Enzymatic mechanisms for catalysis of enolization: ketosteroid isomerase.

Abstract:

:Breaking a carbon-hydrogen bond adjacent to a carbonyl is a slow step in a large number of chemical reactions. However, many enzymes are capable of catalyzing this reaction with great efficiency. One of the most proficient of these enzymes is 3-oxo-Delta5-steroid isomerase (KSI), which catalyzes the isomerization of a wide variety of 3-oxo-Delta5-steroids to their Delta4-conjugated isomers. In this review, the mechanism of KSI is discussed, with particular emphasis on energetic considerations. Both experimental and theoretical approaches are considered to explain the mechanistic details of the reaction.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Pollack RM

doi

10.1016/j.bioorg.2004.06.005

subject

Has Abstract

pub_date

2004-10-01 00:00:00

pages

341-53

issue

5

eissn

0045-2068

issn

1090-2120

pii

S0045206804000550

journal_volume

32

pub_type

杂志文章,评审
  • Design, synthesis, molecular modeling, in vivo studies and anticancer activity evaluation of new phthalazine derivatives as potential DNA intercalators and topoisomerase II inhibitors.

    abstract::Herein we report the design and synthesis of a new series of phthalazine derivatives as Topo II inhibitors and DNA intercalators. The synthesized compounds were in vitro evaluated for their cytotoxic activities against HepG-2, MCF-7 and HCT-116 cell lines. Additionally, Topo II inhibitory activity and DNA intercalatin...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104233

    authors: El-Helby AA,Sakr H,Ayyad RR,Mahdy HA,Khalifa MM,Belal A,Rashed M,El-Sharkawy A,Metwaly AM,Elhendawy MA,Radwan MM,ElSohly MA,Eissa IH

    更新日期:2020-10-01 00:00:00

  • An alkali tolerant α-l-rhamnosidase from Fusarium moniliforme MTCC-2088 used in de-rhamnosylation of natural glycosides.

    abstract::Analkali tolerant α-l-rhamnosidase has been purified to homogeneity from the culture filtrate of a new fungal strain, Fusarium moniliforme MTCC-2088, using concentration by ultrafiltration and cation exchange chromatography on CM cellulose column. The molecular mass of the purified enzyme has been found to be 36.0 kDa...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.11.027

    authors: Kumar D,Yadav S,Yadava S,Yadav KDS

    更新日期:2019-03-01 00:00:00

  • Structural elucidation and in vivo anti-arthritic activity of β-amyrin and polpunonic acid isolated from the root bark of Ziziphus abyssinica HochstEx. A Rich (Rhamnaceae).

    abstract::Two natural products, compounds 1 and 2 were isolated from the root bark of Ziziphus abyssinica for the first time and were structurally elucidated as β-amyrin and polpunonic acid, respectively. Both compounds were further subjected to an in vivo study in rats to evaluate their anti-arthritic potency. Compared to the ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.103744

    authors: Henneh IT,Huang B,Musayev FN,Hashimi RA,Safo MK,Armah FA,Ameyaw EO,Adokoh CK,Ekor M,Zhang Y

    更新日期:2020-05-01 00:00:00

  • Synthesis, biological evaluation and molecular docking studies of novel 3,5-disubstituted 2,4-thiazolidinediones derivatives.

    abstract::A series of thirteen novel 2,4-thiazolidinedione derivatives were synthesized through three step reaction procedure. The title compounds were synthesized by Knoevenagel condensation at the 5th position of the 2,4-thiazolidinedione ring. Various physicochemical and spectral studies were conducted to characterize the sy...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.102993

    authors: Ranjan Srivastava A,Bhatia R,Chawla P

    更新日期:2019-08-01 00:00:00

  • Synthesis of 4,6-dideoxy-3-fluoro-2-keto-beta-D-glucopyranosyl analogues of 5-fluorouracil, N6-benzoyl adenine, uracil, thymine, N4-benzoyl cytosine and evaluation of their antitumor activities.

    abstract::The synthesis of the unsaturated 4,6-dideoxy-3-fluoro-2-keto-beta-d-glucopyranosyl nucleosides of 5-fluorouracil (6a), N(6)-benzoyl adenine (6b), uracil (6c), thymine (6d) and N(4)-benzoyl cytosine (6e), is described. Monoiodination of compounds 1a,b, followed by acetylation, catalytic hydrogenation and finally regios...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2009.11.001

    authors: Manta S,Tsoukala E,Tzioumaki N,Kiritsis C,Balzarini J,Komiotis D

    更新日期:2010-04-01 00:00:00

  • Bioactive sesquiterpene coumarins from the resin of Ferula sinkiangensis targeted on over-activation of microglia.

    abstract::Nine undescribed (1-4, 6-10) sesquiterpene coumarins, together with a new natural one (5) and ten known ones (11-20), were isolated from the low polarity fraction of the 95% ethanol extract of the resin of Ferula sinkiangensis. Their structures were elucidated based on the comprehensive analysis of HRESIMS, 1D and 2D ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104338

    authors: Guo T,Zhou D,Yang Y,Zhang X,Chen G,Lin B,Sun Y,Ni H,Liu J,Hou Y,Li N

    更新日期:2020-11-01 00:00:00

  • Synthesis and in-vitro anti-leishmanial activity of (4-arylpiperazin-1-yl)(1-(thiophen-2-yl)-9H-pyrido[3,4-b]indol-3-yl)methanone derivatives.

    abstract::In the present study, we have reported synthesis and biological evaluation of a series of fifteen 1-(thiophen-2-yl)-9H-pyrido[3,4-b]indole derivatives against both promastigotes and amastigotes of Leishmania parasites responsible for visceral (L. donovani) and cutaneous (L. amazonensis) leishmaniasis. Among these repo...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2016.11.013

    authors: Ashok P,Chander S,Chow LM,Wong IL,Singh RP,Jha PN,Sankaranarayanan M

    更新日期:2017-02-01 00:00:00

  • Benzoxaboroles as dynamic covalent receptors for bioconjugation and transport of nucleosides and related drugs: Proof of action in HeLa cells.

    abstract::In this work we describe not previously explored binding studies on the reversible interaction of benzoxaborole with ligands of medical and pharmaceutical interest such as nucleosidic drugs gemcitabine and capecitabine, as well as the hydrophobic chemotherapeutic doxorubicin. We include functional derivatives of benzo...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103059

    authors: Samaniego Lopez C,Martínez JH,Acebedo SL,Spagnuolo CC

    更新日期:2019-09-01 00:00:00

  • Synthesis and molecular docking study of some 3,4-dihydrothieno[2,3-d]pyrimidine derivatives as potential antimicrobial agents.

    abstract::In continuation of our research program aiming at developing new potent antimicrobial agents, new series of substituted 3,4-dihydrothieno[2,3-d]pyrimidines was synthesized. The newly synthesized compounds were preliminary tested for their in vitro activity against six bacterial and three fungal strains using the agar ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.102934

    authors: Shaaban OG,Issa DAE,El-Tombary AA,Abd El Wahab SM,Abdel Wahab AE,Abdelwahab IA

    更新日期:2019-07-01 00:00:00

  • Design, synthesis and biological evaluation of novel indole derivatives as potential HDAC/BRD4 dual inhibitors and anti-leukemia agents.

    abstract::HDAC inhibitors and BRD4 inhibitors were considered to be potent anti-cancer agents. Recent studies have demonstrated that HDAC and BRD4 participate in the regulation of some signal paths like PI3K-AKT. In this work, a series of indole derivatives that combine the inhibitory activities of BRD4 and HDAC into one molecu...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.12.011

    authors: Cheng G,Wang Z,Yang J,Bao Y,Xu Q,Zhao L,Liu D

    更新日期:2019-03-01 00:00:00

  • Aryl- or heteroaryl-based hydrazinylphthalazine derivatives as new potential antitrypanosomal agents.

    abstract::A series of twenty phthalazinyl-hydrazones were synthesized and tested as potential anti-Trypanosoma cruzi agents. The phthalazines containing 5-nitroheteroaryl moiety 3l and 3m displayed an excellent in vitro antitrypanosomal profile, exhibiting low micromolar EC50 values against proliferative epimastigote of T. cruz...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2017.03.008

    authors: Romero AH,Rodríguez J,García-Marchan Y,Leañez J,Serrano-Martín X,López SE

    更新日期:2017-06-01 00:00:00

  • Ellagitannin and flavonoid constituents from Agrimonia pilosa Ledeb. with their protein tyrosine phosphatase and acetylcholinesterase inhibitory activities.

    abstract::A new ellagitannin, agritannin (1), a new flavone glycoside, agriflavone (2), and another flavone glycoside with spectroscopic data reported for the first time, kaempferol-3-O-[(S)-3-hydroxy-3-methylglutaryl (1→6)]-β-d-glucoside (3), along with 16 known compounds were isolated from the aerial parts of Agrimonia pilosa...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2017.04.017

    authors: Nguyen DH,Seo UM,Zhao BT,Le DD,Seong SH,Choi JS,Min BS,Woo MH

    更新日期:2017-06-01 00:00:00

  • Chemoenzymatic synthesis of enantiomerically enriched diprophylline and xanthinol nicotinate.

    abstract::A concise chemoenzymatic route toward enantiomerically enriched active pharmaceutical ingredients (API) - diprophylline and xanthinol nicotinate - is reported for the first time. The decisive step is an enantioselective lipase-mediated methanolysis of racemic chlorohydrin-synthon acetate, namely 1-chloro-3-(1,3-dimeth...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104448

    authors: Borowiecki P,Młynek M,Dranka M

    更新日期:2021-01-01 00:00:00

  • Effect of an E461G mutation of beta-galactosidase (Escherichia coli, lac Z) on pL rate profiles and solvent deuterium isotope effects.

    abstract::An E461G mutation of beta-galactosidase results in the disappearance of the high pL (L = H, D) downward break in the rate profiles for k(cat)/K(m) for wild-type enzyme-catalyzed hydrolysis of 4-nitrophenyl beta-D-galactopyranoside (Gal-OPNP) and a decrease from (k(cat))(HOH)/(k(cat))(DOD) = 1.7 to (k(cat))(HOH)/(k(cat...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1006/bioo.2001.1206

    authors: Richard JP,Huber RE,McCall DA

    更新日期:2001-06-01 00:00:00

  • Photoactivable analogs for labeling 25-hydroxyvitamin D3 serum binding protein and for 1,25-dihydroxyvitamin D3 intestinal receptor protein.

    abstract::3-Azidobenzoates and 3-azidonitrobenzoates of 25-hydroxyvitamin D3 as well as 3-deoxy-3-azido-25-hydroxyvitamin D3 and 3-deoxy-3-azido-1,25-dihydroxyvitamin D3 were prepared as photoaffinity labels for vitamin D serum binding protein and 1,25-dihydroxyvitamin D3 intestinal receptor protein. The compounds prepared wer...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/0045-2068(86)90023-4

    authors: Kutner A,Link RP,Schnoes HK,DeLuca HF

    更新日期:1986-01-01 00:00:00

  • Reaction of epichlorohydrin with adenosine, 2'-deoxyadenosine and calf thymus DNA: identification of adducts.

    abstract::Epichlorohydrin (a probable human carcinogen) was allowed to react with adenosine and the adducts were characterized by NMR and UV spectroscopy, and mass spectrometry. The adduct initially formed was 1-(3-chloro-2-hydroxypropyl)-adenosine, which subsequently ring closures to 1,N(6)-(2-hydroxypropyl)-adenosine at neutr...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2006.01.005

    authors: Sund P,Kronberg L

    更新日期:2006-06-01 00:00:00

  • An NMR spectroscopy study of bendaline-albumin interactions.

    abstract::The complete assignment of the 1H and 13C NMR spectra of bendaline (BNDL) was performed by mono-dimensional and homo- and hetero-correlated two-dimensional NMR experiments. The interaction between bendaline and albumin was also studied by the analysis of the motional parameters spin-lattice relaxation times, allowing ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/s0045-2068(03)00078-6

    authors: Delfini M,Bianchetti C,Di Cocco ME,Pescosolido N,Porcelli F,Rosa R,Rugo G

    更新日期:2003-10-01 00:00:00

  • Evaluation of guanylhydrazone derivatives as inhibitors of Candida rugosa digestive lipase: Biological, biophysical, theoretical studies and biotechnological application.

    abstract::This work aimed to evaluate the inhibition of Candida rugosa lipase by five guanylhydrazone derivatives through biological, biophysical and theoretical studies simulating physiologic conditions. The compound LQM11 (IC50 = 14.70 μM) presented the highest inhibition against the enzyme. Therefore, for a better understand...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.03.030

    authors: Santana CC,Silva-Júnior EF,Santos JCN,Rodrigues ÉEDS,da Silva IM,Araújo-Júnior JX,do Nascimento TG,Oliveira Barbosa LA,Dornelas CB,Figueiredo IM,Santos JCC,Grillo LAM

    更新日期:2019-06-01 00:00:00

  • ent-Pimarane diterpenoids from Siegesbeckia glabrescens with anti-inflammatory activity.

    abstract::Nine new ent-pimarane-type diterpenoids, siegesbeckia A-I (1-9), together with four known analogues ent-3α,15,16,19-tetrahydroxypimar-8(14)-ene (10), 15,16-dihydroxypimar-8(14)-en-3-one (11), 14β,16-epoxy-7-pimarene-3α,15β-diol (12) and darutigenol (13), were obtained from the aerial parts of Siegesbeckia glabrescens ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.103854

    authors: Gao X,Rong Z,Long G,Hu G,Yan T,Li N,Jia J,Wang A

    更新日期:2020-06-01 00:00:00

  • Discovery of imidazopyridine derivatives as novel c-Met kinase inhibitors: Synthesis, SAR study, and biological activity.

    abstract::Receptor tyrosine kinase c-Met acts as an alternative angiogenic pathway in the process and contents of cancers. A series of imidazopyridine derivatives were designed and synthesized according to the established docking studies as possible c-Met inhibitors. Most of these imidazopyridine derivatives displayed nanomolar...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2016.12.002

    authors: Yang Y,Zhang Y,Yang L,Zhao L,Si L,Zhang H,Liu Q,Zhou J

    更新日期:2017-02-01 00:00:00

  • Discovery of potent PTP1B inhibitors via structure-based drug design, synthesis and in vitro bioassay of Norathyriol derivatives.

    abstract::Protein tyrosine phosphatase 1B (PTP1B) has recently been identified as a potential target of Norathyriol. Unfortunately, Norathyriol is not a potent PTP1B inhibitor, which somewhat hinders its further application. Based on the fact that no study on the relationship of chemical structure and PTP1B inhibitory activity ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.01.059

    authors: Xue W,Tian J,Wang XS,Xia J,Wu S

    更新日期:2019-05-01 00:00:00

  • New heterocyclic compounds from Ranunculus ternatus Thunb.

    abstract::Five new heterocyclic compounds, 5-α-d-fructofuranosylmethyl-furfural (1), 5-β-d-fructofuranosylmethyl-furfural (2), 5-β-d-fructopyranosylmethyl-furfural (3), 4-(2-((2S-2,3-dihydroxypropoxy)methyl)-5-formyl-1H-pyrrol-1-yl)butanoic acid (4), and 3S,4S-4,5,8-trihydroxy-3-(prop-1-en-2-yl)isochroman-1-one (5), were obtain...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2017.07.004

    authors: Feng ZM,Zhan ZL,Yang YN,Jiang JS,Zhang PC

    更新日期:2017-10-01 00:00:00

  • Synthesis of triphenylphosphonium dibenzothiophene S-oxide derivatives and their effect on cell cycle as photodeoxygenation-based cytotoxic agents.

    abstract::Photodeoxygenation of Dibenzothiophene-S-oxide (DBTO) in UV-A light produces atomic oxygen [O(3P)] and the corresponding sulfide, dibenzothiophene (DBT). Recently, DBTO has been derivatized to study the effect of UV-A light-driven photodeoxygenation in lipids, proteins, and nucleic acids. In this study, two DBTO deriv...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104442

    authors: Isor A,O'Dea AT,Petroff JT 2nd,Skubic KN,Grady SF,Arnatt CK,McCulla RD

    更新日期:2020-12-01 00:00:00

  • Functional studies of rat hydroxymethylbilane synthase.

    abstract::The structurally related tetrapyrrolic pigments are a group of natural products that participate in many of the fundamental biosynthetic and catabolic processes of living organisms. Hydroxymethylbilane synthase catalyzes a rate-limiting step for the biosyntheses of tetrapyrrolic natural products. We carried out extens...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2008.07.001

    authors: Li N,Chu X,Wu L,Liu X,Li D

    更新日期:2008-10-01 00:00:00

  • Withanolides from Physalis peruviana showing nitric oxide inhibitory effects and affinities with iNOS.

    abstract::A phytochemical study to obtain new nitric oxide (NO) inhibitors resulted in the isolation of five new withanolides from the whole plants of Physalis peruviana. The structures were determined on the basis of extensive NMR spectroscopic data analysis as well as the time-dependent density functional theory (TDDFT) elect...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.03.051

    authors: Dong B,An L,Yang X,Zhang X,Zhang J,Tuerhong M,Jin DQ,Ohizumi Y,Lee D,Xu J,Guo Y

    更新日期:2019-06-01 00:00:00

  • A novel bi-functional chalcone inhibits multi-drug resistant Staphylococcus aureus and potentiates the activity of fluoroquinolones.

    abstract::Staphylococcus aureus is the leading cause of bacteraemia and the dwindling supply of effective antibacterials has exacerbated the problem of managing infections caused by this bacterium. Isoliquiritigenin (ISL) is a plant flavonoid that displays therapeutic potential against S. aureus. The present study identified a ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.10.024

    authors: Gupta VK,Gaur R,Sharma A,Akther J,Saini M,Bhakuni RS,Pathania R

    更新日期:2019-03-01 00:00:00

  • Inula japonica ameliorated bleomycin-induced pulmonary fibrosis via inhibiting soluble epoxide hydrolase.

    abstract::Pulmonary fibrosis is a progressive, irreversible, and fatal fibrotic lung disease with a high mortality and morbidity, and commonly nonresponsive to conventional therapy. Inula japonica Thunb. is a traditional Chinese medicine, known as "Xuan Fu Hua" in Chinese, and has been widely applied to relieve cough and dyspne...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104065

    authors: Zhao WY,Luan ZL,Liu TT,Ming WH,Huo XK,Huang HL,Sun CP,Zhang BJ,Ma XC

    更新日期:2020-09-01 00:00:00

  • Design, synthesis and photoinduced DNA cleavage studies of [1,2,4]-triazolo[4,3-a]quinoxalin-4(5H)-ones.

    abstract::An expedient and eco-friendly synthesis of 1-aryl/heteroaryl-[1,2,4]-triazolo[4,3-a]quinoxalin-4(5H)-ones (4) has been accomplished via iodobenzene diacetate mediated oxidative intramolecular cyclization of 3-(2-(aryl/heteroarylidene)hydrazinyl)-quinoxalin-2(1H)-ones (3). Ten synthesized compounds 3 and 4 (10-40 μg) o...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.102932

    authors: Sumran G,Aggarwal R,Mittal A,Aggarwal A,Gupta A

    更新日期:2019-07-01 00:00:00

  • Macrocyclic diterpenoids from the seeds of Euphorbia peplus with potential activity in inducing lysosomal biogenesis.

    abstract::The first phytochemical investigation of the seeds of Euphorbia peplus led to the isolation and characterization of five new (1-5), named euphopepluanones A-E, and five known diterpenoids (6-10). Their structures were established by extensive spectroscopic analysis and X-ray crystallographic experiments. Euphopepluano...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104464

    authors: Chen YN,Ding X,Lu QY,Li DM,Li BT,Liu S,Yang L,Zhang Y,Di YT,Fang X,Hao XJ

    更新日期:2020-12-01 00:00:00

  • Facile synthesis of 1,2,3-triazole-fused indolo- and pyrrolo[1,4]diazepines, DNA-binding and evaluation of their anticancer activity.

    abstract::A facile synthetic strategy has been developed for the generation of structurally diverse N-fused heterocycles. The formation of fused 1,2,3-triazole indolo and pyrrolodiazepines proceeds through an initial Knoevenagel condensation followed by intramolecular azide-alkyne cycloaddition reaction at room temperature with...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103306

    authors: Gour J,Gatadi S,Pooladanda V,Ghouse SM,Malasala S,Madhavi YV,Godugu C,Nanduri S

    更新日期:2019-12-01 00:00:00