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P9375

Sigma-Aldrich

1,10-Phenanthroline monohydrate

reagent grade

Synonym(s):

o-Phenanthroline monohydrate

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About This Item

Empirical Formula (Hill Notation):
C12H8N2 · H2O
CAS Number:
5144-89-8
Molecular Weight:
198.22
Beilstein:
4008096
EC Number:
200-629-2
MDL number:
MFCD00149973
UNSPSC Code:
12352116
PubChem Substance ID:
24278663
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

grade

reagent grade

form

powder

mp

100-104 °C (lit.)

solubility

methanol: 200 mM (Stock solution is stable for months at –20° C.)

SMILES string

O.c1cnc2c(c1)ccc3cccnc23

InChI

1S/C12H8N2.H2O/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1;/h1-8H;1H2

InChI key

PPQJCISYYXZCAE-UHFFFAOYSA-N

Gene Information

human ... FNTA(2339)

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General description

Phenanthroline is a heterocyclic organic compound, which forms complexes with metal ions. These complexes have wide applications in biochemistry, catalysis and analytical chemistry. It complexes with iron and is exploited as a redox indicator.

Application

1,10-Phenanthroline monohydrate has been used:
  • as an inhibitor of metalloproteinase (MMP) in MDA-MB-231 breast cancer cells
  • as a negative control in in situ zymography of mice heart samples
  • in in vitro resveratrol chelation and reducing activities assays to chelate iron

When complexed with copper, it possesses nuclease activity that has been used to study DNA-protein interactions.

Biochem/physiol Actions

Metalloprotease inhibitor; chelates iron, zinc and other divalent metals. Effective concentration 1-10 mM.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301,H410

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000377981
0000377981
0000342743
0000342744
0000296790

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Electrochemical and DFT study of the reduction of substituted phenanthrolines
Ferreira H, et al.
Polyhedron, 122, 147-154 (2017)
The transmodulation of HER2 and EGFR by substance P in breast cancer cells requires c-Src and metalloproteinase activation
Garcia-Recio S, et al.
PLoS ONE, 10(6), e0129661-e0129661 (2015)
Katy Satué et al.
Acta veterinaria Hungarica, 68(1), 79-84 (2020-05-10)
In women and females of different species of laboratory animals, oestrogens stimulate the renin-angiotensin-aldosterone system (RAAS) by increasing tissue and circulating levels of angiotensinogen and renin during the preovulatory period. Progesterone and cortisol compete with aldosterone for mineralocorticoid receptors, which
Central Role of Phenanthroline Mono-N-oxide in the Decomposition Reactions of Tris (1, 10-phenanthroline) iron (II) and-iron (III) Complexes
Beller G, et al.
Inorganic Chemistry, 49(9), 3968-3970 (2010)
Overexpression of TFAM or twinkle increases mtDNA copy number and facilitates cardioprotection associated with limited mitochondrial oxidative stress
Ikeda M, et al.
PLoS ONE, 10(3), e0119687-e0119687 (2015)
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