Research progress of inhibitors of peptides and peptidomimetic acting on P53-MDM2 interface

LI Xiang; ZOU Yan; WU Maocheng; HUANG Ting; HU Honggang; WU Qiuye

doi:10.3969/j.issn.1006-0111.2015.06.004

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2015 > 33(6): 494-497,512

LI Xiang, ZOU Yan, WU Maocheng, HUANG Ting, HU Honggang, WU Qiuye. Research progress of inhibitors of peptides and peptidomimetic acting on P53-MDM2 interface[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(6): 494-497,512. doi: 10.3969/j.issn.1006-0111.2015.06.004

Citation:

LI Xiang, ZOU Yan, WU Maocheng, HUANG Ting, HU Honggang, WU Qiuye. Research progress of inhibitors of peptides and peptidomimetic acting on P53-MDM2 interface[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(6): 494-497,512. doi: 10.3969/j.issn.1006-0111.2015.06.004

Research progress of inhibitors of peptides and peptidomimetic acting on P53-MDM2 interface

doi: 10.3969/j.issn.1006-0111.2015.06.004

Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2013-11-25
Rev Recd Date: 2014-03-31

Abstract

Tumor diseases have attracted great attention of the society because of the increasing morbidity in recent years. To inhibit the P53-MDM2 interaction has become an important target for design of cancer drug, and a lot of peptide and small molecule inhibitors have been found with various kinds of drug screening and research tools. This paper summarized the recent progress of the peptide and peptidomimetic inhibitors of P53-MDM2 at home and abroad lately.
- P53-MDM2,
- peptide,
- inhibitor

References

[1]	Oliner JD, Kinzler KW, Meltzer PS, et al. Amplication of a gene encoding a p53-associated protein in human sarcomas[J]. Nature, 1992, 358: 80-83.
[2]	Levine AJ. P53, the cellular gate keeper for growth and division[J]. Cell, 1997, 88(3): 323-331.
[3]	Bert V, David L, Arnold JL. Surfing the p53 network[J]. Nature, 408: 307-310.
[4]	Oliner JD, Pietenpol JA, Thiagalingam S, et al. Oncoprotein MDM2 conceals the activation domain of tumour suppressor p53[J]. Nature, 1993, 362: 857-860.
[5]	Pickskey SM, Lane DP. The p53-mdm2 autoregulatory feedback loop: a paradigm for the regulation of growth control by p53[J]. BioEssays, 1993, 15: 689-690.
[6]	Raymond EM, Melanie C, Tina ND, et al. Direct inhibition of the NOTCH transcription factor complex[J]. Nature, 2009, 462(7270): 182-188.
[7]	Wu X, Bayle JH, Olson D, et al. The P53-mdm-2 autoregulatory feedback loop[J]. Genes Devel, 1993, 7(7a): 1126-1132.
[8]	Almerico AM, Tutone M, Pantano L, et al. Molecular dynamics studies on Mdm2 complexes: an analysis of the inhibitor influence[J]. Biochem Biophys Res Commun, 2012, 424(2): 341-347.
[9]	Meng W, Brigance RP, Chao HJ,et al. Discovery of 6-(aminomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxa mides as potent, selective dipeptidyl peptidase-4 (DPP4) inhibitors[J]. J Med Chem, 2010, 53(15): 5620-5628.
[10]	Vassilev LT, Vu BT, Graves B, et al. In vivo activation of the P53 pathway by small-molecule antagonists of MDM2[J]. Science, 2004, 303(5659): 844-848.
[11]	Wang B, Fang L, Zhao H, et al. MDM2 inhibitor nutlin-3a suppresses proliferation and promotes apoptosis in osteosarcoma cells[J]. Acta Biochim Biophys Sin (Shanghai), 2012, 44(8): 685-691.
[12]	Warner WA, Sanchez R, Dawoodian A, et al. Identification of FDA-approved drugs that computationally bind to MDM2[J]. Chem Biol Drug Des, 2012, 80(4): 631-637.
[13]	Zhuang C, Miao Z, Zhu L, et al. Synthesis and biological evaluation of thio-benzodiazepines as novel small molecule inhibitors of the P53-MDM2 protein-protein interaction[J]. Eur J Med Chem, 2011, 46(11): 5654-5661.
[14]	Grasberger BL, Lu T, Schubert C, et al. Discovery and cocrystalstructure of benzodiazepinedione MDM2 antagonists that activate P53 in cells. J Med Chem, 2005, 48(4): 909-912.
[15]	Mohammad RM, Wu J, Azmi AS, et al. An MDM2 antagonist (MI-319) restores p53 functions and increases the life span of orally treated follicular lymphoma bearing animals[J]. Mol Cancer, 2009, 8: 115.
[16]	Andrea GC. Protein-protein interfaces: mimics and inhibitors[J]. Curr Opin Chem Biol, 2001, 5:654-659.
[17]	Arkin MR and Wells JA. Small-molecule inhibitors of protein-protein interactions: progressing towards the dream[J]. Nat Rev Drug Discov, 2004, 3(4): 301-317.
[18]	Pazgier M, Liu M, Zou G, et al. Structural basis for high-affinity peptide inhibition of p53 interactions with MDM2 and MDMX[J]. Proc Natl Acad Sci(USA), 2009, 106(12): 4665-4670.
[19]	Chang YS, Graves B, Guerlavais V, et al. Stapled alpha-helical peptide drug development: a potent dual inhibitor of MDM2 and MDMX for p53-dependent cancer therapy[J]. Proc Natl Acad Sci USA, 2013, 110(36): E3445-E3454.
[20]	Li C, Pazgier M, Liu M, et al. Apamin as a template for structure-based rational design of potent peptide activators of p53[J]. Angew Chem Int Ed Engl, 2009, 48(46): 8712-8715.
[21]	Li C, Zhan C, Zhao L, et al. Functional consequences of retro-inverso isomerization of a miniature protein inhibitor of the p53-MDM2 interaction[J]. Bioorg Med Chem, 2013, 21(14): 4045-4050.
[22]	Hu Y, Li X, Sebti SM, et al. Design and synthesis of peptides: a new class of peptide mimics[J]. Bioorg Med Chem Lett, 2011, 21(5): 1469-1471.
[23]	Noguchi T, Oishi S, Honda K, et al. Affinity-based screening of MDM2/MDMX-p53 interaction inhibitors by chemical array: identification of novel peptidic inhibitors[J]. Bioorg Med Chem Lett, 2013, 23(13): 3802-3805.
[24]	Duncan SJ, Gruschow S, Williams DH, et al. Isolation and structure elucidation of chlorofusin, a novel P53-MDM2 antagonist from a Fusarium sp[J]. J Am Chem Soc, 2001, 123: 554-560.
[25]	Lee SY and Boger DL. Synthesis of the chlorofusin cyclic peptide[J]. Tetrahedron, 2009, 65(16): 3281-3284.
[26]	Sakurai K and Kahne D. Design and synthesis of functionalized trisaccharides as P53-peptide mimics[J]. Tetrahedron Lett, 2010, 51(29): 3724-3727.
[27]	Phan J, Li Z, Kasprzak A, et al. Structure-based design of high affinity peptides inhibiting the interaction of p53 with MDM2 and MDMX[J]. J Biol Chem, 2010, 285(3): 2174-2183.
[28]	Liu M, Pazgier M, Li C, et al. A left-handed solution to peptide inhibition of the P53-MDM2 interaction[J]. Angew Chem Int Ed Engl, 2010, 49(21): 3649-3652.
[29]	Li C, Pazgier M, Li J, et al. Limitations of peptide retro-inverso isomerization in molecular mimicry[J]. J Biol Chem, 2010, 285(25): 19572-19581.
[30]	Harker EA and Schepartz A. Cell-permeable beta-peptide inhibitors of p53/hDM2 complexation[J]. Chembiochem, 2009, 10(6): 990-993.
[31]	Hintersteiner M, Kimmerlin T, Garavel G, et al. A highly potent and cellularly active beta-peptidic inhibitor of the p53/hDM2 interaction[J]. Chembiochem, 2009, 10(6): 994-998.
[32]	Yamada S, Kanno H and Kawahara N. Trans-membrane peptide therapy for malignant glioma by use of a peptide derived from the MDM2 binding site of p53[J]. J Neurooncol, 2012, 109(1): 7-14.
[33]	Li C, Shen J, Wei X, et al. Targeted delivery of a novel palmitylated D-peptide for antiglioblastoma molecular therapy[J]. J Drug Target, 2012, 20(3): 264-271.
[34]	Jeong WJ, Lee MS and Lim YB. Helix stabilized, thermostable, and protease-resistant self-assembled peptide nanostructures as potential inhibitors of protein-protein interactions[J]. Biomacromolecules, 2013, 14(8): 2684-2689.
[35]	Muppidi A, Wang Z, Li X, et al. Achieving cell penetration with distance-matching cysteine cross-linkers: a facile route to cell-permeable peptide dual inhibitors of Mdm2/Mdmx[J]. Chem Commun (Camb), 2011, 47(33): 9396-9398.
[36]	Muppidi A, Li X, Chen J, et al. Conjugation of spermine enhances cellular uptake of the stapled peptide-based inhibitors of p53-Mdm2 interaction[J]. Bioorg Med Chem Lett, 2011, 21(24): 7412-7415.
[37]	Madden MM, Muppidi A, Li Z, et al. Synthesis of cell-permeable stapled peptide dual inhibitors of the p53-Mdm2/Mdmx interactions via photoinduced cycloaddition[J]. Bioorg Med Chem Lett, 2011, 21(5): 1472-1476.

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通讯作者: 陈斌, [email protected]

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沈阳化工大学材料科学与工程学院沈阳 110142

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Research progress of inhibitors of peptides and peptidomimetic acting on P53-MDM2 interface

Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2013-11-25

Rev Recd Date: 2014-03-31

Key words:

P53-MDM2 /
peptide /
inhibitor

Abstract: Tumor diseases have attracted great attention of the society because of the increasing morbidity in recent years. To inhibit the P53-MDM2 interaction has become an important target for design of cancer drug, and a lot of peptide and small molecule inhibitors have been found with various kinds of drug screening and research tools. This paper summarized the recent progress of the peptide and peptidomimetic inhibitors of P53-MDM2 at home and abroad lately.

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Reference (37)

[1]	Oliner JD, Kinzler KW, Meltzer PS, et al. Amplication of a gene encoding a p53-associated protein in human sarcomas[J]. Nature, 1992, 358: 80-83.
[2]	Levine AJ. P53, the cellular gate keeper for growth and division[J]. Cell, 1997, 88(3): 323-331.
[3]	Bert V, David L, Arnold JL. Surfing the p53 network[J]. Nature, 408: 307-310.
[4]	Oliner JD, Pietenpol JA, Thiagalingam S, et al. Oncoprotein MDM2 conceals the activation domain of tumour suppressor p53[J]. Nature, 1993, 362: 857-860.
[5]	Pickskey SM, Lane DP. The p53-mdm2 autoregulatory feedback loop: a paradigm for the regulation of growth control by p53[J]. BioEssays, 1993, 15: 689-690.
[6]	Raymond EM, Melanie C, Tina ND, et al. Direct inhibition of the NOTCH transcription factor complex[J]. Nature, 2009, 462(7270): 182-188.
[7]	Wu X, Bayle JH, Olson D, et al. The P53-mdm-2 autoregulatory feedback loop[J]. Genes Devel, 1993, 7(7a): 1126-1132.
[8]	Almerico AM, Tutone M, Pantano L, et al. Molecular dynamics studies on Mdm2 complexes: an analysis of the inhibitor influence[J]. Biochem Biophys Res Commun, 2012, 424(2): 341-347.
[9]	Meng W, Brigance RP, Chao HJ,et al. Discovery of 6-(aminomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxa mides as potent, selective dipeptidyl peptidase-4 (DPP4) inhibitors[J]. J Med Chem, 2010, 53(15): 5620-5628.
[10]	Vassilev LT, Vu BT, Graves B, et al. In vivo activation of the P53 pathway by small-molecule antagonists of MDM2[J]. Science, 2004, 303(5659): 844-848.
[11]	Wang B, Fang L, Zhao H, et al. MDM2 inhibitor nutlin-3a suppresses proliferation and promotes apoptosis in osteosarcoma cells[J]. Acta Biochim Biophys Sin (Shanghai), 2012, 44(8): 685-691.
[12]	Warner WA, Sanchez R, Dawoodian A, et al. Identification of FDA-approved drugs that computationally bind to MDM2[J]. Chem Biol Drug Des, 2012, 80(4): 631-637.
[13]	Zhuang C, Miao Z, Zhu L, et al. Synthesis and biological evaluation of thio-benzodiazepines as novel small molecule inhibitors of the P53-MDM2 protein-protein interaction[J]. Eur J Med Chem, 2011, 46(11): 5654-5661.
[14]	Grasberger BL, Lu T, Schubert C, et al. Discovery and cocrystalstructure of benzodiazepinedione MDM2 antagonists that activate P53 in cells. J Med Chem, 2005, 48(4): 909-912.
[15]	Mohammad RM, Wu J, Azmi AS, et al. An MDM2 antagonist (MI-319) restores p53 functions and increases the life span of orally treated follicular lymphoma bearing animals[J]. Mol Cancer, 2009, 8: 115.
[16]	Andrea GC. Protein-protein interfaces: mimics and inhibitors[J]. Curr Opin Chem Biol, 2001, 5:654-659.
[17]	Arkin MR and Wells JA. Small-molecule inhibitors of protein-protein interactions: progressing towards the dream[J]. Nat Rev Drug Discov, 2004, 3(4): 301-317.
[18]	Pazgier M, Liu M, Zou G, et al. Structural basis for high-affinity peptide inhibition of p53 interactions with MDM2 and MDMX[J]. Proc Natl Acad Sci(USA), 2009, 106(12): 4665-4670.
[19]	Chang YS, Graves B, Guerlavais V, et al. Stapled alpha-helical peptide drug development: a potent dual inhibitor of MDM2 and MDMX for p53-dependent cancer therapy[J]. Proc Natl Acad Sci USA, 2013, 110(36): E3445-E3454.
[20]	Li C, Pazgier M, Liu M, et al. Apamin as a template for structure-based rational design of potent peptide activators of p53[J]. Angew Chem Int Ed Engl, 2009, 48(46): 8712-8715.
[21]	Li C, Zhan C, Zhao L, et al. Functional consequences of retro-inverso isomerization of a miniature protein inhibitor of the p53-MDM2 interaction[J]. Bioorg Med Chem, 2013, 21(14): 4045-4050.
[22]	Hu Y, Li X, Sebti SM, et al. Design and synthesis of peptides: a new class of peptide mimics[J]. Bioorg Med Chem Lett, 2011, 21(5): 1469-1471.
[23]	Noguchi T, Oishi S, Honda K, et al. Affinity-based screening of MDM2/MDMX-p53 interaction inhibitors by chemical array: identification of novel peptidic inhibitors[J]. Bioorg Med Chem Lett, 2013, 23(13): 3802-3805.
[24]	Duncan SJ, Gruschow S, Williams DH, et al. Isolation and structure elucidation of chlorofusin, a novel P53-MDM2 antagonist from a Fusarium sp[J]. J Am Chem Soc, 2001, 123: 554-560.
[25]	Lee SY and Boger DL. Synthesis of the chlorofusin cyclic peptide[J]. Tetrahedron, 2009, 65(16): 3281-3284.
[26]	Sakurai K and Kahne D. Design and synthesis of functionalized trisaccharides as P53-peptide mimics[J]. Tetrahedron Lett, 2010, 51(29): 3724-3727.
[27]	Phan J, Li Z, Kasprzak A, et al. Structure-based design of high affinity peptides inhibiting the interaction of p53 with MDM2 and MDMX[J]. J Biol Chem, 2010, 285(3): 2174-2183.
[28]	Liu M, Pazgier M, Li C, et al. A left-handed solution to peptide inhibition of the P53-MDM2 interaction[J]. Angew Chem Int Ed Engl, 2010, 49(21): 3649-3652.
[29]	Li C, Pazgier M, Li J, et al. Limitations of peptide retro-inverso isomerization in molecular mimicry[J]. J Biol Chem, 2010, 285(25): 19572-19581.
[30]	Harker EA and Schepartz A. Cell-permeable beta-peptide inhibitors of p53/hDM2 complexation[J]. Chembiochem, 2009, 10(6): 990-993.
[31]	Hintersteiner M, Kimmerlin T, Garavel G, et al. A highly potent and cellularly active beta-peptidic inhibitor of the p53/hDM2 interaction[J]. Chembiochem, 2009, 10(6): 994-998.
[32]	Yamada S, Kanno H and Kawahara N. Trans-membrane peptide therapy for malignant glioma by use of a peptide derived from the MDM2 binding site of p53[J]. J Neurooncol, 2012, 109(1): 7-14.
[33]	Li C, Shen J, Wei X, et al. Targeted delivery of a novel palmitylated D-peptide for antiglioblastoma molecular therapy[J]. J Drug Target, 2012, 20(3): 264-271.
[34]	Jeong WJ, Lee MS and Lim YB. Helix stabilized, thermostable, and protease-resistant self-assembled peptide nanostructures as potential inhibitors of protein-protein interactions[J]. Biomacromolecules, 2013, 14(8): 2684-2689.
[35]	Muppidi A, Wang Z, Li X, et al. Achieving cell penetration with distance-matching cysteine cross-linkers: a facile route to cell-permeable peptide dual inhibitors of Mdm2/Mdmx[J]. Chem Commun (Camb), 2011, 47(33): 9396-9398.
[36]	Muppidi A, Li X, Chen J, et al. Conjugation of spermine enhances cellular uptake of the stapled peptide-based inhibitors of p53-Mdm2 interaction[J]. Bioorg Med Chem Lett, 2011, 21(24): 7412-7415.
[37]	Madden MM, Muppidi A, Li Z, et al. Synthesis of cell-permeable stapled peptide dual inhibitors of the p53-Mdm2/Mdmx interactions via photoinduced cycloaddition[J]. Bioorg Med Chem Lett, 2011, 21(5): 1472-1476.

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Research progress of inhibitors of peptides and peptidomimetic acting on P53-MDM2 interface

doi: 10.3969/j.issn.1006-0111.2015.06.004

Abstract

References

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通讯作者: 陈斌, [email protected]

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