40. Mann BS, Johnson JR, He K, Sridhara R, Abraham S, Booth BP, Verbois L, Morse DE, Jee JM,
Pope S, Harapanhalli RS, Dagher R, Farrell A, Justice R, Pazdur R (2007) Vorinostat for
treatment of cutaneous manifestations of advanced primary cutaneous T-cell lymphoma.
Clin Cancer Res 13(8):2318–2322
41. Day JA, Cohen SM (2013) Investigating the selectivity of metalloenzyme inhibitors. J Med
Chem 56(20):7997–8007
42. Chen Y, Cohen SM (2015) Investigating the selectivity of metalloenzyme inhibitors in the
presence of competing metalloproteins. ChemMedChem 10(10):1733–1738
43. Chen Y, Lai B, Zhang Z, Cohen SM (2017) The effect of metalloprotein inhibitors on
cellular metal ion content and distribution. Metallomics 9(3):250–257
44. Shen S, Kozikowski AP (2016) Why hydroxamates may not be the best histone deacetylase
inhibitors—what some may have forgotten or would rather forget? ChemMedChem 11(1):
15–21
45. Nishino N, Jose B, Shinta R, Kato T, Komatsu Y, Yoshida M (2004) Chlamydocin–hydroxamic
acid analogues as histone deacetylase inhibitors. Biorg Med Chem 12(22):5777–5784
46. Islam N, Islam S, Hoque A, Kato T, Nishino N (2015) Synthetic strategy for bicyclic
tetrapeptides HDAC inhibitors using ring closing metathesis. J Chem Sci 127(9):1563–1569
47. Meinke PT, Colletti SL, Ayer MB, Darkin-Rattray SJ, Myers RW, Schmatz DM, Wyvratt MJ,
Fisher MH (2000) Synthesis of side chain modified apicidin derivatives: potent mechanismbased histone deacetylase inhibitors. Tetrahedron Lett 41(41):7831–7835
48. Wen S, Carey KL, Nakao Y, Fusetani N, Packham G, Ganesan A (2007) Total synthesis of
azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a
more potent analogue. Org Lett 9(6):1105–1108
49. Kitir B, Maolanon AR, Ohm RG, Colaço AR, Fristrup P, Madsen AS, Olsen CA (2017)
Chemical editing of macrocyclic natural products provides HDAC inhibitors with picomolar affinities. Biochemistry 56(38):5134–5146
50. Thouin E, Lubell WD (2000) Effective synthesis of enantiopure hydroxamates by displacement
of resin-bound esters with hydroxylamine. Tetrahedron Lett 41(4):457–460
51. Floyd CD, Lewis CN, Patel SR, Whittaker M (1996) A method for the synthesis of hydroxamic
acids on solid phase. Tetrahedron Lett 37(44):8045–8048
52. Ngu K, Patel DV (1997) A new and efficient solid phase synthesis of hydroxamic acids. J Org
Chem 62(21):7088–7089
53. Gordeev MF, Hui HC, Gordon EM, Patel DV (1997) A general and efficient solid phase synthesis of quinazoline-2, 4-diones. Tetrahedron Lett 38(10):1729–1732
54. Chen JJ, Spatola AF (1997) Solid phase synthesis of peptide hydroxamic acids. Tetrahedron
Lett 38(9):1511–1514
55. Richter LS, Desai MC (1997) A TFA-cleavable linkage for solid-phase synthesis of hydroxamic
acids. Tetrahedron Lett 38(3):321–322
56. Barlaam B, Koza P, Berriot J (1999) Solid-phase synthesis of hydroxamic acid based TNF-α
convertase inhibitors. Tetrahedron 55(23):7221–7232
57. Mellor SL, McGuire C, Chan WC (1997) N-Fmoc-aminooxy-2-chlorotrityl polystyrene resin: a
facile solid-phase methodology for the synthesis of hydroxamic acids. Tetrahedron Lett 38(18):
3311–3314
58. Bauer U, Ho W-B, Koskinen AM (1997) A novel linkage for the solid-phase synthesis of
hydroxamic acids. Tetrahedron Lett 38(41):7233–7236
59. Bang CG, Jensen JF, O’Hanlon Cohrt E, Olsen LB, Siyum SG, Mortensen KT, Skovgaard T,
Berthelsen J, Yang L, Givskov M (2017) A linker for the solid-phase synthesis of hydroxamic
acids and identification of HDAC6 inhibitors. ACS Comb Sci 19(10):657–669
60. Montero A, Beierle JM, Olsen CA, Ghadiri MR (2009) Design, synthesis, biological evaluation,
and structural characterization of potent histone deacetylase inhibitors based on
cyclic Α/Β-tetrapeptide architectures. J Am Chem Soc 131(8):3033–3041
61. Olsen CA, Ghadiri MR (2009) Discovery of potent and selective histone deacetylase inhibitors
via focused combinatorial libraries of cyclic Α3β-tetrapeptides. J Med Chem 52(23):7836–7846
Hydroxamic Acid-Containing Peptides in the Study of Histone Deacetylases
51
Pope S, Harapanhalli RS, Dagher R, Farrell A, Justice R, Pazdur R (2007) Vorinostat for
treatment of cutaneous manifestations of advanced primary cutaneous T-cell lymphoma.
Clin Cancer Res 13(8):2318–2322
41. Day JA, Cohen SM (2013) Investigating the selectivity of metalloenzyme inhibitors. J Med
Chem 56(20):7997–8007
42. Chen Y, Cohen SM (2015) Investigating the selectivity of metalloenzyme inhibitors in the
presence of competing metalloproteins. ChemMedChem 10(10):1733–1738
43. Chen Y, Lai B, Zhang Z, Cohen SM (2017) The effect of metalloprotein inhibitors on
cellular metal ion content and distribution. Metallomics 9(3):250–257
44. Shen S, Kozikowski AP (2016) Why hydroxamates may not be the best histone deacetylase
inhibitors—what some may have forgotten or would rather forget? ChemMedChem 11(1):
15–21
45. Nishino N, Jose B, Shinta R, Kato T, Komatsu Y, Yoshida M (2004) Chlamydocin–hydroxamic
acid analogues as histone deacetylase inhibitors. Biorg Med Chem 12(22):5777–5784
46. Islam N, Islam S, Hoque A, Kato T, Nishino N (2015) Synthetic strategy for bicyclic
tetrapeptides HDAC inhibitors using ring closing metathesis. J Chem Sci 127(9):1563–1569
47. Meinke PT, Colletti SL, Ayer MB, Darkin-Rattray SJ, Myers RW, Schmatz DM, Wyvratt MJ,
Fisher MH (2000) Synthesis of side chain modified apicidin derivatives: potent mechanismbased histone deacetylase inhibitors. Tetrahedron Lett 41(41):7831–7835
48. Wen S, Carey KL, Nakao Y, Fusetani N, Packham G, Ganesan A (2007) Total synthesis of
azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a
more potent analogue. Org Lett 9(6):1105–1108
49. Kitir B, Maolanon AR, Ohm RG, Colaço AR, Fristrup P, Madsen AS, Olsen CA (2017)
Chemical editing of macrocyclic natural products provides HDAC inhibitors with picomolar affinities. Biochemistry 56(38):5134–5146
50. Thouin E, Lubell WD (2000) Effective synthesis of enantiopure hydroxamates by displacement
of resin-bound esters with hydroxylamine. Tetrahedron Lett 41(4):457–460
51. Floyd CD, Lewis CN, Patel SR, Whittaker M (1996) A method for the synthesis of hydroxamic
acids on solid phase. Tetrahedron Lett 37(44):8045–8048
52. Ngu K, Patel DV (1997) A new and efficient solid phase synthesis of hydroxamic acids. J Org
Chem 62(21):7088–7089
53. Gordeev MF, Hui HC, Gordon EM, Patel DV (1997) A general and efficient solid phase synthesis of quinazoline-2, 4-diones. Tetrahedron Lett 38(10):1729–1732
54. Chen JJ, Spatola AF (1997) Solid phase synthesis of peptide hydroxamic acids. Tetrahedron
Lett 38(9):1511–1514
55. Richter LS, Desai MC (1997) A TFA-cleavable linkage for solid-phase synthesis of hydroxamic
acids. Tetrahedron Lett 38(3):321–322
56. Barlaam B, Koza P, Berriot J (1999) Solid-phase synthesis of hydroxamic acid based TNF-α
convertase inhibitors. Tetrahedron 55(23):7221–7232
57. Mellor SL, McGuire C, Chan WC (1997) N-Fmoc-aminooxy-2-chlorotrityl polystyrene resin: a
facile solid-phase methodology for the synthesis of hydroxamic acids. Tetrahedron Lett 38(18):
3311–3314
58. Bauer U, Ho W-B, Koskinen AM (1997) A novel linkage for the solid-phase synthesis of
hydroxamic acids. Tetrahedron Lett 38(41):7233–7236
59. Bang CG, Jensen JF, O’Hanlon Cohrt E, Olsen LB, Siyum SG, Mortensen KT, Skovgaard T,
Berthelsen J, Yang L, Givskov M (2017) A linker for the solid-phase synthesis of hydroxamic
acids and identification of HDAC6 inhibitors. ACS Comb Sci 19(10):657–669
60. Montero A, Beierle JM, Olsen CA, Ghadiri MR (2009) Design, synthesis, biological evaluation,
and structural characterization of potent histone deacetylase inhibitors based on
cyclic Α/Β-tetrapeptide architectures. J Am Chem Soc 131(8):3033–3041
61. Olsen CA, Ghadiri MR (2009) Discovery of potent and selective histone deacetylase inhibitors
via focused combinatorial libraries of cyclic Α3β-tetrapeptides. J Med Chem 52(23):7836–7846
Hydroxamic Acid-Containing Peptides in the Study of Histone Deacetylases
51