2024

Quantitative analysis of protein lipidation and acyl-CoAs reveals substrate preferences of the S-acylation machinery

Busquets-Hernández C, Ribó S, Gratacós-Batlle E, Carbajo D, Tsiotsia A, Blanco-Canosa JB, Chamberlain LH, Triola G. . Chem Sci. 2024 Jul 9;15(32):12845-12855. doi: 10.1039/d4sc02235a.

2023

High-throughput discovery of novel small-molecule inhibitors of acid Ceramidase.

Aseeri M, Abad JL, Delgado A, Fabriàs G, Triola G, Casas J.

Enzyme Inhib Med Chem. 2023 Dec;38(1):343-348. doi: 10.1080/14756366.2022.2150183.

2022

Dinuclear silver and gold bisNHC complexes as drug candidates for cancer therapy.

Quintana M, Rodriguez-Rius A, Vellé A, Vives S, Sanz Miguel PJ, Triola G.

Bioorg Med Chem. 2022 Aug 1;67:116814. doi: 10.1016/j.bmc.2022.116814. Epub 2022 May 10.

A versatile o-aminoanilide linker for native chemical ligation

Sánchez-Campillo I, Miguel-Gracia J, Karamanis P, Blanco-Canosa JB.

Chem Sci. 2022 Aug 26;13(36):10904-10913. doi: 10.1039/d2sc04158h.

2021

Palmitoylation as a Key Regulator of Ras Localization and Function.

Busquets-Hernández, C., Triola, G.

Front Mol Biosci. 2021, Mar 17; 8:659861. doi: 10.3389/fmolb.2021.659861

2020

Native Chemical Ligation via N-Acylurea Thioester Surrogates Obtained by Fmoc Solid-Phase Peptide Synthesis.

Palà-Pujadas J, Blanco-Canosa JB.

Methods Mol Biol. 2020;2133:141-161. doi: 10.1007/978-1-0716-0434-2_7.

DAPLE protein inhibits nucleotide exchange on Gαs and Gαq via the same motif that activates Gαi.

Marivin A, Maziarz M, Zhao J, DiGiacomo V, Olmos Calvo I, Mann EA, Ear J, Blanco-Canosa JB, Ross EM, Ghosh P, Garcia-Marcos M. J

Biol Chem. 2020 Feb 21;295(8):2270-2284. doi: 10.1074/jbc.RA119.011648

2019

A hydroxylamine probe for profiling S-acylated fatty acids on proteins.

Schulte-Zweckel J , Dwivedi M , Brockmeyer A , Janning P , Winter R , Triola G .

Chem Commun (Camb). 2019;55(75):11183-11186. doi:10.1039/c9cc05989j

Identification of benzo[cd]indol-2(1H)-ones as novel Atg4B inhibitors via a structure-based virtual screening and a novel AlphaScreen assay.

Quintana M, Bilbao A, Comas-Barceló J, Bujons J, Triola G.

Eur J Med Chem. 2019;178:648-666. doi:10.1016/j.ejmech.2019.05.086

Activity-Based Imaging of Acid Ceramidase in Living Cells.

Ordóñez YF, Abad JL, Aseeri M, Casas J, Garcia V, Casasampere M, Schuchman EH, Levade T, Delgado A, Triola G, Fabrias G.

J Am Chem Soc. 2019;141(19):7736-7742. doi:10.1021/jacs.8b11687

Cancer Immunotherapy of TLR4 Agonist-Antigen Constructs Enhanced with Pathogen-Mimicking Magnetite Nanoparticles and Checkpoint Blockade of PD-L1.

Traini G, Ruiz-de-Angulo A, Blanco-Canosa JB, Zamacola Bascarán K, Molinaro A, Silipo A, Escors D, Mareque-Rivas JC.

Small. 2019;15(4):e1803993. doi:10.1002/smll.201803993

2018

Peptide Ligations by Using Aryloxycarbonyl-o-methylaminoanilides: Chemical Synthesis of Palmitoylated Sonic Hedgehog.

Palà-Pujadas J, Albericio F, Blanco-Canosa JB.

Angew Chem Int Ed Engl. 2018;57(49):16120-16125. doi:10.1002/anie.201810712

A biochemical and genetic discovery pipeline identifies PLCδ4b as a nonreceptor activator of heterotrimeric G-proteins.

Maziarz M, Broselid S, DiGiacomo V, Park JC, Luebbers A, Garcia-Navarrete L, Blanco-Canosa JB, Baillie GS, Garcia-Marcos M.

J Biol Chem. 2018;293(44):16964-16983. doi:10.1074/jbc.RA118.003580

One-Pot Peptide Ligation-Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides.

Spengler J, Blanco-Canosa JB, Forni L, Albericio F.

Org Lett. 2018;20(14):4306-4309. doi:10.1021/acs.orglett.8b01741

2017

Specific inhibition of GPCR-independent G protein signaling by a rationally engineered protein.

Leyme A, Marivin A, Maziarz M, DiGiacomo V, Papakonstantinou MP, Patel PP, Blanco-Canosa JB, Walawalkar IA, Rodriguez-Davila G, Dominguez I, Garcia-Marcos M.

Proc Natl Acad Sci U S A. 2017;114(48):E10319-E10328. doi:10.1073/pnas.1707992114

The Gαi-GIV binding interface is a druggable protein-protein interaction.

DiGiacomo V, de Opakua AI, Papakonstantinou MP, Nguyen LT, Merino N, Blanco-Canosa JB, Blanco FJ, Garcia-Marcos M.

Sci Rep. 2017;7(1):8575. doi:10.1038/s41598-017-08829-7

Molecular mechanism of Gαi activation by non-GPCR proteins with a Gα-Binding and Activating motif.

de Opakua AI, Parag-Sharma K, DiGiacomo V, Merino N, Leyme A, Marivin A, Villate M, Nguyen LT, de la Cruz-Morcillo MA, Blanco-Canosa JB, Ramachandran S, Baillie GS, Cerione RA, Blanco FJ, Garcia-Marcos M.

Nat Commun. 2017;8:15163. doi:10.1038/ncomms15163doi:10.1038/ncomms15163

Concurrent Modulation of Quantum Dot Photoluminescence Using a Combination of Charge Transfer and Förster Resonance Energy Transfer: Competitive Quenching and Multiplexed Biosensing Modality

Algar WR, Khachatrian A, Melinger JS, Huston AL, Stewart MH, Susumu K, Blanco-Canosa JB, Oh E, Dawson PE, Medintz IL.

J Am Chem Soc. 2017;139(1):363-372. doi:10.1021/jacs.6b11042

2016

GIV/Girdin activates Gαi and inhibits Gαs via the same motif.

Gupta V, Bhandari D, Leyme A, Aznar N, Midde KK, Lo IC, Ear J, Niesman I, López-Sánchez I,Blanco-Canosa JB, von Zastrow M, Garcia-Marcos M, Farquhar MG, Ghosh P.

Proc Natl Acad Sci U S A. 2016;113(39):E5721-E5730. doi:10.1073/pnas.1609502113

High Affinity Immobilization of Proteins Using the CrAsH/TC Tag.

Schulte-Zweckel J, Rosi F, Sreenu D, Schröder H, Niemeyer CM, Triola G.

Molecules. 2016;21(6):750. doi:10.3390/molecules21060750

Guidelines for the use and interpretation of assays for monitoring autophagy

Klionsky DJ, Abdelmohsen K, Abe A, Abedin MJ, Abeliovich H, Acevedo Arozena A, Adachi H, Adams CM, Adams PD, Adeli K, Adhihetty PJ, Adler SG, Agam G, Agarwal R, Aghi MK, Agnello M, Agostinis P, Aguilar PV, Aguirre-Ghiso et al.

Autophagy. 2016;12(1):1-222. doi:10.1080/15548627.2015.1100356

2015

Specificity of Lipoprotein Chaperones for the Characteristic Lipidated Structural Motifs of their Cognate Lipoproteins.

Mejuch T, van Hattum H, Triola G, Jaiswal M, Waldmann H.

Chembiochem. 2015;16(17):2460-2465. doi:10.1002/cbic.201500355

Chemical Protein Synthesis Using a Second-Generation N-Acylurea Linker for the Preparation of Peptide-Thioester Precursors.

Blanco-Canosa JB, Nardone B, Albericio F, Dawson PE.

J Am Chem Soc. 2015;137(22):7197-7209. doi:10.1021/jacs.5b03504

2014

Site-specific, reversible and fluorescent immobilization of proteins on CrAsH-modified surfaces for microarray analytics.

Schulte-Zweckel J, Rosi F, Sreenu D, Schröder H, Niemeyer CM, Triola G.

Chem Commun (Camb). 2014;50(84):12761-12764. doi:10.1039/c4cc04120h

Structure guided design and kinetic analysis of highly potent benzimidazole inhibitors targeting the PDEδ prenyl binding site.

Zimmermann G, Schultz-Fademrecht C, Küchler P, Murarka S, Ismail S, Triola G, Nussbaumer P, Wittinghofer A, Waldmann H.

J Med Chem. 2014;57(12):5435-5448. doi:10.1021/jm500632s

Interaction of the human N-Ras protein with lipid raft model membranes of varying degrees of complexity.

Vogel A, Nikolaus J, Weise K, Triola G, Waldmann H, Winter R, Herrmann A, Huster D.

Biol Chem. 2014;395(7-8):779-789. doi:10.1515/hsz-2013-0294

Probing the Quenching of Quantum Dot Photoluminescence by Peptide-Labeled Ruthenium(II) Complexes.

Scott AM, Algar WR, Stewart MH, Trammell SA, Blanco-Canosa JB, Dawson PE, Deschamps JR, Goswami R, Oh E, Huston AL, Medintz IL.

J Phys Chem C Nanomater Interfaces. 2014;118(17):9239-9250. doi:10.1021/jp501039w

2013

Rotational and translational dynamics of ras proteins upon binding to model membrane systems.

Werkmüller A, Triola G, Waldmann H, Winter R.

Chemphyschem. 2013;14(16):3698-3705. doi:10.1002/cphc.201300617

Synthesis of lipidated peptides.

Rosi F, Triola G.

Methods Mol Biol. 2013;1047:161-189. doi:10.1007/978-1-62703-544-6_12

Synthesizing and modifying peptides for chemoselective ligation and assembly into quantum dot-peptide bioconjugates.

Algar WR, Blanco-Canosa JB, Manthe RL, Susumu K, Stewart MH, Dawson PE, Medintz IL.

Methods Mol Biol. 2013;1025:47-73. doi:10.1007/978-1-62703-462-3_5

Cytotoxicity of quantum dots used for in vitro cellular labeling: role of QD surface ligand, delivery modality, cell type, and direct comparison to organic fluorophores.

Bradburne CE, Delehanty JB, Boeneman Gemmill K, Mei BC, Mattoussi H, Susumu K, Blanco-Canosa JB, Dawson PE, Medintz IL.

Bioconjug Chem. 2013;24(9):1570-1583. doi:10.1021/bc4001917

Site-specific cellular delivery of quantum dots with chemoselectively-assembled modular peptides.

Delehanty JB, Blanco-Canosa JB, Bradburne CE, Susumu K, Stewart MH, Prasuhn DE, Dawson PE, Medintz IL.

Chem Commun (Camb). 2013;49(72):7878-7880. doi:10.1039/c3cc42781a

Imidazole-1-sulfonyl azide-based diazo-transfer reaction for the preparation of azido solid supports for solid-phase synthesis.

Castro V, Blanco-Canosa JB, Rodriguez H, Albericio F.

ACS Comb Sci. 2013;15(7):331-334.

Semisynthetic lipidated LC3 protein mediates membrane fusion.

Chembiochem. 2013;14(11):1296-1300. Yang A, Li Y, Pantoom S, Triola G, Wu YW.

doi:10.1002/cbic.201300344

Gibbs energy determinants of lipoprotein insertion into lipid membranes: the case study of Ras proteins.

Weise K, Huster D, Kapoor S, Triola G, Waldmann H, Winter R.

Faraday Discuss. 2013;161:549-589. doi:10.1039/c2fd20100c

Selecting improved peptidyl motifs for cytosolic delivery of disparate protein and nanoparticle materials.

Boeneman K, Delehanty JB, Blanco-Canosa JB, Susumu K, Stewart MH, Oh E, Huston AL, Dawson G, Ingale S, Walters R, Domowicz M, Deschamps JR, Algar WR, Dimaggio S, Manono J, Spillmann CM, Thompson D, Jennings TL, Dawson PE, Medintz IL.

ACS Nano. 2013;7(5):3778-3796. doi:10.1021/nn400702r

Small molecule inhibition of the KRAS-PDEδ interaction impairs oncogenic KRAS signalling.

Zimmermann G, Papke B, Ismail S, Vartak N, Chandra A, Hoffmann M, Hahn SA, Triola G, Wittinghofer A, Bastiaens PI, Waldmann H.

Nature. 2013;497(7451):638-642. doi:10.1038/nature12205

2012

N-Ras forms dimers at POPC membranes.

Güldenhaupt J, Rudack T, Bachler P, Mann D, Triola G, Waldmann H, Kötting C, Gerwert K.

Biophys J. 2012;103(7):1585-1593. doi:10.1016/j.bpj.2012.08.043

Direct immobilization of oxyamine-modified proteins from cell lysates.

Yi L, Chen YX, Lin PC, Schröder H, Niemeyer CM, Wu YW, Goody RS, Triola G, Waldmann H.

Chem Commun (Camb). 2012;48(88):10829-10831. doi:10.1039/c2cc35237k

The role of G-domain orientation and nucleotide state on the Ras isoform-specific membrane interaction.

Kapoor S, Weise K, Erlkamp M, Triola G, Waldmann H, Winter R.

Eur Biophys J. 2012;41(10):801-813. doi:10.1007/s00249-012-0841-5

Dissociation of the K-Ras4B/PDEδ complex upon contact with lipid membranes: membrane delivery instead of extraction.

Weise K, Kapoor S, Werkmüller A, Möbitz S, Zimmermann G, Triola G, Waldmann H, Winter R.

J Am Chem Soc. 2012;134(28):11503-11510. doi:10.1021/ja305518h

Proteolytic activity at quantum dot-conjugates: kinetic analysis reveals enhanced enzyme activity and localized interfacial "hopping".

Algar WR, Malonoski A, Deschamps JR, Blanco-Canosa JB, Susumu K, Stewart MH, Johnson BJ, Dawson PE, Medintz IL.

Nano Lett. 2012;12(7):3793-3802. doi:10.1021/nl301727k

Complex Förster energy transfer interactions between semiconductor quantum dots and a redox-active osmium assembly.

Stewart MH, Huston AL, Scott AM, Efros AL, Melinger JS, Gemmill KB, Trammell SA, Blanco-Canosa JB, Dawson PE, Medintz IL.

ACS Nano. 2012;6(6):5330-5347. doi:10.1021/nn301177h

Chemical-biological exploration of the limits of the Ras de- and repalmitoylating machinery.

Görmer K, Bürger M, Kruijtzer JA, Vetter I, Vartak N, Brunsveld L, Bastiaens PI, Liskamp RM, Triola G, Waldmann H.

Chembiochem. 2012;13(7):1017-1023. doi:10.1002/cbic.201200078

Multimodal characterization of a linear DNA-based nanostructure.

Buckhout-White S, Ancona M, Oh E, Deschamps JR, Stewart MH, Blanco-Canosa JB, Dawson PE, Goldman ER, Medintz IL.

ACS Nano. 2012;6(2):1026-1043. doi:10.1021/nn204680r

Revealing conformational substates of lipidated N-Ras protein by pressure modulation.

Kapoor S, Triola G, Vetter IR, Erlkamp M, Waldmann H, Winter R.

Proc Natl Acad Sci U S A. 2012;109(2):460-465. doi:10.1073/pnas.1110553109

Chemical biology of lipidated proteins.

Triola G, Waldmann H, Hedberg C.

ACS Chem Biol. 2012;7(1):87-99. doi:10.1021/cb200460u

Quantum dots as simultaneous acceptors and donors in time-gated Förster resonance energy transfer relays: characterization and biosensing.

Algar WR, Wegner D, Huston AL, Blanco-Canosa JB, Stewart MH, Armstrong A, Dawson PE, Hildebrandt N, Medintz IL.

J Am Chem Soc. 2012;134(3):1876-1891.

2011

Arl2-GTP and Arl3-GTP regulate a GDI-like transport system for farnesylated cargo.

Ismail SA, Chen YX, Rusinova A, Chandra A, Bierbaum M, Gremer L, Triola G, Waldmann H, Bastiaens PI, Wittinghofer A.

Nat Chem Biol. 2011 Oct 16;7(12):942-9. doi: 10.1038/nchembio.686.

Identification of acyl protein thioesterases 1 and 2 as the cellular targets of the Ras-signaling modulators palmostatin B and M.

Rusch M, Zimmermann TJ, Bürger M, Dekker FJ, Görmer K, Triola G, Brockmeyer A, Janning P, Böttcher T, Sieber SA, Vetter IR, Hedberg C, Waldmann H.

Angew Chem Int Ed Engl. 2011 Oct 10;50(42):9838-42. doi: 10.1002/anie.201102967.

Bioorthogonal chemistry for site-specific labeling and surface immobilization of proteins.

Chen YX, Triola G, Waldmann H.

Acc Chem Res. 2011 Sep 20;44(9):762-73. doi: 10.1021/ar200046h.

One-pot dual-labeling of a protein by two chemoselective reactions.

Yi L, Sun H, Itzen A, Triola G, Waldmann H, Goody RS, Wu YW.

Angew Chem Int Ed Engl. 2011 Aug 29;50(36):8287-90. doi: 10.1002/anie.201100840.

Membrane-mediated induction and sorting of K-Ras microdomain signaling platforms.

Weise K, Kapoor S, Denter C, Nikolaus J, Opitz N, Koch S, Triola G, Herrmann A, Waldmann H, Winter R.

J Am Chem Soc. 2011 Feb 2;133(4):880-7. doi: 10.1021/ja107532q.

2010

A highly efficient strategy for modification of proteins at the C terminus.

Yi L, Sun H, Wu YW, Triola G, Waldmann H, Goody RS.

Angew Chem Int Ed Engl. 2010 Dec 3;49(49):9417-21. doi: 10.1002/anie.201003834.

Synthesis of the Rheb and K-Ras4B GTPases.

Chen YX, Koch S, Uhlenbrock K, Weise K, Das D, Gremer L, Brunsveld L, Wittinghofer A, Winter R, Triola G, Waldmann H.

Angew Chem Int Ed Engl. 2010 Aug 16;49(35):6090-5. doi: 10.1002/anie.201001884.

Solid-phase synthesis of lipidated Ras peptides employing the Ellman sulfonamide linker.

Triola G, Gerauer M, Görmer K, Brunsveld L, Waldmann H.

Chemistry. 2010 Aug 16;16(31):9585-91. doi: 10.1002/chem.201001642.

Influence of the lipid anchor motif of N-ras on the interaction with lipid membranes: a surface plasmon resonance study.

Gohlke A, Triola G, Waldmann H, Winter R.

Biophys J. 2010 May 19;98(10):2226-35. doi: 10.1016/j.bpj.2010.02.005.

Efficient microwave-assisted synthesis of unsymmetrical disulfides.

Görmer K, Waldmann H, Triola G.

J Org Chem. 2010 Mar 5;75(5):1811-3. doi: 10.1021/jo902695a.

Visualizing association of lipidated signaling proteins in heterogeneous membranes--partitioning into subdomains, lipid sorting, interfacial adsorption, and protein association.

Weise K, Triola G, Janosch S, Waldmann H, Winter R.

Biochim Biophys Acta. 2010 Jul;1798(7):1409-17. doi: 10.1016/j.bbamem.2009.12.006.

2009

cis- versus trans-ceramides: effects of the double bond on conformation and H-bonding interactions.

Phillips SC, Triola G, Fabrias G, Goñi FM, DuPré DB, Yappert MC.

J Phys Chem B. 2009 Nov 19;113(46):15249-55. doi: 10.1021/jp903000m.

The lipid modifications of Ras that sense membrane environments and induce local enrichment.

Vogel A, Reuther G, Weise K, Triola G, Nikolaus J, Tan KT, Nowak C, Herrmann A, Waldmann H, Winter R, Huster D.

Angew Chem Int Ed Engl. 2009;48(46):8784-7. doi: 10.1002/anie.200903396.

Influence of the lipidation motif on the partitioning and association of N-Ras in model membrane subdomains.

Weise K, Triola G, Brunsveld L, Waldmann H, Winter R.

J Am Chem Soc. 2009 Feb 4;131(4):1557-64. doi: 10.1021/ja808691r.

ATP competitive inhibitors of D-alanine-D-alanine ligase based on protein kinase inhibitor scaffolds.

Triola G, Wetzel S, Ellinger B, Koch MA, Hübel K, Rauh D, Waldmann H. Bioorg Med Chem. 2009 Feb 1;17(3):1079-87. doi: 10.1016/j.bmc.2008.02.046

2008

Racemization-free synthesis of S-alkylated cysteines via thiol-ene reaction.

Triola G, Brunsveld L, Waldmann H.

J Org Chem. 2008 May 2;73(9):3646-9. doi: 10.1021/jo800198s.

2006

Design, synthesis and activity as acid ceramidase inhibitors of 2-oxooctanoyl and N-oleoylethanolamine analogues.

Grijalvo S, Bedia C, Triola G, Casas J, Llebaria A, Teixidó J, Rabal O, Levade T, Delgado A, Fabriàs G.

Chem Phys Lipids. 2006 Oct;144(1):69-84. doi: 10.1016/j.chemphyslip.2006.07.001.

2005

Analogs of the dihydroceramide desaturase inhibitor GT11 modified at the amide function: synthesis and biological activities.

Bedia C, Triola G, Casas J, Llebaria A, Fabriàs G.

Org Biomol Chem. 2005 Oct 21;3(20):3707-12. doi: 10.1039/b510198k.

2004

Specificity of the dihydroceramide desaturase inhibitor N-[(1R,2S)-2-hydroxy-1-hydroxymethyl-2-(2-tridecyl-1-cyclopropenyl)ethyl]octanamide (GT11) in primary cultured cerebellar neurons.

Triola G, Fabrias G, Dragusin M, Niederhausen L, Broere R, Llebaria A, van Echten-Deckert G.

Mol Pharmacol. 2004 Dec;66(6):1671-8. doi: 10.1124/mol.104.003681.

2003

Synthesis of cyclopropene analogues of ceramide and their effect on dihydroceramide desaturase.

Triola G, Fabriàs G, Casas J, Llebaria A.

J Org Chem. 2003 Dec 26;68(26):9924-32. doi: 10.1021/jo030141u.

2001

Synthesis of a Cyclopropene Analogue of Ceramide, a Potent Inhibitor of Dihydroceramide Desaturase

Triola G, Fabriàs G, Llebaria A.

Angew Chem Int Ed Engl. 2001 May 18;40(10):1960-1962.