62. Watson PJ, Millard CJ, Riley AM, Robertson NS, Wright LC, Godage HY, Cowley SM,
Jamieson AG, Potter BVL, Schwabe JWR (2016) Insights into the activation mechanism of
class I HDAC complexes by inositol phosphates. Nat Commun 7(11262):1–13
63. Wilson DM, Silverman LN, Bergauer M, Keshari KR (2013) Solid phase synthesis of
hydroxamate peptides for histone deacetylase inhibition. Tetrahedron Lett 54(2):151–153
64. Dose A, Sindlinger J, Bierlmeier J, Bakirbas A, Schulze-Osthoff K, Einsele-Scholz S, Hartl M,
Essmann F, Finkemeier I, Schwarzer D (2016) Interrogating substrate selectivity and composition of endogenous histone deacetylase complexes with chemical probes. Angew Chem Int Ed
55(3):1192–1195
65. Nielsen DS, Shepherd NE, Xu W, Lucke AJ, Stoermer MJ, Fairlie DP (2017) Orally absorbed
cyclic peptides. Chem Rev 117(12):8094–8128
66. Craik DJ, Fairlie DP, Liras S, Price D (2013) The future of peptide-based drugs. Chem Biol
Drug Des 81(1):136–147
67. Maolanon A, Kristensen H, Leman L, Ghadiri R, Olsen CA (2017) Natural and synthetic
macrocyclic inhibitors of the histone deacetylase enzymes. ChemBioChem 18(1):5–49
68. Furumai R, Komatsu Y, Nishino N, Khochbin S, Yoshida M, Horinouchi S (2001)
Potent histone deacetylase inhibitors built from trichostatin A and cyclic tetrapeptide antibiotics
including trapoxin. PNAS 98(1):87–92
69. Yoshida M, Furumai R, Nishiyama M, Komatsu Y, Nishino N, Horinouchi S (2001) Histone
deacetylase as a new target for cancer chemotherapy. Cancer Chemother Pharmacol 48:
S20–S26
70. Komatsu Y, Tomizaki K-Y, Tsukamoto M, Kato T, Nishino N, Sato S, Yamori T, Tsuruo T,
Furumai R, Yoshida M, Horinouchi S, Hayashi H (2001) Cyclic hydroxamic-acid-containing
peptide 31, a potent synthetic histone deacetylase inhibitor with antitumor activity. Cancer Res
61(11):4459–4466
71. Wang S, Li X, Wei Y, Xiu Z, Nishino N (2014) Discovery of potent HDAC inhibitors based on
chlamydocin with inhibitory effects on cell migration. ChemMedChem 9(3):627–637
72. Islam NM, Kato T, Nishino N, Kim H-J, Ito A, Yoshida M (2010) Bicyclic peptides as potent
inhibitors of histone deacetylases: optimization of alkyl loop length. Bioorg Med Chem Lett
20(3):997–999
73. Li X-H, Huang M-L, Wang S-M, Wang Q (2013) Selective inhibition of bicyclic tetrapeptide
histone deacetylase inhibitor on HDAC4 and K562 leukemia cell. Asian Pac J Cancer Prev
14(12):7095–7100
74. Jose B, Okamura S, Kato T, Nishino N, Sumida Y, Yoshida M (2004) Toward an HDAC6
inhibitor: synthesis and conformational analysis of cyclic hexapeptide hydroxamic acid
designed from α-tubulin sequence. Biorg Med Chem 12(6):1351–1356
75. Nakao Y, Yoshida S, Matsunaga S, Shindoh N, Terada Y, Nagai K, Yamashita JK, Ganesan A,
van Soest RWM, Fusetani N (2006) Azumamides A–E: histone deacetylase inhibitory cyclic
tetrapeptides from the marine sponge mycale izuensis. Angew Chem Int Ed 45(45):7553–7557
76. Maulucci N, Chini MG, Di Micco S, Izzo I, Cafaro E, Russo A, Gallinari P, Paolini C, Nardi
MC, Casapullo A (2007) Molecular insights into azumamide E histone deacetylases inhibitory
activity. J Am Chem Soc 129(10):3007–3012
77. Kranz M, Murray PJ, Taylor S, Upton RJ, Clegg W, Elsegood MRJ (2006) Solution, solid phase
and computational structures of apicidin and its backbone-reduced analogs. J Pept Sci
12(6):383–388
78. Izzo I, Maulucci N, Bifulco G, De Riccardis F (2006) Total synthesis of azumamides A and
E. Angew Chem Int Ed 45(45):7557–7560
79. Kawai M, Jasensky RD, Rich DH (1983) Conformational analysis by NMR spectrometry of the
highly substituted cyclic tetrapeptides, chlamydocin and Ala4-chlamydocin. Evidence for a
unique amide bond sequence in dimethyl sulfoxide-d6. J Am Chem Soc 105(13):4456–4462
80. Rich DH, Kawai M, Jasensky RD (1983) Conformational studies of cyclic tetrapeptides.
Chem Biol Drug Des 21(1):35–42
81. Kawai M, Rich DH, Walton JD (1983) The structure and conformation of HC-toxin.
Biochem Biophys Res Commun 111(2):398–403
52
C. Moreno-Yruela and C. A. Olsen
Jamieson AG, Potter BVL, Schwabe JWR (2016) Insights into the activation mechanism of
class I HDAC complexes by inositol phosphates. Nat Commun 7(11262):1–13
63. Wilson DM, Silverman LN, Bergauer M, Keshari KR (2013) Solid phase synthesis of
hydroxamate peptides for histone deacetylase inhibition. Tetrahedron Lett 54(2):151–153
64. Dose A, Sindlinger J, Bierlmeier J, Bakirbas A, Schulze-Osthoff K, Einsele-Scholz S, Hartl M,
Essmann F, Finkemeier I, Schwarzer D (2016) Interrogating substrate selectivity and composition of endogenous histone deacetylase complexes with chemical probes. Angew Chem Int Ed
55(3):1192–1195
65. Nielsen DS, Shepherd NE, Xu W, Lucke AJ, Stoermer MJ, Fairlie DP (2017) Orally absorbed
cyclic peptides. Chem Rev 117(12):8094–8128
66. Craik DJ, Fairlie DP, Liras S, Price D (2013) The future of peptide-based drugs. Chem Biol
Drug Des 81(1):136–147
67. Maolanon A, Kristensen H, Leman L, Ghadiri R, Olsen CA (2017) Natural and synthetic
macrocyclic inhibitors of the histone deacetylase enzymes. ChemBioChem 18(1):5–49
68. Furumai R, Komatsu Y, Nishino N, Khochbin S, Yoshida M, Horinouchi S (2001)
Potent histone deacetylase inhibitors built from trichostatin A and cyclic tetrapeptide antibiotics
including trapoxin. PNAS 98(1):87–92
69. Yoshida M, Furumai R, Nishiyama M, Komatsu Y, Nishino N, Horinouchi S (2001) Histone
deacetylase as a new target for cancer chemotherapy. Cancer Chemother Pharmacol 48:
S20–S26
70. Komatsu Y, Tomizaki K-Y, Tsukamoto M, Kato T, Nishino N, Sato S, Yamori T, Tsuruo T,
Furumai R, Yoshida M, Horinouchi S, Hayashi H (2001) Cyclic hydroxamic-acid-containing
peptide 31, a potent synthetic histone deacetylase inhibitor with antitumor activity. Cancer Res
61(11):4459–4466
71. Wang S, Li X, Wei Y, Xiu Z, Nishino N (2014) Discovery of potent HDAC inhibitors based on
chlamydocin with inhibitory effects on cell migration. ChemMedChem 9(3):627–637
72. Islam NM, Kato T, Nishino N, Kim H-J, Ito A, Yoshida M (2010) Bicyclic peptides as potent
inhibitors of histone deacetylases: optimization of alkyl loop length. Bioorg Med Chem Lett
20(3):997–999
73. Li X-H, Huang M-L, Wang S-M, Wang Q (2013) Selective inhibition of bicyclic tetrapeptide
histone deacetylase inhibitor on HDAC4 and K562 leukemia cell. Asian Pac J Cancer Prev
14(12):7095–7100
74. Jose B, Okamura S, Kato T, Nishino N, Sumida Y, Yoshida M (2004) Toward an HDAC6
inhibitor: synthesis and conformational analysis of cyclic hexapeptide hydroxamic acid
designed from α-tubulin sequence. Biorg Med Chem 12(6):1351–1356
75. Nakao Y, Yoshida S, Matsunaga S, Shindoh N, Terada Y, Nagai K, Yamashita JK, Ganesan A,
van Soest RWM, Fusetani N (2006) Azumamides A–E: histone deacetylase inhibitory cyclic
tetrapeptides from the marine sponge mycale izuensis. Angew Chem Int Ed 45(45):7553–7557
76. Maulucci N, Chini MG, Di Micco S, Izzo I, Cafaro E, Russo A, Gallinari P, Paolini C, Nardi
MC, Casapullo A (2007) Molecular insights into azumamide E histone deacetylases inhibitory
activity. J Am Chem Soc 129(10):3007–3012
77. Kranz M, Murray PJ, Taylor S, Upton RJ, Clegg W, Elsegood MRJ (2006) Solution, solid phase
and computational structures of apicidin and its backbone-reduced analogs. J Pept Sci
12(6):383–388
78. Izzo I, Maulucci N, Bifulco G, De Riccardis F (2006) Total synthesis of azumamides A and
E. Angew Chem Int Ed 45(45):7557–7560
79. Kawai M, Jasensky RD, Rich DH (1983) Conformational analysis by NMR spectrometry of the
highly substituted cyclic tetrapeptides, chlamydocin and Ala4-chlamydocin. Evidence for a
unique amide bond sequence in dimethyl sulfoxide-d6. J Am Chem Soc 105(13):4456–4462
80. Rich DH, Kawai M, Jasensky RD (1983) Conformational studies of cyclic tetrapeptides.
Chem Biol Drug Des 21(1):35–42
81. Kawai M, Rich DH, Walton JD (1983) The structure and conformation of HC-toxin.
Biochem Biophys Res Commun 111(2):398–403
52
C. Moreno-Yruela and C. A. Olsen