Research progress on tumor-targeting paclitaxel prodrugs

CHENG Dan; XU Youfa; FU Zhiqin; CHEN Jianming

doi:10.3969/j.issn.1006-0111.2018.01.001

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Volume 36 Issue 1

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2018 > 36(1): 1-8

CHENG Dan, XU Youfa, FU Zhiqin, CHEN Jianming. Research progress on tumor-targeting paclitaxel prodrugs[J]. Journal of Pharmaceutical Practice and Service, 2018, 36(1): 1-8. doi: 10.3969/j.issn.1006-0111.2018.01.001

Citation:

CHENG Dan, XU Youfa, FU Zhiqin, CHEN Jianming. Research progress on tumor-targeting paclitaxel prodrugs[J]. Journal of Pharmaceutical Practice and Service, 2018, 36(1): 1-8. doi: 10.3969/j.issn.1006-0111.2018.01.001

Research progress on tumor-targeting paclitaxel prodrugs

doi: 10.3969/j.issn.1006-0111.2018.01.001

1.
School of Pharmacy, Second Military Medical University, Shanghai 200433, China
2.
School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122, China
3.
School of Pharmacy, Second Military Medical University, Shanghai 200433, China;School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122, China;Tasly Group Co. Ltd., Tianjin 300402, China

Received Date: 2017-09-13
Rev Recd Date: 2017-10-17

Abstract

Paclitaxel is a natural compound with efficient broad-spectrum antitumor activity. However, the clinical application has been limited owing to the undesirable drawbacks, such as the poor water-solubility, cardiovascular toxicity and neurotoxicity. The design of paclitaxel prodrugs is an effective measure which can improve the drug's druggability, alleviate its toxicity adverse effect and enhance its antitumor effect. With the in-depth research of prodrugs, tumor-targeting paclitaxel prodrugs which using the excessive receptors, specific enzymes, transporters, reactive oxide species, glutathione in tumor tissues as well as acidosis and hypoxia in tumors as specific targets, have made great progress. The relevant literature about paclitaxel prodrugs were reviewed in this paper, which targeted to the specific pathological and physiological features of tumor microenvironment in recent years.
- paclitaxel prodrug,
- tumor microenvironment,
- targeting,
- antitumor

References

[1]	Wani M C, Taylor H L, Wall M E, et al. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia.[J]. J Amer Chem Soc, 1971, 93(9):2325-2327.
[2]	Yusuf RZ, Duan Z, Lamendola DE, et al. Paclitaxel resistance:molecular mechanisms and pharmacologic manipulation[J]. Curr Cancer Drug Targets, 2003,3(1):1-19.
[3]	Scripture CD, Figg WD, Sparreboom A. Paclitaxel chemotherapy:from empiricism to a mechanism-based formulation strategy[J]. Ther Clin Risk Manag, 2005,1(2):107-114.
[4]	Wang Y, Li X, Wang L, et al. Formulation and pharmacokinetic evaluation of a paclitaxel nanosuspension for intravenous delivery[J]. Int J Nanomed, 2011,6:1497-1507.
[5]	Webster L, Linsenmeyer M, Millward M, et al. Measurement of cremophor EL following taxol:plasma levels sufficient to reverse drug exclusion mediated by the multidrug-resistant phenotype[J]. JNCI, 1993, 85(20):1685-1690.
[6]	Chervinsky DS, Brecher ML, Hoelcle MJ. Cremophor-EL enhances taxol efficacy in a multi-drug resistant C1300 neuroblastoma cell line[J]. Anticancer Res, 1993, 13(1):93-96.
[7]	张珏, 吕加国, 朱驹. 抗肿瘤药物紫杉醇的化学研究进展[J]. 中国新药杂志, 2006,15(3):178-181.
[8]	Meerum Terwogt JM, ten Bokkel Huinink WW, Schellens JH, et al. Phase I clinical and pharmacokinetic study of PNU166945, a novel water-soluble polymer-conjugated prodrug of paclitaxel.[J]. Anticancer Drugs, 2001,12(4):315-323.
[9]	Tr dan O, Galmarini CM, Patel K, et al. Drug Resistance and the Solid Tumor Microenvironment[J]. JNCI, 2007,99(19):1441-1454.
[10]	Misra S, Hascall VC, Markwald RR, et al. Interactions between Hyaluronan and Its Receptors (CD44, RHAMM) Regulate the Activities of Inflammation and Cancer[J]. Front Immunol, 2015,6:201.
[11]	Shahbaz M, Ruliang F, Xu Z, et al. mRNA expression of somatostatin receptor subtypes SSTR-2, SSTR-3, and SSTR-5 and its significance in pancreatic cancer[J]. World J Surg Oncol, 2015,13:46.
[12]	Barar J, Kafil V, Majd MH, et al. Multifunctional mitoxantrone-conjugated magnetic nanosystem for targeted therapy of folate receptor-overexpressing malignant cells[J]. J Nanobiotechnol, 2015,13:26.
[13]	Huo M, Zhu Q, Wu Q, et al. Somatostatin receptor-mediated specific delivery of paclitaxel prodrugs for efficient cancer therapy[J]. J Pharm Sci-US, 2015, 104(6):2018-2028.
[14]	Zhong Y, Goltsche K, Cheng L, et al. Hyaluronic acid-shelled acid-activatable paclitaxel prodrug micelles effectively target and treat CD44-overexpressing human breast tumor xenografts in vivo[J]. Biomaterials, 2016, 84:250-261.
[15]	Alaoui AE, Saha N, Schmidt F, et al. New Taxol(paclitaxel) prodrugs designed for ADEPT and PMT strategies in cancer chemotherapy[J]. Bioorg Med Chem, 2006, 14(14):5012-5019.
[16]	Satsangi A, Roy SS, Satsangi RK, et al. Design of a paclitaxel prodrug conjugate for active targeting of an enzyme upregulated in breast cancer cells[J]. Mol Pharm, 2014, 11(6):1906-1918.
[17]	Li N, Cai H, Jiang L, et al. Enzyme-Sensitive and Amphiphilic PEGylated Dendrimer-Paclitaxel Prodrug Based Nanoparticles for Enhanced Stability and Anticancer Efficacy[J]. ACS Appl Mater Interfaces, 2017,9(8),6865-6877.
[18]	樊健, 俞光荣. 葡萄糖转运蛋白1与恶性肿瘤相关性的研究进展[J]. 中国肿瘤生物治疗杂志, 2010,17(2):232-236.
[19]	Liu DZ, Sinchaikul S, Reddy PV, et al. Synthesis of 2'-paclitaxel methyl 2-glucopyranosyl succinate for specific targeted delivery to cancer cells[J]. Bioorg Med Chem Lett, 2007, 17(3):617-620.
[20]	常彬霞, 貌盼勇. 谷胱甘肽S转移酶的研究进展及其与肿瘤的相关性[J]. 解放军医学杂志, 2012,37(8):838-842.
[21]	Ushio-Fukai M, Nakamura Y. Reactive oxygen species and angiogenesis:NADPH oxidase as target for cancer therapy[J]. Cancer Lett, 2008,266(1):37-52.
[22]	Jiang Y,Wang X,Liu X, et al. Enhanced antiglioma efficacy of ultrahigh loading capacity paclitaxel prodrug conjugate self-assembled targeted nanoparticles[J]. ACS Appl Mater Interfaces, 2017, 9(1):211-217.
[23]	Luo C, Sun J, Liu D, et al. Self-Assembled Redox Dual-Responsive Prodrug-Nanosystem Formed by Single Thioether-Bridged Paclitaxel-Fatty Acid Conjugate for Cancer Chemotherapy[J]. Nano Lett, 2016, 16(9):5401-5408.
[24]	Yang LV, Castellone RD, Dong L. Targeting Tumor Microenvironments for Cancer Prevention and Therapy[M]. InTech, 2012:1811-1814.
[25]	Ling L, Du Y, Ismail M, et al. Self-assembled liposomes of dual paclitaxel-phospholipid prodrug for anticancer therapy[J]. Int J Pharm, 2017, 526(1-2):11-22.
[26]	杜征臻, 张琰, 叶金海,等. 聚己内酯-紫杉醇高分子前药的合成及性能研究[J]. 化学学报, 2015, 73(4):349-356.
[27]	Chen L, Endler A, Shibasaki F. Hypoxia and angiogenesis:regulation of hypoxia-inducible factors via novel binding factors.[J]. Experimental & Molecular Medicine, 2009, 41(12):849-857.
[28]	Damen EW, Nevalainen TJ, van den Bergh TJ, et al. Synthesis of novel paclitaxel prodrugs designed for bioreductive activation in hypoxic tumour tissue[J]. Bioorg Med Chem, 2002, 10(1):71-77.
[29]	Wang J, Luo T, Li S, et al. The powerful applications of polyunsaturated fatty acids in improving the therapeutic efficacy of anticancer drugs[J]. Expert Opin Drug Deliv, 2012,9(1):1-7.
[30]	Kuznetsova L, Chen J, Sun L, et al. Syntheses and evaluation of novel fatty acid-second-generation taxoid conjugates as promising anticancer agents[J]. Bioorg Med Chem Lett, 2006,16(4):974-977.
[31]	Bouvier E, Thirot S, Schmidt F, et al. A new paclitaxel prodrug for use in ADEPT strategy[J]. Org Biomol Chem,2003,1(19):3343-3352.
[32]	Nawa A, Tanino T, Luo C, et al. Gene directed enzyme prodrug therapy for ovarian cancer:could GDEPT become a promising treatment against ovarian cancer?[J]. Anticancer Agents Med Chem, 2008, 8(2):232-239.

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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Research progress on tumor-targeting paclitaxel prodrugs

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

2. School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122, China

3. School of Pharmacy, Second Military Medical University, Shanghai 200433, China;School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122, China;Tasly Group Co. Ltd., Tianjin 300402, China

Received Date: 2017-09-13

Rev Recd Date: 2017-10-17

Key words:

Abstract: Paclitaxel is a natural compound with efficient broad-spectrum antitumor activity. However, the clinical application has been limited owing to the undesirable drawbacks, such as the poor water-solubility, cardiovascular toxicity and neurotoxicity. The design of paclitaxel prodrugs is an effective measure which can improve the drug's druggability, alleviate its toxicity adverse effect and enhance its antitumor effect. With the in-depth research of prodrugs, tumor-targeting paclitaxel prodrugs which using the excessive receptors, specific enzymes, transporters, reactive oxide species, glutathione in tumor tissues as well as acidosis and hypoxia in tumors as specific targets, have made great progress. The relevant literature about paclitaxel prodrugs were reviewed in this paper, which targeted to the specific pathological and physiological features of tumor microenvironment in recent years.

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Reference (32)

[1]	Wani M C, Taylor H L, Wall M E, et al. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia.[J]. J Amer Chem Soc, 1971, 93(9):2325-2327.
[2]	Yusuf RZ, Duan Z, Lamendola DE, et al. Paclitaxel resistance:molecular mechanisms and pharmacologic manipulation[J]. Curr Cancer Drug Targets, 2003,3(1):1-19.
[3]	Scripture CD, Figg WD, Sparreboom A. Paclitaxel chemotherapy:from empiricism to a mechanism-based formulation strategy[J]. Ther Clin Risk Manag, 2005,1(2):107-114.
[4]	Wang Y, Li X, Wang L, et al. Formulation and pharmacokinetic evaluation of a paclitaxel nanosuspension for intravenous delivery[J]. Int J Nanomed, 2011,6:1497-1507.
[5]	Webster L, Linsenmeyer M, Millward M, et al. Measurement of cremophor EL following taxol:plasma levels sufficient to reverse drug exclusion mediated by the multidrug-resistant phenotype[J]. JNCI, 1993, 85(20):1685-1690.
[6]	Chervinsky DS, Brecher ML, Hoelcle MJ. Cremophor-EL enhances taxol efficacy in a multi-drug resistant C1300 neuroblastoma cell line[J]. Anticancer Res, 1993, 13(1):93-96.
[7]	张珏, 吕加国, 朱驹. 抗肿瘤药物紫杉醇的化学研究进展[J]. 中国新药杂志, 2006,15(3):178-181.
[8]	Meerum Terwogt JM, ten Bokkel Huinink WW, Schellens JH, et al. Phase I clinical and pharmacokinetic study of PNU166945, a novel water-soluble polymer-conjugated prodrug of paclitaxel.[J]. Anticancer Drugs, 2001,12(4):315-323.
[9]	Tr dan O, Galmarini CM, Patel K, et al. Drug Resistance and the Solid Tumor Microenvironment[J]. JNCI, 2007,99(19):1441-1454.
[10]	Misra S, Hascall VC, Markwald RR, et al. Interactions between Hyaluronan and Its Receptors (CD44, RHAMM) Regulate the Activities of Inflammation and Cancer[J]. Front Immunol, 2015,6:201.
[11]	Shahbaz M, Ruliang F, Xu Z, et al. mRNA expression of somatostatin receptor subtypes SSTR-2, SSTR-3, and SSTR-5 and its significance in pancreatic cancer[J]. World J Surg Oncol, 2015,13:46.
[12]	Barar J, Kafil V, Majd MH, et al. Multifunctional mitoxantrone-conjugated magnetic nanosystem for targeted therapy of folate receptor-overexpressing malignant cells[J]. J Nanobiotechnol, 2015,13:26.
[13]	Huo M, Zhu Q, Wu Q, et al. Somatostatin receptor-mediated specific delivery of paclitaxel prodrugs for efficient cancer therapy[J]. J Pharm Sci-US, 2015, 104(6):2018-2028.
[14]	Zhong Y, Goltsche K, Cheng L, et al. Hyaluronic acid-shelled acid-activatable paclitaxel prodrug micelles effectively target and treat CD44-overexpressing human breast tumor xenografts in vivo[J]. Biomaterials, 2016, 84:250-261.
[15]	Alaoui AE, Saha N, Schmidt F, et al. New Taxol(paclitaxel) prodrugs designed for ADEPT and PMT strategies in cancer chemotherapy[J]. Bioorg Med Chem, 2006, 14(14):5012-5019.
[16]	Satsangi A, Roy SS, Satsangi RK, et al. Design of a paclitaxel prodrug conjugate for active targeting of an enzyme upregulated in breast cancer cells[J]. Mol Pharm, 2014, 11(6):1906-1918.
[17]	Li N, Cai H, Jiang L, et al. Enzyme-Sensitive and Amphiphilic PEGylated Dendrimer-Paclitaxel Prodrug Based Nanoparticles for Enhanced Stability and Anticancer Efficacy[J]. ACS Appl Mater Interfaces, 2017,9(8),6865-6877.
[18]	樊健, 俞光荣. 葡萄糖转运蛋白1与恶性肿瘤相关性的研究进展[J]. 中国肿瘤生物治疗杂志, 2010,17(2):232-236.
[19]	Liu DZ, Sinchaikul S, Reddy PV, et al. Synthesis of 2'-paclitaxel methyl 2-glucopyranosyl succinate for specific targeted delivery to cancer cells[J]. Bioorg Med Chem Lett, 2007, 17(3):617-620.
[20]	常彬霞, 貌盼勇. 谷胱甘肽S转移酶的研究进展及其与肿瘤的相关性[J]. 解放军医学杂志, 2012,37(8):838-842.
[21]	Ushio-Fukai M, Nakamura Y. Reactive oxygen species and angiogenesis:NADPH oxidase as target for cancer therapy[J]. Cancer Lett, 2008,266(1):37-52.
[22]	Jiang Y,Wang X,Liu X, et al. Enhanced antiglioma efficacy of ultrahigh loading capacity paclitaxel prodrug conjugate self-assembled targeted nanoparticles[J]. ACS Appl Mater Interfaces, 2017, 9(1):211-217.
[23]	Luo C, Sun J, Liu D, et al. Self-Assembled Redox Dual-Responsive Prodrug-Nanosystem Formed by Single Thioether-Bridged Paclitaxel-Fatty Acid Conjugate for Cancer Chemotherapy[J]. Nano Lett, 2016, 16(9):5401-5408.
[24]	Yang LV, Castellone RD, Dong L. Targeting Tumor Microenvironments for Cancer Prevention and Therapy[M]. InTech, 2012:1811-1814.
[25]	Ling L, Du Y, Ismail M, et al. Self-assembled liposomes of dual paclitaxel-phospholipid prodrug for anticancer therapy[J]. Int J Pharm, 2017, 526(1-2):11-22.
[26]	杜征臻, 张琰, 叶金海,等. 聚己内酯-紫杉醇高分子前药的合成及性能研究[J]. 化学学报, 2015, 73(4):349-356.
[27]	Chen L, Endler A, Shibasaki F. Hypoxia and angiogenesis:regulation of hypoxia-inducible factors via novel binding factors.[J]. Experimental & Molecular Medicine, 2009, 41(12):849-857.
[28]	Damen EW, Nevalainen TJ, van den Bergh TJ, et al. Synthesis of novel paclitaxel prodrugs designed for bioreductive activation in hypoxic tumour tissue[J]. Bioorg Med Chem, 2002, 10(1):71-77.
[29]	Wang J, Luo T, Li S, et al. The powerful applications of polyunsaturated fatty acids in improving the therapeutic efficacy of anticancer drugs[J]. Expert Opin Drug Deliv, 2012,9(1):1-7.
[30]	Kuznetsova L, Chen J, Sun L, et al. Syntheses and evaluation of novel fatty acid-second-generation taxoid conjugates as promising anticancer agents[J]. Bioorg Med Chem Lett, 2006,16(4):974-977.
[31]	Bouvier E, Thirot S, Schmidt F, et al. A new paclitaxel prodrug for use in ADEPT strategy[J]. Org Biomol Chem,2003,1(19):3343-3352.
[32]	Nawa A, Tanino T, Luo C, et al. Gene directed enzyme prodrug therapy for ovarian cancer:could GDEPT become a promising treatment against ovarian cancer?[J]. Anticancer Agents Med Chem, 2008, 8(2):232-239.

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Research progress on tumor-targeting paclitaxel prodrugs

doi: 10.3969/j.issn.1006-0111.2018.01.001

Abstract

References

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通讯作者: 陈斌, bchen63@163.com

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