1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C

ara-Cytidine-5′-alkylphosphonophosphates and the corresponding -diphosphates were found to be cytostatically active in vitro against the human mammary epithelial cell line H184 A1N4 and the human mammary tumor cell line MaTu. Our results indicate that the replacement of the diphosphate by the phosph...
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Gespeichert in:

Autor*in:	H. Brachwitz [verfasserIn] J. Bergmann [verfasserIn] I. Fichtner [verfasserIn] Y. Thomas [verfasserIn] C. Vollgraf [verfasserIn] P. Langen [verfasserIn] W.E. Berdel [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	1998

Schlagwörter:	ara-C derivatives alkylphospholipids calcium antiproliferative activity in vivo studies in vitro studies

Übergeordnetes Werk:	In: Journal of Lipid Research - Elsevier, 2021, 39(1998), 1, Seite 162-172
Übergeordnetes Werk:	volume:39 ; year:1998 ; number:1 ; pages:162-172

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.1016/S0022-2275(20)34212-7

Katalog-ID:	DOAJ067434975

Internformat


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allfields	10.1016/S0022-2275(20)34212-7 doi (DE-627)DOAJ067434975 (DE-599)DOAJee54a9fb9ac342ee9e56858e84282ad7 DE-627 ger DE-627 rakwb eng QD415-436 H. Brachwitz verfasserin aut 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C 1998 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier ara-Cytidine-5′-alkylphosphonophosphates and the corresponding -diphosphates were found to be cytostatically active in vitro against the human mammary epithelial cell line H184 A1N4 and the human mammary tumor cell line MaTu. Our results indicate that the replacement of the diphosphate by the phosphonophosphate group has no influence on antiproliferative activity in this case. The compounds were more active than the corresponding cytidine phospholipid conjugates and related compounds lacking a cytostatically active nucleoside, the ara-C prodrug Cytoros, and were slightly less active than ara-C. The cytostatic effect was prevented by 2′-deoxycytidine indicating their action as prodrugs of ara-C. In contrast to ara-C, they increase [Ca2+]1 in H184 A1N4 cells, pointing to a different mechanism of action in addition to their prodrug effect. In combination with phospholipid analogs, synergistic effects could be observed. Further studies within the disease-oriented in vitro Anticancer Screening Program of the National Cancer Institute show selectivity for certain cancer cell lines. The hexadecyl derivatives revealed a significant antitumor activity in vivo against the murine lymphatic leukemia P 388 cells being equally potent or even superior to ara-C. In contrast to ara-C, they were found to be orally active. Side effects measured as leukopenia and body weight reduction were less pronounced than with the parent drug.—Brachwitz, H., J. Bergmann, I. Fichtner, Y. Thomas, C. Vollgraf, P. Langen, and W. E. Berdel. 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C. J. Lipid Res. 1998. 39: 162–172. ara-C derivatives alkylphospholipids calcium antiproliferative activity in vivo studies in vitro studies Biochemistry J. Bergmann verfasserin aut I. Fichtner verfasserin aut Y. Thomas verfasserin aut C. Vollgraf verfasserin aut P. Langen verfasserin aut W.E. Berdel verfasserin aut In Journal of Lipid Research Elsevier, 2021 39(1998), 1, Seite 162-172 (DE-627)26601593X (DE-600)1466675-3 15397262 nnns volume:39 year:1998 number:1 pages:162-172 https://doi.org/10.1016/S0022-2275(20)34212-7 kostenfrei https://doaj.org/article/ee54a9fb9ac342ee9e56858e84282ad7 kostenfrei http://www.sciencedirect.com/science/article/pii/S0022227520342127 kostenfrei https://doaj.org/toc/0022-2275 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_252 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2006 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 39 1998 1 162-172
spelling	10.1016/S0022-2275(20)34212-7 doi (DE-627)DOAJ067434975 (DE-599)DOAJee54a9fb9ac342ee9e56858e84282ad7 DE-627 ger DE-627 rakwb eng QD415-436 H. Brachwitz verfasserin aut 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C 1998 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier ara-Cytidine-5′-alkylphosphonophosphates and the corresponding -diphosphates were found to be cytostatically active in vitro against the human mammary epithelial cell line H184 A1N4 and the human mammary tumor cell line MaTu. Our results indicate that the replacement of the diphosphate by the phosphonophosphate group has no influence on antiproliferative activity in this case. The compounds were more active than the corresponding cytidine phospholipid conjugates and related compounds lacking a cytostatically active nucleoside, the ara-C prodrug Cytoros, and were slightly less active than ara-C. The cytostatic effect was prevented by 2′-deoxycytidine indicating their action as prodrugs of ara-C. In contrast to ara-C, they increase [Ca2+]1 in H184 A1N4 cells, pointing to a different mechanism of action in addition to their prodrug effect. In combination with phospholipid analogs, synergistic effects could be observed. Further studies within the disease-oriented in vitro Anticancer Screening Program of the National Cancer Institute show selectivity for certain cancer cell lines. The hexadecyl derivatives revealed a significant antitumor activity in vivo against the murine lymphatic leukemia P 388 cells being equally potent or even superior to ara-C. In contrast to ara-C, they were found to be orally active. Side effects measured as leukopenia and body weight reduction were less pronounced than with the parent drug.—Brachwitz, H., J. Bergmann, I. Fichtner, Y. Thomas, C. Vollgraf, P. Langen, and W. E. Berdel. 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C. J. Lipid Res. 1998. 39: 162–172. ara-C derivatives alkylphospholipids calcium antiproliferative activity in vivo studies in vitro studies Biochemistry J. Bergmann verfasserin aut I. Fichtner verfasserin aut Y. Thomas verfasserin aut C. Vollgraf verfasserin aut P. Langen verfasserin aut W.E. Berdel verfasserin aut In Journal of Lipid Research Elsevier, 2021 39(1998), 1, Seite 162-172 (DE-627)26601593X (DE-600)1466675-3 15397262 nnns volume:39 year:1998 number:1 pages:162-172 https://doi.org/10.1016/S0022-2275(20)34212-7 kostenfrei https://doaj.org/article/ee54a9fb9ac342ee9e56858e84282ad7 kostenfrei http://www.sciencedirect.com/science/article/pii/S0022227520342127 kostenfrei https://doaj.org/toc/0022-2275 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_252 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2006 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 39 1998 1 162-172
allfields_unstemmed	10.1016/S0022-2275(20)34212-7 doi (DE-627)DOAJ067434975 (DE-599)DOAJee54a9fb9ac342ee9e56858e84282ad7 DE-627 ger DE-627 rakwb eng QD415-436 H. Brachwitz verfasserin aut 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C 1998 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier ara-Cytidine-5′-alkylphosphonophosphates and the corresponding -diphosphates were found to be cytostatically active in vitro against the human mammary epithelial cell line H184 A1N4 and the human mammary tumor cell line MaTu. Our results indicate that the replacement of the diphosphate by the phosphonophosphate group has no influence on antiproliferative activity in this case. The compounds were more active than the corresponding cytidine phospholipid conjugates and related compounds lacking a cytostatically active nucleoside, the ara-C prodrug Cytoros, and were slightly less active than ara-C. The cytostatic effect was prevented by 2′-deoxycytidine indicating their action as prodrugs of ara-C. In contrast to ara-C, they increase [Ca2+]1 in H184 A1N4 cells, pointing to a different mechanism of action in addition to their prodrug effect. In combination with phospholipid analogs, synergistic effects could be observed. Further studies within the disease-oriented in vitro Anticancer Screening Program of the National Cancer Institute show selectivity for certain cancer cell lines. The hexadecyl derivatives revealed a significant antitumor activity in vivo against the murine lymphatic leukemia P 388 cells being equally potent or even superior to ara-C. In contrast to ara-C, they were found to be orally active. Side effects measured as leukopenia and body weight reduction were less pronounced than with the parent drug.—Brachwitz, H., J. Bergmann, I. Fichtner, Y. Thomas, C. Vollgraf, P. Langen, and W. E. Berdel. 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C. J. Lipid Res. 1998. 39: 162–172. ara-C derivatives alkylphospholipids calcium antiproliferative activity in vivo studies in vitro studies Biochemistry J. Bergmann verfasserin aut I. Fichtner verfasserin aut Y. Thomas verfasserin aut C. Vollgraf verfasserin aut P. Langen verfasserin aut W.E. Berdel verfasserin aut In Journal of Lipid Research Elsevier, 2021 39(1998), 1, Seite 162-172 (DE-627)26601593X (DE-600)1466675-3 15397262 nnns volume:39 year:1998 number:1 pages:162-172 https://doi.org/10.1016/S0022-2275(20)34212-7 kostenfrei https://doaj.org/article/ee54a9fb9ac342ee9e56858e84282ad7 kostenfrei http://www.sciencedirect.com/science/article/pii/S0022227520342127 kostenfrei https://doaj.org/toc/0022-2275 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_252 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2006 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 39 1998 1 162-172
allfieldsGer	10.1016/S0022-2275(20)34212-7 doi (DE-627)DOAJ067434975 (DE-599)DOAJee54a9fb9ac342ee9e56858e84282ad7 DE-627 ger DE-627 rakwb eng QD415-436 H. Brachwitz verfasserin aut 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C 1998 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier ara-Cytidine-5′-alkylphosphonophosphates and the corresponding -diphosphates were found to be cytostatically active in vitro against the human mammary epithelial cell line H184 A1N4 and the human mammary tumor cell line MaTu. Our results indicate that the replacement of the diphosphate by the phosphonophosphate group has no influence on antiproliferative activity in this case. The compounds were more active than the corresponding cytidine phospholipid conjugates and related compounds lacking a cytostatically active nucleoside, the ara-C prodrug Cytoros, and were slightly less active than ara-C. The cytostatic effect was prevented by 2′-deoxycytidine indicating their action as prodrugs of ara-C. In contrast to ara-C, they increase [Ca2+]1 in H184 A1N4 cells, pointing to a different mechanism of action in addition to their prodrug effect. In combination with phospholipid analogs, synergistic effects could be observed. Further studies within the disease-oriented in vitro Anticancer Screening Program of the National Cancer Institute show selectivity for certain cancer cell lines. The hexadecyl derivatives revealed a significant antitumor activity in vivo against the murine lymphatic leukemia P 388 cells being equally potent or even superior to ara-C. In contrast to ara-C, they were found to be orally active. Side effects measured as leukopenia and body weight reduction were less pronounced than with the parent drug.—Brachwitz, H., J. Bergmann, I. Fichtner, Y. Thomas, C. Vollgraf, P. Langen, and W. E. Berdel. 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C. J. Lipid Res. 1998. 39: 162–172. ara-C derivatives alkylphospholipids calcium antiproliferative activity in vivo studies in vitro studies Biochemistry J. Bergmann verfasserin aut I. Fichtner verfasserin aut Y. Thomas verfasserin aut C. Vollgraf verfasserin aut P. Langen verfasserin aut W.E. Berdel verfasserin aut In Journal of Lipid Research Elsevier, 2021 39(1998), 1, Seite 162-172 (DE-627)26601593X (DE-600)1466675-3 15397262 nnns volume:39 year:1998 number:1 pages:162-172 https://doi.org/10.1016/S0022-2275(20)34212-7 kostenfrei https://doaj.org/article/ee54a9fb9ac342ee9e56858e84282ad7 kostenfrei http://www.sciencedirect.com/science/article/pii/S0022227520342127 kostenfrei https://doaj.org/toc/0022-2275 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_252 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2006 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 39 1998 1 162-172
allfieldsSound	10.1016/S0022-2275(20)34212-7 doi (DE-627)DOAJ067434975 (DE-599)DOAJee54a9fb9ac342ee9e56858e84282ad7 DE-627 ger DE-627 rakwb eng QD415-436 H. Brachwitz verfasserin aut 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C 1998 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier ara-Cytidine-5′-alkylphosphonophosphates and the corresponding -diphosphates were found to be cytostatically active in vitro against the human mammary epithelial cell line H184 A1N4 and the human mammary tumor cell line MaTu. Our results indicate that the replacement of the diphosphate by the phosphonophosphate group has no influence on antiproliferative activity in this case. The compounds were more active than the corresponding cytidine phospholipid conjugates and related compounds lacking a cytostatically active nucleoside, the ara-C prodrug Cytoros, and were slightly less active than ara-C. The cytostatic effect was prevented by 2′-deoxycytidine indicating their action as prodrugs of ara-C. In contrast to ara-C, they increase [Ca2+]1 in H184 A1N4 cells, pointing to a different mechanism of action in addition to their prodrug effect. In combination with phospholipid analogs, synergistic effects could be observed. Further studies within the disease-oriented in vitro Anticancer Screening Program of the National Cancer Institute show selectivity for certain cancer cell lines. The hexadecyl derivatives revealed a significant antitumor activity in vivo against the murine lymphatic leukemia P 388 cells being equally potent or even superior to ara-C. In contrast to ara-C, they were found to be orally active. Side effects measured as leukopenia and body weight reduction were less pronounced than with the parent drug.—Brachwitz, H., J. Bergmann, I. Fichtner, Y. Thomas, C. Vollgraf, P. Langen, and W. E. Berdel. 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C. J. Lipid Res. 1998. 39: 162–172. ara-C derivatives alkylphospholipids calcium antiproliferative activity in vivo studies in vitro studies Biochemistry J. Bergmann verfasserin aut I. Fichtner verfasserin aut Y. Thomas verfasserin aut C. Vollgraf verfasserin aut P. Langen verfasserin aut W.E. Berdel verfasserin aut In Journal of Lipid Research Elsevier, 2021 39(1998), 1, Seite 162-172 (DE-627)26601593X (DE-600)1466675-3 15397262 nnns volume:39 year:1998 number:1 pages:162-172 https://doi.org/10.1016/S0022-2275(20)34212-7 kostenfrei https://doaj.org/article/ee54a9fb9ac342ee9e56858e84282ad7 kostenfrei http://www.sciencedirect.com/science/article/pii/S0022227520342127 kostenfrei https://doaj.org/toc/0022-2275 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_252 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2006 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 39 1998 1 162-172
language	English
source	In Journal of Lipid Research 39(1998), 1, Seite 162-172 volume:39 year:1998 number:1 pages:162-172
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callnumber-first	Q - Science
author	H. Brachwitz
spellingShingle	H. Brachwitz misc QD415-436 misc ara-C derivatives misc alkylphospholipids misc calcium misc antiproliferative activity misc in vivo studies misc in vitro studies misc Biochemistry 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C
authorStr	H. Brachwitz
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topic_title	QD415-436 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C ara-C derivatives alkylphospholipids calcium antiproliferative activity in vivo studies in vitro studies
topic	misc QD415-436 misc ara-C derivatives misc alkylphospholipids misc calcium misc antiproliferative activity misc in vivo studies misc in vitro studies misc Biochemistry
topic_unstemmed	misc QD415-436 misc ara-C derivatives misc alkylphospholipids misc calcium misc antiproliferative activity misc in vivo studies misc in vitro studies misc Biochemistry
topic_browse	misc QD415-436 misc ara-C derivatives misc alkylphospholipids misc calcium misc antiproliferative activity misc in vivo studies misc in vitro studies misc Biochemistry
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title	1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C
ctrlnum	(DE-627)DOAJ067434975 (DE-599)DOAJee54a9fb9ac342ee9e56858e84282ad7
title_full	1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C
author_sort	H. Brachwitz
journal	Journal of Lipid Research
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author_browse	H. Brachwitz J. Bergmann I. Fichtner Y. Thomas C. Vollgraf P. Langen W.E. Berdel
container_volume	39
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author-letter	H. Brachwitz
doi_str_mv	10.1016/S0022-2275(20)34212-7
author2-role	verfasserin
title_sort	1-β-d-arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-c
callnumber	QD415-436
title_auth	1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C
abstract	ara-Cytidine-5′-alkylphosphonophosphates and the corresponding -diphosphates were found to be cytostatically active in vitro against the human mammary epithelial cell line H184 A1N4 and the human mammary tumor cell line MaTu. Our results indicate that the replacement of the diphosphate by the phosphonophosphate group has no influence on antiproliferative activity in this case. The compounds were more active than the corresponding cytidine phospholipid conjugates and related compounds lacking a cytostatically active nucleoside, the ara-C prodrug Cytoros, and were slightly less active than ara-C. The cytostatic effect was prevented by 2′-deoxycytidine indicating their action as prodrugs of ara-C. In contrast to ara-C, they increase [Ca2+]1 in H184 A1N4 cells, pointing to a different mechanism of action in addition to their prodrug effect. In combination with phospholipid analogs, synergistic effects could be observed. Further studies within the disease-oriented in vitro Anticancer Screening Program of the National Cancer Institute show selectivity for certain cancer cell lines. The hexadecyl derivatives revealed a significant antitumor activity in vivo against the murine lymphatic leukemia P 388 cells being equally potent or even superior to ara-C. In contrast to ara-C, they were found to be orally active. Side effects measured as leukopenia and body weight reduction were less pronounced than with the parent drug.—Brachwitz, H., J. Bergmann, I. Fichtner, Y. Thomas, C. Vollgraf, P. Langen, and W. E. Berdel. 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C. J. Lipid Res. 1998. 39: 162–172.
abstractGer	ara-Cytidine-5′-alkylphosphonophosphates and the corresponding -diphosphates were found to be cytostatically active in vitro against the human mammary epithelial cell line H184 A1N4 and the human mammary tumor cell line MaTu. Our results indicate that the replacement of the diphosphate by the phosphonophosphate group has no influence on antiproliferative activity in this case. The compounds were more active than the corresponding cytidine phospholipid conjugates and related compounds lacking a cytostatically active nucleoside, the ara-C prodrug Cytoros, and were slightly less active than ara-C. The cytostatic effect was prevented by 2′-deoxycytidine indicating their action as prodrugs of ara-C. In contrast to ara-C, they increase [Ca2+]1 in H184 A1N4 cells, pointing to a different mechanism of action in addition to their prodrug effect. In combination with phospholipid analogs, synergistic effects could be observed. Further studies within the disease-oriented in vitro Anticancer Screening Program of the National Cancer Institute show selectivity for certain cancer cell lines. The hexadecyl derivatives revealed a significant antitumor activity in vivo against the murine lymphatic leukemia P 388 cells being equally potent or even superior to ara-C. In contrast to ara-C, they were found to be orally active. Side effects measured as leukopenia and body weight reduction were less pronounced than with the parent drug.—Brachwitz, H., J. Bergmann, I. Fichtner, Y. Thomas, C. Vollgraf, P. Langen, and W. E. Berdel. 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C. J. Lipid Res. 1998. 39: 162–172.
abstract_unstemmed	ara-Cytidine-5′-alkylphosphonophosphates and the corresponding -diphosphates were found to be cytostatically active in vitro against the human mammary epithelial cell line H184 A1N4 and the human mammary tumor cell line MaTu. Our results indicate that the replacement of the diphosphate by the phosphonophosphate group has no influence on antiproliferative activity in this case. The compounds were more active than the corresponding cytidine phospholipid conjugates and related compounds lacking a cytostatically active nucleoside, the ara-C prodrug Cytoros, and were slightly less active than ara-C. The cytostatic effect was prevented by 2′-deoxycytidine indicating their action as prodrugs of ara-C. In contrast to ara-C, they increase [Ca2+]1 in H184 A1N4 cells, pointing to a different mechanism of action in addition to their prodrug effect. In combination with phospholipid analogs, synergistic effects could be observed. Further studies within the disease-oriented in vitro Anticancer Screening Program of the National Cancer Institute show selectivity for certain cancer cell lines. The hexadecyl derivatives revealed a significant antitumor activity in vivo against the murine lymphatic leukemia P 388 cells being equally potent or even superior to ara-C. In contrast to ara-C, they were found to be orally active. Side effects measured as leukopenia and body weight reduction were less pronounced than with the parent drug.—Brachwitz, H., J. Bergmann, I. Fichtner, Y. Thomas, C. Vollgraf, P. Langen, and W. E. Berdel. 1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C. J. Lipid Res. 1998. 39: 162–172.
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title_short	1-β-d-Arabinofuranosylcytosine-5′-alkylphosphonophosphates and diphosphates: new orally active derivatives of ara-C
url	https://doi.org/10.1016/S0022-2275(20)34212-7 https://doaj.org/article/ee54a9fb9ac342ee9e56858e84282ad7 http://www.sciencedirect.com/science/article/pii/S0022227520342127 https://doaj.org/toc/0022-2275
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