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Contents |
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* Residue conservation analysis
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Enzyme class:
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Chains H, L:
E.C.3.4.21.5
- thrombin.
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Reaction:
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Preferential cleavage: Arg-|-Gly; activates fibrinogen to fibrin and releases fibrinopeptide A and B.
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DOI no:
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Science
317:1881-1886
(2007)
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PubMed id:
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Fluorine in pharmaceuticals: looking beyond intuition.
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K.Müller,
C.Faeh,
F.Diederich.
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ABSTRACT
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Fluorine substituents have become a widespread and important drug component,
their introduction facilitated by the development of safe and selective
fluorinating agents. Organofluorine affects nearly all physical and adsorption,
distribution, metabolism, and excretion properties of a lead compound. Its
inductive effects are relatively well understood, enhancing bioavailability, for
example, by reducing the basicity of neighboring amines. In contrast,
exploration of the specific influence of carbon-fluorine single bonds on docking
interactions, whether through direct contact with the protein or through
stereoelectronic effects on molecular conformation of the drug, has only
recently begun. Here, we review experimental progress in this vein and add
complementary analysis based on comprehensive searches in the Cambridge
Structural Database and the Protein Data Bank.
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Selected figure(s)
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Figure 3.
Fig. 3. (A) Aryl–OCHF[2] fragment (  = 19°) of
roflumilast bound to phosphordiesterase 4 (table S1, entry 7)
shows a multipolar C–F···C=O contact with
the backbone amide of Trp332. (B) Aryl–OCF[3] fragment ( =
81°) of an inhibitor bound to the Ser protease trypsin
(table S1, entry 13). Protein Cs are shown in gray (also applies
to Fig. 5 and the SOM).
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Figure 5.
Fig. 5. (A) Fluorine interacts favorably with peptidic N–H
(ligand Cs in green) and C=O (ligand Cs in purple) moieties. (B)
Fluorine undergoes dipolar interactions with side-chain amides
of Gln and Asp (ligand Cs in yellow). (C) The C–F residue of a
tricyclic inhibitor undergoes a multipolar interaction with the
backbone C=O of Asn98 in the D pocket of thrombin (table S1,
entry 23). (D) A dipolar N–H···F–C
interaction induces the shown conformation of a thrombin
inhibitor within the enzyme (fig. S3 and table S1, entry 22).
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The above figures are
reprinted
by permission from the AAAs:
Science
(2007,
317,
1881-1886)
copyright 2007.
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Figures were
selected
by the author.
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Literature references that cite this PDB file's key reference
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PubMed id
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Reference
|
|
|
|
|
|
A.J.Hickman,
and
M.S.Sanford
(2012).
High-valent organometallic copper and palladium in catalysis.
|
| |
Nature,
484,
177-185.
|
|
|
|
|
|
|
Y.Fujiwara,
J.A.Dixon,
F.O'Hara,
E.D.Funder,
D.D.Dixon,
R.A.Rodriguez,
R.D.Baxter,
B.Herlé,
N.Sach,
M.R.Collins,
Y.Ishihara,
and
P.S.Baran
(2012).
Practical and innate carbon-hydrogen functionalization of heterocycles.
|
| |
Nature,
492,
95-99.
|
|
|
|
|
|
|
C.Dalvit,
and
A.Vulpetti
(2011).
Fluorine-protein interactions and ¹⁹F NMR isotropic chemical shifts: An empirical correlation with implications for drug design.
|
| |
ChemMedChem,
6,
104-114.
|
|
|
|
|
|
|
D.A.Nagib,
and
D.W.MacMillan
(2011).
Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis.
|
| |
Nature,
480,
224-228.
|
|
|
|
|
|
|
G.Landelle,
M.Bergeron,
M.O.Turcotte-Savard,
and
J.F.Paquin
(2011).
Synthetic approaches to monofluoroalkenes.
|
| |
Chem Soc Rev,
40,
2867-2908.
|
|
|
|
|
|
|
G.Mehta,
and
S.Sen
(2011).
(1S*,3S*,8S*,10S*)-10-Fluoro-15-oxa-tetra-cyclo-[6.6.1.0.0]penta-deca-5,12-dien-3-ol.
|
| |
Acta Crystallogr Sect E Struct Rep Online,
67,
o1985.
|
|
|
|
|
|
|
J.M.Narayanam,
and
C.R.Stephenson
(2011).
Visible light photoredox catalysis: applications in organic synthesis.
|
| |
Chem Soc Rev,
40,
102-113.
|
|
|
|
|
|
|
J.P.Brand,
D.Fernández González,
S.Nicolai,
and
J.Waser
(2011).
Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions.
|
| |
Chem Commun (Camb),
47,
102-115.
|
|
|
|
|
|
|
J.R.Pliego
(2011).
Chemical reactions inside structured nano-environment: S(N)2 vs. E2 reactions for the F(-) + CH(3)CH(2)Cl system.
|
| |
Phys Chem Chem Phys,
13,
779-782.
|
|
|
|
|
|
|
J.Xu,
D.F.Luo,
B.Xiao,
Z.J.Liu,
T.J.Gong,
Y.Fu,
and
L.Liu
(2011).
Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3+ reagent.
|
| |
Chem Commun (Camb),
47,
4300-4302.
|
|
|
|
|
|
|
J.Zhu,
H.Xie,
Z.Chen,
S.Li,
and
Y.Wu
(2011).
Synthesis of 6-trifluoromethylindolo[1,2-c]quinazolines and related heterocycles using N-(2-iodophenyl)trifluoroacetimidoyl chlorides as starting material via C-H bond functionalization.
|
| |
Chem Commun (Camb),
47,
1512-1514.
|
|
|
|
|
|
|
L.L.Wu,
C.L.Yang,
F.C.Lo,
C.H.Chiang,
C.W.Chang,
K.Y.Ng,
H.H.Chou,
H.Y.Hung,
S.I.Chan,
and
S.S.Yu
(2011).
Tuning the regio- and stereoselectivity of C-H activation in n-octanes by cytochrome P450 BM-3 with fluorine substituents: evidence for interactions between a C-F bond and aromatic π systems.
|
| |
Chemistry,
17,
4774-4787.
|
|
|
|
|
|
|
M.Saito,
K.Miyamoto,
and
M.Ochiai
(2011).
Hypervalent phenyl-λ(3)-iodane-mediated para-selective aromatic fluorination of 3-phenylpropyl ethers.
|
| |
Chem Commun (Camb),
47,
3410-3412.
|
|
|
|
|
|
|
N.H.Campbell,
D.L.Smith,
A.P.Reszka,
S.Neidle,
and
D.O'Hagan
(2011).
Fluorine in medicinal chemistry: β-fluorination of peripheral pyrrolidines attached to acridine ligands affects their interactions with G-quadruplex DNA.
|
| |
Org Biomol Chem,
9,
1328-1331.
|
|
|
PDB codes:
|
|
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|
|
|
|
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S.Fustero,
V.Rodrigo,
M.Sánchez-Roselló,
C.del Pozo,
J.Timoneda,
M.Frizler,
M.T.Sisay,
J.Bajorath,
L.P.Calle,
F.J.Cañada,
J.Jiménez-Barbero,
and
M.Gütschow
(2011).
New cathepsin inhibitors to explore the fluorophilic properties of the S2 pocket of cathepsin B: design, synthesis, and biological evaluation.
|
| |
Chemistry,
17,
5256-5260.
|
|
|
|
|
|
|
S.L.Zhang,
H.X.Xie,
J.Zhu,
H.Li,
X.S.Zhang,
J.Li,
and
W.Wang
(2011).
Organocatalytic enantioselective β-functionalization of aldehydes by oxidation of enamines and their application in cascade reactions.
|
| |
Nat Commun,
2,
211.
|
|
|
|
|
|
|
T.Furuya,
A.S.Kamlet,
and
T.Ritter
(2011).
Catalysis for fluorination and trifluoromethylation.
|
| |
Nature,
473,
470-477.
|
|
|
|
|
|
|
A.D.Sun,
and
J.A.Love
(2010).
Cross coupling reactions of polyfluoroarenes via C-F activation.
|
| |
Dalton Trans,
39,
10362-10374.
|
|
|
|
|
|
|
A.E.Allen,
and
D.W.Macmillan
(2010).
The productive merger of iodonium salts and organocatalysis: a non-photolytic approach to the enantioselective alpha-trifluoromethylation of aldehydes.
|
| |
J Am Chem Soc,
132,
4986-4987.
|
|
|
|
|
|
|
A.L'heureux,
F.Beaulieu,
C.Bennett,
D.R.Bill,
S.Clayton,
F.Laflamme,
M.Mirmehrabi,
S.Tadayon,
D.Tovell,
and
M.Couturier
(2010).
Aminodifluorosulfinium salts: selective fluorination reagents with enhanced thermal stability and ease of handling.
|
| |
J Org Chem,
75,
3401-3411.
|
|
|
|
|
|
|
A.M.Saraiva,
I.Cardoso,
M.C.Pereira,
M.A.Coelho,
M.J.Saraiva,
H.Möhwald,
and
G.Brezesinski
(2010).
Controlling amyloid-beta peptide(1-42) oligomerization and toxicity by fluorinated nanoparticles.
|
| |
Chembiochem,
11,
1905-1913.
|
|
|
|
|
|
|
A.N.Koller,
J.Bozilovic,
J.W.Engels,
and
H.Gohlke
(2010).
Aromatic N versus aromatic F: bioisosterism discovered in RNA base pairing interactions leads to a novel class of universal base analogs.
|
| |
Nucleic Acids Res,
38,
3133-3146.
|
|
|
|
|
|
|
A.S.Eustáquio,
D.O'Hagan,
and
B.S.Moore
(2010).
Engineering fluorometabolite production: fluorinase expression in Salinispora tropica Yields Fluorosalinosporamide.
|
| |
J Nat Prod,
73,
378-382.
|
|
|
|
|
|
|
A.Vulpetti,
N.Schiering,
and
C.Dalvit
(2010).
Combined use of computational chemistry, NMR screening, and X-ray crystallography for identification and characterization of fluorophilic protein environments.
|
| |
Proteins,
78,
3281-3291.
|
|
|
PDB codes:
|
|
|
|
|
|
|
|
C.Bissantz,
B.Kuhn,
and
M.Stahl
(2010).
A medicinal chemist's guide to molecular interactions.
|
| |
J Med Chem,
53,
5061-5084.
|
|
|
|
|
|
|
C.Diehl,
O.Engström,
T.Delaine,
M.Håkansson,
S.Genheden,
K.Modig,
H.Leffler,
U.Ryde,
U.J.Nilsson,
and
M.Akke
(2010).
Protein flexibility and conformational entropy in ligand design targeting the carbohydrate recognition domain of galectin-3.
|
| |
J Am Chem Soc,
132,
14577-14589.
|
|
|
PDB code:
|
|
|
|
|
|
|
|
C.Madelaine,
O.Buriez,
B.Crousse,
I.Florent,
P.Grellier,
P.Retailleau,
and
Y.Six
(2010).
Aminocyclopropanes as precursors of endoperoxides with antimalarial activity.
|
| |
Org Biomol Chem,
8,
5591-5601.
|
|
|
|
|
|
|
D.Breyer,
T.Braun,
and
A.Penner
(2010).
Isolation and reactivity of palladium hydrido complexes: intermediates in the hydrodefluorination of pentafluoropyridine.
|
| |
Dalton Trans,
39,
7513-7520.
|
|
|
|
|
|
|
E.J.Cho,
T.D.Senecal,
T.Kinzel,
Y.Zhang,
D.A.Watson,
and
S.L.Buchwald
(2010).
The palladium-catalyzed trifluoromethylation of aryl chlorides.
|
| |
Science,
328,
1679-1681.
|
|
|
|
|
|
|
G.Blay,
I.Fernández,
M.C.Muñoz,
J.R.Pedro,
and
C.Vila
(2010).
Synthesis of functionalized indoles with a trifluoromethyl-substituted stereogenic tertiary carbon atom through an enantioselective Friedel-Crafts alkylation with beta-trifluoromethyl-alpha,beta-enones.
|
| |
Chemistry,
16,
9117-9122.
|
|
|
|
|
|
|
G.Kokotos,
Y.H.Hsu,
J.E.Burke,
C.Baskakis,
C.G.Kokotos,
V.Magrioti,
and
E.A.Dennis
(2010).
Potent and selective fluoroketone inhibitors of group VIA calcium-independent phospholipase A2.
|
| |
J Med Chem,
53,
3602-3610.
|
|
|
|
|
|
|
G.Verniest,
K.Piron,
E.Van Hende,
J.W.Thuring,
G.Macdonald,
F.Deroose,
and
N.De Kimpe
(2010).
Synthesis of aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines.
|
| |
Org Biomol Chem,
8,
2509-2512.
|
|
|
|
|
|
|
J.Liu,
and
J.Hu
(2010).
Highly diastereoselective synthesis of α-difluoromethyl amines from N-tert-butylsulfinyl ketimines and difluoromethyl phenyl sulfone.
|
| |
Chemistry,
16,
11443-11454.
|
|
|
|
|
|
|
J.N.Baraniuk,
and
M.J.Jamieson
(2010).
Rhinorrhea, cough and fatigue in patients taking sitagliptin.
|
| |
Allergy Asthma Clin Immunol,
6,
8.
|
|
|
|
|
|
|
K.Fujimura,
and
Y.Sasabuchi
(2010).
The role of fluorine atoms in a fluorinated prostaglandin agonist.
|
| |
ChemMedChem,
5,
1254-1257.
|
|
|
|
|
|
|
K.S.Kanyiva,
N.Kashihara,
Y.Nakao,
T.Hiyama,
M.Ohashi,
and
S.Ogoshi
(2010).
Hydrofluoroarylation of alkynes with fluoroarenes.
|
| |
Dalton Trans,
39,
10483-10494.
|
|
|
|
|
|
|
K.Zheng,
Y.Yang,
J.Zhao,
C.Yin,
L.Lin,
X.Liu,
and
X.Feng
(2010).
The magnesium(II)-catalyzed asymmetric ketone-ene reaction under solvent-free conditions: stereocontrolled access to enantioenriched trifluoromethyl-substituted compounds.
|
| |
Chemistry,
16,
9969-9972.
|
|
|
|
|
|
|
L.M.Hughes,
R.Covian,
G.W.Gribble,
and
B.L.Trumpower
(2010).
Probing binding determinants in center P of the cytochrome bc(1) complex using novel hydroxy-naphthoquinones.
|
| |
Biochim Biophys Acta,
1797,
38-43.
|
|
|
|
|
|
|
N.Xiao,
and
Y.B.Yu
(2010).
Separation of Fluorinated Amino Acids and Oligopeptides from their Non-fluorinated Counterparts using High-performance Liquid Chromatography.
|
| |
J Fluor Chem,
131,
439-445.
|
|
|
|
|
|
|
O.H.Kwon,
T.H.Yoo,
C.M.Othon,
J.A.Van Deventer,
D.A.Tirrell,
and
A.H.Zewail
(2010).
Hydration dynamics at fluorinated protein surfaces.
|
| |
Proc Natl Acad Sci U S A,
107,
17101-17106.
|
|
|
|
|
|
|
O.Pàmies,
P.G.Andersson,
and
M.Diéguez
(2010).
Asymmetric hydrogenation of minimally functionalised terminal olefins: an alternative sustainable and direct strategy for preparing enantioenriched hydrocarbons.
|
| |
Chemistry,
16,
14232-14240.
|
|
|
|
|
|
|
S.Fan,
C.Y.He,
and
X.Zhang
(2010).
Direct Pd-catalyzed benzylation of highly electron-deficient perfluoroarenes.
|
| |
Chem Commun (Camb),
46,
4926-4928.
|
|
|
|
|
|
|
T.A.Gulder,
and
B.S.Moore
(2010).
Salinosporamide natural products: potent 20 s proteasome inhibitors as promising cancer chemotherapeutics.
|
| |
Angew Chem Int Ed Engl,
49,
9346-9367.
|
|
|
|
|
|
|
T.Furuya,
D.Benitez,
E.Tkatchouk,
A.E.Strom,
P.Tang,
W.A.Goddard,
and
T.Ritter
(2010).
Mechanism of C-F reductive elimination from palladium(IV) fluorides.
|
| |
J Am Chem Soc,
132,
3793-3807.
|
|
|
|
|
|
|
T.Vagt,
E.Nyakatura,
M.Salwiczek,
C.Jäckel,
and
B.Koksch
(2010).
Towards identifying preferred interaction partners of fluorinated amino acids within the hydrophobic environment of a dimeric coiled coil peptide.
|
| |
Org Biomol Chem,
8,
1382-1386.
|
|
|
|
|
|
|
V.Capriati,
S.Florio,
F.M.Perna,
and
A.Salomone
(2010).
Lithiated fluorinated styrene oxides: configurational stability, synthetic applications, and mechanistic insight.
|
| |
Chemistry,
16,
9778-9788.
|
|
|
|
|
|
|
V.Hugenberg,
R.Fröhlich,
and
G.Haufe
(2010).
Oxidative desulfurization-fluorination of thioethers. Application for the synthesis of fluorinated nitrogen containing building blocks.
|
| |
Org Biomol Chem,
8,
5682-5691.
|
|
|
|
|
|
|
Y.P.Pang,
J.Davis,
S.Wang,
J.G.Park,
M.P.Nambiar,
J.J.Schmidt,
and
C.B.Millard
(2010).
Small molecules showing significant protection of mice against botulinum neurotoxin serotype A.
|
| |
PLoS One,
5,
e10129.
|
|
|
|
|
|
|
A.Caravano,
R.A.Field,
J.M.Percy,
G.Rinaudo,
R.Roig,
and
K.Singh
(2009).
Developing an asymmetric, stereodivergent route to selected 6-deoxy-6-fluoro-hexoses.
|
| |
Org Biomol Chem,
7,
996.
|
|
|
|
|
|
|
A.D.Scott,
C.Phillips,
A.Alex,
M.Flocco,
A.Bent,
A.Randall,
R.O'Brien,
L.Damian,
and
L.H.Jones
(2009).
Thermodynamic Optimisation in Drug Discovery: A Case Study using Carbonic Anhydrase Inhibitors.
|
| |
ChemMedChem,
4,
1985-1989.
|
|
|
PDB codes:
|
|
|
|
|
|
|
|
A.Rentmeister,
F.H.Arnold,
and
R.Fasan
(2009).
Chemo-enzymatic fluorination of unactivated organic compounds.
|
| |
Nat Chem Biol,
5,
26-28.
|
|
|
|
|
|
|
A.Schiefner,
M.Fujio,
D.Wu,
C.H.Wong,
and
I.A.Wilson
(2009).
Structural evaluation of potent NKT cell agonists: implications for design of novel stimulatory ligands.
|
| |
J Mol Biol,
394,
71-82.
|
|
|
PDB codes:
|
|
|
|
|
|
|
|
B.Linclau,
A.J.Boydell,
R.S.Timofte,
K.J.Brown,
V.Vinader,
and
A.C.Weymouth-Wilson
(2009).
Enantioselective synthesis of tetrafluorinated ribose and fructose.
|
| |
Org Biomol Chem,
7,
803-814.
|
|
|
|
|
|
|
B.Stump,
C.Eberle,
W.B.Schweizer,
M.Kaiser,
R.Brun,
R.L.Krauth-Siegel,
D.Lentz,
and
F.Diederich
(2009).
Pentafluorosulfanyl as a novel building block for enzyme inhibitors: trypanothione reductase inhibition and antiprotozoal activities of diarylamines.
|
| |
Chembiochem,
10,
79-83.
|
|
|
|
|
|
|
C.Fäh,
L.A.Hardegger,
L.Baitsch,
W.B.Schweizer,
S.Meyer,
D.Bur,
and
F.Diederich
(2009).
New organofluorine building blocks: inhibition of the malarial aspartic proteases plasmepsin II and IV by alicyclic alpha,alpha-difluoroketone hydrates.
|
| |
Org Biomol Chem,
7,
3947-3957.
|
|
|
|
|
|
|
C.S.Ananda Kumar,
C.V.Kavitha,
K.Vinaya,
S.B.Benaka Prasad,
N.R.Thimmegowda,
S.Chandrappa,
S.C.Raghavan,
and
K.S.Rangappa
(2009).
Synthesis and in vitro cytotoxic evaluation of novel diazaspiro bicyclo hydantoin derivatives in human leukemia cells: a SAR study.
|
| |
Invest New Drugs,
27,
327-337.
|
|
|
|
|
|
|
D.A.Watson,
M.Su,
G.Teverovskiy,
Y.Zhang,
J.García-Fortanet,
T.Kinzel,
and
S.L.Buchwald
(2009).
Formation of ArF from LPdAr(F): catalytic conversion of aryl triflates to aryl fluorides.
|
| |
Science,
325,
1661-1664.
|
|
|
|
|
|
|
E.L.Luzina,
and
A.V.Popov
(2009).
Synthesis and anticancer activity of N-bis(trifluoromethyl)alkyl-N'-thiazolyl and N-bis(trifluoromethyl)alkyl-N'-benzothiazolyl ureas.
|
| |
Eur J Med Chem,
44,
4944-4953.
|
|
|
|
|
|
|
G.Sandford
(2009).
Engineering fluorination.
|
| |
Nat Chem Biol,
5,
6-7.
|
|
|
|
|
|
|
H.Ji,
S.Tan,
J.Igarashi,
H.Li,
M.Derrick,
P.Martásek,
L.J.Roman,
J.Vásquez-Vivar,
T.L.Poulos,
and
R.B.Silverman
(2009).
Selective neuronal nitric oxide synthase inhibitors and the prevention of cerebral palsy.
|
| |
Ann Neurol,
65,
209-217.
|
|
|
|
|
|
|
H.Li,
S.Zhang,
C.Yu,
X.Song,
and
W.Wang
(2009).
Organocatalytic asymmetric synthesis of chiral fluorinated quaternary carbon containing beta-ketoesters.
|
| |
Chem Commun (Camb),
(),
2136-2138.
|
|
|
|
|
|
|
J.A.Garnett,
Y.Liu,
E.Leon,
S.A.Allman,
N.Friedrich,
S.Saouros,
S.Curry,
D.Soldati-Favre,
B.G.Davis,
T.Feizi,
and
S.Matthews
(2009).
Detailed insights from microarray and crystallographic studies into carbohydrate recognition by microneme protein 1 (MIC1) of Toxoplasma gondii.
|
| |
Protein Sci,
18,
1935-1947.
|
|
|
PDB codes:
|
|
|
|
|
|
|
|
J.C.Errey,
M.C.Mann,
S.A.Fairhurst,
L.Hill,
M.R.McNeil,
J.H.Naismith,
J.M.Percy,
C.Whitfield,
and
R.A.Field
(2009).
Sugar nucleotide recognition by Klebsiella pneumoniae UDP-D-galactopyranose mutase: fluorinated substrates, kinetics and equilibria.
|
| |
Org Biomol Chem,
7,
1009-1016.
|
|
|
|
|
|
|
J.C.Lewis,
S.Bastian,
C.S.Bennett,
Y.Fu,
Y.Mitsuda,
M.M.Chen,
W.A.Greenberg,
C.H.Wong,
and
F.H.Arnold
(2009).
Chemoenzymatic elaboration of monosaccharides using engineered cytochrome P450BM3 demethylases.
|
| |
Proc Natl Acad Sci U S A,
106,
16550-16555.
|
|
|
|
|
|
|
J.Nie,
G.W.Zhang,
L.Wang,
A.Fu,
Y.Zheng,
and
J.A.Ma
(2009).
A perfect double role of CF3 groups in activating substrates and stabilizing adducts: the chiral Brønsted acid-catalyzed direct arylation of trifluoromethyl ketones.
|
| |
Chem Commun (Camb),
(),
2356-2358.
|
|
|
|
|
|
|
J.S.Stehouwer,
and
M.M.Goodman
(2009).
Fluorine-18 Radiolabeled PET Tracers for Imaging Monoamine Transporters: Dopamine, Serotonin, and Norepinephrine.
|
| |
PET Clin,
4,
101-128.
|
|
|
|
|
|
|
K.H.Piepenbrink,
O.Y.Borbulevych,
R.F.Sommese,
J.Clemens,
K.M.Armstrong,
C.Desmond,
P.Do,
and
B.M.Baker
(2009).
Fluorine substitutions in an antigenic peptide selectively modulate T-cell receptor binding in a minimally perturbing manner.
|
| |
Biochem J,
423,
353-361.
|
|
|
PDB codes:
|
|
|
|
|
|
|
|
M.Jagodzinska,
F.Huguenot,
G.Candiani,
and
M.Zanda
(2009).
Assessing the bioisosterism of the trifluoromethyl group with a protease probe.
|
| |
ChemMedChem,
4,
49-51.
|
|
|
|
|
|
|
M.Molteni,
M.C.Bellucci,
S.Bigotti,
S.Mazzini,
A.Volonterio,
and
M.Zanda
(2009).
Psi[CH(CF(3))NH]Gly-peptides: synthesis and conformation analysis.
|
| |
Org Biomol Chem,
7,
2286-2296.
|
|
|
|
|
|
|
M.T.Kirchner,
D.Bläser,
R.Boese,
T.S.Thakur,
and
G.R.Desiraju
(2009).
1,3-Difluoro-benzene.
|
| |
Acta Crystallogr Sect E Struct Rep Online,
65,
o2668-o2669.
|
|
|
|
|
|
|
M.T.Kirchner,
D.Bläser,
R.Boese,
T.S.Thakur,
and
G.R.Desiraju
(2009).
1,2,3-Trifluoro-benzene.
|
| |
Acta Crystallogr Sect E Struct Rep Online,
65,
o2670.
|
|
|
|
|
|
|
P.Jing,
P.J.Rodgers,
and
S.Amemiya
(2009).
High lipophilicity of perfluoroalkyl carboxylate and sulfonate: implications for their membrane permeability.
|
| |
J Am Chem Soc,
131,
2290-2296.
|
|
|
|
|
|
|
P.Restorp,
O.B.Berryman,
A.C.Sather,
D.Ajami,
and
J.Rebek
(2009).
A synthetic receptor for hydrogen-bonding to fluorines of trifluoroborates.
|
| |
Chem Commun (Camb),
(),
5692-5694.
|
|
|
|
|
|
|
R.Koller,
Q.Huchet,
P.Battaglia,
J.M.Welch,
and
A.Togni
(2009).
Acid-mediated formation of trifluoromethyl sulfonates from sulfonic acids and a hypervalent iodine trifluoromethylating agent.
|
| |
Chem Commun (Camb),
(),
5993-5995.
|
|
|
|
|
|
|
S.Grüschow,
E.J.Rackham,
B.Elkins,
P.L.Newill,
L.M.Hill,
and
R.J.Goss
(2009).
New pacidamycin antibiotics through precursor-directed biosynthesis.
|
| |
Chembiochem,
10,
355-360.
|
|
|
|
|
|
|
S.Zhang,
Y.Zhang,
Y.Ji,
H.Li,
and
W.Wang
(2009).
Catalytic enantioselective conjugate addition of fluorobis(phenylsulfonyl)methane to enals: synthesis of chiral monofluoromethyl compounds.
|
| |
Chem Commun (Camb),
(),
4886-4888.
|
|
|
|
|
|
|
V.Gouverneur
(2009).
Chemistry. A new departure in fluorination chemistry.
|
| |
Science,
325,
1630-1631.
|
|
|
|
|
|
|
X.Han,
J.Luo,
C.Liu,
and
Y.Lu
(2009).
Asymmetric generation of fluorine-containing quaternary carbons adjacent to tertiary stereocenters: uses of fluorinated methines as nucleophiles.
|
| |
Chem Commun (Camb),
(),
2044-2046.
|
|
|
|
|
|
|
Z.Zhou,
J.Zhen,
N.K.Karpowich,
C.J.Law,
M.E.Reith,
and
D.N.Wang
(2009).
Antidepressant specificity of serotonin transporter suggested by three LeuT-SSRI structures.
|
| |
Nat Struct Mol Biol,
16,
652-657.
|
|
|
PDB codes:
|
|
|
|
|
|
|
|
A.Memic,
and
M.R.Spaller
(2008).
How do halogen substituents contribute to protein-binding interactions? A thermodynamic study of peptide ligands with diverse aryl halides.
|
| |
Chembiochem,
9,
2793-2795.
|
|
|
|
|
|
|
C.Baskakis,
V.Magrioti,
N.Cotton,
D.Stephens,
V.Constantinou-Kokotou,
E.A.Dennis,
and
G.Kokotos
(2008).
Synthesis of polyfluoro ketones for selective inhibition of human phospholipase A2 enzymes.
|
| |
J Med Chem,
51,
8027-8037.
|
|
|
|
|
|
|
D.B.Berkowitz,
K.R.Karukurichi,
R.de la Salud-Bea,
D.L.Nelson,
and
C.D.McCune
(2008).
Use of Fluorinated Functionality in Enzyme Inhibitor Development: Mechanistic and Analytical Advantages.
|
| |
J Fluor Chem,
129,
731-742.
|
|
|
|
|
|
|
D.O'Hagan
(2008).
Themed series in organo-fluorine chemistry.
|
| |
Beilstein J Org Chem,
4,
11.
|
|
|
|
|
|
|
D.Zhou,
T.L.Sharp,
N.M.Fettig,
H.Lee,
J.S.Lewis,
J.A.Katzenellenbogen,
and
M.J.Welch
(2008).
Evaluation of a bromine-76-labeled progestin 16alpha,17alpha-dioxolane for breast tumor imaging and radiotherapy: in vivo biodistribution and metabolic stability studies.
|
| |
Nucl Med Biol,
35,
655-663.
|
|
|
|
|
|
|
H.Kopitz,
A.Zivković,
J.W.Engels,
and
H.Gohlke
(2008).
Determinants of the unexpected stability of RNA fluorobenzene self pairs.
|
| |
Chembiochem,
9,
2619-2622.
|
|
|
|
|
|
|
H.Meng,
S.T.Krishnaji,
M.Beinborn,
and
K.Kumar
(2008).
Influence of selective fluorination on the biological activity and proteolytic stability of glucagon-like peptide-1.
|
| |
J Med Chem,
51,
7303-7307.
|
|
|
|
|
|
|
H.Q.Do,
and
O.Daugulis
(2008).
Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds.
|
| |
J Am Chem Soc,
130,
1128-1129.
|
|
|
|
|
|
|
J.J.Aerts,
A.R.Plenevaux,
C.F.Lemaire,
F.Giacomelli,
G.I.Warnock,
C.L.Phillips,
and
A.J.Luxen
(2008).
Metabolism of no-carrier-added 2-[18F]fluoro-L-tyrosine in rats.
|
| |
BMC Med Phys,
8,
4.
|
|
|
|
|
|
|
J.S.Stehouwer,
N.Jarkas,
F.Zeng,
R.J.Voll,
L.Williams,
V.M.Camp,
E.J.Malveaux,
J.R.Votaw,
L.Howell,
M.J.Owens,
and
M.M.Goodman
(2008).
Synthesis, radiosynthesis, and biological evaluation of fluorine-18-labeled 2beta-carbo(fluoroalkoxy)-3beta-(3'-((Z)-2-haloethenyl)phenyl)nortropanes: candidate radioligands for in vivo imaging of the serotonin transporter with positron emission tomography.
|
| |
J Med Chem,
51,
7788-7799.
|
|
|
|
|
|
|
K.Shibatomi,
and
H.Yamamoto
(2008).
Stereoselective synthesis of alpha,alpha-chlorofluoro carbonyl compounds leading to the construction of fluorinated chiral quaternary carbon centers.
|
| |
Angew Chem Int Ed Engl,
47,
5796-5798.
|
|
|
|
|
|
|
L.Hunter,
and
D.O'Hagan
(2008).
Multi-vicinal fluoroalkanes: a new class of organofluorine compounds.
|
| |
Org Biomol Chem,
6,
2843-2848.
|
|
|
|
|
|
|
M.Katayama,
Y.Masui,
E.Kageyama,
Y.Kawabata,
and
K.Kanayama
(2008).
Synthesis and biological activities of 4-trifluoromethylindole-3-acetic acid: a new fluorinated indole auxin.
|
| |
Biosci Biotechnol Biochem,
72,
2025-2033.
|
|
|
|
|
|
|
N.B.Barhate,
R.N.Barhate,
P.Cekan,
G.Drobny,
and
S.T.Sigurdsson
(2008).
A nonafluoro nucleoside as a sensitive 19f NMR probe of nucleic acid conformation.
|
| |
Org Lett,
10,
2745-2747.
|
|
|
|
|
|
|
P.Beier,
A.V.Alexandrova,
M.Zibinsky,
and
G.K.Prakash
(2008).
Nucleophilic difluoromethylation and difluoromethylenation of aldehydes and ketones using diethyl difluoromethylphosphonate.
|
| |
Tetrahedron,
64,
10977-10985.
|
|
|
|
|
|
|
P.J.Riss,
and
F.Rösch
(2008).
A convenient chemo-enzymatic synthesis and 18F-labelling of both enantiomers of trans-1-toluenesulfonyloxymethyl-2-fluoromethyl-cyclopropane.
|
| |
Org Biomol Chem,
6,
4567-4574.
|
|
|
|
|
|
|
S.Purser,
P.R.Moore,
S.Swallow,
and
V.Gouverneur
(2008).
Fluorine in medicinal chemistry.
|
| |
Chem Soc Rev,
37,
320-330.
|
|
|
|
|
|
|
T.Gustafsson,
R.Gilmour,
and
P.H.Seeberger
(2008).
Fluorination reactions in microreactors.
|
| |
Chem Commun (Camb),
(),
3022-3024.
|
|
|
|
|
|
|
T.L.Mavencamp,
J.F.Rhoderick,
R.J.Bridges,
and
C.S.Esslinger
(2008).
Synthesis and preliminary pharmacological evaluation of novel derivatives of L-beta-threo-benzylaspartate as inhibitors of the neuronal glutamate transporter EAAT3.
|
| |
Bioorg Med Chem,
16,
7740-7748.
|
|
|
|
|
|
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Citation data come partly from CiteXplore and partly
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so more and more references will be included with time.
Where a reference describes a PDB structure, the PDB
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