Neocuproine | CAS#484-11-7 | chelator

MedKoo Cat#: 584849 | Name: Neocuproine

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Description:

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

Neocuproine is a copper(I) chelator.

Chemical Structure

Neocuproine

CAS#484-11-7

Theoretical Analysis

MedKoo Cat#: 584849

Name: Neocuproine

CAS#: 484-11-7

Chemical Formula: C14H12N2

Exact Mass: 208.1000

Molecular Weight: 208.26

Elemental Analysis: C, 80.74; H, 5.81; N, 13.45

Price and Availability

Size	Price	Availability	Quantity
1g	USD 210.00
5g	USD 380.00
25g	USD 720.00

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Related CAS #

No Data

Synonym

Neocuproine; Neocuproin

IUPAC/Chemical Name

1,10-Phenanthroline, 2,9-dimethyl-

InChi Key

IYRGXJIJGHOCFS-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H12N2/c1-9-3-5-11-7-8-12-6-4-10(2)16-14(12)13(11)15-9/h3-8H,1-2H3

SMILES Code

CC1=NC2=C3N=C(C)C=CC3=CC=C2C=C1

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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Neocuproine is a copper(I) chelator.

In vitro activity:

A novel amperometric method is presented for the determination of total antioxidant capacity in flow injection analysis (FIA) system using copper(II)-neocuproine complex modified on Nafion-functionalized multi-walled carbon nanotube-glassy carbon electrode ([Cu(Ncp)22+]/Nf@f-MWCNT/GCE). Cyclic voltammetric studies showed that the modified electrode exhibits a very well-formed reversible redox couple for Cu(II)-/Cu(I)-complex. Reference: Mikrochim Acta. 2022 Mar 31;189(4):167. https://pubmed.ncbi.nlm.nih.gov/35359164/

In vivo activity:

Neocuproine (100 microM) significantly suppressed the amplitude and frequency of the spontaneous contractions in the ovariectomized non-pregnant rat uterus while this agent facilitated the frequency of the spontaneous or oxytocin-induced contractions in the pregnant rat and human uterus without altering the amplitude of these contractions. At high concentration of 200 microM, neocuproine could enhance the amplitude of the contractions in the pregnant uterus. Reference: Eur J Pharmacol. 2009 Mar 1;605(1-3):158-63. https://pubmed.ncbi.nlm.nih.gov/19248249/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	120.04
	DMSO	25.0	120.04
	DMSO:PBS (pH 7.2) (1:4)	0.2	0.96
	Ethanol	10.0	48.02

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 208.26 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. Ayaz S, Üzer A, Dilgin Y, Apak R. A novel flow injection amperometric method for sensitive determination of total antioxidant capacity at cupric-neocuproine complex modified MWCNT glassy carbon electrode. Mikrochim Acta. 2022 Mar 31;189(4):167. doi: 10.1007/s00604-022-05271-z. PMID: 35359164. 2. Zhang Y, Wang J, Yang Z, Zhang Z, He X, Chen G, Huang G, Lu X. Hydrazine Hydrate Accelerates Neocuproine-Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation. J Org Chem. 2021 Dec 17;86(24):17696-17709. doi: 10.1021/acs.joc.1c01803. Epub 2021 Nov 24. PMID: 34818024. 3. Kumcu EK, Büyüknacar HS, Göçmen C, Evrüke IC, Onder S. Differential effect of neocuproine, a copper(I) chelator, on contractile activity in isolated ovariectomized non-pregnant rat, pregnant rat and pregnant human uterus. Eur J Pharmacol. 2009 Mar 1;605(1-3):158-63. doi: 10.1016/j.ejphar.2009.01.008. PMID: 19248249. 4. Göçmen C, Kumcu EK, Büyüknacar HS, Onder S, Singirik E. Neocuproine, a copper (I) chelator, potentiates purinergic component of vas deferens contractions elicited by electrical field stimulation. Pharmacology. 2005 Oct;75(2):69-75. doi: 10.1159/000087007. Epub 2005 Jul 11. PMID: 16020948.

In vitro protocol:

In vivo protocol:

1. Kumcu EK, Büyüknacar HS, Göçmen C, Evrüke IC, Onder S. Differential effect of neocuproine, a copper(I) chelator, on contractile activity in isolated ovariectomized non-pregnant rat, pregnant rat and pregnant human uterus. Eur J Pharmacol. 2009 Mar 1;605(1-3):158-63. doi: 10.1016/j.ejphar.2009.01.008. PMID: 19248249. 2. Göçmen C, Kumcu EK, Büyüknacar HS, Onder S, Singirik E. Neocuproine, a copper (I) chelator, potentiates purinergic component of vas deferens contractions elicited by electrical field stimulation. Pharmacology. 2005 Oct;75(2):69-75. doi: 10.1159/000087007. Epub 2005 Jul 11. PMID: 16020948.

1: Castro PA, Ramirez A, Sepúlveda FJ, Peters C, Fierro H, Waldron J, Luza S, Fuentealba J, Muñoz FJ, De Ferrari GV, Bush AI, Aguayo LG, Opazo CM. Copper-uptake is critical for the down regulation of synapsin and dynamin induced by neocuproine: modulation of synaptic activity in hippocampal neurons. Front Aging Neurosci. 2014 Dec 3;6:319. doi: 10.3389/fnagi.2014.00319. eCollection 2014. PubMed PMID: 25520655; PubMed Central PMCID: PMC4253966. 2: Patel OV, Wilson WB, Qin Z. Production of LPS-induced inflammatory mediators in murine peritoneal macrophages: neocuproine as a broad inhibitor and ATP7A as a selective regulator. Biometals. 2013 Jun;26(3):415-25. doi: 10.1007/s10534-013-9624-4. Epub 2013 Apr 19. PubMed PMID: 23604539. 3: Kumcu EK, Büyüknacar HS, Göçmen C, Evrüke IC, Onder S. Differential effect of neocuproine, a copper(I) chelator, on contractile activity in isolated ovariectomized non-pregnant rat, pregnant rat and pregnant human uterus. Eur J Pharmacol. 2009 Mar 1;605(1-3):158-63. doi: 10.1016/j.ejphar.2009.01.008. PubMed PMID: 19248249. 4: Soares SAR, Costa SSL, Araujo RGO, Teixeira LSG, Dantas AF. Comparison of Spectrophotometric Methods for the Determination of Copper in Sugar Cane Spirit. J AOAC Int. 2018 May 1;101(3):876-882. doi: 10.5740/jaoacint.17-0154. Epub 2017 Sep 15. PubMed PMID: 28911344. 5: Ho WC, Chung K, Ingram AJ, Waymouth RM. Pd-Catalyzed Aerobic Oxidation Reactions: Strategies To Increase Catalyst Lifetimes. J Am Chem Soc. 2018 Jan 17;140(2):748-757. doi: 10.1021/jacs.7b11372. Epub 2018 Jan 5. PubMed PMID: 29244945. 6: Zhu BZ, Chevion M. Copper-mediated toxicity of 2,4,5-trichlorophenol: biphasic effect of the copper(I)-specific chelator neocuproine. Arch Biochem Biophys. 2000 Aug 15;380(2):267-73. PubMed PMID: 10933881. 7: Paul BD, Snyder SH. Protein sulfhydration. Methods Enzymol. 2015;555:79-90. doi: 10.1016/bs.mie.2014.11.021. Epub 2015 Jan 14. PubMed PMID: 25747476. 8: Roohparvar R, Shamspur T, Mostafavi A. Application of silica coated magnetite nanoparticles modified with Cu(I)-neocuproine as nanosorbent to simultaneous separation-preconcentration of trace amounts of nitrate and nitrite. Nitric Oxide. 2018 Feb 28;73:9-14. doi: 10.1016/j.niox.2017.12.003. Epub 2017 Dec 14. PubMed PMID: 29248688. 9: Tütem E, Apak R, Günaydı E, Sözgen K. Spectrophotometric determination of vitamin E (alpha-tocopherol) using copper(II)-neocuproine reagent. Talanta. 1997 Feb;44(2):249-55. PubMed PMID: 18966741. 10: Arnal N, de Alaniz MJ, Marra CA. Carnosine and neocuproine as neutralizing agents for copper overload-induced damages in cultured human cells. Chem Biol Interact. 2011 Jul 15;192(3):257-63. doi: 10.1016/j.cbi.2011.03.017. Epub 2011 Apr 8. PubMed PMID: 21501601. 11: Nandal P, Khatkar SP, Kumar R, Khatkar A, Taxak VB. Synthesis, Optical Investigation and Biological Properties of Europium(III) Complexes with 2-(4-Chlorophenyl)-1-(2-Hydroxy-4-Methoxyphenyl)Ethan-1-one and Ancillary Ligands. J Fluoresc. 2017 Jan;27(1):1-11. doi: 10.1007/s10895-016-1930-0. Epub 2016 Sep 19. PubMed PMID: 27646650. 12: Al-Sa'doni HH, Megson IL, Bisland S, Butler AR, Flitney FW. Neocuproine, a selective Cu(I) chelator, and the relaxation of rat vascular smooth muscle by S-nitrosothiols. Br J Pharmacol. 1997 Jul;121(6):1047-50. PubMed PMID: 9249237; PubMed Central PMCID: PMC1564784. 13: De Man JG, Moreels TG, De Winter BY, Herman AG, Pelckmans PA. Neocuproine potentiates the activity of the nitrergic neurotransmitter but inhibits that of S-nitrosothiols. Eur J Pharmacol. 1999 Sep 24;381(2-3):151-9. PubMed PMID: 10554883. 14: Göçmen C, Göktürk HS, Ertuğ PU, Onder S, Dikmen A, Baysal F. Effect of neocuproine, a selective Cu(I) chelator, on nitrergic relaxations in the mouse corpus cavernosum. Eur J Pharmacol. 2000 Oct 13;406(2):293-300. PubMed PMID: 11020493. 15: Starosta R, Bykowska A, Kyzioł A, Płotek M, Florek M, Król J, Jeżowska-Bojczuk M. Copper(I) (pseudo)halide complexes with neocuproine and aminomethylphosphines derived from morpholine and thiomorpholine - in vitro cytotoxic and antimicrobial activity and the interactions with DNA and serum albumins. Chem Biol Drug Des. 2013 Nov;82(5):579-86. doi: 10.1111/cbdd.12187. Epub 2013 Aug 10. PubMed PMID: 23841542. 16: Vanin AF, Serezhenkov VA, Malenkova IV. Nitric oxide initiates iron binding to neocuproine. Nitric Oxide. 2001 Apr;5(2):166-75. PubMed PMID: 11292366. 17: Apak R, Güçlü K, Ozyürek M, Karademir SE, Altun M. Total antioxidant capacity assay of human serum using copper(II)-neocuproine as chromogenic oxidant: the CUPRAC method. Free Radic Res. 2005 Sep;39(9):949-61. PubMed PMID: 16087476. 18: Byrnes RW, Antholine WE, Petering DH. Oxidation-reduction reactions in Ehrlich cells treated with copper-neocuproine. Free Radic Biol Med. 1992 Nov;13(5):469-78. PubMed PMID: 1334027. 19: Vercruysse KP, Lauwers AR, Demeester JM. Kinetic investigation of the action of hyaluronidase on hyaluronan using the Morgan-Elson and neocuproine assays. Biochem J. 1995 Aug 15;310 ( Pt 1):55-9. PubMed PMID: 7646472; PubMed Central PMCID: PMC1135853. 20: Applebaum YJ, Kuvin J, Borman JB, Uretzky G, Chevion M. The protective role of neocuproine against cardiac damage in isolated perfused rat hearts. Free Radic Biol Med. 1990;8(2):133-43. PubMed PMID: 2332193.