CA2387539C - Method for protecting normal cells from cytotoxicity of chemotherapeutic agents - Google Patents

Info

Publication number

CA2387539C

CA2387539C CA2387539A CA2387539A CA2387539C CA 2387539 C CA2387539 C CA 2387539C CA 2387539 A CA2387539 A CA 2387539A CA 2387539 A CA2387539 A CA 2387539A CA 2387539 C CA2387539 C CA 2387539C

Authority

CA

Canada

Prior art keywords

group

phenyl

mol

sulfone

pharmaceutically acceptable

Prior art date

1999-10-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

Links

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• 239000002246 antineoplastic agent Substances 0.000 title abstract description 14
• 238000000034 method Methods 0.000 title description 104
• 229940127089 cytotoxic agent Drugs 0.000 title description 24
• 230000003013 cytotoxicity Effects 0.000 title description 7
• 231100000135 cytotoxicity Toxicity 0.000 title description 7
• -1 sulfone compound Chemical class 0.000 claims abstract description 127
• 230000000394 mitotic effect Effects 0.000 claims abstract description 26
• 229940123587 Cell cycle inhibitor Drugs 0.000 claims abstract description 23
• 231100000433 cytotoxic Toxicity 0.000 claims abstract description 19
• 230000001472 cytotoxic effect Effects 0.000 claims abstract description 19
• 230000000694 effects Effects 0.000 claims abstract description 18
• 239000003534 dna topoisomerase inhibitor Substances 0.000 claims abstract description 15
• 229940044693 topoisomerase inhibitor Drugs 0.000 claims abstract description 15
• 150000001875 compounds Chemical class 0.000 claims description 128
• 229910052739 hydrogen Inorganic materials 0.000 claims description 55
• 229930012538 Paclitaxel Natural products 0.000 claims description 38
• 229960001592 paclitaxel Drugs 0.000 claims description 38
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 38
• LRHCIAKITMHSNT-OGBZJDJUSA-N 1-[(e)-3-(4-chlorophenyl)-3-[(e)-1-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-enyl]sulfonylprop-1-enyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C=CC(F)=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 LRHCIAKITMHSNT-OGBZJDJUSA-N 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 229960004528 vincristine Drugs 0.000 claims description 22
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 22
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• 239000000203 mixture Substances 0.000 claims description 15
• 241001465754 Metazoa Species 0.000 claims description 14
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 13
• 241000282414 Homo sapiens Species 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
• QAADMTMRLCWAME-UHFFFAOYSA-N 2-(benzenesulfonyl)-3-(4-fluorophenyl)-1-phenylprop-2-en-1-one Chemical compound C1=CC(F)=CC=C1C=C(S(=O)(=O)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 QAADMTMRLCWAME-UHFFFAOYSA-N 0.000 claims description 5
• SNGZRCQJDGCGEF-OGBZJDJUSA-N 4-[(e)-3-[(e)-3-(4-carboxyphenyl)-1-(4-chlorophenyl)prop-2-enyl]sulfonyl-3-(4-chlorophenyl)prop-1-enyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C=CC(=CC=1)C(O)=O)C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 SNGZRCQJDGCGEF-OGBZJDJUSA-N 0.000 claims description 5
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims description 4
• MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 claims description 4
• WXVZZCHUAIGQKJ-MDZDMXLPSA-N 1-chloro-4-[[(e)-2-(4-chlorophenyl)ethenyl]sulfonylmethyl]benzene Chemical compound C1=CC(Cl)=CC=C1CS(=O)(=O)\C=C\C1=CC=C(Cl)C=C1 WXVZZCHUAIGQKJ-MDZDMXLPSA-N 0.000 claims description 4
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
• CMXFGRBYOKHMGL-IAGONARPSA-N 2,4-dichloro-1-[(e)-1-[(e)-1-(2,4-dichlorophenyl)-3-(4-fluorophenyl)prop-2-enyl]sulfonyl-3-(4-fluorophenyl)prop-2-enyl]benzene Chemical compound C1=CC(F)=CC=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C=CC(F)=CC=1)C=1C(=CC(Cl)=CC=1)Cl)C1=CC=C(Cl)C=C1Cl CMXFGRBYOKHMGL-IAGONARPSA-N 0.000 claims description 4
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• SKUSOFLZORLIEM-WXUKJITCSA-N 2,6-dichloro-5-[[4,6-dichloro-6-[(E)-2-(4-fluorophenyl)ethenyl]cyclohexa-2,4-dien-1-yl]methylsulfonylmethyl]-6-[(E)-2-(4-fluorophenyl)ethenyl]cyclohexa-1,3-diene Chemical compound ClC1(C(CS(=O)(=O)CC2C(C=C(C=C2)Cl)(Cl)\C=C\C2=CC=C(C=C2)F)C=CC(=C1)Cl)\C=C\C1=CC=C(C=C1)F SKUSOFLZORLIEM-WXUKJITCSA-N 0.000 claims description 3
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 3
• 229940127093 camptothecin Drugs 0.000 claims description 3
• VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical group C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 3
• VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 3
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
• 229960005420 etoposide Drugs 0.000 claims description 3
• 229940123237 Taxane Drugs 0.000 claims description 2
• 229940122803 Vinca alkaloid Drugs 0.000 claims description 2
• 229960001338 colchicine Drugs 0.000 claims description 2
• 229960001842 estramustine Drugs 0.000 claims description 2
• FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 claims description 2
• 239000003120 macrolide antibiotic agent Substances 0.000 claims description 2
• 229940041033 macrolides Drugs 0.000 claims description 2
• 229960001156 mitoxantrone Drugs 0.000 claims description 2
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 2
• 125000005362 aryl sulfone group Chemical group 0.000 abstract description 33
• 230000001120 cytoprotective effect Effects 0.000 abstract description 30
• 230000001093 anti-cancer Effects 0.000 abstract description 7
• 238000002512 chemotherapy Methods 0.000 abstract description 4
• 230000001965 increasing effect Effects 0.000 abstract description 3
• 238000002203 pretreatment Methods 0.000 abstract description 2
• 230000000973 chemotherapeutic effect Effects 0.000 abstract 1
• 230000015572 biosynthetic process Effects 0.000 description 84
• 238000003786 synthesis reaction Methods 0.000 description 83
• 239000000243 solution Substances 0.000 description 81
• 210000004027 cell Anatomy 0.000 description 74
• 125000003118 aryl group Chemical group 0.000 description 35
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 23
• XJNHONCWGODPIZ-PHEQNACWSA-N [(e)-2-[(e)-2-phenylethenyl]sulfonylethenyl]benzene Chemical group C=1C=CC=CC=1/C=C/S(=O)(=O)\C=C\C1=CC=CC=C1 XJNHONCWGODPIZ-PHEQNACWSA-N 0.000 description 23
• 125000004429 atom Chemical group 0.000 description 23
• 239000011734 sodium Substances 0.000 description 23
• 229910052708 sodium Inorganic materials 0.000 description 23
• 230000003647 oxidation Effects 0.000 description 22
• 238000007254 oxidation reaction Methods 0.000 description 22
• 238000011282 treatment Methods 0.000 description 21
• 101150041968 CDC13 gene Proteins 0.000 description 20
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
• 238000002844 melting Methods 0.000 description 19
• 230000008018 melting Effects 0.000 description 19
• UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
• 206010028980 Neoplasm Diseases 0.000 description 17
• 229940079593 drug Drugs 0.000 description 17
• 239000003814 drug Substances 0.000 description 17
• 150000003457 sulfones Chemical class 0.000 description 17
• 239000002254 cytotoxic agent Substances 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 239000003795 chemical substances by application Substances 0.000 description 15
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
• ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 13
• 201000011510 cancer Diseases 0.000 description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• HPWAJMXOEYIERK-UHFFFAOYSA-N 2-benzylsulfonylacetic acid Chemical class OC(=O)CS(=O)(=O)CC1=CC=CC=C1 HPWAJMXOEYIERK-UHFFFAOYSA-N 0.000 description 11
• UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 11
• AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 10
• 150000002431 hydrogen Chemical class 0.000 description 10
• YYXBXAYHHCTPEF-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylsulfonyl]acetic acid Chemical compound OC(=O)CS(=O)(=O)CC1=CC=C(Cl)C=C1 YYXBXAYHHCTPEF-UHFFFAOYSA-N 0.000 description 9
• 239000003112 inhibitor Substances 0.000 description 9
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• 108020004414 DNA Proteins 0.000 description 8
• 229960000583 acetic acid Drugs 0.000 description 8
• UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 8
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• MRTIWTGAGMZREP-QXMHVHEDSA-N [(z)-2-phenylethenyl]sulfonylmethylbenzene Chemical class C=1C=CC=CC=1\C=C/S(=O)(=O)CC1=CC=CC=C1 MRTIWTGAGMZREP-QXMHVHEDSA-N 0.000 description 7
• 210000002950 fibroblast Anatomy 0.000 description 7
• 239000012362 glacial acetic acid Substances 0.000 description 7
• WCOXFTGMNJJABC-SREVYHEPSA-N 2-[(z)-2-phenylethenyl]sulfonylacetic acid Chemical compound OC(=O)CS(=O)(=O)\C=C/C1=CC=CC=C1 WCOXFTGMNJJABC-SREVYHEPSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 238000005481 NMR spectroscopy Methods 0.000 description 6
• 239000013543 active substance Substances 0.000 description 6
• 150000003934 aromatic aldehydes Chemical class 0.000 description 6
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
• 230000016507 interphase Effects 0.000 description 6
• 230000002062 proliferating effect Effects 0.000 description 6
• 230000001988 toxicity Effects 0.000 description 6
• 231100000419 toxicity Toxicity 0.000 description 6
• 210000004881 tumor cell Anatomy 0.000 description 6
• WWFIIZLHSNBNTC-UHFFFAOYSA-N (2-chlorophenyl)methanethiol Chemical compound SCC1=CC=CC=C1Cl WWFIIZLHSNBNTC-UHFFFAOYSA-N 0.000 description 5
• GKQXPTHQTXCXEV-UHFFFAOYSA-N (4-chlorophenyl)methanethiol Chemical compound SCC1=CC=C(Cl)C=C1 GKQXPTHQTXCXEV-UHFFFAOYSA-N 0.000 description 5
• RKTRHMNWVZRZJQ-UHFFFAOYSA-N (4-fluorophenyl)methanethiol Chemical compound FC1=CC=C(CS)C=C1 RKTRHMNWVZRZJQ-UHFFFAOYSA-N 0.000 description 5
• YTEFAALYDTWTLB-UHFFFAOYSA-N 2-(benzenesulfonyl)acetic acid Chemical class OC(=O)CS(=O)(=O)C1=CC=CC=C1 YTEFAALYDTWTLB-UHFFFAOYSA-N 0.000 description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
• 229910052731 fluorine Inorganic materials 0.000 description 5
• 239000011737 fluorine Substances 0.000 description 5
• 230000011278 mitosis Effects 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• LTLVZQZDXQWLHU-UHFFFAOYSA-N 1-bromo-4-ethynylbenzene Chemical group BrC1=CC=C(C#C)C=C1 LTLVZQZDXQWLHU-UHFFFAOYSA-N 0.000 description 4
• LFZJRTMTKGYJRS-UHFFFAOYSA-N 1-chloro-4-ethynylbenzene Chemical group ClC1=CC=C(C#C)C=C1 LFZJRTMTKGYJRS-UHFFFAOYSA-N 0.000 description 4
• QXSWHQGIEKUBAS-UHFFFAOYSA-N 1-ethynyl-4-fluorobenzene Chemical group FC1=CC=C(C#C)C=C1 QXSWHQGIEKUBAS-UHFFFAOYSA-N 0.000 description 4
• IAONCYGNBVHNCT-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfonylacetic acid Chemical compound OC(=O)CS(=O)(=O)C1=CC=C(Cl)C=C1 IAONCYGNBVHNCT-UHFFFAOYSA-N 0.000 description 4
• JZLMLFCJWFMZMC-UHFFFAOYSA-N 3-phenylpropanethioic s-acid Chemical compound SC(=O)CCC1=CC=CC=C1 JZLMLFCJWFMZMC-UHFFFAOYSA-N 0.000 description 4
• KSZVOXHGCKKOLL-UHFFFAOYSA-N 4-Ethynyltoluene Chemical group CC1=CC=C(C#C)C=C1 KSZVOXHGCKKOLL-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
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• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• 238000004566 IR spectroscopy Methods 0.000 description 4
• 241000699670 Mus sp. Species 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• 101710183280 Topoisomerase Proteins 0.000 description 4
• WZDKIPVHBCBPCR-QXMHVHEDSA-N [(z)-2-benzylsulfanylethenyl]benzene Chemical compound C=1C=CC=CC=1CS\C=C/C1=CC=CC=C1 WZDKIPVHBCBPCR-QXMHVHEDSA-N 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• 230000002927 anti-mitotic effect Effects 0.000 description 4
• 230000000259 anti-tumor effect Effects 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 230000022131 cell cycle Effects 0.000 description 4
• 231100000599 cytotoxic agent Toxicity 0.000 description 4
• 238000001704 evaporation Methods 0.000 description 4
• 230000008020 evaporation Effects 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 238000007747 plating Methods 0.000 description 4
• 238000002360 preparation method Methods 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 230000002441 reversible effect Effects 0.000 description 4
• 231100000331 toxic Toxicity 0.000 description 4
• 230000002588 toxic effect Effects 0.000 description 4
• JPMYPWYPVNCINE-UHFFFAOYSA-N 2-(benzenesulfonyl)-1,3-diphenylprop-2-en-1-one Chemical class C=1C=CC=CC=1C(=O)C(S(=O)(=O)C=1C=CC=CC=1)=CC1=CC=CC=C1 JPMYPWYPVNCINE-UHFFFAOYSA-N 0.000 description 3
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