recent publications
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academic article
- Campos, K. R., Coleman, P. J., Alvarez, J. C., Dreher, S. D., Garbaccio, R. M., Terrett, N. K., Tillyer, R. D., Truppo, M. D., Parmee, E. R. The importance of synthetic chemistry in the pharmaceutical industry Science 2019 363 DOI:10.1126/science.aat0805 PMID:30655413
- Brandish, P. E., Palmieri, A., Antonenko, S., Beaumont, M., Benso, L., Cancilla, M., Cheng, M., Fayadat-Dilman, L., Feng, G., Figueroa, I., Firdos, J., Garbaccio, R., et al. Development of anti-CD74 antibody-drug conjugates to target glucocorticoids to immune cells Bioconjugate Chemistry 2018 29:2357-2369 DOI:10.1021/acs.bioconjchem.8b00312 PMID:29923706
- Kern, J. C., Dooney, D., Zhang, R., Liang, L., Brandish, P. E., Cheng, M., Feng, G., Beck, A., Bresson, D., Firdos, J., Gately, D., Knudsen, N., et al. Novel phosphate modified cathepsin B linkers: improving aqueous solubility and enhancing payload scope of ADCs Bioconjugate Chemistry 2016 27:2081-2088 DOI:10.1021/acs.bioconjchem.6b00337 PMID:27469406
- Pero, J. E., Rossi, M. A., Kelly, M. J., Lehman, Hdgf, Layton, M. E., Garbaccio, R. M., O'Brien, J. A., Magliaro, B. C., Uslaner, J. M., Huszar, S. L., Fillgrove, K. L., Tang, C., et al. Optimization of novel Aza-benzimidazolone mGluR2 PAMs with respect to LLE and PK properties and mitigation of CYP TDI ACS Medicinal Chemistry Letters 2016 7:312-317 DOI:10.1021/acsmedchemlett.5b00459 PMID:26985321 PMCID:PMC4789683
- Layton, M. E., Reif, A. J., Hartingh, T. J., Rodzinak, K., Dudkin, V., Wang, C., Arrington, K., Kelly, M. J., Garbaccio, R. M., O'Brien, J. A., Magliaro, B. C., Uslaner, J. M., et al. Discovery of 5-aryl-1,3-dihydro-2H-imidazo 4,5-b pyridin-2-ones as positive allosteric modulators of metabotropic glutamate subtype-2 (mGlu2) receptors with efficacy in a preclinical model of psychosis Bioorganic & Medicinal Chemistry Letters 2016 26:1260-1264 DOI:10.1016/j.bmcl.2016.01.021 PMID:26810316
- Kern, J. C., Cancilla, M., Dooney, D., Kwasnjuk, K., Zhang, R., Beaumont, M., Figueroa, I., Hsieh, S., Liang, L. D., Tomazela, D., Zhang, J., Brandish, P. E., et al. Discovery of pyrophosphate diesters as tunable, soluble, and bioorthogonal linkers for site-specific antibody-drug conjugates Journal of the American Chemical Society 2016 138:1430-1445 DOI:10.1021/jacs.5b12547
- Pei, T., Liao, J., Williams, J. M., Xiang, R., Garbaccio, R. M., Barrett, S. E., Guidry, E. N. Size controlled synthesis of ornithine‐based polypeptides by ring‐opening polymerization of α‐(amino acid)‐N‐carboxyanhydrides Journal of Polymer Science Part a-Polymer Chemistry 2016 54:311-315 DOI:10.1002/pola.27920
- Garbaccio, R. M., Parmee, E. R. The impact of chemical probes in drug discovery: a pharmaceutical industry perspective Cell Chemical Biology 2016 23:10-17 DOI:10.1016/j.chembiol.2015.11.011
- Garbaccio, R. M., Johnson, D. S., Hong, J., Disney, M. D. Recent advances in medicinal chemistry and chemical biology. Preface. Bioorganic & Medicinal Chemistry Letters 2015 25:4714-4714 DOI:10.1016/j.bmcl.2015.08.083
- Converso, A., Hartingh, T., Fraley, M. E., Garbaccio, R. M., Hartman, G. D., Huang, S. Y., Majercak, J. M., McCampbell, A., Na, S. J., Ray, W. J., Savage, M. J., Wolffe, C., et al. Adenosine analogue inhibitors of S-adenosylhomocysteine hydrolase Bioorganic & Medicinal Chemistry Letters 2014 24:2737-2740 DOI:10.1016/j.bmcl.2014.04.034 PMID:24813734
- Barrett, S. E., Burke, R. S., Abrams, M. T., Bason, C., Busuek, M., Carlini, E., Carr, B. A., Crocker, L. S., Fan, H., Garbaccio, R. M., Guidry, E. N., Heo, J. H., et al. Development of a liver-targeted siRNA delivery platform with a broad therapeutic window utilizing biodegradable polypeptide-based polymer conjugates Journal of Controlled Release 2014 183:124-137 DOI:10.1016/j.jconrel.2014.03.028 PMID:24657948
- Barrett, S. E., Abrams, M. T., Burke, R., Carr, B. A., Crocker, L. S., Garbaccio, R. M., Howell, B. J., Kemp, E. A., Kowtoniuk, R. A., Latham, A. H., Leander, K. R., Leone, A. M., et al. An in vivo evaluation of amphiphilic, biodegradable peptide copolymers as siRNA delivery agents International Journal of Pharmaceutics 2014 466:58-67 DOI:10.1016/j.ijpharm.2014.03.011 PMID:24607208
- Kowtoniuk, R. A., Pei, T., DeAngelo, C. M., Waldman, J. H., Guidry, E. N., Williams, J. M., Garbaccio, R. M., Barrett, S. E. Optimization of an α‐(Amino acid)‐N‐carboxyanhydride polymerization using the high vacuum technique: Examining the effects of monomer concentration, polymerization kinetics, polymer molecular weight, and monomer purity Journal of Polymer Science Part a-Polymer Chemistry 2014 52:1385-1391 DOI:10.1002/pola.27132
- Parmar, R. G., Poslusney, M., Busuek, M., Williams, J. M., Garbaccio, R., Leander, K., Walsh, E., Howell, B., Sepp-Lorenzino, L., Riley, S., Patel, M., Kemp, E., et al. Novel endosomolytic poly(amido amine) polymer conjugates for systemic delivery of siRNA to hepatocytes in rodents and nonhuman primates Bioconjugate Chemistry 2014 25:896-906 DOI:10.1021/bc400527e PMID:24742200
- Guidry, E. N., Farand, J., Soheili, A., Parish, C. A., Kevin, N. J., Pipik, B., Calati, K. B., Ikemoto, N., Waldman, J. H., Latham, A. H., Howell, B. J., Leone, A., et al. Improving the in vivo therapeutic index of siRNA polymer conjugates through increasing pH responsiveness Bioconjugate Chemistry 2014 25:296-307 DOI:10.1021/bc400442p PMID:24409989
- Parmar, R. G., Busuek, M., Walsh, E. S., Leander, K. R., Howell, B. J., Sepp-Lorenzino, L., Kemp, E., Crocker, L. S., Leone, A., Kochansky, C. J., Carr, B. A., Garbaccio, R. M., et al. Endosomolytic bioreducible poly(amido amine disulfide) polymer conjugates for the in vivo systemic delivery of siRNA therapeutics Bioconjugate Chemistry 2013 24:640-647 DOI:10.1021/bc300600a PMID:23496378
- Cox, C. D., Garbaccio, R. M. Discovery of allosteric inhibitors of kinesin spindle protein (KSP) for the treatment of taxane-refractory cancer: MK-0731 and analogs Anti-Cancer Agents in Medicinal Chemistry 2010 10:697-712 DOI:10.2174/187152010794479807 PMID:21235439
- Garbaccio, R. M., Brnardic, E. J., Fraley, M. E., Hartman, G. D., Hutson, P. H., O'Brien, J. A., Magliaro, B. C., Uslaner, J. M., Huszar, S. L., Fillgrove, K. L., Small, J. H., Tang, C., et al. Discovery of oxazolobenzimidazoles as positive allosteric modulators for the mGluR2 receptor ACS Medicinal Chemistry Letters 2010 1:406-410 DOI:10.1021/ml100115a PMID:24900224 PMCID:PMC4007895
- Brnardic, E. J., Fraley, M. E., Garbaccio, R. M., Layton, M. E., Sanders, J. M., Culberson, C., Jacobson, M. A., Magliaro, B. C., Hutson, P. H., O'Brien, J. A., Huszar, S. L., Uslaner, J. M., et al. 3-Aryl-5-phenoxymethyl-1,3-oxazolidin-2-ones as positive allosteric modulators of mGluR2 for the treatment of schizophrenia: Hit-to-lead efforts Bioorganic & Medicinal Chemistry Letters 2010 20:3129-3133 DOI:10.1016/j.bmcl.2010.03.089 PMID:20409708
- Li, C., Lu, B., Garbaccio, R. M., Tasber, E. S., Fraley, M. E., Hartman, G. D., Ye, J., Harrelson, J. C., Prueksaritanont, T. Stereospecific reduction of a potent kinesin spindle protein (KSP) inhibitor in human tissues Biochemical Pharmacology 2010 79:1526-1533 DOI:10.1016/j.bcp.2010.01.024 PMID:20109439
- Converso, A., Hartingh, T., Garbaccio, R. M., Tasber, E., Rickert, K., Fraley, M. E., Yan, Y., Kreatsoulas, C., Stirdivant, S., Drakas, B., Walsh, E. S., Hamilton, K., et al. Development of thioquinazolinones, allosteric Chk1 kinase inhibitors Bioorganic & Medicinal Chemistry Letters 2009 19:1240-1244 DOI:10.1016/j.bmcl.2008.12.076 PMID:19155174
- Cox, C. D., Coleman, P. J., Breslin, M. J., Whitman, D. B., Garbaccio, R. M., Fraley, M. E., Buser, C. A., Walsh, E. S., Hamilton, K., Schaber, M. D., Lobell, R. B., Tao, W., et al. Kinesin spindle protein (KSP) inhibitors. 9. Discovery of (2S)-4-(2,5-difluorophenyl)-N-[(3R,4S)-3-fluoro-1-methylpiperidin-4-yl]- 2-(hydroxymethyl)-N-methyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide (MK-0731) for the treatment of taxane-refractory cancer Journal of Medicinal Chemistry 2008 51:4239-4252 DOI:10.1021/jm800386y PMID:18578472
- Rickert, K. W., Schaber, M., Torrent, M., Neilson, L. A., Tasber, E. S., Garbaccio, R., Coleman, P. J., Harvey, D., Zhang, Y., Yang, Y., Marshall, G., Lee, L., et al. Discovery and biochemical characterization of selective ATP competitive inhibitors of the human mitotic kinesin KSP Archives of Biochemistry and Biophysics 2008 469:220-231 DOI:10.1016/j.abb.2007.10.016 PMID:17999913
- Garbaccio, R. M., Huang, S., Tasber, E. S., Fraley, M. E., Yan, Y., Munshi, S., Ikuta, M., Kuo, L., Kreatsoulas, C., Stirdivant, S., Drakas, B., Rickert, K., et al. Synthesis and evaluation of substituted benzoisoquinolinones as potent inhibitors of Chk1 kinase Bioorganic & Medicinal Chemistry Letters 2007 17:6280-6285 DOI:10.1016/j.bmc1.2007.09.007 PMID:17900896
- Brnardic, E. J., Garbaccio, R. M., Fraley, M. E., Tasber, E. S., Steen, J. T., Arrington, K. L., Dudkin, V. Y., Hartman, G. D., Stirdivant, S. M., Drakas, B. A., Rickert, K., Walsh, E. S., et al. Optimization of a pyrazoloquinolinone class of Chk1 kinase inhibitors Bioorganic & Medicinal Chemistry Letters 2007 17:5989-5994 DOI:10.1016/j.bmcl.2007.07.051 PMID:17804227
- Garbaccio, R. M., Tasbera, E. S., Neilson, L. A., Coleman, P. J., Fraley, M. E., Olson, C., Bergman, J., Torrent, M., Buser, C. A., Rickert, K., Walsh, E. S., Hamilton, K., et al. Kinesin spindle protein (KSP) inhibitors. Part 7: Design and synthesis of 3,3-disubstituted dihydropyrazolobenzoxazines as potent inhibitors of the mitotic kinesin KSP Bioorganic & Medicinal Chemistry Letters 2007 17:5671-5676 DOI:10.1016/j.bmcl.2007.07.067 PMID:17804233
- Coleman, P. J., Schreler, J. D., Cox, C. D., Fraley, M. E., Garbaccio, R. M., Buser, C. A., Walsh, E. S., Hamilton, K., Lobell, R. B., Rickert, K., Tao, W. K., Diehl, R. E., et al. Kinesin spindle protein (KSP) inhibitors. Part 6: Design and synthesis of 3,5-diaryl-4,5-dihydropyrazole amides as potent inhibitors of the mitotic kinesin KSP Bioorganic & Medicinal Chemistry Letters 2007 17:5390-5395 DOI:10.1016/j.bmcl.2007.07.046 PMID:17761419
- Cox, C. D., Breslin, M. J., Whitman, D. B., Coleman, P. J., Garbaccio, R. M., Fraley, M. E., Zrada, M. M., Buser, C. A., Walsh, E. S., Hamilton, K., Lobell, R. B., Tao, W., et al. Kinesin spindle protein (KSP) inhibitors. Part V: Discovery of 2-propylamino-2,4-diaryl-2,5-dihydropyrroles as potent, water-soluble KSP inhibitors, and modulation of their basicity by beta-fluorination to overcome cellular efflux by P-glycoprotein Bioorganic & Medicinal Chemistry Letters 2007 17:2697-2702 DOI:10.1016/j.bmcl.2007.03.006 PMID:17395460
- Huang, S. E., Garbaccio, R. M., Fraley, M. E., Steen, J., Kreatsoulas, C., Hartman, G., Stirdivant, S., Drakas, B., Rickert, K., Walsh, E., Hamilton, K., Buser, C. A., et al. Development of 6-substituted indolylquinolinones as potent Chek1 kinase inhibitors Bioorganic & Medicinal Chemistry Letters 2006 16:5907-5912 DOI:10.1016/j.bmcl.2006.08.053 PMID:16990002
- Fraley, M. E., Garbaccio, R. M., Arrington, K. L., Hoffman, W. F., Tasber, E. S., Coleman, P. J., Buser, C. A., Walsh, E. S., Hamilton, K., Fernandes, C., Schaber, M. D., Lobell, R. B., et al. Kinesin spindle protein (KSP) inhibitors. Part 2: The design, synthesis, and characterization of 2,4-diaryl-2,5-dihydropyrrole inhibitors of the mitotic kinesin KSP Bioorganic & Medicinal Chemistry Letters 2006 16:1775-1779 DOI:10.1016/j.bmcl.2006.01.030 PMID:16439123
- Garbaccio, R. M., Fraley, M. E., Tasber, E. S., Olson, C. M., Hoffman, W. F., Arrington, K. L., Torrent, M., Buser, C. A., Walsh, E. S., Hamilton, K., Schaber, M. D., Fernandes, C., et al. Kinesin spindle protein (KSP) inhibitors. Part 3: Synthesis and evaluation of phenolic 2,4-diaryl-2,5-dihydropyrroles with reduced hERG binding and employment of a phosphate prodrug strategy for aqueous solubility Bioorganic & Medicinal Chemistry Letters 2006 16:1780-1783 DOI:10.1016/j.bmcl.2005.12.094 PMID:16439122
- Tasber, E. S., Garbaccio, R. M. Thermodynamic equilibration of dihydropyridone enolates: application to the total synthesis of (+/-)-epiuleine Tetrahedron Letters 2003 44:9185-9188 DOI:10.1016/j.tetlet.2003.10.030
- Yamamoto, K., Garbaccio, R. M., Stachel, S. J., Solit, D. B., Chiosis, G., Rosen, N., Danishefsky, S. J. Total synthesis as a resource in the discovery of potentially valuable antitumor agents: cycloproparadicicol Angewandte Chemie - International Edition 2003 42:1280-1284 DOI:10.1002/anie.200390329 PMID:12645064
- Garbaccio, R. M., Stachel, S. J., Baeschlin, D. K., Danishefsky, S. J. Concise asymmetric syntheses of radicicol and monocillin I Journal of the American Chemical Society 2001 123:10903-10908 DOI:10.1021/ja011364+ PMID:11686693
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Boger, D. L., Brunette, S. R., Garbaccio, R. M.
Synthesis and evaluation of a series of C3-substituted CBI analogues of CC-1065 and the duocarmycins
Journal of Organic Chemistry
2001
66:5163-5173
DOI:10.1021/jo010309g
PMID:11463270
- Garbaccio, R. M., Danishefsky, S. J. Efficient asymmetric synthesis of radicicol dimethyl ether: A novel application of ring-forming olefin metathesis Organic Letters 2000 2:3127-3129 DOI:10.1021/ol0063252 PMID:11009362
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Boger, D. L.*, Garbaccio, R. M.*
Shape-dependent catalysis: Insights into the source of catalysis for the CC-1065 and duocarmycin DNA alkylation reaction
Accounts of Chemical Research
1999
32:1043-1052
DOI:10.1021/ar9800946
(* = equal contribution)
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Boger, D. L.*, Garbaccio, R. M.*
A novel class of CC-1065 and duocarmycin analogues subject to mitomycin-related reductive activation
Journal of Organic Chemistry
1999
64:8350-8362
DOI:10.1021/jo991301y
PMID:11674758
(* = equal contribution)
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Boger, D. L.*, Garbaccio, R. M.*
Are the duocarmycin and CC-1065 DNA alkylation reactions acid-catalyzed? Solvolysis pH-rate profiles suggest they are not
Journal of Organic Chemistry
1999
64:5666-5669
DOI:10.1021/jo990762g
PMID:11674637
(* = equal contribution)
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Boger, D. L.*, Boyce, C. W.*, Garbaccio, R. M., Searcey, M., Jin, Q.
CBI prodrug analogs of CC-1065 and the duocarmycins
Synthesis-Stuttgart
1999
1505-1509
(* = equal contribution)
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Boger, D. L., Schaum, R. P., Garbaccio, R. M.
Regioselective inverse electron demand Diels-Alder reactions of N-acyl 6-amino-3-(methylthio)-1,2,4,5-tetrazines
Journal of Organic Chemistry
1998
63:6329-6337
DOI:10.1021/jo980795g
PMID:11672266
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Boger, D. L.*, Boyce, C. W.*, Garbaccio, R. M., Searcey, M.
Synthesis of CC-1065 and duocarmycin analogs via intramolecular aryl radical cyclization of a tethered vinyl chloride
Tetrahedron Letters
1998
39:2227-2230
DOI:10.1016/s0040-4039(98)00232-9
(* = equal contribution)
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Boger, D. L.*, Garbaccio, R. M.*, Jin, Q.
Synthesis and evaluation of CC-1065 and duocarmycin analogues incorporating the iso-CI and iso-CBI alkylation subunits: impact of relocation of the C-4 carbonyl
Journal of Organic Chemistry
1997
62:8875-8891
DOI:10.1021/jo971686p
(* = equal contribution)
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Boger, D. L., Bollinger, B., Hertzog, D. L., Johnson, D. S., Cai, H., Mesini, P., Garbaccio, R. M., Jin, Q., Kitos, P. A.
Reversed and sandwiched analogs of duocarmycin SA: Establishment of the origin of the sequence-selective alkylation of DNA and new insights into the source of catalysis
Journal of the American Chemical Society
1997
119:4987-4998
DOI:10.1021/ja9637210
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Boger, D. L.*, Boyce, C. W.*, Garbaccio, R. M., Goldberg, J. A.
CC-1065 and the duocarmycins: Synthetic studies
Chemical Reviews
1997
97:787-828
DOI:10.1021/cr960095g
PMID:11848889
(* = equal contribution)
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Boger, D. L.*, Garbaccio, R. M.*
Catalysis of the CC-1065 and duocarmycin DNA alkylation reaction: DNA binding induced conformational change in the agent results in activation
Bioorganic & Medicinal Chemistry
1997
5:263-276
DOI:10.1016/s0968-0896(96)00238-6
PMID:9061191
(* = equal contribution)
- Panek, J. S.*, Garbaccio, R. M.*, Jain, N. F. Diastereoselectivity in cyclopropanation and epoxidation reactions of chiral (E)-crotylsilanes: asymmetric synthesis of substituted tetrahydrofurans Tetrahedron Letters 1994 35:6453-6456 DOI:10.1016/s0040-4039(00)78244-x (* = equal contribution)