In Situ Photoregulation of Carbonic Anhydrase Activity Using Azobenzenesulfonamides.

Abstract:

:We report two small molecule azobenzenesulfonamide probes, CAP1 and CAP2, capable of photomodulating the activity of carbonic anhydrase (CA) on demand. In the trans form, CAP azobenzene probes adopt a linear shape, making them suitable for occupying the CA active site and interacting with Zn2+, thereby inhibiting enzyme activity. Following irradiation with either 365 or 410 nm light, the CAP probes isomerize to their cis form. Because of the change in steric profile, the probe exits the active site, and the activity of the enzyme is restored. The cis isomer can revert back to the trans isomer through thermal relaxation or via photoirradiation with 460 nm light and thereby inhibit protein activity again. This process can be repeated multiple times without any photodegradation and thus can be used to inhibit or activate the protein reversibly. Importantly, we demonstrate our ability to apply CAP azobenzene probes to regulate CA activity both in an isolated protein solution and in live cells, where the two isomers of CAP1 differentially regulate the intracellular cytosolic pH.

journal_name

Biochemistry

journal_title

Biochemistry

authors

Aggarwal K,Banik M,Medellin B,Que EL

doi

10.1021/acs.biochem.8b00947

subject

Has Abstract

pub_date

2019-01-08 00:00:00

pages

48-53

issue

1

eissn

0006-2960

issn

1520-4995

journal_volume

58

pub_type

杂志文章
  • HIV-1 gp41 transmembrane domain interacts with the fusion peptide: implication in lipid mixing and inhibition of virus-cell fusion.

    abstract::Fusion of the human immunodeficiency virus (HIV) with target cells is mediated by the gp41 subunit of the envelope protein. Mutation and deletion studies within the transmembrane domain (TMD) of intact gp41 influenced its fusion activity. In addition, current models suggest that the TMD is in proximity with the fusion...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi201721r

    authors: Reuven EM,Dadon Y,Viard M,Manukovsky N,Blumenthal R,Shai Y

    更新日期:2012-04-03 00:00:00

  • Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthesis of the antitumor antibiotic sibiromycin by Streptosporangium sibiricum.

    abstract::The biosynthesis of the antitumor antibiotic sibiromycin by Streptosporangium sibiricum requires the construction of four units: the amino sugar from glucose; the anthranilate ring from DL-tryptophan probably via kynurenine; the aromatic methyl group from methionine; the propylidene proline from L-tyrosine with the lo...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00586a029

    authors: Hurley LH,Lasswell WL,Malhotra RK,Das NV

    更新日期:1979-09-18 00:00:00

  • Translation of collagen messenger RNA in a cell-free system derived from wheat germ.

    abstract::A cell-free system for synthesizing protein from wheat germ was used to translate the messenger RNA extracted from 16-day embryonic chick calvaria. A part of the product had properties similar to collagenous peptides and served as a substrate for prolyl hydroxylase, an enzyme specific for collagen. The level of potass...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00649a016

    authors: Benveniste K,Wilczek J,Ruggieri A,Stern R

    更新日期:1976-02-24 00:00:00

  • Amphipathic polymers: tools to fold integral membrane proteins to their active form.

    abstract::Among the major obstacles to pharmacological and structural studies of integral membrane proteins (MPs) are their natural scarcity and the difficulty in overproducing them in their native form. MPs can be overexpressed in the non-native state as inclusion bodies, but inducing them to achieve their functional three-dim...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi0616706

    authors: Pocanschi CL,Dahmane T,Gohon Y,Rappaport F,Apell HJ,Kleinschmidt JH,Popot JL

    更新日期:2006-11-28 00:00:00

  • Membrane topography of the photosynthetic reaction center polypeptides of Rhodopseudomonas sphaeroides.

    abstract::The topography of the photosynthetic reaction center (RC) polypeptides (H, M, and L) was investigated by proteolysis and radioiodination of membrane vesicles isolated from Rhodopseudomonas sphaeroides. Chromatophores, obtained from French-pressed cell lysates, are closed vesicles' and oriented inside out with respect ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00519a012

    authors: Bachmann RC,Gillies K,Takemoto JY

    更新日期:1981-08-04 00:00:00

  • Sequence-Dependent Promoter Escape Efficiency Is Strongly Influenced by Bias for the Pretranslocated State during Initial Transcription.

    abstract::Abortive transcription initiation can be rate-limiting for promoter escape and therefore represents a barrier to productive gene expression. The mechanism for abortive initiation is unknown, but the amount of abortive transcript is known to vary with the composition of the initial transcribed sequence (ITS). Here, we ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.5b00272

    authors: Skancke J,Bar N,Kuiper M,Hsu LM

    更新日期:2015-07-21 00:00:00

  • Preferential assembly of the tropomyosin heterodimer: equilibrium studies.

    abstract::Thermal unfolding/refolding studies of the three tropomyosin dimers, alpha alpha, alpha beta, and beta beta, from chicken gizzard muscle were performed to explain the preferential assembly of alpha- and beta-tropomyosin subunits into heterodimers, alpha beta [Lehrer, S. S., & Qian, Y. (1989) J. Biol. Chem. 265, 1134]....

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00237a007

    authors: Lehrer SS,Stafford WF 3rd

    更新日期:1991-06-11 00:00:00

  • Conformational heterogeneity at position U37 of an all-RNA hairpin ribozyme with implications for metal binding and the catalytic structure of the S-turn.

    abstract::The hairpin ribozyme is an RNA enzyme that performs site-specific phosphodiester bond cleavage between nucleotides A-1 and G+1 within its cognate substrate. Previous functional studies revealed that the minimal hairpin ribozyme exhibited "gain-of-function" cleavage properties resulting from U39C or U39 to propyl linke...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi051550i

    authors: Alam S,Grum-Tokars V,Krucinska J,Kundracik ML,Wedekind JE

    更新日期:2005-11-08 00:00:00

  • Use of azidobestatin as a photoaffinity label to identify the active site peptide of leucine aminopeptidase.

    abstract::Aminopeptidases catalyze the hydrolysis of amino acid residues from the amino terminus of peptide substrates. They are found in most cells and tissues, and their activity has been implicated in myriad fundamental biochemical and physiological processes. Nevertheless, little is known about the structure of the aminopep...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00131a034

    authors: Taylor A,Peltier CZ,Jahngen EG Jr,Laxman E,Szewczuk Z,Torre FJ

    更新日期:1992-04-28 00:00:00

  • Biochemical properties of acteylcholine receptor subunits from Torpedo californica.

    abstract::Four polypeptide chains composing acetylcholine receptors from the electric organ of Torpedo californica were purified by preparative electrophoresis in sodium dodecyl sulfate. Their apparent mole ratio alpha/beta/gamma/delta is 2:1:1:1. These chains are not readily distinguished by amino acid or carbohydrate composit...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00588a003

    authors: Lindstrom J,Merlie J,Yogeeswaran G

    更新日期:1979-10-16 00:00:00

  • Hemin inhibits ubiquitin-dependent proteolysis in both a higher plant and yeast.

    abstract::In eukaryotes, a major route for ATP-dependent protein breakdown proceeds through covalent intermediates of target proteins destined for degradation and the highly conserved, 76 amino acid protein ubiquitin. In rabbit reticulocytes, it has been shown that hemin effectively inhibits this pathway by blocking the catabol...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00409a025

    authors: Vierstra RD,Sullivan ML

    更新日期:1988-05-03 00:00:00

  • Fragment reconstitution of a small protein: folding energetics of the reconstituted immunoglobulin binding domain B1 of streptococcal protein G.

    abstract::To elucidate early stages in protein folding, we have adopted a fragment reconstitution method for small proteins. This approach is expected to provide nuclei for protein folding and to allow us to investigate folding mechanisms. In previous work [Kobayashi, N., et al. (1995) FEBS Lett. 366, 99-103.] we demonstrated t...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi982271g

    authors: Honda S,Kobayashi N,Munekata E,Uedaira H

    更新日期:1999-01-26 00:00:00

  • Binding kinetics of glucose and allosteric activators to human glucokinase reveal multiple conformational states.

    abstract::Slow conformational changes have been proposed to be responsible for the kinetic positive cooperativity of glucokinase (GK) with glucose. Induced-fit and preexisting equilibrium kinetic models have been previously suggested. In the present study, equilibrium and pre-steady-state fluorescence spectroscopy has been used...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi900374c

    authors: Antoine M,Boutin JA,Ferry G

    更新日期:2009-06-16 00:00:00

  • Differential cytotoxicity of human wild type and mutant alpha-synuclein in human neuroblastoma SH-SY5Y cells in the presence of dopamine.

    abstract::Parkinson's disease (PD) involves loss of dopaminergic neurons in the substantia nigra and is characterized by intracellular inclusions, Lewy bodies, consisting primarily of aggregated alpha-synuclein. Two substitution mutations (A53T and A30P) in alpha-synuclein gene have been identified in familial early-onset PD. T...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi036114f

    authors: Moussa CE,Wersinger C,Tomita Y,Sidhu A

    更新日期:2004-05-11 00:00:00

  • Crystal Structure of the Zorbamycin-Binding Protein ZbmA, the Primary Self-Resistance Element in Streptomyces flavoviridis ATCC21892.

    abstract::The bleomycins (BLMs), tallysomycins (TLMs), phleomycin, and zorbamycin (ZBM) are members of the BLM family of glycopeptide-derived antitumor antibiotics. The BLM-producing Streptomyces verticillus ATCC15003 and the TLM-producing Streptoalloteichus hindustanus E465-94 ATCC31158 both possess at least two self-resistanc...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.5b01008

    authors: Rudolf JD,Bigelow L,Chang C,Cuff ME,Lohman JR,Chang CY,Ma M,Yang D,Clancy S,Babnigg G,Joachimiak A,Phillips GN Jr,Shen B

    更新日期:2015-11-17 00:00:00

  • Hypertriglyceridemic VLDL decreases plasminogen binding to endothelial cells and surface-localized fibrinolysis.

    abstract::The effect of normo (NTG)- and hypertriglyceridemic (HTG)-VLDL on cultured human umbilical vein endothelial cell (HUVEC) surface-localized fibrinolysis was examined following pre-incubation with NTG-, HTG-VLDL, LDL (1-20 micrograms/mL) or buffer (control). Ligand binding assays, using 125I-labeled tcu-PA, t-PA, or Glu...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi952032i

    authors: Li XN,Koons JC,Benza RL,Parks JM,Varma VK,Bradley WA,Gianturco SH,Taylor KB,Grammer JR,Tabengwa EM,Booyse FM

    更新日期:1996-05-14 00:00:00

  • Reactivity of C-terminal cysteines with HNO.

    abstract::Nitroxyl (HNO), a potential heart failure therapeutic, is known to target cysteine residues to form sulfinamides and/or disulfides. Because HNO-derived modifications may depend on their local environment, we have investigated the reactivity of HNO with cysteine derivatives and C-terminal cysteine-containing peptides a...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi500360x

    authors: Keceli G,Toscano JP

    更新日期:2014-06-10 00:00:00

  • Leaving group dependence and proton inventory studies of the phosphorylation of a cytoplasmic phosphotyrosyl protein phosphatase from bovine heart.

    abstract::The kcat and Km values for the bovine heart low molecular weight phosphotyrosyl protein phosphatase catalyzed hydrolysis of 16 aryl phosphate monoesters and of five alkyl phosphate monoesters having the structure Ar(CH2)nOPO3H2 (n = 1-5) were measured at pH 5.0 and 37 degrees C. With the exception of alpha-naphthyl ph...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00101a006

    authors: Zhang ZY,Van Etten RL

    更新日期:1991-09-17 00:00:00

  • Splicing Site Recognition by Synergy of Three Domains in Splicing Factor RBM10.

    abstract::Splicing factor RBM10 and its close homologues RBM5 and RBM6 govern the splicing of oncogenes such as Fas, NUMB, and Bcl-X. The molecular architecture of these proteins includes zinc fingers (ZnFs) and RNA recognition motifs (RRMs). Three of these domains in RBM10 that constitute the RNA binding part of this splicing ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.7b01242

    authors: Serrano P,Hammond JA,Geralt M,Wüthrich K

    更新日期:2018-03-13 00:00:00

  • Purification and characterization of a tissue plasminogen activator-inhibitor complex from human umbilical vein endothelial cell conditioned medium.

    abstract::Tissue plasminogen activator-inhibitor complexes were purified from the conditioned medium of human umbilical vein endothelial cells by affinity chromatography followed by gel filtration. It was found that a single complex was isolated which can exist in two distinct interconvertible conformations. These may be separa...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00397a037

    authors: Sanzo MA,Marasa JC,Wittwer AJ,Siegel NR,Harakas NK,Feder J

    更新日期:1987-11-17 00:00:00

  • Trihydroxynaphthalene reductase from Magnaporthe grisea: realization of an active center inhibitor and elucidation of the kinetic mechanism.

    abstract::Active trihydroxynaphthalene reductase (3HNR) is essential for the biosynthesis of fungal melanin by Magnaporthe grisea and is a focus of inhibitor design studies directed toward control of blast disease in rice. Tricyclazole, a preventative fungicide against rice blast, has been previously characterized as inhibiting...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi962355u

    authors: Thompson JE,Basarab GS,Andersson A,Lindqvist Y,Jordan DB

    更新日期:1997-02-18 00:00:00

  • Cross-linking of trans reentrant loops in the Na(+)-citrate transporter CitS of Klebsiella pneumoniae.

    abstract::The membrane topology model of the Na(+)-citrate transporter CitS of Klebsiella pneumoniae shows a core of two homologous domains with opposite orientation in the membrane and each containing a so-called reentrant loop. A split version of CitS was constructed to study domain interactions and proximity relationships of...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi100336s

    authors: Dobrowolski A,Fusetti F,Lolkema JS

    更新日期:2010-06-01 00:00:00

  • Pinpoint chemical modification of Asp160 in the 49 kDa subunit of bovine mitochondrial complex I via a combination of ligand-directed tosyl chemistry and click chemistry.

    abstract::Through a ligand-directed tosyl (LDT) chemistry strategy using the synthetic acetogenin ligand AL1, we succeeded in the pinpoint alkynylation (-C≡CH) of Asp160 in the 49 kDa subunit of bovine complex I, which may be located in the inner part of the putative quinone binding cavity of the enzyme [Masuya, T., et al. (201...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi501342w

    authors: Masuya T,Murai M,Morisaka H,Miyoshi H

    更新日期:2014-12-16 00:00:00

  • Bis(pyrrolecarboxamide) linked to intercalating chromophore oxazolopyridocarbazole (OPC): selective binding to DNA and polynucleotides.

    abstract::We have investigated some properties related to interaction with DNA and recognition of AT-rich sequences of netropsin-oxazolopyridocarbazole (Net-OPC) (Mrani et al., 1990), which is a hybrid groove-binder-intercalator. The hybrid molecule Net-OPC binds to poly[d(A-T)] at two different sites with Kapp values close to ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00220a029

    authors: Subra F,Carteau S,Pager J,Paoletti J,Paoletti C,Auclair C,Mrani D,Gosselin G,Imbach JL

    更新日期:1991-02-12 00:00:00

  • Unique guanine nucleotide binding properties of the human placental GTP-binding protein Gp.

    abstract::Gp is a major GTP-binding protein of human placenta and platelets [Evans, T., Brown, M. L., Fraser, E. D., & Northup, J. K. (1986) J. Biol. Chem. 261, 7052-7059]. High-affinity guanine nucleotide binding is associated with a polypeptide migrating identically with H-ras on SDS-PAGE. We have characterized the interactio...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00482a002

    authors: Tamir A,Fawzi AB,Northup JK

    更新日期:1990-07-31 00:00:00

  • Determination of proton transfer rates by chemical rescue: application to bacterial reaction centers.

    abstract::The bacterial reaction center (RC) converts light into chemical energy through the reduction of an internal quinone molecule Q(B) to Q(B)H(2). In the native RC, proton transfer is coupled to electron transfer and is not rate-controlling. Consequently, proton transfer is not directly observable, and its rate was unknow...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi020419x

    authors: Paddock ML,Adelroth P,Feher G,Okamura MY,Beatty JT

    更新日期:2002-12-17 00:00:00

  • Functional roles of metal binding domains of the Archaeoglobus fulgidus Cu(+)-ATPase CopA.

    abstract::CopA, a thermophilic membrane ATPase from Archaeoglobus fulgidus, drives the outward movement of Cu(+) or Ag(+) [Mandal et al. (2002) J. Biol. Chem. 277, 7201-7208]. This, as other P(IB)-ATPases, is characterized by a putative metal binding sequence (C(380)PC(382)) in its sixth transmembrane fragment and cytoplasmic m...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi034806y

    authors: Mandal AK,Argüello JM

    更新日期:2003-09-23 00:00:00

  • Truncation of the amino terminus of human apolipoprotein A-I substantially alters only the lipid-free conformation.

    abstract::An amino-terminal deletion mutant (residues 1-43) of human apolipoprotein A-I (apo hA-I) has been produced from a bacterial expression system to explore the structural and functional role of these amino acids, encoded by exon 3, in apo hA-I. Lipid binding of apo delta (1-43)A-I and lipid binding of apo hA-I are very s...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi961876e

    authors: Rogers DP,Brouillette CG,Engler JA,Tendian SW,Roberts L,Mishra VK,Anantharamaiah GM,Lund-Katz S,Phillips MC,Ray MJ

    更新日期:1997-01-14 00:00:00

  • A deuterium and phosphorus-31 nuclear magnetic resonance study of the interaction of melittin with dimyristoylphosphatidylcholine bilayers and the effects of contaminating phospholipase A2.

    abstract::The interaction of bee venom melittin with dimyristolphosphatidylcholine (DMPC) selectively deuteriated in the choline head group has been studied by deuterium and phosphorus-31 nuclear magnetic resonance (NMR) spectroscopy. The action of residual phospholipase A2 in melittin samples resulted in mixtures of DMPC and i...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00392a033

    authors: Dempsey CE,Watts A

    更新日期:1987-09-08 00:00:00

  • Direct spectroscopic and kinetic evidence for the involvement of a peroxodiferric intermediate during the ferroxidase reaction in fast ferritin mineralization.

    abstract::Rapid freeze-quench (RFQ) Mössbauer and stopped-flow absorption spectroscopy were used to monitor the ferritin ferroxidase reaction using recombinant (apo) frog M ferritin; the initial transient ferric species could be trapped by the RFQ method using low iron loading (36 Fe2+/ferritin molecule). Biphasic kinetics of f...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi980847w

    authors: Pereira AS,Small W,Krebs C,Tavares P,Edmondson DE,Theil EC,Huynh BH

    更新日期:1998-07-14 00:00:00