NQTrp | CAS#185351-19-3 |

MedKoo Cat#: 563305 | Name: NQTrp

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Description:

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

NQTrp is a potent inhibitor of Aβ oligomer and fibril formation (IC50 = 50 nM for formation of fibrils from Aβ1-42).

Chemical Structure

NQTrp

CAS#185351-19-3

Theoretical Analysis

MedKoo Cat#: 563305

Name: NQTrp

CAS#: 185351-19-3

Chemical Formula: C21H16N2O4

Exact Mass: 360.1110

Molecular Weight: 360.37

Elemental Analysis: C, 69.99; H, 4.48; N, 7.77; O, 17.76

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 260.00
10mg	USD 400.00
25mg	USD 710.00

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Related CAS #

No Data

Synonym

NQTrp; NQ-Trp; NQ Trp;

IUPAC/Chemical Name

(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-L-tryptophan

InChi Key

DZZUYZXINNHEGM-SFHVURJKSA-N

InChi Code

InChI=1S/C21H16N2O4/c24-19-10-17(20(25)15-7-2-1-6-14(15)19)23-18(21(26)27)9-12-11-22-16-8-4-3-5-13(12)16/h1-8,10-11,18,22-23H,9H2,(H,26,27)/t18-/m0/s1

SMILES Code

O=C(O)[C@H](CC1=CNC2=C1C=CC=C2)NC(C3=O)=CC(C4=C3C=CC=C4)=O

Appearance

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

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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

NQTrp is an inhibitor of the aggregation of the tau protein with generic anti-amyloidogenic effects.

In vitro activity:

This study shows that the naphthoquinone tryptophan (NQTrp) hybrid molecule significantly inhibited PAP f39 aggregation in vitro in a dose-dependent manner as observed from the ThT assay, ANS assay, and transmission electron microscopy imaging. This study found that even at a sub-molar concentration of 20:1 [PAP f39:NQTrp], NQTrp could reduce >50% amyloid formation. NQTrp inhibition of PAP f39 aggregation resulted in non-toxic intermediate species as determined by the vesicle leakage assay. Reference: Molecules. 2018 Dec 11;23(12):3279. https://pubmed.ncbi.nlm.nih.gov/30544943/

In vivo activity:

This compound, 1,4-naphthoquinon-2-yl-L-tryptophan (NQTrp), combines the recognition capacities of both quinone and tryptophan moieties and completely inhibited Abeta oligomerization and fibrillization, as well as the cytotoxic effect of Abeta oligomers towards cultured neuronal cell line. Furthermore, when fed to transgenic Alzheimer's disease Drosophila model it prolonged their life span and completely abolished their defective locomotion. Analysis of the brains of these flies showed a significant reduction in oligomeric species of Abeta while immuno-staining of the 3(rd) instar larval brains showed a significant reduction in Abeta accumulation. Reference: PLoS One. 2010 Jun 14;5(6):e11101. https://pubmed.ncbi.nlm.nih.gov/20559435/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	55.50
	DMF:PBS (pH 7.2) (1:1)	0.5	1.39
	DMSO	72.5	201.18
	Ethanol	1.0	2.78

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 360.37 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. Viswanathan GK, Mohapatra S, Paul A, Arad E, Jelinek R, Gazit E, Segal D. Inhibitory Effect of Naphthoquinone-Tryptophan Hybrid towards Aggregation of PAP f39 Semen Amyloid. Molecules. 2018 Dec 11;23(12):3279. doi: 10.3390/molecules23123279. PMID: 30544943; PMCID: PMC6320874. 2. Scherzer-Attali R, Convertino M, Pellarin R, Gazit E, Segal D, Caflisch A. Methylations of tryptophan-modified naphthoquinone affect its inhibitory potential toward Aβ aggregation. J Phys Chem B. 2013 Feb 14;117(6):1780-9. doi: 10.1021/jp309066p. Epub 2013 Jan 31. PMID: 23259849. 3. Scherzer-Attali R, Pellarin R, Convertino M, Frydman-Marom A, Egoz-Matia N, Peled S, Levy-Sakin M, Shalev DE, Caflisch A, Gazit E, Segal D. Complete phenotypic recovery of an Alzheimer's disease model by a quinone-tryptophan hybrid aggregation inhibitor. PLoS One. 2010 Jun 14;5(6):e11101. doi: 10.1371/journal.pone.0011101. PMID: 20559435; PMCID: PMC2885425.

In vitro protocol:

In vivo protocol:

1. Scherzer-Attali R, Pellarin R, Convertino M, Frydman-Marom A, Egoz-Matia N, Peled S, Levy-Sakin M, Shalev DE, Caflisch A, Gazit E, Segal D. Complete phenotypic recovery of an Alzheimer's disease model by a quinone-tryptophan hybrid aggregation inhibitor. PLoS One. 2010 Jun 14;5(6):e11101. doi: 10.1371/journal.pone.0011101. PMID: 20559435; PMCID: PMC2885425.

1: KrishnaKumar VG, Paul A, Gazit E, Segal D. Mechanistic insights into remodeled Tau-derived PHF6 peptide fibrils by Naphthoquinone-Tryptophan hybrids. Sci Rep. 2018 Jan 8;8(1):71. doi: 10.1038/s41598-017-18443-2. PubMed PMID: 29311706; PubMed Central PMCID: PMC5758761. 2: Frenkel-Pinter M, Tal S, Scherzer-Attali R, Abu-Hussien M, Alyagor I, Eisenbaum T, Gazit E, Segal D. 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. doi: 10.1159/000448518. Epub 2016 Oct 20. PubMed PMID: 27760426. 3: Frenkel-Pinter M, Tal S, Scherzer-Attali R, Abu-Hussien M, Alyagor I, Eisenbaum T, Gazit E, Segal D. Naphthoquinone-Tryptophan Hybrid Inhibits Aggregation of the Tau-Derived Peptide PHF6 and Reduces Neurotoxicity. J Alzheimers Dis. 2016;51(1):165-78. doi: 10.3233/JAD-150927. PubMed PMID: 26836184. 4: Tarus B, Nguyen PH, Berthoumieu O, Faller P, Doig AJ, Derreumaux P. Molecular structure of the NQTrp inhibitor with the Alzheimer Aβ1-28 monomer. Eur J Med Chem. 2015 Feb 16;91:43-50. doi: 10.1016/j.ejmech.2014.07.002. Epub 2014 Jul 1. PubMed PMID: 25011560. 5: Zhang T, Xu W, Mu Y, Derreumaux P. Atomic and dynamic insights into the beneficial effect of the 1,4-naphthoquinon-2-yl-L-tryptophan inhibitor on Alzheimer's Aβ1-42 dimer in terms of aggregation and toxicity. ACS Chem Neurosci. 2014 Feb 19;5(2):148-59. doi: 10.1021/cn400197x. Epub 2013 Nov 22. PubMed PMID: 24246047; PubMed Central PMCID: PMC3930991. 6: Scherzer-Attali R, Convertino M, Pellarin R, Gazit E, Segal D, Caflisch A. Methylations of tryptophan-modified naphthoquinone affect its inhibitory potential toward Aβ aggregation. J Phys Chem B. 2013 Feb 14;117(6):1780-9. doi: 10.1021/jp309066p. Epub 2013 Jan 31. PubMed PMID: 23259849. 7: Scherzer-Attali R, Farfara D, Cooper I, Levin A, Ben-Romano T, Trudler D, Vientrov M, Shaltiel-Karyo R, Shalev DE, Segev-Amzaleg N, Gazit E, Segal D, Frenkel D. Naphthoquinone-tyrptophan reduces neurotoxic Aβ*56 levels and improves cognition in Alzheimer's disease animal model. Neurobiol Dis. 2012 Jun;46(3):663-72. doi: 10.1016/j.nbd.2012.03.005. Epub 2012 Mar 19. PubMed PMID: 22449754. 8: Chebaro Y, Jiang P, Zang T, Mu Y, Nguyen PH, Mousseau N, Derreumaux P. Structures of Aβ17-42 trimers in isolation and with five small-molecule drugs using a hierarchical computational procedure. J Phys Chem B. 2012 Jul 26;116(29):8412-22. doi: 10.1021/jp2118778. Epub 2012 Feb 10. PubMed PMID: 22283547. 9: Scherzer-Attali R, Pellarin R, Convertino M, Frydman-Marom A, Egoz-Matia N, Peled S, Levy-Sakin M, Shalev DE, Caflisch A, Gazit E, Segal D. Complete phenotypic recovery of an Alzheimer's disease model by a quinone-tryptophan hybrid aggregation inhibitor. PLoS One. 2010 Jun 14;5(6):e11101. doi: 10.1371/journal.pone.0011101. PubMed PMID: 20559435; PubMed Central PMCID: PMC2885425.