O-PHENANTHROLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H8N2
Molecular Weight	180.2053
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1=CN=C2C(C=CC3=C2N=CC=C3)=C1

InChI

InChIKey=DGEZNRSVGBDHLK-UHFFFAOYSA-N

InChI=1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H

HIDE SMILES / InChI

Molecular Formula	C12H8N2
Molecular Weight	180.2053
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30344448 | https://www.ncbi.nlm.nih.gov/pubmed/30970890 | https://www.ncbi.nlm.nih.gov/pubmed/26396770

o-Phenanthroline is a metal chelating agent that prevents the induction of chromosomal aberrations in streptozotocin-treated cells. Acts as a general MMP (matrix metalloproteinase) inhibitor. o-Phenanthroline has been employed as a photometric reagent for iron. o-Phenanthroline forms a complex with Fe2+, but not with Fe3+. NH2OH can be added to the solution to reduce the Fe3+ to Fe2+ for analysis of iron. Due to the o-Phenanthroline's strong UV absorbance, it may interfere with spectrophotometric assays. When complexed with copper, it possesses nuclease activity that has been employed in studying DNA-protein interactions.

Approval Year

PubMed

Title	Date	PubMed
Mitochondrial processing of newly synthesized steroidogenic acute regulatory protein (StAR), but not total StAR, mediates cholesterol transfer to cytochrome P450 side chain cleavage enzyme in adrenal cells.	2001-12-07	11579102
Structural and functional characterization of the Zn(II) site in dimethylargininase-1 (DDAH-1) from bovine brain. Zn(II) release activates DDAH-1.	2001-11-02	11546769
Allosteric interaction of minor groove binding ligands with UL9-DNA complexes.	2001-10-23	11601987
Proximity of transmembrane segments M3 and M1 of the alpha subunit of Na+,K+-ATPase revealed by specific oxidative cleavage mediated by a complex of Cu2+ ions and 4,7-diphenyl-1,10-phenanthroline.	2001-10-23	11601974
Use of SDS micelles to stabilize a ternary intermediate in the reaction of ferrioxamine B and 1,10-phenanthroline.	2001-10-08	11578189
Relative binding energies of gas-phase pyridyl ligand/metal complexes by energy-variable collisionally activated dissociation in a quadrupole ion trap.	2001-10-08	11578185
Phenanthrolines--a new class of CFTR chloride channel openers.	2001-10	11606326
Functional expression and characterization of the cytoplasmic aminopeptidase P of Caenorhabditis elegans.	2001-10	11606206
Study of metallopeptidase isozymes from malted barley (Hordeum vulgare cv. Morex).	2001-10	11600042
CaALK8, an alkane assimilating cytochrome P450, confers multidrug resistance when expressed in a hypersensitive strain of Candida albicans.	2001-09-15	11536334
Cell surface antigens in renal tumour cells: detection by immunoluminescence and enzymatic analysis.	2001-09-14	11556847
mu-Opioid receptor-mediated ERK activation involves calmodulin-dependent epidermal growth factor receptor transactivation.	2001-09-07	11457825
Characterization of a secretase activity for placental leucine aminopeptidase.	2001-09-01	11516173
Isomerization of DNA-bound distilbazolium ligand induced by electron transfer from photoexcited tris(1,10-phenanthroline)Ru(II).	2001-09	11594051
Stress proteins in oligodendrocytes: differential effects of heat shock and oxidative stress.	2001-09	11579132
Characteristics of an alpha-galactosidase associated with grape flesh.	2001-09	11551541
Matrix metalloproteinase activities of turkey (Meleagris gallopavo) bile.	2001-09	11544146
[Study of ribosome structure using the biochemical methods: judgment day].	2001-08-30	11524944
Influence of carbon disulphide on hydroxyl radicals in the phenanthroline chemiluminescence system.	2001-08-21	11512146
Identical flow injection spectrophotometric manifold for determination of protein, phosphorus, calcium, chloride, copper, manganese, iron, and zinc in feeds or premixes.	2001-08-15	11501921
Intracellular iron, but not copper, plays a critical role in hydrogen peroxide-induced DNA damage.	2001-08-15	11498282
Conformational isomerism and weak molecular and magnetic interactions in ternary copper(II) complexes of [Cu(AA)L']ClO4.nH2O, where AA = L-phenylalanine and L-histidine, L' = 1,10-phenanthroline and 2,2-bipyridine, and n = 1 or 1.5: synthesis, single-crystal X-ray structures, and magnetic resonance investigations.	2001-08-13	11487335
Heterobimetallic oxalato-bridged Cu(II)Re(IV) complexes. Synthesis, crystal structure and magnetic properties.	2001-08-13	11487328
Bis(4,7-dimethyl and 5-dinitro-1,10-phenanthroline) sulfato-oxovanadium(IV)-mediated in vivo male germ cell apoptosis.	2001-08-02	11481668
Lysine aminopeptidase of Aspergillus niger.	2001-08	11495983
Mn K-edge XANES and Kbeta XES studies of two Mn-oxo binuclear complexes: investigation of three different oxidation states relevant to the oxygen-evolving complex of photosystem II.	2001-07-25	11459481
Synthesis and characterization of a ruthenium(II)-based redox conjugate for reagentless biosensing.	2001-07-19	11459471
Solid-state coordination chemistry: structural influences of copper-phenanthroline subunits on oxovanadium organophosphonate phases. hydrothermal synthesis and structural characterization of the two-dimensional materials [Cu(phen)(VO)(O3PCH2PO3)(H2O)], [[Cu(phen)]2(V2O5)(O3PCH2CH2PO3)], and [[Cu(phen)]2(V3O5)(O3PCH2CH2CH2PO3)2(H2O)] and the three-dimensional phase [[Cu(phen)]2(V3O5)(O3PCH2PO3)2(H2O)].	2001-07-16	11442373
Formation and structure of a complex of sucrose with cobalt(III)bis(phenanthroline).	2001-07-12	11448682
Purification and characterisation of a haemorrhagic fraction from the venom of the Uracoan rattlesnake Crotalus vegrandis.	2001-07-09	11451438
Matrix metalloproteinase-2 in platelet adhesion to fibrinogen: interactions with nitric oxide.	2001-07-04	11433190
Iron(II) complexes containing a ferrocenyl framework attached to 2,2'-bipyridine or 1,10-phenanthroline subunits: formation of stable Fe-bis(2,2'-bipyridine)-like and Fe-bis(1,10-phenanthroline)-like complexes.	2001-07-02	11421719
Energy-transfer rate in crystals of double-complex salts composed of [Ru(N-N)3](2+) (N-N = 2,2'-bipyridine or 1,10-phenanthroline) and [Cr(CN)6](3-): effect of relative orientation between donor and acceptor.	2001-07-02	11421686
Fluxional behavior of the dinitrogen ligand 2,9-dimethyl-1,10-phenanthroline in cationic methyl platinum(II) complexes.	2001-07-02	11421672
Determination of trace metals by capillary electrophoresis.	2001-07	11504052
Inhibition of human gelatinases by metals released from dental amalgam.	2001-07	11426881
Isotachophoretic separation behavior of rare-earth EDTA chelates and analysis of minor rare-earth elements in an iron ore by bidirectional isotachophoresis-particle-induced X-ray emission.	2001-06-15	11442049
Inactivation of the serpin alpha(2)-antiplasmin by stromelysin-1.	2001-06-11	11410276
Soluble CD44 inhibits melanoma tumor growth by blocking cell surface CD44 binding to hyaluronic acid.	2001-06-07	11423990
Purification and characterization of a 43.5 kDa keratinolytic metalloprotease from Microsporum canis.	2001-06	11446530
A robust multi-syringe system for process flow analysis. Part 3. Time based injection applied to the spectrophotometric determination of nickel(II) and iron speciation.	2001-06	11445960
Chemiluminescent flow-through sensor for 1,10-phenanthroline based on the combination of molecular imprinting and chemiluminescence.	2001-06	11445942
Biological activity of alpha-thujaplicin, the minor component of Thujopsis dolabrata SIEB. et ZUCC. var. hondai MAKINO.	2001-06	11411545
Synthesis of [Ru(phen)(2)dppz](2+)-tethered oligo-DNA and studies on the metallointercalation mode into the DNA duplex.	2001-04-18	11472126
H2O2-induced cell death in human glioma cells: role of lipid peroxidation and PARP activation.	2001-04	11495343
Modulator of heme biosynthesis induces apoptosis in leukemia cells.	2001-04	11443791
Cyclization/hydrosilylation of functionalized diynes catalyzed by a cationic platinum phenanthroline complex.	2001-02-08	11428020
Cycloisomerization of functionalized 1,5- and 1,6-dienes catalyzed by cationic palladium phenanthroline complexes.	2001-01-26	11429845
Friedländer synthesis of chiral alkyl-substituted 1,10-phenanthrolines.	2001-01-26	11429806
Processing of the insulin-like growth factor-II-mannose 6-phosphate receptor in isolated liver subcellular fractions.	2001	11527216

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:15:15 GMT 2025` Edited by `admin` on `Mon Mar 31 19:15:15 GMT 2025`
Record UNII	W4X6ZO7939
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-203545

Preferred Name

English

O-PHENANTHROLINE

Common Name

English

PHENANTHROLINE, 1,10-

Systematic Name

English

4,5-PHENANTHROLINE

Systematic Name

English

1,10-PHENANTHROLINE

Systematic Name

English

PHENANTHROLINE, O-

Common Name

English

NSC-4265

Code

English

O-PHENANTHROLINE [MI]

Common Name

English

Code System Code Type Description

EVMPD

SUB179387