Synonym
Dihydrokainic acid; DHK; Dihydrokainate
IUPAC/Chemical Name
(2S,3S,4R)-2-carboxy-4-(1-methylethyl)-3-pyrrolidineacetic acid
InChi Key
JQPDCKOQOOQUSC-OOZYFLPDSA-N
InChi Code
InChI=1S/C10H17NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h5-7,9,11H,3-4H2,1-2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1
SMILES Code
OC([C@@H]1[C@@H](CC(O)=O)[C@@H](C(C)C)CN1)=O
Purity
>95% (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
>3 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:
Dihydrokainic acid (DHK) is a glutamate transporter GLT1 (EAAT2) inhibitor.
In vivo activity:
In the novel object recognition test, the Cef-induced reversal on recognition index in APP/PS1 AD mice was inhibited after the administration of DHK in DHK + Cef group compared with Cef group (Figures 3A,B) [test 1: F(3,53) = 10.503, p < 0.001; test 2: F(3,58) = 4.860, p = 0.004, ANOVA]. Meanwhile, the suppression on mGluR2 expression in APP/PS1 AD mice induced by Cef was also reversed by the administration of DHK (Figure 3C) [F(3,20) = 30.966, p < 0.001, ANOVA]. The results suggested that Cef-induced reversals on the recognition memory deficits and suppression on the mGluR2 upregulation in APP/PS1 AD mice were dependent on GLT-1.
Reference: Front Neurosci. 2022 Jul 4;16:905403. https://pubmed.ncbi.nlm.nih.gov/35860293/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| Water |
5.4 |
24.99 |
|
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
215.25
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. Fan S, Li L, Liu L, Li H, Xian X, Li W. Ceftriaxone Suppresses Group II Metabotropic Glutamate Receptor Expression Contributing to Reversal of Recognition Memory Deficits of Amyloid Precursor Protein/Presenilin 1 AD Mice. Front Neurosci. 2022 Jul 4;16:905403. doi: 10.3389/fnins.2022.905403. PMID: 35860293; PMCID: PMC9289516.
2. Chen Y, Shen M, Liu X, Xu J, Wang C. The Regulation of Glutamate Transporter 1 in the Rapid Antidepressant-Like Effect of Ketamine in Mice. Front Behav Neurosci. 2022 Mar 2;16:789524. doi: 10.3389/fnbeh.2022.789524. PMID: 35309681; PMCID: PMC8926310.
In vivo protocol:
1. Fan S, Li L, Liu L, Li H, Xian X, Li W. Ceftriaxone Suppresses Group II Metabotropic Glutamate Receptor Expression Contributing to Reversal of Recognition Memory Deficits of Amyloid Precursor Protein/Presenilin 1 AD Mice. Front Neurosci. 2022 Jul 4;16:905403. doi: 10.3389/fnins.2022.905403. PMID: 35860293; PMCID: PMC9289516.
2. Chen Y, Shen M, Liu X, Xu J, Wang C. The Regulation of Glutamate Transporter 1 in the Rapid Antidepressant-Like Effect of Ketamine in Mice. Front Behav Neurosci. 2022 Mar 2;16:789524. doi: 10.3389/fnbeh.2022.789524. PMID: 35309681; PMCID: PMC8926310.
1. Arriza, J.L., Fairman, W.A., Wadiche, J.I., et al. Functional comparisons of three glutamate transporter subtypes cloned from human motor cortex. J. Neurosci. 14(9), 5559-5569 (1994).
2. Gasull-Camós, J., Tarrés-Gatius, M., Artigas, F., et al. Glial GLT-1 blockade in infralimbic cortex as a new strategy to evoke rapid antidepressant-like effects in rats. Transl. Psychiatry 7(2), e1038 (2017).
3. Gasull-Camós, J., Martínez-Torres, S., Tarrés-Gatius, M., et al. Serotonergic mechanisms involved in antidepressant-like responses evoked by GLT-1 blockade in rat infralimbic cortex. Neuropharmacology 139, 41-51 (2018).
4. John, C.S., Smith, K.L., Van't Veer, A., et al. Blockade of astrocytic glutamate uptake in the prefrontal cortex induces anhedonia. Neuropsychopharmacology 37(11), 2467-2475 (2012).
5. Tian, S.-W., Yu, X.-D., Cen, L., et al. Glutamate transporter GLT1 inhibitor dihydrokainic acid impairs novel object recognition memory performance in mice. Physiol. Behav. 199, 28-32 (2019).
