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Key Documents

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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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Doxorubicin Hydrochloride InSolution, ≥98%

504042

Doxorubicin Hydrochloride

mode of action

DNA synthesis | interferes

mode of action

-

mode of action

DNA synthesis | interferes, enzyme | inhibits

mode of action

-

antibiotic activity spectrum

viruses

antibiotic activity spectrum

-

antibiotic activity spectrum

neoplastics

antibiotic activity spectrum

-

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

200

assay

98.0-102.0% (HPLC)

assay

-

assay

98.0-102.0% (HPLC)

assay

≥98% (HPLC)

form

powder

form

powder

form

solid

form

liquid

biological source

synthetic (organic)

biological source

-

biological source

synthetic

biological source

-

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.[1] It complexes with iron and is exploited as a redox indicator.[2]

Application

1,10-Phenanthroline monohydrate has been used:
  • as an inhibitor of metalloproteinase (MMP) in MDA-MB-231 breast cancer cells[3]
  • as a negative control in in situ zymography of mice heart samples[4]
  • in in vitro resveratrol chelation and reducing activities assays to chelate iron[5]

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
    0000434933
    0000434933
    0000424774
    0000424774
    0000377981

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    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)
    Electrochemical and DFT study of the reduction of substituted phenanthrolines
    Ferreira H, et al.
    Polyhedron, 122, 147-154 (2017)
    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)
    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
    Resveratrol attenuates iron-induced toxicity in a chronic post-treatment paradigm in Caenorhabditis elegans
    Soares MV, et al.
    Free Radical Research, 52(9), 939-951 (2018)
    View All Related Papers

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