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Volumn 13, Issue 10, 2008, Pages 2370-2384

Radiation- and photo-induced activation of 5-fluorouracil prodrugs as a strategy for the selective treatment of solid tumors

Author keywords

5 Fluorouracil; Hydrated electrons; Hypoxia; Photolysis; Prodrugs; Radiolysis

Indexed keywords

FLUOROURACIL; PRODRUG;

EID: 55249084962     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13102370     Document Type: Review
Times cited : (31)

References (65)
  • 1
    • 0021970675 scopus 로고
    • Radiation-therapy alone or in combination with chemotherapy in the treatment of residual or inoperable carcinoma of the rectum and rectosigmoid or pelvic recurrence following colorectal surgery - Radiation-therapy oncology group-study
    • Rominger, C.J.; Gelber, R.D.; Gunderson, L.L; Conner, N. Radiation-therapy alone or in combination with chemotherapy in the treatment of residual or inoperable carcinoma of the rectum and rectosigmoid or pelvic recurrence following colorectal surgery - Radiation-therapy oncology group-study. Am. J. Clin. Oncol. 1985, 8, 118-127.
    • (1985) Am. J. Clin. Oncol , vol.8 , pp. 118-127
    • Rominger, C.J.1    Gelber, R.D.2    Gunderson, L.L.3    Conner, N.4
  • 3
    • 0029051690 scopus 로고
    • Thymidine phosphorylase mediates the sensitivity of human colon-carcinoma cells to 5-fluorouracil
    • Schwartz, E.L.; Baptiste, N.; Wadler, S.; Makower, D. Thymidine phosphorylase mediates the sensitivity of human colon-carcinoma cells to 5-fluorouracil. J. Biol. Chem. 1995, 270, 19073-19077.
    • (1995) J. Biol. Chem , vol.270 , pp. 19073-19077
    • Schwartz, E.L.1    Baptiste, N.2    Wadler, S.3    Makower, D.4
  • 4
    • 0344267645 scopus 로고    scopus 로고
    • Enhancement of 5-fluorouracil cytotoxicity by human thymidine-phosphorylase expression in cancer cells: In vitro and in vivo study
    • Evrard, A.; Cuq, P.; Robert, B.; Vian, L.; Pelegrin, A.; Cano, J.P. Enhancement of 5-fluorouracil cytotoxicity by human thymidine-phosphorylase expression in cancer cells: In vitro and in vivo study. Int. J. Cancer 1999, 80, 465-470.
    • (1999) Int. J. Cancer , vol.80 , pp. 465-470
    • Evrard, A.1    Cuq, P.2    Robert, B.3    Vian, L.4    Pelegrin, A.5    Cano, J.P.6
  • 5
    • 0000875305 scopus 로고
    • Studies on fluorinated pyrimidines. 13. Inhibition of thymidylate synthetase
    • Hartmann, K.U.; Heidelberger, C. Studies on fluorinated pyrimidines. 13. Inhibition of thymidylate synthetase. J. Biol. Chem. 1961, 236, 3006-3013.
    • (1961) J. Biol. Chem , vol.236 , pp. 3006-3013
    • Hartmann, K.U.1    Heidelberger, C.2
  • 7
    • 0032080712 scopus 로고    scopus 로고
    • High expression of thymidylate synthase is associated with the drug resistance of gastric carcinoma to high dose 5-fluorouracil-based systemic chemotherapy
    • Yeh, K.H.; Shun, C.T.; Chen, C.L.; Lin, J.T.; Lee, W.J.; Lee, P.H.; Chen, Y.C.; Cheng, A.L. High expression of thymidylate synthase is associated with the drug resistance of gastric carcinoma to high dose 5-fluorouracil-based systemic chemotherapy. Cancer 1998, 82, 1626-1631.
    • (1998) Cancer , vol.82 , pp. 1626-1631
    • Yeh, K.H.1    Shun, C.T.2    Chen, C.L.3    Lin, J.T.4    Lee, W.J.5    Lee, P.H.6    Chen, Y.C.7    Cheng, A.L.8
  • 8
    • 0001199533 scopus 로고
    • Chemical aspects of selective toxicity
    • Albert, A. Chemical aspects of selective toxicity. Nature 1958, 182, 421-423.
    • (1958) Nature , vol.182 , pp. 421-423
    • Albert, A.1
  • 9
    • 0019276096 scopus 로고
    • Prodrugs and site-specific drug delivery
    • Stella, V.J.; Himmelstein, K.J. Prodrugs and site-specific drug delivery. J. Med. Chem. 1980, 23, 1275-1282.
    • (1980) J. Med. Chem , vol.23 , pp. 1275-1282
    • Stella, V.J.1    Himmelstein, K.J.2
  • 10
  • 13
    • 0018179513 scopus 로고
    • Studies on anti-tumor agents .2. Syntheses and anti-tumor activities of 1-(tetrahydro-2-furanyl)-5-fluorouracil and 1,3-bis(tetrahydro-2-furanyl)-5- fluorouracil
    • Yasumoto, M.; Yamawaki, I.; Marunaka, T.; Hashimoto, S. Studies on anti-tumor agents .2. Syntheses and anti-tumor activities of 1-(tetrahydro-2-furanyl)-5-fluorouracil and 1,3-bis(tetrahydro-2-furanyl)-5- fluorouracil. J. Med. Chem. 1978, 21, 738-741.
    • (1978) J. Med. Chem , vol.21 , pp. 738-741
    • Yasumoto, M.1    Yamawaki, I.2    Marunaka, T.3    Hashimoto, S.4
  • 14
    • 0018918947 scopus 로고
    • Structure of two hydroxylated metabolites of ftorafur
    • Meyer, R.B.; Levenson, C.H. Structure of two hydroxylated metabolites of ftorafur. Biochem. Pharmacol. 1980, 29, 665-668.
    • (1980) Biochem. Pharmacol , vol.29 , pp. 665-668
    • Meyer, R.B.1    Levenson, C.H.2
  • 15
    • 0019477355 scopus 로고
    • The pharmacology of ftorafur (R, S-1-(tetrahydro-2- furanyl)-5-fluorouracil)
    • Au, J.L.; Sadee, W. The pharmacology of ftorafur (R, S-1-(tetrahydro-2- furanyl)-5-fluorouracil). Recent Results Cancer Res. 1981, 76, 100-114.
    • (1981) Recent Results Cancer Res , vol.76 , pp. 100-114
    • Au, J.L.1    Sadee, W.2
  • 16
    • 0018235648 scopus 로고
    • Anti-tumor activity of 1-alkylcarbamoyl derivatives of 5-fluorouracil in a variety of mouse tumors
    • Iigo, M.; Hoshi, A.; Nakamura, A.; Kuretani, K. Anti-tumor activity of 1-alkylcarbamoyl derivatives of 5-fluorouracil in a variety of mouse tumors. Cancer Chemother. Pharmacol. 1978, 1, 203-208.
    • (1978) Cancer Chemother. Pharmacol , vol.1 , pp. 203-208
    • Iigo, M.1    Hoshi, A.2    Nakamura, A.3    Kuretani, K.4
  • 17
    • 0025233669 scopus 로고
    • Transdermal delivery of 5-fluorouracil and its alkylcarbamoyl derivatives
    • Sasaki, H.; Takahashi, T.; Mori, Y. Nakamura, J.; Shibasaki, J. Transdermal delivery of 5-fluorouracil and its alkylcarbamoyl derivatives. Int. J. Pharm. 1990, 60, 1-9.
    • (1990) Int. J. Pharm , vol.60 , pp. 1-9
    • Sasaki, H.1    Takahashi, T.2    Mori, Y.3    Nakamura, J.4    Shibasaki, J.5
  • 18
    • 0033770342 scopus 로고    scopus 로고
    • 5-Fluorouracil: Forty-plus and still ticking. A review of its preclinical and clinical development
    • Grem, J.L. 5-Fluorouracil: forty-plus and still ticking. A review of its preclinical and clinical development. Invest. New Drugs 2000, 18, 299-313.
    • (2000) Invest. New Drugs , vol.18 , pp. 299-313
    • Grem, J.L.1
  • 19
    • 0032006318 scopus 로고    scopus 로고
    • Comparison of 5-fluoro-2′-deoxyuridine with 5-fluorouracil and their role in the treatment of colorectal cancer
    • van Laar, J.A.M.; Rustum, Y.M.; Ackland, S.P.; van Groeningen, C.J.; Peters, G.J. Comparison of 5-fluoro-2′-deoxyuridine with 5-fluorouracil and their role in the treatment of colorectal cancer. Eur. J. Cancer 1998, 34, 296-306.
    • (1998) Eur. J. Cancer , vol.34 , pp. 296-306
    • van Laar, J.A.M.1    Rustum, Y.M.2    Ackland, S.P.3    van Groeningen, C.J.4    Peters, G.J.5
  • 20
    • 0023785929 scopus 로고
    • Subcutaneous polymeric matrix system p(hema-bga) for controlled release of an anticancer drug (5-fluorouracil). 2. Release kinetics
    • Denizli, A.; Kiremitci, M.; Piskin, E. Subcutaneous polymeric matrix system p(hema-bga) for controlled release of an anticancer drug (5-fluorouracil). 2. Release kinetics. Biomaterials 1988, 9, 363-366.
    • (1988) Biomaterials , vol.9 , pp. 363-366
    • Denizli, A.1    Kiremitci, M.2    Piskin, E.3
  • 21
    • 0025981613 scopus 로고
    • Controlled release of 5-fluoro-2′-deoxyuridine by the combination of prodrug and polymer matrix
    • Endoh, H.; Kawaguchi, T.; Seki, T.; Hasegawa, T.; Juni, K. Controlled release of 5-fluoro-2′-deoxyuridine by the combination of prodrug and polymer matrix. Chem. Pharm. Bull. 1991, 39, 458-464.
    • (1991) Chem. Pharm. Bull , vol.39 , pp. 458-464
    • Endoh, H.1    Kawaguchi, T.2    Seki, T.3    Hasegawa, T.4    Juni, K.5
  • 22
    • 0033321793 scopus 로고    scopus 로고
    • Controlled release behavior of prodrugs based on the biodegradable poly(L-glutamic acid) microspheres
    • Kim, K.S.; Kim, T.K.; Graham, N.B. Controlled release behavior of prodrugs based on the biodegradable poly(L-glutamic acid) microspheres. Polym. J. 1999, 31, 813-816.
    • (1999) Polym. J , vol.31 , pp. 813-816
    • Kim, K.S.1    Kim, T.K.2    Graham, N.B.3
  • 24
    • 35848952531 scopus 로고    scopus 로고
    • Design, construction, and in vitro analysis of A33scFv::CDy, a recombinant fusion protein for antibody-directed enzyme prodrug therapy in colon cancer
    • Coelho, V.; Dernedde, J.; Petrausch, U.; Panjideh, H.; Fuchs, H.; Menzel, C.; Dubel, S.; Keilholz, U.; Thiel, E.; Deckert, P.M. Design, construction, and in vitro analysis of A33scFv::CDy, a recombinant fusion protein for antibody-directed enzyme prodrug therapy in colon cancer. Int. J. Oncol. 2007, 31, 951-957.
    • (2007) Int. J. Oncol , vol.31 , pp. 951-957
    • Coelho, V.1    Dernedde, J.2    Petrausch, U.3    Panjideh, H.4    Fuchs, H.5    Menzel, C.6    Dubel, S.7    Keilholz, U.8    Thiel, E.9    Deckert, P.M.10
  • 25
    • 0000819461 scopus 로고    scopus 로고
    • Synthesis of self-immolative glucuronide spacers based on aminomethylcarbamate. Application to 5-fluorouracil prodrugs for antibody-directed enzyme prodrug therapy
    • Madec-Lougerstay, R.; Florent, J.C.; Monneret, C. Synthesis of self-immolative glucuronide spacers based on aminomethylcarbamate. Application to 5-fluorouracil prodrugs for antibody-directed enzyme prodrug therapy. J. Chem. Soc. Perkin Trans. 1 1999, 1369-1375.
    • (1999) J. Chem. Soc. Perkin Trans. 1 , pp. 1369-1375
    • Madec-Lougerstay, R.1    Florent, J.C.2    Monneret, C.3
  • 26
    • 0031833651 scopus 로고    scopus 로고
    • Selective expression of carcinoembryonic antigen promoter in cancer cell lines- Targeting strategy for gene therapy in colorectal cancer
    • Fichera, A.; Michelassi, F.; Arenas, R.B. Selective expression of carcinoembryonic antigen promoter in cancer cell lines- Targeting strategy for gene therapy in colorectal cancer. Dis. Colon Rectum. 1998, 41, 747-754.
    • (1998) Dis. Colon Rectum , vol.41 , pp. 747-754
    • Fichera, A.1    Michelassi, F.2    Arenas, R.B.3
  • 28
    • 0031941292 scopus 로고    scopus 로고
    • Regional 'pro-drug' gene therapy: Intravenous administration of an adenoviral Vector expressing the E-coli cytosine deaminase gene and systemic administration of 5-fluorocytosine suppresses growth of hepatic metastasis of colon carcinoma
    • Topf, N.; Worgall, S.; Hackett, N.R. Regional 'pro-drug' gene therapy: intravenous administration of an adenoviral Vector expressing the E-coli cytosine deaminase gene and systemic administration of 5-fluorocytosine suppresses growth of hepatic metastasis of colon carcinoma. Gene Ther. 1998, 5, 507-513.
    • (1998) Gene Ther , vol.5 , pp. 507-513
    • Topf, N.1    Worgall, S.2    Hackett, N.R.3
  • 29
    • 0038685423 scopus 로고    scopus 로고
    • Prodrugs for gene-directed enzyme-prodrug therapy (suicide gene therapy)
    • Denny, W.A. Prodrugs for gene-directed enzyme-prodrug therapy (suicide gene therapy). J. Biomed. Biotechnol. 2003, 48-70.
    • (2003) J. Biomed. Biotechnol , pp. 48-70
    • Denny, W.A.1
  • 30
    • 0035815157 scopus 로고    scopus 로고
    • N(1)-C(5′)-linked dimer hydrates of 5-substituted uracils produced by anodic oxidation in aqueous solution
    • Hatta, H.; Zhou, L.; Mori, M.; Teshima, S.; Nishimoto, S. N(1)-C(5′)-linked dimer hydrates of 5-substituted uracils produced by anodic oxidation in aqueous solution. J. Org. Chem. 2001, 66, 2232-2239.
    • (2001) J. Org. Chem , vol.66 , pp. 2232-2239
    • Hatta, H.1    Zhou, L.2    Mori, M.3    Teshima, S.4    Nishimoto, S.5
  • 31
    • 0026718848 scopus 로고
    • 1-(5′-Fluoro- 6′-hydroxy-5′,6′-dihydrouracil-5′-yl)-5-fluorouracil, a novel N(1)-C(5′)-linked dimer that releases 5-fluorouracil by radiation activation under hypoxic conditions
    • Nishimoto, S.; Hatta, H.; Ueshima, H.; Kagiya, T. 1-(5′-Fluoro- 6′-hydroxy-5′,6′-dihydrouracil-5′-yl)-5-fluorouracil, a novel N(1)-C(5′)-linked dimer that releases 5-fluorouracil by radiation activation under hypoxic conditions. J. Med. Chem. 1992, 35, 2711-2712.
    • (1992) J. Med. Chem , vol.35 , pp. 2711-2712
    • Nishimoto, S.1    Hatta, H.2    Ueshima, H.3    Kagiya, T.4
  • 32
    • 0024408986 scopus 로고
    • Blood-flow, oxygen and nutrient supply, and metabolic microenvironment of human-tumors- A review
    • Vaupel, P.; Kallinowski, F.; Okunieff, P. Blood-flow, oxygen and nutrient supply, and metabolic microenvironment of human-tumors- A review. Cancer Res.1986, 49, 6449-6465.
    • (1986) Cancer Res , vol.49 , pp. 6449-6465
    • Vaupel, P.1    Kallinowski, F.2    Okunieff, P.3
  • 34
    • 6344282432 scopus 로고    scopus 로고
    • The design of drugs that target tumour hypoxia
    • Denny, W.A. The design of drugs that target tumour hypoxia. Aust. J. Chem. 2004, 57, 821-828.
    • (2004) Aust. J. Chem , vol.57 , pp. 821-828
    • Denny, W.A.1
  • 35
    • 34249930470 scopus 로고    scopus 로고
    • Targeting cytochrome P450 enzymes: A new approach in anti-cancer drug development
    • Bruno, R.D.; Njar, V.C.O. Targeting cytochrome P450 enzymes: A new approach in anti-cancer drug development. Bioorg. Med. Chem. 2007, 15, 5047-5060.
    • (2007) Bioorg. Med. Chem , vol.15 , pp. 5047-5060
    • Bruno, R.D.1    Njar, V.C.O.2
  • 36
    • 21244461192 scopus 로고    scopus 로고
    • Hypoxia-activated anticancer drugs
    • Denny, W.A. Hypoxia-activated anticancer drugs. Expert Opin. Ther. Pat. 2005, 15, 635-646.
    • (2005) Expert Opin. Ther. Pat , vol.15 , pp. 635-646
    • Denny, W.A.1
  • 37
    • 36148939048 scopus 로고    scopus 로고
    • Current molecular design of intelligent drugs and imaging probes targeting tumor-specic microenvironments
    • Tanabe, K.; Zhang, Z.; Ito, T.; Hatta, H.; Nishimoto, S. Current molecular design of intelligent drugs and imaging probes targeting tumor-specic microenvironments. Org. Biomol. Chem. 2007, 5, 3745-3757.
    • (2007) Org. Biomol. Chem , vol.5 , pp. 3745-3757
    • Tanabe, K.1    Zhang, Z.2    Ito, T.3    Hatta, H.4    Nishimoto, S.5
  • 39
    • 0034725814 scopus 로고    scopus 로고
    • Stereoelectronic effect on one-electron reductive release of 5-fluorouracil from 5-fluoro-1-(2′- oxocycloalkyl)uracils as a new class of radiation-activated antitumor prodrugs
    • Mori, M.; Hatta, H.; Nishimoto, S. Stereoelectronic effect on one-electron reductive release of 5-fluorouracil from 5-fluoro-1-(2′- oxocycloalkyl)uracils as a new class of radiation-activated antitumor prodrugs. J. Org. Chem. 2000, 65, 4641-4647.
    • (2000) J. Org. Chem , vol.65 , pp. 4641-4647
    • Mori, M.1    Hatta, H.2    Nishimoto, S.3
  • 40
    • 0034024791 scopus 로고    scopus 로고
    • A novel class of antitumor prodrug, 1-(2 ′-oxopropyl)-5-fluorouracil (OFU001), which releases 5-fluorouracil upon hypoxic irradiation
    • Shibamoto, Y.; Zhou, L.; Hatta, H.; Mori, M.; Nishimoto, S. A novel class of antitumor prodrug, 1-(2 ′-oxopropyl)-5-fluorouracil (OFU001), which releases 5-fluorouracil upon hypoxic irradiation. Jpn. J. Cancer Res. 2000, 91, 433-438.
    • (2000) Jpn. J. Cancer Res , vol.91 , pp. 433-438
    • Shibamoto, Y.1    Zhou, L.2    Hatta, H.3    Mori, M.4    Nishimoto, S.5
  • 41
    • 0035254229 scopus 로고    scopus 로고
    • In vivo evaluation of a novel antitumor prodrug, 1-(2 ′-oxopropyl)-5-fluorouracil (OFU001), which releases 5-fluorouracil upon hypoxic irradiation
    • Shibamoto, Y.; Zhou, L.; Hatta, H.; Mori, M.; Nishimoto, S. In vivo evaluation of a novel antitumor prodrug, 1-(2 ′-oxopropyl)-5-fluorouracil (OFU001), which releases 5-fluorouracil upon hypoxic irradiation. Int. J. Radiat. Oncol. Biol. Phys. 2001, 49, 407-413.
    • (2001) Int. J. Radiat. Oncol. Biol. Phys , vol.49 , pp. 407-413
    • Shibamoto, Y.1    Zhou, L.2    Hatta, H.3    Mori, M.4    Nishimoto, S.5
  • 42
    • 0141504177 scopus 로고    scopus 로고
    • One-electron reduction characteristics of N(3)-substituted 5-fluorodeoxyuridines synthesized as radiation-activated prodrugs
    • Tanabe, K.; Mimasu, Y.; Eto, A.; Tachi, Y.; Sakakibara, S.; Mori, M.; Hatta. H.; Nishimoto, S. One-electron reduction characteristics of N(3)-substituted 5-fluorodeoxyuridines synthesized as radiation-activated prodrugs. Bioorg. Med. Chem. 2003, 11, 4551-4556.
    • (2003) Bioorg. Med. Chem , vol.11 , pp. 4551-4556
    • Tanabe, K.1    Mimasu, Y.2    Eto, A.3    Tachi, Y.4    Sakakibara, S.5    Mori, M.6    Hatta, H.7    Nishimoto, S.8
  • 43
    • 0036693263 scopus 로고    scopus 로고
    • Comparison of 5-fluorouracil and 5-fluoro-2′-deoxyuridine as an effector in radiation-activated prodrugs
    • Shibamoto, Y.; Mimasu, Y.; Tachi, Y.; Hatta. H.; Nishimoto, S. Comparison of 5-fluorouracil and 5-fluoro-2′-deoxyuridine as an effector in radiation-activated prodrugs. J. Chemother. 2002, 14, 390-396.
    • (2002) J. Chemother , vol.14 , pp. 390-396
    • Shibamoto, Y.1    Mimasu, Y.2    Tachi, Y.3    Hatta, H.4    Nishimoto, S.5
  • 44
    • 0942289880 scopus 로고    scopus 로고
    • In vitro and in vivo evaluation of novel antitumor prodrugs of 5-fluoro-2′- deoxyuridine activated by hypoxic irradiation
    • Shibamoto, Y.; Tachi, Y.; Tanabe, K.; Hatta, H.; Nishimoto, S. In vitro and in vivo evaluation of novel antitumor prodrugs of 5-fluoro-2′- deoxyuridine activated by hypoxic irradiation. Int. J. Radiat. Oncol. Biol. Phys. 2004, 58, 397-402.
    • (2004) Int. J. Radiat. Oncol. Biol. Phys , vol.58 , pp. 397-402
    • Shibamoto, Y.1    Tachi, Y.2    Tanabe, K.3    Hatta, H.4    Nishimoto, S.5
  • 45
    • 17144361816 scopus 로고    scopus 로고
    • Hypoxia-selective activation of 5-fluorodeoxyuridine prodrug possessing indolequinone structure: Radiolytic reduction and cytotoxicity characteristics
    • Tanabe, K.; Makimura, Y.; Tachi, Y. Imagawa-Sato, A.; Nishimoto, S. Hypoxia-selective activation of 5-fluorodeoxyuridine prodrug possessing indolequinone structure: Radiolytic reduction and cytotoxicity characteristics. Bioorg. Med. Chem. Lett. 2005, 15, 2321-2324.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 2321-2324
    • Tanabe, K.1    Makimura, Y.2    Tachi, Y.3    Imagawa-Sato, A.4    Nishimoto, S.5
  • 47
    • 0035959970 scopus 로고    scopus 로고
    • Indolequinone antitumor agents: Correlation between quinine structure and rate of metabolism by recombinant human NAD(P)H: quinine oxidoreductase. Part 2
    • Swann, E.; Barraja, P.; Oberlander, A. M.; Gardipee, W. T.; Hudnott, A. R.; Beall, H. D.; Moody, C. J. Indolequinone antitumor agents: correlation between quinine structure and rate of metabolism by recombinant human NAD(P)H: quinine oxidoreductase. Part 2. J. Med. Chem. 2001, 44, 3311-3319.
    • (2001) J. Med. Chem , vol.44 , pp. 3311-3319
    • Swann, E.1    Barraja, P.2    Oberlander, A.M.3    Gardipee, W.T.4    Hudnott, A.R.5    Beall, H.D.6    Moody, C.J.7
  • 48
    • 0036682238 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of indolequinone phosphoramidate prodrugs targeted to DT-diaphorase
    • Hernick, M.; Flader, C.; Borch, R. F. Design, synthesis, and biological evaluation of indolequinone phosphoramidate prodrugs targeted to DT-diaphorase. J. Med. Chem. 2002, 45, 3540-3548.
    • (2002) J. Med. Chem , vol.45 , pp. 3540-3548
    • Hernick, M.1    Flader, C.2    Borch, R.F.3
  • 50
    • 0034848005 scopus 로고    scopus 로고
    • Recognition and cleavage at the DNA major groove
    • Skibo, E. B.; Xing, C.; Groy, T. Recognition and cleavage at the DNA major groove. Bioorg. Med. Chem. 2001, 9, 2445-2459.
    • (2001) Bioorg. Med. Chem , vol.9 , pp. 2445-2459
    • Skibo, E.B.1    Xing, C.2    Groy, T.3
  • 51
    • 0033951038 scopus 로고    scopus 로고
    • Using photolabile ligands in drug discovery and development
    • Dormán, G.; Prestwich, G.D. Using photolabile ligands in drug discovery and development. Trends Biotech. 2000, 18, 64-77.
    • (2000) Trends Biotech , vol.18 , pp. 64-77
    • Dormán, G.1    Prestwich, G.D.2
  • 52
    • 0032540405 scopus 로고    scopus 로고
    • Nitrobenzyl-based photosensitive phosphoramide mustards: Synthesis and photochemical properties of potential prodrugs for cancer therapy
    • Reinhard, R.; Schmidt, B.F. Nitrobenzyl-based photosensitive phosphoramide mustards: Synthesis and photochemical properties of potential prodrugs for cancer therapy. J. Org. Chem. 1998, 63, 2434-2441.
    • (1998) J. Org. Chem , vol.63 , pp. 2434-2441
    • Reinhard, R.1    Schmidt, B.F.2
  • 53
    • 0034694705 scopus 로고    scopus 로고
    • New dendritic caged compounds: Synthesis, mass spectrometric characterization, and photochemical properties of dentrimers with a-carboxy-2-nitrobenzyl caged compounds at their periphery
    • Watanabe, S.; Sato, M.; Sakamoto, S.; Yamaguchi, K.; Iwamura, M. New dendritic caged compounds: synthesis, mass spectrometric characterization, and photochemical properties of dentrimers with a-carboxy-2-nitrobenzyl caged compounds at their periphery. J. Am. Chem. Soc. 2000, 122, 12588-12589.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 12588-12589
    • Watanabe, S.1    Sato, M.2    Sakamoto, S.3    Yamaguchi, K.4    Iwamura, M.5
  • 54
    • 0036152653 scopus 로고    scopus 로고
    • Design, synthesis, photochemical properties and cytotoxic activities of water-soluble caged Lleucyl-L-leucine methyl esters that control apoptosis of immune cells
    • Mizuta, H.; Watanabe, S.; Sakurai, Y.; Nishiyama, K.; Furuta, T.; Kobayashi, Y.; Iwamura, M. Design, synthesis, photochemical properties and cytotoxic activities of water-soluble caged Lleucyl-L-leucine methyl esters that control apoptosis of immune cells. Bioorg. Med. Chem. 2002, 10, 675-683.
    • (2002) Bioorg. Med. Chem , vol.10 , pp. 675-683
    • Mizuta, H.1    Watanabe, S.2    Sakurai, Y.3    Nishiyama, K.4    Furuta, T.5    Kobayashi, Y.6    Iwamura, M.7
  • 57
    • 33644969545 scopus 로고    scopus 로고
    • Synthesis and DNA cleavage reaction characteristics of enediyne prodrugs activated via an allylic rearrangement by base or UV irradiation
    • Tachi, Y.; Dai, W.-M.; Tanabe, K.; Nishimoto, S. Synthesis and DNA cleavage reaction characteristics of enediyne prodrugs activated via an allylic rearrangement by base or UV irradiation. Bioorg. Med. Chem. 2006, 14, 3199-3209.
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 3199-3209
    • Tachi, Y.1    Dai, W.-M.2    Tanabe, K.3    Nishimoto, S.4
  • 59
    • 43749100667 scopus 로고    scopus 로고
    • Development of novel water-soluble photocleavable protecting group and its application for design of photoresponsive paclitaxel prodrugs
    • Noguchi, M.; Skwarczynski, M.; Prakash, H.; Hirota, S.; Kimura, T.; Hayashi, Y.; Kiso, Y. Development of novel water-soluble photocleavable protecting group and its application for design of photoresponsive paclitaxel prodrugs. Bioorg. Med. Chem. 2008, 16, 5389-5397.
    • (2008) Bioorg. Med. Chem , vol.16 , pp. 5389-5397
    • Noguchi, M.1    Skwarczynski, M.2    Prakash, H.3    Hirota, S.4    Kimura, T.5    Hayashi, Y.6    Kiso, Y.7
  • 62
    • 14544287702 scopus 로고    scopus 로고
    • Synthesis and photochemical properties of photoactivated antitumor prodrugs releasing 5-fluorouracil
    • Zhang, Z.; Hatta, H.; Ito, T.; Nishimoto, S. Synthesis and photochemical properties of photoactivated antitumor prodrugs releasing 5-fluorouracil. Org. Biomol. Chem. 2005, 3, 592-596.
    • (2005) Org. Biomol. Chem , vol.3 , pp. 592-596
    • Zhang, Z.1    Hatta, H.2    Ito, T.3    Nishimoto, S.4
  • 63
    • 53649105098 scopus 로고    scopus 로고
    • A model for light-triggered porphyrin anticancer prodrugs based on an o-nitrobenzyl photolabile group
    • Lin, W.; Peng, D.; Wang, B.; Long, L.; Guo, C.; Yuan, J. A model for light-triggered porphyrin anticancer prodrugs based on an o-nitrobenzyl photolabile group. Eur. J. Org. Chem. 2008, 793-796.
    • (2008) Eur. J. Org. Chem , pp. 793-796
    • Lin, W.1    Peng, D.2    Wang, B.3    Long, L.4    Guo, C.5    Yuan, J.6
  • 64
    • 0031879628 scopus 로고    scopus 로고
    • Uracil-tegafur in gastric carcinoma: A comprehensive review
    • Takiuchi, H.; Ajani, J. A. Uracil-tegafur in gastric carcinoma: a comprehensive review. J. Clin. Oncol. 1998, 16, 2877-2885.
    • (1998) J. Clin. Oncol , vol.16 , pp. 2877-2885
    • Takiuchi, H.1    Ajani, J.A.2
  • 65
    • 45849101264 scopus 로고    scopus 로고
    • Synthesis, characterization, and properties evaluation of methylcoumarin end-functionalized poly(methyl methacrylate) for photoinduced drug release
    • Sinkel, C.; Greiner, A.; Agarwal, S. Synthesis, characterization, and properties evaluation of methylcoumarin end-functionalized poly(methyl methacrylate) for photoinduced drug release. Macromolecules 2008, 41, 3460-3467.
    • (2008) Macromolecules , vol.41 , pp. 3460-3467
    • Sinkel, C.1    Greiner, A.2    Agarwal, S.3


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