131. Wan H et al (2009) Benzo[d]imidazole inhibitors of coactivator associated arginine
methyltransferase 1 (CARM1)-hit to Lead studies. Bioorg Med Chem Lett 19:5063–5066
132. Therrien E et al (2009) 1,2-diamines as inhibitors of co-activator associated arginine
methyltransferase 1 (CARM1). Bioorg Med Chem Lett 19:6725–6732
133. Sack JS et al (2011) Structural basis for CARM1 inhibition by indole and pyrazole inhibitors.
Biochem J 436:331–339
134. Ferreira De Freitas R et al (2016) Discovery of a potent class i protein arginine
methyltransferase fragment inhibitor. J Med Chem 59:1176–1183
135. Shen Y et al (2016) Discovery of a potent, selective, and cell-active dual inhibitor of protein
arginine methyltransferase 4 and protein arginine methyltransferase 6. J Med Chem
59:9124–9139
136. Kaniskan HÜ et al (2016) Design and synthesis of selective, small molecule inhibitors of
coactivator-associated arginine methyltransferase 1 (CARM1). Med Chem Commun
7:1793–1796
137. Nakayama K et al (2018) TP-064, a potent and selective small molecule inhibitor of PRMT4
for multiple myeloma. Oncotarget 9:18480–18493
138. Ferreira de Freitas R et al (2016) Discovery of a potent and selective coactivator associated
arginine methyltransferase 1 (CARM1) inhibitor by virtual screening. J Med Chem
59:6838–6847
139. Cheng DH et al (2011) Novel 3,5-bis(bromohydroxybenzylidene)piperidin-4-ones as
coactivator-associated arginine methyltransferase 1 inhibitors: enzyme selectivity and cellular
activity. J Med Chem 54:4928–4932
140. Selvi BR et al (2010) Identification of a novel inhibitor of coactivator-associated arginine
methyltransferase 1 (CARM1)-mediated methylation of histone H3 Arg-17. J Biol Chem
285:7143–7152
141. van Haren MJ et al (2017) Transition state mimics are valuable mechanistic probes for
structural studies with the arginine methyltransferase CARM1. Proc Natl Acad Sci U S A
114:3625–3630
142. Pollack BP et al (1999) The human homologue of the yeast proteins Skb1 and Hsl7p interacts
with Jak kinases and contains protein methyltransferase activity. J Biol Chem
274:31531–31542
143. Wei H et al (2013) PRMT5 dimethylates R30 of the p65 subunit to activate NF- B. Proc Natl
Acad Sci U S A 110:13516–13521
144. Migliori V et al (2012) Symmetric dimethylation of H3R2 is a newly identified histone mark
that supports euchromatin maintenance. Nat Struct Mol Biol 19:136–144
145. Ren J et al (2010) Methylation of ribosomal protein S10 by protein-arginine methyltransferase
5 regulates ribosome biogenesis. J Biol Chem 285:12695–12705
146. Jansson M et al (2008) Arginine methylation regulates the p53 response. Nat Cell Biol
10:1431–1439
147. Zheng S et al (2013) Arginine methylation-dependent reader-writer interplay governs growth
control by E2F-1. Mol Cell 52:37–51
148. Powers MA et al (2011) Protein arginine methyltransferase 5 accelerates tumor growth by
arginine methylation of the tumor suppressor programmed cell death 4. Cancer Res
71:5579–5587
149. Andreu-Perez P et al (2011) Protein arginine methyltransferase 5 regulates ERK1/2 signal
transduction amplitude and cell fate through CRAF. Sci Signal 4:ra58
150. Antonysamy S et al (2012) Crystal structure of the human PRMT5:MEP50 complex. Proc Natl
Acad Sci U S A 109:17960–17965
151. Ho M-C et al (2013) Structure of the arginine methyltransferase PRMT5-MEP50 reveals a
mechanism for substrate specificity. PLoS One 8:e57008
152. Morales Y et al (2016) Biochemistry and regulation of the protein arginine methyltransferases
(PRMTs). Arch Biochem Biophys 590:138–152
194
M. J. van Haren and N. I. Martin
methyltransferase 1 (CARM1)-hit to Lead studies. Bioorg Med Chem Lett 19:5063–5066
132. Therrien E et al (2009) 1,2-diamines as inhibitors of co-activator associated arginine
methyltransferase 1 (CARM1). Bioorg Med Chem Lett 19:6725–6732
133. Sack JS et al (2011) Structural basis for CARM1 inhibition by indole and pyrazole inhibitors.
Biochem J 436:331–339
134. Ferreira De Freitas R et al (2016) Discovery of a potent class i protein arginine
methyltransferase fragment inhibitor. J Med Chem 59:1176–1183
135. Shen Y et al (2016) Discovery of a potent, selective, and cell-active dual inhibitor of protein
arginine methyltransferase 4 and protein arginine methyltransferase 6. J Med Chem
59:9124–9139
136. Kaniskan HÜ et al (2016) Design and synthesis of selective, small molecule inhibitors of
coactivator-associated arginine methyltransferase 1 (CARM1). Med Chem Commun
7:1793–1796
137. Nakayama K et al (2018) TP-064, a potent and selective small molecule inhibitor of PRMT4
for multiple myeloma. Oncotarget 9:18480–18493
138. Ferreira de Freitas R et al (2016) Discovery of a potent and selective coactivator associated
arginine methyltransferase 1 (CARM1) inhibitor by virtual screening. J Med Chem
59:6838–6847
139. Cheng DH et al (2011) Novel 3,5-bis(bromohydroxybenzylidene)piperidin-4-ones as
coactivator-associated arginine methyltransferase 1 inhibitors: enzyme selectivity and cellular
activity. J Med Chem 54:4928–4932
140. Selvi BR et al (2010) Identification of a novel inhibitor of coactivator-associated arginine
methyltransferase 1 (CARM1)-mediated methylation of histone H3 Arg-17. J Biol Chem
285:7143–7152
141. van Haren MJ et al (2017) Transition state mimics are valuable mechanistic probes for
structural studies with the arginine methyltransferase CARM1. Proc Natl Acad Sci U S A
114:3625–3630
142. Pollack BP et al (1999) The human homologue of the yeast proteins Skb1 and Hsl7p interacts
with Jak kinases and contains protein methyltransferase activity. J Biol Chem
274:31531–31542
143. Wei H et al (2013) PRMT5 dimethylates R30 of the p65 subunit to activate NF- B. Proc Natl
Acad Sci U S A 110:13516–13521
144. Migliori V et al (2012) Symmetric dimethylation of H3R2 is a newly identified histone mark
that supports euchromatin maintenance. Nat Struct Mol Biol 19:136–144
145. Ren J et al (2010) Methylation of ribosomal protein S10 by protein-arginine methyltransferase
5 regulates ribosome biogenesis. J Biol Chem 285:12695–12705
146. Jansson M et al (2008) Arginine methylation regulates the p53 response. Nat Cell Biol
10:1431–1439
147. Zheng S et al (2013) Arginine methylation-dependent reader-writer interplay governs growth
control by E2F-1. Mol Cell 52:37–51
148. Powers MA et al (2011) Protein arginine methyltransferase 5 accelerates tumor growth by
arginine methylation of the tumor suppressor programmed cell death 4. Cancer Res
71:5579–5587
149. Andreu-Perez P et al (2011) Protein arginine methyltransferase 5 regulates ERK1/2 signal
transduction amplitude and cell fate through CRAF. Sci Signal 4:ra58
150. Antonysamy S et al (2012) Crystal structure of the human PRMT5:MEP50 complex. Proc Natl
Acad Sci U S A 109:17960–17965
151. Ho M-C et al (2013) Structure of the arginine methyltransferase PRMT5-MEP50 reveals a
mechanism for substrate specificity. PLoS One 8:e57008
152. Morales Y et al (2016) Biochemistry and regulation of the protein arginine methyltransferases
(PRMTs). Arch Biochem Biophys 590:138–152
194
M. J. van Haren and N. I. Martin