JP2013522189A5 - - Google Patents
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- Publication number
- JP2013522189A5 JP2013522189A5 JP2012557010A JP2012557010A JP2013522189A5 JP 2013522189 A5 JP2013522189 A5 JP 2013522189A5 JP 2012557010 A JP2012557010 A JP 2012557010A JP 2012557010 A JP2012557010 A JP 2012557010A JP 2013522189 A5 JP2013522189 A5 JP 2013522189A5
- Authority
- JP
- Japan
- Prior art keywords
- flavonoid
- anticancer drug
- group
- delivery vehicle
- conjugate
- Prior art date
- 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.)
- Granted
Links
- 239000002246 antineoplastic agent Substances 0.000 claims 32
- 229930003935 flavonoid Natural products 0.000 claims 26
- 235000017173 flavonoids Nutrition 0.000 claims 26
- 150000002215 flavonoids Chemical class 0.000 claims 26
- 229940041181 antineoplastic drug Drugs 0.000 claims 23
- 239000003981 vehicle Substances 0.000 claims 20
- 238000000034 method Methods 0.000 claims 19
- 238000012377 drug delivery Methods 0.000 claims 14
- 229920001223 polyethylene glycol Polymers 0.000 claims 12
- 229920000642 polymer Polymers 0.000 claims 12
- 239000000126 substance Substances 0.000 claims 9
- 229930014124 (-)-epigallocatechin gallate Natural products 0.000 claims 8
- 235000004911 (-)-epigallocatechin gallate Nutrition 0.000 claims 8
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 claims 8
- VFSWRBJYBQXUTE-UHFFFAOYSA-N epi-Gallocatechin 3-O-gallate Natural products Oc1ccc2C(=O)C(OC(=O)c3cc(O)c(O)c(O)c3)C(Oc2c1)c4cc(O)c(O)c(O)c4 VFSWRBJYBQXUTE-UHFFFAOYSA-N 0.000 claims 8
- 125000000524 functional group Chemical group 0.000 claims 8
- 229940124447 delivery agent Drugs 0.000 claims 7
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims 6
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 6
- 229920002674 hyaluronan Polymers 0.000 claims 6
- 229960003160 hyaluronic acid Drugs 0.000 claims 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 6
- 230000021615 conjugation Effects 0.000 claims 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 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 claims 4
- 125000003172 aldehyde group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 239000000412 dendrimer Substances 0.000 claims 4
- 229920000736 dendritic polymer Polymers 0.000 claims 4
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- -1 phenoxymethyl (methyl hydrazono) Chemical class 0.000 claims 4
- 229960003732 tyramine Drugs 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 3
- 229930013915 (+)-catechin Natural products 0.000 claims 2
- 235000007219 (+)-catechin Nutrition 0.000 claims 2
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 claims 2
- 229930013783 (-)-epicatechin Natural products 0.000 claims 2
- 235000007355 (-)-epicatechin Nutrition 0.000 claims 2
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 claims 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 2
- DZKXDEWNLDOXQH-UHFFFAOYSA-N 1,3,5,2,4,6-triazatriphosphinine Chemical compound N1=PN=PN=P1 DZKXDEWNLDOXQH-UHFFFAOYSA-N 0.000 claims 2
- 108020004414 DNA Proteins 0.000 claims 2
- 102000053602 DNA Human genes 0.000 claims 2
- LSHVYAFMTMFKBA-UHFFFAOYSA-N ECG Natural products C=1C=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical group 0.000 claims 2
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims 2
- 235000005487 catechin Nutrition 0.000 claims 2
- 229950001002 cianidanol Drugs 0.000 claims 2
- 229960004316 cisplatin Drugs 0.000 claims 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 2
- 230000001268 conjugating effect Effects 0.000 claims 2
- 229960004679 doxorubicin Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 2
- 229940022353 herceptin Drugs 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 125000001863 phosphorothioyl group Chemical group *P(*)(*)=S 0.000 claims 2
- 229960000575 trastuzumab Drugs 0.000 claims 2
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims 1
- 102000040650 (ribonucleotides)n+m Human genes 0.000 claims 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- 102000004127 Cytokines Human genes 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 108700011259 MicroRNAs Proteins 0.000 claims 1
- 229930012538 Paclitaxel Natural products 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 108020004682 Single-Stranded DNA Proteins 0.000 claims 1
- 108091027967 Small hairpin RNA Proteins 0.000 claims 1
- 108020004459 Small interfering RNA Proteins 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 1
- 229940121369 angiogenesis inhibitor Drugs 0.000 claims 1
- 238000011394 anticancer treatment Methods 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 229960000975 daunorubicin Drugs 0.000 claims 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000003102 growth factor Substances 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 claims 1
- 238000002513 implantation Methods 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002679 microRNA Substances 0.000 claims 1
- 108020004707 nucleic acids Proteins 0.000 claims 1
- 102000039446 nucleic acids Human genes 0.000 claims 1
- 150000007523 nucleic acids Chemical class 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000004055 small Interfering RNA Substances 0.000 claims 1
- 150000003384 small molecules Chemical class 0.000 claims 1
- 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 1
- 238000011200 topical administration Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31288510P | 2010-03-11 | 2010-03-11 | |
| US61/312,885 | 2010-03-11 | ||
| PCT/SG2011/000100 WO2011112156A1 (en) | 2010-03-11 | 2011-03-11 | Anti-cancer agent delivery vehicles capable of improved laoding |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016053960A Division JP2016153415A (ja) | 2010-03-11 | 2016-03-17 | 負荷率の改善が可能な抗癌剤送達ビヒクル |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013522189A JP2013522189A (ja) | 2013-06-13 |
| JP2013522189A5 true JP2013522189A5 (enExample) | 2014-04-24 |
| JP5954877B2 JP5954877B2 (ja) | 2016-07-20 |
Family
ID=44563737
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012557010A Active JP5954877B2 (ja) | 2010-03-11 | 2011-03-11 | 負荷率の改善が可能な抗癌剤送達ビヒクル |
| JP2016053960A Pending JP2016153415A (ja) | 2010-03-11 | 2016-03-17 | 負荷率の改善が可能な抗癌剤送達ビヒクル |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016053960A Pending JP2016153415A (ja) | 2010-03-11 | 2016-03-17 | 負荷率の改善が可能な抗癌剤送達ビヒクル |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9687464B2 (enExample) |
| EP (1) | EP2544768A4 (enExample) |
| JP (2) | JP5954877B2 (enExample) |
| SG (2) | SG184027A1 (enExample) |
| WO (1) | WO2011112156A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009054813A1 (en) * | 2007-10-23 | 2009-04-30 | Agency For Science, Technology And Research | Method of delivering an anti-cancer agent to a cell |
| EP2435504B1 (en) | 2009-05-29 | 2020-03-11 | Agency For Science, Technology And Research | Flavonoid hydrogel |
| US8933078B2 (en) | 2011-07-14 | 2015-01-13 | Research Cancer Institute Of America | Method of treating cancer with combinations of histone deacetylase inhibitors (HDAC1) substances |
| WO2015034436A1 (en) | 2013-09-03 | 2015-03-12 | Agency For Science, Technology And Research | Polymer-flavonoid conjugates and hydrogels for biomedical applications |
| JP6307631B2 (ja) * | 2014-05-09 | 2018-04-04 | エージェンシー フォー サイエンス， テクノロジー アンド リサーチ | ミセルナノ錯体 |
| WO2015183970A1 (en) * | 2014-05-28 | 2015-12-03 | Stealth Peptides International, Inc. | Therapeutic compositions including flavonoid and uses thereof |
| US11241520B2 (en) | 2014-08-07 | 2022-02-08 | Cook Medical Technologies Llc | Compositions and devices incorporating water-insoluble therapeutic agents and methods of the use thereof |
| US9180226B1 (en) | 2014-08-07 | 2015-11-10 | Cook Medical Technologies Llc | Compositions and devices incorporating water-insoluble therapeutic agents and methods of the use thereof |
| US9655998B2 (en) | 2014-08-07 | 2017-05-23 | Cook Medical Technologies Llc | Encapsulated drug compositions and methods of use thereof |
| WO2018124970A1 (en) * | 2016-12-30 | 2018-07-05 | Agency For Science, Technology And Research | A nanocomplex |
| WO2018157081A1 (en) | 2017-02-27 | 2018-08-30 | Research Cancer Institute Of America | Compositions, methods, systems and/or kits for preventing and/or treating neoplasms |
| US11369585B2 (en) | 2017-03-17 | 2022-06-28 | Research Cancer Institute Of America | Compositions, methods, systems and/or kits for preventing and/or treating neoplasms |
| US12213958B2 (en) | 2017-11-17 | 2025-02-04 | Research Cancer Institute Of America | Compositions, methods, systems and/or kits for preventing and/or treating neoplasms |
| CN111973754A (zh) * | 2019-05-21 | 2020-11-24 | 杭州磐田生物技术有限公司 | 含药物纳米颗粒及其制备方法和应用 |
| WO2023224883A1 (en) * | 2022-05-16 | 2023-11-23 | Suntec Medical, Inc. | Method for treating autoimmune disease |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6586612B2 (en) * | 2001-11-16 | 2003-07-01 | Crompton Corporation | Process for the preparation of secondary and tertiary amino-functional silanes, iminoorganosilanes and/or imidoorganosilanes |
| CN101180319B (zh) * | 2005-05-20 | 2012-06-27 | 新加坡科技研究局 | 醛结合的类黄酮制剂 |
| US7858080B2 (en) * | 2005-05-20 | 2010-12-28 | Agency For Science, Technology And Research | Aldehyde conjugated flavonoid preparations |
| ES2776100T3 (es) * | 2006-03-31 | 2020-07-29 | Massachusetts Inst Technology | Sistema para el suministro dirigido de agentes terapéuticos |
| WO2009054813A1 (en) * | 2007-10-23 | 2009-04-30 | Agency For Science, Technology And Research | Method of delivering an anti-cancer agent to a cell |
| EP2435504B1 (en) * | 2009-05-29 | 2020-03-11 | Agency For Science, Technology And Research | Flavonoid hydrogel |
| US8753687B2 (en) * | 2009-08-11 | 2014-06-17 | Agency For Science, Technology And Research | Particulate hyaluronic acid/flavonoid suspensions for cellular delivery of bioactive agents |
-
2011
- 2011-03-11 WO PCT/SG2011/000100 patent/WO2011112156A1/en not_active Ceased
- 2011-03-11 SG SG2012067575A patent/SG184027A1/en unknown
- 2011-03-11 SG SG10201501829YA patent/SG10201501829YA/en unknown
- 2011-03-11 US US13/634,036 patent/US9687464B2/en not_active Expired - Fee Related
- 2011-03-11 JP JP2012557010A patent/JP5954877B2/ja active Active
- 2011-03-11 EP EP11753700.1A patent/EP2544768A4/en not_active Withdrawn
-
2016
- 2016-03-17 JP JP2016053960A patent/JP2016153415A/ja active Pending
-
2017
- 2017-05-18 US US15/598,407 patent/US20170258757A1/en not_active Abandoned
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