Recent advances of tyrosyl-DNA phosdiesterase Ⅰ (TdpⅠ) inhibitors

HUANG Yahui; DONG Guoqiang; ZHANG Wannian; SHENG Chunquan

doi:10.3969/j.issn.1006-0111.2015.04.003

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2015 > 33(4): 298-302

HUANG Yahui, DONG Guoqiang, ZHANG Wannian, SHENG Chunquan. Recent advances of tyrosyl-DNA phosdiesterase Ⅰ (TdpⅠ) inhibitors[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(4): 298-302. doi: 10.3969/j.issn.1006-0111.2015.04.003

Citation:

HUANG Yahui, DONG Guoqiang, ZHANG Wannian, SHENG Chunquan. Recent advances of tyrosyl-DNA phosdiesterase Ⅰ (TdpⅠ) inhibitors[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(4): 298-302. doi: 10.3969/j.issn.1006-0111.2015.04.003

Recent advances of tyrosyl-DNA phosdiesterase Ⅰ (TdpⅠ) inhibitors

doi: 10.3969/j.issn.1006-0111.2015.04.003

School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2014-07-14
Rev Recd Date: 2014-10-27

Abstract

Tyrosyl-DNA phosphodiesterase Ⅰ (TdpⅠ) is a recently discovered proteinthat catalyzes the hydrolysis of 3'-phosphotyrosyl bonds. Such linkages form in vivo during the interaction of DNA and topoisomerase Ⅰ (TopⅠ). TdpⅠ has been regarded as a potential therapeutic co-target of TopⅠ because it has the functions of repairing TopⅠ compound and counteracting the effects of TopⅠ inhibitors. TdpⅠ inhibitors can not only synergizing with TopⅠ-targeting drugs (camptothecins), but also strength the function of bleomycin, topoisomerase Ⅱ (TopⅡ) inhibitors (etoposide, doxorubicin) and DNA alkylating agents. We summarized the researching advance of TdpⅠ inhibitors and focused on the introduction of the mechanism, bioactivity and structure-activity relationship.
- tyrosyl-DNA phosphodiesterase Ⅰ (TdpⅠ),
- topoisomerase Ⅰ (TopⅠ),
- anti-tumor inhibitors,
- structure and activity relationship

References

[1]	Wang JC. DNA topoisomerases[J]. Annu Rev Biochem, 1996, 65:635-692.
[2]	Pommier Y. Topoisomerase I inhibitors: camptothecins and beyond[J]. Nat Rev Cancer, 2006, 6(10):789-802.
[3]	Champoux JJ. DNA topoisomerases: structure, function, and mechanism[J]. Annu Rev Biochem, 2001, 70:369-413.
[4]	Pourquier P, Pommier Y. Topoisomerase I-mediated DNA damage[J]. Adv Cancer Res, 2001, 80:189-216.
[5]	Pourquier P, Pilon AA, Kohlhagen G, et al. Trapping of mammalian topoisomerase I and recombinations induced by damaged DNA containing nicks or gaps. Importance of DNA end phosphorylation and camptothecin effects[J]. J Biol Chem, 1997, 272(42):26441-26447.
[6]	Yang SW, Burgin AB,, Huizenga BN Jr, et al. A eukaryotic enzyme that can disjoin dead-end covalent complexes between DNA and type I topoisomerases[J]. Proc Natl Acad Sci U S A, 1996, 93(21):11534-11539.
[7]	Pouliot JJ, Yao KC, Robertson CA, et al. Yeast gene for a Tyr-DNA phosphodiesterase that repairs topoisomerase I complexes[J]. Science, 1999, 286(5439):552-555.
[8]	El-Khamisy SF, Saifi GM, Weinfeld M, et al. Defective DNA single-strand break repair in spinocerebellar ataxia with axonal neuropathy-1[J]. Nature, 2005, 434(7029):108-113.
[9]	Plo I, Liao ZY, Barcelo JM, et al. Association of XRCC1 and tyrosyl DNA phosphodiesterase (Tdp1) for the repair of topoisomerase I-mediated DNA lesions[J]. DNA Repair (Amst), 2003, 2(10):1087-1100.
[10]	Whitehouse CJ, Taylor RM, Thistlethwaite A, et al. XRCC1 stimulates human polynucleotide kinase activity at damaged DNA termini and accelerates DNA single-strand break repair[J]. Cell, 2001, 104(1):107-117.
[11]	Pommier Y, Redon C, Rao VA, et al. Repair of and checkpoint response to topoisomerase I-mediated DNA damage[J]. Mutat Res, 2003, 532(1-2):173-203.
[12]	Takashima H, Boerkoel CF, John J, et al. Mutation of TDP1, encoding a topoisomerase I-dependent DNA damage repair enzyme, in spinocerebellar ataxia with axonal neuropathy[J]. Nat Genet, 2002, 32(2):267-272.
[13]	El-Khamisy SF, Katyal S, Patel P, et al. Synergistic decrease of DNA single-strand break repair rates in mouse neural cells lacking both Tdp1 and aprataxin[J]. DNA Repair (Amst), 2009, 8(6):760-766.
[14]	Das BB, Antony S, Gupta S, et al. Optimal function of the DNA repair enzyme TDP1 requires its phosphorylation by ATM and/or DNA-PK[J]. EMBO J, 2009, 28(23):3667-3680.
[15]	Katyal S, el-Khamisy SF, Russell HR, et al. TDP1 facilitates chromosomal single-strand break repair in neurons and is neuroprotective in vivo[J]. EMBO J, 2007, 26(22):4720-4731.
[16]	Hirano R, Interthal H, Huang C, et al. Spinocerebellar ataxia with axonal neuropathy: consequence of a Tdp1 recessive neomorphic mutation?[J]. EMBO J, 2007, 26(22):4732-4743.
[17]	Barthelmes HU, Habermeyer M, Christensen MO, et al. TDP1 overexpression in human cells counteracts DNA damage mediated by topoisomerases I and II[J]. J Biol Chem, 2004, 279(53):55618-55625.
[18]	Nivens MC, Felder T, Galloway AH, et al. Engineered resistance to camptothecin and antifolates by retroviral coexpression of tyrosyl DNA phosphodiesterase-I and thymidylate synthase[J]. Cancer Chemother Pharmacol, 2004, 53(2):107-115.
[19]	Pommier Y, Barcelo JM, Rao VA, et al. Repair of topoisomerase I-mediated DNA damage[J]. Prog Nucleic Acid Res Mol Biol, 2006, 81:179-229.
[20]	Dexheimer TS, Antony S, Marchand C, et al. Tyrosyl-DNA phosphodiesterase as a target for anticancer therapy[J]. Anticancer Agents Med Chem, 2008, 8(4):381-389.
[21]	Liao Z, Thibaut L, Jobson A, et al. Inhibition of human tyrosyl-DNA phosphodiesterase by aminoglycoside antibiotics and ribosome inhibitors[J]. Mol Pharmacol, 2006, 70(1):366-372.
[22]	Antony S, Marchand C, Stephen AG, et al. Novel high-throughput electrochemiluminescent assay for identification of human tyrosyl-DNA phosphodiesterase (Tdp1) inhibitors and characterization of furamidine (NSC 305831) as an inhibitor of Tdp1[J]. Nucleic Acids Res, 2007, 35(13):4474-4484.
[23]	Marchand C, Lea WA, Jadhav A, et al. Identification of phosphotyrosine mimetic inhibitors of human tyrosyl-DNA phosphodiesterase I by a novel AlphaScreen high-throughput assay[J]. Mol Cancer Ther, 2009, 8(1):240-248.
[24]	Dexheimer TS, Gediya LK, Stephen AG, et al. 4-Pregnen-21-ol-3,20-dione-21-(4-bromobenzenesulfonate) (NSC 88915) and related novel steroid derivatives as tyrosyl-DNA phosphodiesterase (Tdp1) inhibitors[J]. J Med Chem, 2009, 52(22):7122-7131.
[25]	Weidlich IE, Dexheimer T, Marchand C, et al. Inhibitors of human tyrosyl-DNA phospodiesterase (hTdp1) developed by virtual screening using ligand-based pharmacophores[J]. Bioorg Med Chem, 2010, 18(1):182-189.
[26]	Takagi M, Ueda JY, Hwang JH, et al. Tyrosyl-DNA phosphodiesterase 1 inhibitor from an anamorphic fungus[J]. J Nat Prod, 2012, 75(4):764-767.
[27]	Nguyen TX, Morrell A, Conda-Sheridan M, et al. Synthesis and biological evaluation of the first dual tyrosyl-DNA phosphodiesterase I (Tdp1)-topoisomerase I (Top1) inhibitors[J]. J Med Chem, 2012, 55(9):4457-4478.
[28]	Sirivolu VR, Vernekar SK, Marchand C, et al. 5-Arylidenethioxothiazolidinones as inhibitors of tyrosyl-DNA phosphodiesterase I[J]. J Med Chem, 2012, 55(20):8671-8684.

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通讯作者: 陈斌, bchen63@163.com

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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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Recent advances of tyrosyl-DNA phosdiesterase Ⅰ (TdpⅠ) inhibitors

School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2014-07-14

Rev Recd Date: 2014-10-27

Key words:

tyrosyl-DNA phosphodiesterase Ⅰ (TdpⅠ) /
topoisomerase Ⅰ (TopⅠ) /
anti-tumor inhibitors /
structure and activity relationship

Abstract: Tyrosyl-DNA phosphodiesterase Ⅰ (TdpⅠ) is a recently discovered proteinthat catalyzes the hydrolysis of 3'-phosphotyrosyl bonds. Such linkages form in vivo during the interaction of DNA and topoisomerase Ⅰ (TopⅠ). TdpⅠ has been regarded as a potential therapeutic co-target of TopⅠ because it has the functions of repairing TopⅠ compound and counteracting the effects of TopⅠ inhibitors. TdpⅠ inhibitors can not only synergizing with TopⅠ-targeting drugs (camptothecins), but also strength the function of bleomycin, topoisomerase Ⅱ (TopⅡ) inhibitors (etoposide, doxorubicin) and DNA alkylating agents. We summarized the researching advance of TdpⅠ inhibitors and focused on the introduction of the mechanism, bioactivity and structure-activity relationship.

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Reference (28)

[1]	Wang JC. DNA topoisomerases[J]. Annu Rev Biochem, 1996, 65:635-692.
[2]	Pommier Y. Topoisomerase I inhibitors: camptothecins and beyond[J]. Nat Rev Cancer, 2006, 6(10):789-802.
[3]	Champoux JJ. DNA topoisomerases: structure, function, and mechanism[J]. Annu Rev Biochem, 2001, 70:369-413.
[4]	Pourquier P, Pommier Y. Topoisomerase I-mediated DNA damage[J]. Adv Cancer Res, 2001, 80:189-216.
[5]	Pourquier P, Pilon AA, Kohlhagen G, et al. Trapping of mammalian topoisomerase I and recombinations induced by damaged DNA containing nicks or gaps. Importance of DNA end phosphorylation and camptothecin effects[J]. J Biol Chem, 1997, 272(42):26441-26447.
[6]	Yang SW, Burgin AB,, Huizenga BN Jr, et al. A eukaryotic enzyme that can disjoin dead-end covalent complexes between DNA and type I topoisomerases[J]. Proc Natl Acad Sci U S A, 1996, 93(21):11534-11539.
[7]	Pouliot JJ, Yao KC, Robertson CA, et al. Yeast gene for a Tyr-DNA phosphodiesterase that repairs topoisomerase I complexes[J]. Science, 1999, 286(5439):552-555.
[8]	El-Khamisy SF, Saifi GM, Weinfeld M, et al. Defective DNA single-strand break repair in spinocerebellar ataxia with axonal neuropathy-1[J]. Nature, 2005, 434(7029):108-113.
[9]	Plo I, Liao ZY, Barcelo JM, et al. Association of XRCC1 and tyrosyl DNA phosphodiesterase (Tdp1) for the repair of topoisomerase I-mediated DNA lesions[J]. DNA Repair (Amst), 2003, 2(10):1087-1100.
[10]	Whitehouse CJ, Taylor RM, Thistlethwaite A, et al. XRCC1 stimulates human polynucleotide kinase activity at damaged DNA termini and accelerates DNA single-strand break repair[J]. Cell, 2001, 104(1):107-117.
[11]	Pommier Y, Redon C, Rao VA, et al. Repair of and checkpoint response to topoisomerase I-mediated DNA damage[J]. Mutat Res, 2003, 532(1-2):173-203.
[12]	Takashima H, Boerkoel CF, John J, et al. Mutation of TDP1, encoding a topoisomerase I-dependent DNA damage repair enzyme, in spinocerebellar ataxia with axonal neuropathy[J]. Nat Genet, 2002, 32(2):267-272.
[13]	El-Khamisy SF, Katyal S, Patel P, et al. Synergistic decrease of DNA single-strand break repair rates in mouse neural cells lacking both Tdp1 and aprataxin[J]. DNA Repair (Amst), 2009, 8(6):760-766.
[14]	Das BB, Antony S, Gupta S, et al. Optimal function of the DNA repair enzyme TDP1 requires its phosphorylation by ATM and/or DNA-PK[J]. EMBO J, 2009, 28(23):3667-3680.
[15]	Katyal S, el-Khamisy SF, Russell HR, et al. TDP1 facilitates chromosomal single-strand break repair in neurons and is neuroprotective in vivo[J]. EMBO J, 2007, 26(22):4720-4731.
[16]	Hirano R, Interthal H, Huang C, et al. Spinocerebellar ataxia with axonal neuropathy: consequence of a Tdp1 recessive neomorphic mutation?[J]. EMBO J, 2007, 26(22):4732-4743.
[17]	Barthelmes HU, Habermeyer M, Christensen MO, et al. TDP1 overexpression in human cells counteracts DNA damage mediated by topoisomerases I and II[J]. J Biol Chem, 2004, 279(53):55618-55625.
[18]	Nivens MC, Felder T, Galloway AH, et al. Engineered resistance to camptothecin and antifolates by retroviral coexpression of tyrosyl DNA phosphodiesterase-I and thymidylate synthase[J]. Cancer Chemother Pharmacol, 2004, 53(2):107-115.
[19]	Pommier Y, Barcelo JM, Rao VA, et al. Repair of topoisomerase I-mediated DNA damage[J]. Prog Nucleic Acid Res Mol Biol, 2006, 81:179-229.
[20]	Dexheimer TS, Antony S, Marchand C, et al. Tyrosyl-DNA phosphodiesterase as a target for anticancer therapy[J]. Anticancer Agents Med Chem, 2008, 8(4):381-389.
[21]	Liao Z, Thibaut L, Jobson A, et al. Inhibition of human tyrosyl-DNA phosphodiesterase by aminoglycoside antibiotics and ribosome inhibitors[J]. Mol Pharmacol, 2006, 70(1):366-372.
[22]	Antony S, Marchand C, Stephen AG, et al. Novel high-throughput electrochemiluminescent assay for identification of human tyrosyl-DNA phosphodiesterase (Tdp1) inhibitors and characterization of furamidine (NSC 305831) as an inhibitor of Tdp1[J]. Nucleic Acids Res, 2007, 35(13):4474-4484.
[23]	Marchand C, Lea WA, Jadhav A, et al. Identification of phosphotyrosine mimetic inhibitors of human tyrosyl-DNA phosphodiesterase I by a novel AlphaScreen high-throughput assay[J]. Mol Cancer Ther, 2009, 8(1):240-248.
[24]	Dexheimer TS, Gediya LK, Stephen AG, et al. 4-Pregnen-21-ol-3,20-dione-21-(4-bromobenzenesulfonate) (NSC 88915) and related novel steroid derivatives as tyrosyl-DNA phosphodiesterase (Tdp1) inhibitors[J]. J Med Chem, 2009, 52(22):7122-7131.
[25]	Weidlich IE, Dexheimer T, Marchand C, et al. Inhibitors of human tyrosyl-DNA phospodiesterase (hTdp1) developed by virtual screening using ligand-based pharmacophores[J]. Bioorg Med Chem, 2010, 18(1):182-189.
[26]	Takagi M, Ueda JY, Hwang JH, et al. Tyrosyl-DNA phosphodiesterase 1 inhibitor from an anamorphic fungus[J]. J Nat Prod, 2012, 75(4):764-767.
[27]	Nguyen TX, Morrell A, Conda-Sheridan M, et al. Synthesis and biological evaluation of the first dual tyrosyl-DNA phosphodiesterase I (Tdp1)-topoisomerase I (Top1) inhibitors[J]. J Med Chem, 2012, 55(9):4457-4478.
[28]	Sirivolu VR, Vernekar SK, Marchand C, et al. 5-Arylidenethioxothiazolidinones as inhibitors of tyrosyl-DNA phosphodiesterase I[J]. J Med Chem, 2012, 55(20):8671-8684.

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Recent advances of tyrosyl-DNA phosdiesterase Ⅰ (TdpⅠ) inhibitors

doi: 10.3969/j.issn.1006-0111.2015.04.003

Abstract

References

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通讯作者: 陈斌, bchen63@163.com

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