Physicochemical Properties
| Molecular Formula | C21H15N2O4CL |
| Molecular Weight | 394.808 |
| Exact Mass | 394.072 |
| CAS # | 185351-23-9 |
| PubChem CID | 1427125 |
| Appearance | Brown to reddish brown solid powder |
| LogP | 4.2 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 28 |
| Complexity | 707 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | ClC1C(=O)C2C(=CC=CC=2)C(=O)C=1N[C@H](C(O)=O)CC1C2=C(C=CC=C2)NC=1 |
| InChi Key | ZKNQSBBALRSDBQ-INIZCTEOSA-N |
| InChi Code | InChI=1S/C21H15ClN2O4/c22-17-18(20(26)14-7-2-1-6-13(14)19(17)25)24-16(21(27)28)9-11-10-23-15-8-4-3-5-12(11)15/h1-8,10,16,23-24H,9H2,(H,27,28)/t16-/m0/s1 |
| Chemical Name | (2S)-2-[(3-chloro-1,4-dioxonaphthalen-2-yl)amino]-3-(1H-indol-3-yl)propanoic acid |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | Using Cl-NQTrp, pre-formed PHF6 peptide fibrils were effectively disassembled[1]. PHF6 peptide oligomers may undergo structural modifications as a result of Cl-NQTrp[1]. |
| ln Vivo | Since Cl-NQTrp targets both Aβ and tau aggregation, it may offer a novel therapeutic option for AD[2]. The shortened life span of htau-expressing flies is greatly reduced by Cl-NQTrp, resulting in 58% viability on day 29[2]. |
| Animal Protocol |
Animal/Disease Models: Virgin females, carrying either the eye GMR -Gal4 driver or the pan-neuronal driver elavc155 -Gal4 on chromosome X, were collected and crossed with males carrying UAS-h tau on the 2nd chromosome or with wild-type Oregon- R (OR) males as a control[2]. Doses: 0.75 mg/mL. Route of Administration: Dripped every other day. Experimental Results: Inhibited PHF6 aggregation and ameliorates eye neurodegeneration Drosophila overexpressing the human tau protein (htau). |
| References |
[1]. Mechanistic insights into remodeled Tau-derived PHF6 peptide fibrils by Naphthoquinone-Tryptophan hybrids. Sci Rep. 2018 Jan 8;8(1):71. [2]. Cl-NQTrp Alleviates Tauopathy Symptoms in a Model Organism through the Inhibition of Tau Aggregation-Engendered Toxicity. Neurodegener Dis. 2017;17(2-3):73-82. |
Solubility Data
| Solubility (In Vitro) | DMSO: 250 mg/mL (633.22 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.27 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.27 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5329 mL | 12.6643 mL | 25.3286 mL | |
| 5 mM | 0.5066 mL | 2.5329 mL | 5.0657 mL | |
| 10 mM | 0.2533 mL | 1.2664 mL | 2.5329 mL |