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1.
Science ; 379(6627): 94-99, 2023 01 06.
Article in English | MEDLINE | ID: mdl-36603079

ABSTRACT

Maize (Zea mays) is a major staple crop in Africa, where its yield and the livelihood of millions are compromised by the parasitic witchweed Striga. Germination of Striga is induced by strigolactones exuded from maize roots into the rhizosphere. In a maize germplasm collection, we identified two strigolactones, zealactol and zealactonoic acid, which stimulate less Striga germination than the major maize strigolactone, zealactone. We then showed that a single cytochrome P450, ZmCYP706C37, catalyzes a series of oxidative steps in the maize-strigolactone biosynthetic pathway. Reduction in activity of this enzyme and two others involved in the pathway, ZmMAX1b and ZmCLAMT1, can change strigolactone composition and reduce Striga germination and infection. These results offer prospects for breeding Striga-resistant maize.


Subject(s)
Lactones , Striga , Zea mays , Germination , Lactones/metabolism , Plant Breeding , Striga/growth & development , Zea mays/genetics , Zea mays/metabolism
2.
Gene Ther ; 20(4): 435-43, 2013 Apr.
Article in English | MEDLINE | ID: mdl-22809997

ABSTRACT

High-risk Human Papillomaviruses (HPV) has been found to be associated with carcinomas of the cervix, penis, vulva/vagina, anus, mouth and oro-pharynx. As the main tumorigenic effects of the HPV have been attributed to the expression of E6 and E7 genes, different gene therapy approaches have been directed to block their expression such as antisense oligonucleotides (ASO), ribozymes and small interfering RNAs. In order to develop a gene-specific therapy for HPV-related cancers, we investigated a potential therapeutic strategy of gene silencing activated under illumination. Our aim according to this antisense therapy consisted in regulating the HPV16 E6 oncogene by using an E6-ASO derivatized with a polyazaaromatic ruthenium (Ru(II)) complex (E6-Ru-ASO) able, under visible illumination, to crosslink irreversibly the targeted sequence. We examined the effects of E6-Ru-ASO on the expression of E6 and on the cell growth of cervical cancer cells. We demonstrated using HPV16(+) SiHa cervical cancer cells that E6-Ru-ASO induces after illumination, a reactivation of p53, the most important target of E6, as well as the inhibition of cell proliferation with a selective repression of E6 at the protein level. These results suggest that E6-Ru ASOs, activated under illumination and specifically targeting E6, are capable of inhibiting HPV16(+) cervical cancer cell proliferation.


Subject(s)
Cell Proliferation/drug effects , Light , Oligonucleotides/genetics , Oncogene Proteins, Viral/genetics , Repressor Proteins/genetics , Ruthenium Compounds/radiation effects , Tumor Suppressor Protein p53/metabolism , Uterine Cervical Neoplasms/therapy , Cell Line, Tumor , Cross-Linking Reagents/chemistry , Female , Gene Silencing , Genes, p53 , Genetic Therapy , Humans , Oligonucleotides/chemistry , Oncogene Proteins, Viral/metabolism , Repressor Proteins/metabolism , Ruthenium Compounds/chemistry , Uterine Cervical Neoplasms/virology
3.
Dalton Trans ; (5): 852-6, 2005 Mar 07.
Article in English | MEDLINE | ID: mdl-15726135

ABSTRACT

The emission properties of a non intercalating complex, [Ru(TAP)2(dip)]2+ (TAP = 1,4,5,8-tetraazaphenanthrene; dip = 4,7-diphenyl-1,10-phenanthroline), tethered to 17-mer single-stranded oligodeoxyribonucleotides (ODNs) either in the middle or at the 5'-end of the sequence, are determined. The results highlight the fact that the luminescence of this metallic compound is sufficiently sensitive to its microenvironment to probe self-structuration of these short single-stranded ODNs. It is shown that the weighted averaged emission lifetimes (tau(M)) along with the quenching rate constants of luminescence by oxygen reflect particularly well different structures adopted by the different ODNs sequences. The determination of these parameters thus offers an elegant way to examine possible structurations of synthetic single-stranded ODNs that play important roles in biological applications.


Subject(s)
DNA, Single-Stranded/chemistry , Luminescence , Oligonucleotides/chemistry , Phenanthrolines/chemistry , Ruthenium/chemistry , DNA, Single-Stranded/metabolism , Models, Molecular , Nucleic Acid Conformation , Phenanthrolines/metabolism
5.
Chembiochem ; 4(2-3): 195-202, 2003 Mar 03.
Article in English | MEDLINE | ID: mdl-12616633

ABSTRACT

The formation of a photoadduct between a [Ru(1,4,5,8-tetraazaphenanthrene)(2)4,7-diphenylphenanthroline](2+) complex chemically attached to a synthetic oligonucleotide, and a guanine moiety in a complementary targeted single-stranded DNA molecule was studied for ten 17-mer duplexes by denaturing gel electrophoresis. This photoadduct formation leads to photocrosslinking of the two strands. The percentage quenching of luminescence of the complex by electron transfer was compared to the resulting yield of photocrosslinked product. This yield does not only depend on the ionisation potential of the guanine bases, which are electron donors, but also on other factors, such as the position of the guanine bases as compared to the site of attachment of the complex. The photocrosslinking yield is higher when the guanine moieties are towards the 3' end on the complementary strand as compared to the tethering site. Computer modelling results are in agreement with this preference for the 3' side for the photoreaction. Interestingly, the photocrosslink is not alkali labile. Moreover, a type III exonuclease enzyme is blocked at the position of photocrosslinking.


Subject(s)
Cross-Linking Reagents/radiation effects , Oligonucleotides/chemistry , Ruthenium Radioisotopes , Electron Transport , Guanine , Isotope Labeling , Photochemistry
6.
Biophys J ; 82(2): 978-87, 2002 Feb.
Article in English | MEDLINE | ID: mdl-11806937

ABSTRACT

The yield of hole injection into guanines of different oligonucleotide duplexes by a photooxidizing tethered Ru(II) complex is examined by measuring the luminescence quenching of the excited complex. This yield is investigated as a function of the anchoring site of the complex (on a thymine nucleobase in the middle of the sequence or on the 5' terminal phosphate) and the number and position of the guanine bases as compared with the site of attachment of the Ru(II) compound. In contrast to other studies, the tethered complex, [Ru(tap)(2)(dip)](2+), is a non-intercalating compound and has been shown previously to produce an irreversible photocrosslinking between the two strands as the ultimate step of hole injection. The study of luminescence quenching of the anchored complex by emission intensity and lifetime measurements for the different duplexes indicates that a direct contact between the complex and the guanine nucleobase is needed for the electron transfer to take place. Moreover, for none of the sequences a clear contribution of a static quenching is evidenced independently of the two types of attachment of the [Ru(tap)(2)(dip)](2+) complex to the oligonucleotide. A comparison of the fastest hole-injection process by electron transfer to the excited anchored [Ru(tap)(2)(dip)](2+), with the rate of the photo-electron transfer between the same complex free in solution and guanosine-5'-monophosphate, indicates that the hole injection by the anchored complex is slower by a factor of 10 at least. A bad overlap between donor and acceptor orbitals is probably the cause of this slow rate, which could be attributed to some steric hindrance induced by the complex linker.


Subject(s)
DNA/chemistry , Light , Ruthenium/chemistry , Binding Sites , DNA/metabolism , Electron Transport , Electrons , Guanine/chemistry , Kinetics , Models, Chemical , Models, Molecular , Nucleic Acid Conformation , Oligonucleotides/chemistry , Ultraviolet Rays
7.
Chemistry ; 6(8): 1331-6, 2000 Apr 14.
Article in English | MEDLINE | ID: mdl-10840955

ABSTRACT

Scanning tunneling microscopy (STM) and molecular mechanics calculations were used to investigate the long-range packing and the structure of an heptanuclear ruthenium (II) dendritic species, as a PF6- salt. STM imaging was carried out on a mono-add layer of the ruthenium dendrimer formed by physisorption from a 1,2,4-trichlorobenzene solution at the liquid-graphite interface. The packing of the molecules on the surface was visualised by the formation of ordered patterns and a distance of 27 +/- 2 A was measured between two adjacent lamellae. The comparison of this dimension with the molecular-modelling data indicates that the lamellae were formed by rows of dendrimer molecules in which the counterions (PF6-) were strongly associated with the Ru atoms. The images acquired with higher spatial resolution revealed the presence of repeating units within the lamellae. The comparison of the STM images with the modelling results allowed the attribution of the repeating units observed in the imaged pattern to the STM signature of single dendrimer molecules.

8.
Acc Chem Res ; 33(4): 215-24, 2000 Apr.
Article in English | MEDLINE | ID: mdl-10775314

ABSTRACT

In this paper we summarize our efforts toward optimizing key reactions on the solid phase which tolerate a variety of functional groups. These groups were sequentially modified, allowing the production of novel and diverse compound libraries on the solid phase.


Subject(s)
Chemistry, Organic , Animals , Cyclization , Humans , Organic Chemistry Phenomena , Palladium
9.
J Photochem Photobiol B ; 40(2): 91-106, 1997 Sep.
Article in English | MEDLINE | ID: mdl-9345780

ABSTRACT

The design of Ru(II) and Os(II) complexes which are photoreactive with deoxyribonucleic acid (DNA) represents one of the main targets for the development of novel molecular tools for the study of DNA and, in the future, for the production of new, metal-based, anti-tumor drugs. In this review, we explain how it is possible to make a complex photoreactive with nucleobases and nucleic acids. According to the photophysical behaviour of the Ru(II) compounds, two types of photochemistry are expected: (1) photosubstitution of a ligand by a nucleobase and another monodentate ligand, which takes place from the triplet, metal-centred (3MC) state; this state is populated thermally from the lowest lying triplet metal to ligand charge transfer (3MLCT) state; (2) photoreaction from the 3MLCT state, corresponding to photoredox processes with DNA bases. The two photoreactivities are in competition. By modulating appropriately the redox properties of the 3MLCT state, an electron transfer process from the base to the excited complex takes place, and is directly correlated with DNA cleavage or the formation of an adduct of the complex to DNA. In this adduct, guanine is linked by N2 to the alpha-position of a non-chelating nitrogen of the polyazaaromatic ligand without destruction of the complex. Different strategies are explained which increase the affinity of the complexes for DNA and direct the complex photoreactivity to sites of special DNA topology or targeted sequences of bases. Moreover, the replacement of the Ru(II) ion by the Os(II) ion in the photoreactive complexes leads to an increased specificity of photoreaction. Indeed, only one type of photoreactivity (from the 3MLCT state) is present for the Os(II) complexes because the 3MC state is too high in energy to be populated at room temperature.


Subject(s)
DNA/chemistry , Osmium Compounds/chemistry , Ruthenium Compounds/chemistry , DNA Adducts , Electron Transport , Light , Photochemistry
10.
11.
Science ; 272(5258): 18c-9c, 1996 Apr 05.
Article in English | MEDLINE | ID: mdl-17789965
12.
Biophys Chem ; 59(1-2): 133-8, 1996 Mar 07.
Article in English | MEDLINE | ID: mdl-8867333

ABSTRACT

The possibility of using sodium-23 spin-lattice relaxation rate measurements to probe the interaction modes of Ru11 polyazaaaromatic complexes with DNA is investigated. The following complexes are considered: Ru(phen)3(2+) (phen = 1.10-phenanthroline), Ru(phen)2HAT2+ (HAT = 1,4,5,8,9,12-hexaazatriphenylene), and Ru(diMeTAP)3(2+) (diMeTAP = 2,7-dimethyl-1,4,5,8-tetraazaphenanthrene). The addition of Ru(diMeTAP)3(2+) to a solution of NaDNA leads to a decrease in the sodium-23 spin-lattice relaxation rate (R1) similar to the effect observed upon addition of Mg2+. This indicates that Ru(diMeTAP)3(2+) interacts like Mg2+ with DNA and consequently that the electrostatic interaction dominates the association with DNA, Ru(phen)3(2+) and Ru(phen)2HAT2+ diminish R1 more efficiently than Mg2+, in a manner similar to ethidium bromide, which is known for its intercalation properties. Thus interactions other than electrostatic occur between these two complexes and DNA. These results are in agreement with data obtained from other techniques, according to which Ru(phen)3(2+) and Ru(phen)2HAT2+ are located partially inside the DNA double helix, in contrast to Ru(diMeTAP)3(2+) which remains in the ionic atmosphere around the phosphate backbone.


Subject(s)
DNA/chemistry , Intercalating Agents/chemistry , Organometallic Compounds/chemistry , Animals , Cattle , Magnetic Resonance Spectroscopy , Quantum Theory , Ruthenium/chemistry , Sodium Isotopes
13.
Curr Opin Struct Biol ; 5(3): 343-55, 1995 Jun.
Article in English | MEDLINE | ID: mdl-7583633

ABSTRACT

In the past year major advances have been made in the design, synthesis and characterization of two classes of modified oligonucleotides. In the first class, the phosphodiester backbone of 2'-deoxyribo-oligonucleotides has been replaced in several different ways. The second group represents a completely different type of oligonucleotide modification in which the backbone and the 2'-deoxyribose moieties are replaced by amino acids. These advances present new possibilities for the pharmaceutical applications of modified oligonucleotides in antisense strategies.


Subject(s)
Nucleic Acids/chemistry , Oligonucleotides/chemistry , Animals , Humans , Molecular Structure , Oligonucleotides/chemical synthesis , Oligonucleotides, Antisense
14.
Bioorg Med Chem ; 3(3): 321-35, 1995 Mar.
Article in English | MEDLINE | ID: mdl-7541696

ABSTRACT

The effect of the replacement of the natural phosphodiester linkage -C3'-O-PO2-O-CH2-C4'- in the DNA strand of RNA.DNA hybrid duplexes by either of the two amide linkages -C3'-CH2-CO-NH-CH2-C4'- or -C3'-CH2-NH-CO-CH2-C4' has been investigated by molecular mechanics (MM) and molecular dynamics (MD) simulations. Conformational analysis has been used to assess various low-energy conformers of the amide-modified backbones. MD simulations have been carried out to study the dynamic behavior of the modified duplexes. The modified RNA.DNA hybrid double helices kept a conservative base pairing scheme during the MD simulations. Although the general behavior has been found to be similar to that of the corresponding wild-type hybrid duplexes, some notable differences, especially regarding the sugar puckering in the amide-modified DNA strands, have been observed. The behavior of the RNA strands in the hybrid duplexes has not been affected by the modified DNA strands and is similar to that in wild-type RNA.DNA duplexes.


Subject(s)
Amides/chemistry , DNA/chemistry , Nucleic Acid Heteroduplexes/chemistry , Oligonucleotides, Antisense/chemistry , RNA/chemistry , Base Sequence , Computer Simulation , Models, Molecular , Molecular Sequence Data , Nucleic Acid Conformation , Nucleic Acid Hybridization
15.
Science ; 267(5195): 237-40, 1995 Jan 13.
Article in English | MEDLINE | ID: mdl-7809628

ABSTRACT

A variant form of a group I ribozyme, optimized by in vitro evolution for its ability to catalyze magnesium-dependent phosphoester transfer reactions involving DNA substrates, also catalyzes the cleavage of an unactivated alkyl amide when that linkage is presented in the context of an oligodeoxynucleotide analog. Substrates containing an amide bond that joins either two DNA oligos, or a DNA oligo and a short peptide, are cleaved in a magnesium-dependent fashion to generate the expected products. The first-order rate constant, kcat, is 0.1 x 10(-5) min-1 to 1 x 10(-5) min-1 for the DNA-flanked substrates, which corresponds to a rate acceleration of more than 10(3) as compared with the uncatalyzed reaction.


Subject(s)
Amides/metabolism , Oligodeoxyribonucleotides/metabolism , RNA, Catalytic/metabolism , Animals , Base Composition , Base Sequence , Kinetics , Magnesium/metabolism , Molecular Sequence Data , Oligopeptides/metabolism , Tetrahymena/enzymology
16.
Nucleic Acids Res ; 22(20): 4187-94, 1994 Oct 11.
Article in English | MEDLINE | ID: mdl-7524037

ABSTRACT

The backbone modification amide-3, in which -CH2-NH-CO-CH2- replaces -C5'H2-O5'-PO2-O3'-, is studied in the duplex d(G1-C2-G3-T4.T5-G6-C7-G8)*mr(C9-G10-C11-A12-A13-C14-G15+ ++-C16) where . indicates the backbone modification and mr indicates the 2'-OMe RNA strand. The majority of the exchangeable and non-exchangeable resonances have been assigned. The assignment procedure differs from standard methods. The methyl substituent of the 2'-OMe position of the RNA strand can be used as a tool in the interpretation. The duplex structure is a right-handed double helix. The sugar conformations of the 2'-OMe RNA strand are predominantly N-type and the 2'-OMe is positioned at the surface of the minor groove. In the complementary strand, only the sugar of residue T4 is found exclusively in N-type conformation. The incorporation of the amide modification does not effect very strongly the duplex structure. All bases are involved in Watson-Crick base pairs.


Subject(s)
Magnetic Resonance Spectroscopy , Nucleic Acid Hybridization , Oligodeoxyribonucleotides/chemistry , RNA/chemistry , Base Composition , Base Sequence , Models, Molecular , Molecular Sequence Data , Molecular Structure , Nucleic Acid Conformation , RNA/metabolism , Temperature
17.
J Photochem Photobiol B ; 23(1): 69-78, 1994 Apr.
Article in English | MEDLINE | ID: mdl-8021753

ABSTRACT

Formation of adducts between Ru(TAP)3(2+) (TAP = 1,4,5,8-tetraazaphenanthrene) and DNA has been monitored by gel electrophoresis, UV-vis spectroscopy and dialysis methods. Adduct formation is found for both single- and double-stranded nucleic acids. The reaction with double-stranded DNA is found to be insensitive to solution pH or aeration. Spectroscopic changes similar to those for DNA are found with GMP in oxygen-free pH 5 solution. However, different reactions occur with GMP at higher pH or when the solution contains oxygen. Comparative experiments with double-stranded poly[d(G-C)] or poly[d(A-T)] indicate that the adduct with DNA involves binding to the guanosine moiety. It is proposed that the product is formed by the reaction of the reduced ruthenium complex and oxidised guanine species produced by photo-induced electron transfer.


Subject(s)
DNA/chemistry , Deoxyguanine Nucleotides , Guanosine Monophosphate , Oligodeoxyribonucleotides/chemistry , Organometallic Compounds/chemistry , Phenanthrenes/chemistry , Radiation-Sensitizing Agents/chemistry , Base Sequence , Molecular Sequence Data , Poly dA-dT/chemistry , Polydeoxyribonucleotides/chemistry , Spectrophotometry
18.
Photochem Photobiol ; 55(5): 681-9, 1992 May.
Article in English | MEDLINE | ID: mdl-1528981

ABSTRACT

The luminescence quenching of ruthenium-tris-1,4,5,8-tetraazaphenanthrene [Ru(tap)3(2+)] by nucleotides approaches the diffusion rate only with guanosine-5'-monophosphate (GMP), the most reducing nucleotide, and leads to an electron transfer with the production of the monoreduced complex and the oxidized base. The resulting deprotonated GMP(-H).radical recombines with the monoreduced complex according to a bimolecular equimolar process. The pH dependence of the decay of the transient reduced complex, in the presence of an oxidant (oxygen or benzoquinone) indicates the formation of Ru(tap)2(tapH)2+, i.e. the reduced protonated species, subsequent to the electron transfer, with a pKa of 7.6 as confirmed from pulse radiolysis experiments. As the non-protonated reduced complex, Ru(tap)2(tap-.)+, has a higher reducing power than the protonated one, oxygen is able to reoxidize only the non-protonated species, whereas benzoquinone reoxidizes both species but with different rate constants. The flash photolysis of Ru(tap)3(2+) in the presence of DNA and the effect of Mg2+ ions and GMP as supplementary additives also show the existence of a photo-induced electron transfer with the nucleic acid, which can be correlated to the photosensitized cleavage of DNA by this complex.


Subject(s)
DNA/radiation effects , Organometallic Compounds/radiation effects , Phenanthrenes/radiation effects , DNA/chemistry , Electron Transport , Models, Chemical , Organometallic Compounds/chemistry , Oxidation-Reduction , Phenanthrenes/chemistry , Photolysis , Radiation-Sensitizing Agents/chemistry , Radiation-Sensitizing Agents/radiation effects
19.
Photochem Photobiol ; 54(4): 499-509, 1991 Oct.
Article in English | MEDLINE | ID: mdl-1796115

ABSTRACT

In the presence of double helical polynucleotides (sodium poly(dA-dT).poly(dA-dT) or calf thymus DNA), the efficiency of oxidative or reductive electron transfer between photoexcited ruthenium(II) chelates Ru(tap)2(hat)2+ or Ru(phen)2+(3) (where tap = 1,4,5,8-tetraazaphenanthrene, hat = 1,4,5,8,9,12-hexaazatriphenylene, and phen = 1,10-phenanthroline) and appropriate cationic quenchers (ethidium, Ru(NH3)3+(6), methyl viologen, or M(phen)3+(3), where M = Co, Rh, Cr) increases 1-2 orders of magnitude compared to the efficiency of the same quenching in microhomogeneous aqueous medium (kq = 0.3-1.8 x 10(9) M-1 s-1). The enhancement is more pronounced when the binding constant of the quencher (10(3) less than Kb less than 10(6) M-1) is large. Similar trends are found when the biopolymers are replaced by sodium poly(styrenesulfonate) (PSS). The accelerated electron transfer process is proposed to be due mainly to the effect of accumulation of the reagents in the electrostatic field of the polymer; if corrections for this effect are introduced (e.g. ratioing [quencher]/[polynucleotide]), the reaction rate becomes essentially independent of the polymer concentration. Based upon a model for electron transfer reaction of the complexes within a small cylindrical interface around the DNA helix, calculations of the bimolecular electron transfer rate constants are computed to be 10(3) times smaller when the reactants are bound to the double-stranded polynucleotides and decreased mobility of the cationic species is apparent. The effect is less pronounced if a simpler polyelectrolyte (PSS) is employed. Emission lifetimes of the Ru(II) polypyridyls bound to the DNA (0.32-2 microseconds, double exponential decays) are discussed as well.


Subject(s)
Chelating Agents , DNA/radiation effects , Organometallic Compounds , Poly dA-dT/radiation effects , Ruthenium , Aza Compounds , Chromium , Cobalt , Electron Transport , Ethidium , Nucleic Acid Conformation , Oxidation-Reduction , Paraquat , Phenanthrenes , Phenanthrolines , Rhodium
20.
Photochem Photobiol ; 52(3): 461-72, 1990 Sep.
Article in English | MEDLINE | ID: mdl-2284340

ABSTRACT

The nature of the interaction in buffered aqueous solution of several homo and heteroleptic ruthenium(II) polypyridyl complexes containing 2,2'-bipyridine (bpy), 2,2'-bipyrazine (bpz), 1,10-phenanthroline (phen), 4,7-diphenyl-1,10-phenanthroline (dip), 3,4,7,8-tetramethyl-1,10-phenanthroline (tmp), 1,4,5,8-tetraazaphenanthrene (tap), and 1,4,5,8,9,12-hexaazatriphenylene (hat) with calf thymus DNA and poly(dA-dT).poly(dA-dT) (pdAT) has been investigated by steady-state spectroscopy and emission lifetime measurements. Those complexes containing two or more tap/hat ligands photo-oxidize the guanine base upon binding to DNA with efficiencies that parallel their excited state redox potentials, but display "normal" behavior (increase of both the emission intensity and lifetime) when bound to pdAT. However Ru(tap)(hat)2+2 and Ru(hat)2+3 even photooxidize the adenine base of pdAT, so that their excited states are also quenched in the presence of either polynucleotide. The electron transfer quenching mechanism has been confirmed previously by detection of the monoreduced complex in laser flash photolysis experiments in the presence of mononucleotides. Most of the complexes investigated appear to bind to DNA, at least in part via intercalation, with affinities being dependent on the nature of the largest ligand (hat shows the highest ability in heteroleptic complexes). From lifetime quenching experiments, in the presence of moderate amounts of NaCl, surface binding does not appear to be a general mode for the complexes investigated, and it has been demonstrated unequivocally only for Ru(phen)2+3. In addition, the intercalation of complexes into DNA increases as the ionic strength of the medium decreases, the DNA/Ru ratio increases, or when water is partially replaced by glycerol.


Subject(s)
2,2'-Dipyridyl/analogs & derivatives , DNA/chemistry , Poly dA-dT/chemistry , Ruthenium , 2,2'-Dipyridyl/chemistry , Kinetics , Ligands , Phenanthrenes/chemistry , Phenanthrolines/chemistry , Pyridines/chemistry , Spectrophotometry/methods
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