- 0.3 microM and 0.52 +/- 0.03 mM for L-690,488 and lithium, respectively). In addition, L-690,488 attenuated the carbachol-induced elevation of inositol 1,4,5-trisphosphate and inositol 1,3,4,5-tetrakisphosphate in m1 CHO cells, an effect reported previously with lithium.
Reference: J Pharmacol Exp Ther. 1994 Jul;270(1):70-6. https://pubmed.ncbi.nlm.nih.gov/8035344/
In vivo activity:
In comparison, a selective IMPase inhibitor (L-690330) attenuated the mouse behavioural response to DOI whereas glycogen synthase kinase inhibitor (AR-A014418) did not.
Reference: Br J Pharmacol. 2018 Jul;175(13):2599-2610. https://pubmed.ncbi.nlm.nih.gov/29488218/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Water |
19.7 |
65.90 |
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
298.12
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. Atack JR, Prior AM, Fletcher SR, Quirk K, McKernan R, Ragan CI. Effects of L-690,488, a prodrug of the bisphosphonate inositol monophosphatase inhibitor L-690,330, on phosphatidylinositol cycle markers. J Pharmacol Exp Ther. 1994 Jul;270(1):70-6. PMID: 8035344.
2. Atack JR, Cook SM, Watt AP, Fletcher SR, Ragan CI. In vitro and in vivo inhibition of inositol monophosphatase by the bisphosphonate L-690,330. J Neurochem. 1993 Feb;60(2):652-8. doi: 10.1111/j.1471-4159.1993.tb03197.x. PMID: 8380439.
3. Antoniadou I, Kouskou M, Arsiwala T, Singh N, Vasudevan SR, Fowler T, Cadirci E, Churchill GC, Sharp T. Ebselen has lithium-like effects on central 5-HT2A receptor function. Br J Pharmacol. 2018 Jul;175(13):2599-2610. doi: 10.1111/bph.14179. Epub 2018 May 22. PMID: 29488218; PMCID: PMC6003638.
4. Shtein L, Toker L, Bersudsky Y, Belmaker RH, Agam G. The inositol monophosphatase inhibitor L-690,330 affects pilocarpine-behavior and the forced swim test. Psychopharmacology (Berl). 2013 Jun;227(3):503-8. doi: 10.1007/s00213-013-2969-0. Epub 2013 Jan 24. PMID: 23344554.
In vitro protocol:
1. Atack JR, Prior AM, Fletcher SR, Quirk K, McKernan R, Ragan CI. Effects of L-690,488, a prodrug of the bisphosphonate inositol monophosphatase inhibitor L-690,330, on phosphatidylinositol cycle markers. J Pharmacol Exp Ther. 1994 Jul;270(1):70-6. PMID: 8035344.
2. Atack JR, Cook SM, Watt AP, Fletcher SR, Ragan CI. In vitro and in vivo inhibition of inositol monophosphatase by the bisphosphonate L-690,330. J Neurochem. 1993 Feb;60(2):652-8. doi: 10.1111/j.1471-4159.1993.tb03197.x. PMID: 8380439.
In vivo protocol:
1. Antoniadou I, Kouskou M, Arsiwala T, Singh N, Vasudevan SR, Fowler T, Cadirci E, Churchill GC, Sharp T. Ebselen has lithium-like effects on central 5-HT2A receptor function. Br J Pharmacol. 2018 Jul;175(13):2599-2610. doi: 10.1111/bph.14179. Epub 2018 May 22. PMID: 29488218; PMCID: PMC6003638.
2. Shtein L, Toker L, Bersudsky Y, Belmaker RH, Agam G. The inositol monophosphatase inhibitor L-690,330 affects pilocarpine-behavior and the forced swim test. Psychopharmacology (Berl). 2013 Jun;227(3):503-8. doi: 10.1007/s00213-013-2969-0. Epub 2013 Jan 24. PMID: 23344554.
1: Shtein L, Toker L, Bersudsky Y, Belmaker RH, Agam G. The inositol monophosphatase inhibitor L-690,330 affects pilocarpine-behavior and the forced swim test. Psychopharmacology (Berl). 2013 Jun;227(3):503-8. doi: 10.1007/s00213-013-2969-0. PubMed PMID: 23344554.
2: Sarkar S, Rubinsztein DC. Inositol and IP3 levels regulate autophagy: biology and therapeutic speculations. Autophagy. 2006 Apr-Jun;2(2):132-4. Review. PubMed PMID: 16874097.
3: Westfall TA, Hjertos B, Slusarski DC. Requirement for intracellular calcium modulation in zebrafish dorsal-ventral patterning. Dev Biol. 2003 Jul 15;259(2):380-91. PubMed PMID: 12871708.
4: Sconzo G, Cascino D, Amore G, Geraci F, Giudice G. Effect of the IMPase inhibitor L690,330 on sea urchin development. Cell Biol Int. 1998;22(2):91-4. PubMed PMID: 9878095.
5: Cui H, Meng Y, Bulleit RF. Inhibition of glycogen synthase kinase 3beta activity regulates proliferation of cultured cerebellar granule cells. Brain Res Dev Brain Res. 1998 Dec 7;111(2):177-88. PubMed PMID: 9838099.
6: Piettre SR, André C, Chanal MC, Ducep JB, Lesur B, Piriou F, Raboisson P, Rondeau JM, Schelcher C, Zimmermann P, Ganzhorn AJ. Monoaryl- and bisaryldihydroxytropolones as potent inhibitors of inositol monophosphatase. J Med Chem. 1997 Dec 19;40(26):4208-21. PubMed PMID: 9435892.
7: Slusarski DC, Corces VG, Moon RT. Interaction of Wnt and a Frizzled homologue triggers G-protein-linked phosphatidylinositol signalling. Nature. 1997 Nov 27;390(6658):410-3. PubMed PMID: 9389482.
8: Atack JR. Inositol monophosphatase inhibitors--lithium mimetics? Med Res Rev. 1997 Mar;17(2):215-24. Review. PubMed PMID: 9057165.
9: Atack JR, Prior AM, Fletcher SR, Quirk K, McKernan R, Ragan CI. Effects of L-690,488, a prodrug of the bisphosphonate inositol monophosphatase inhibitor L-690,330, on phosphatidylinositol cycle markers. J Pharmacol Exp Ther. 1994 Jul;270(1):70-6. PubMed PMID: 8035344.
10: Atack JR, Cook SM, Watt AP, Fletcher SR, Ragan CI. In vitro and in vivo inhibition of inositol monophosphatase by the bisphosphonate L-690,330. J Neurochem. 1993 Feb;60(2):652-8. PubMed PMID: 8380439.
