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 (OSRAM) | 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 (OSRAM) |
| EP (1) | EP2544768A4 (OSRAM) |
| JP (2) | JP5954877B2 (OSRAM) |
| SG (2) | SG184027A1 (OSRAM) |
| WO (1) | WO2011112156A1 (OSRAM) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5612475B2 (ja) * | 2007-10-23 | 2014-10-22 | 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 | 細胞に抗ガン物質を送達する方法 |
| JP5843758B2 (ja) | 2009-05-29 | 2016-01-13 | 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 | フラボノイドハイドロゲル |
| 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 |
| JP6484633B2 (ja) * | 2013-09-03 | 2019-03-13 | エイジェンシー フォー サイエンス，テクノロジー アンド リサーチ | ポリマー−フラボノイド接合体およびバイオメディカル応用のためのヒドロゲル |
| CN106659708B (zh) * | 2014-05-09 | 2022-05-10 | 新加坡科技研究局 | 胶球奈米复合物 |
| WO2015183970A1 (en) * | 2014-05-28 | 2015-12-03 | Stealth Peptides International, Inc. | Therapeutic compositions including flavonoid and uses thereof |
| US9655998B2 (en) | 2014-08-07 | 2017-05-23 | Cook Medical Technologies Llc | Encapsulated drug compositions and methods of 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 |
| 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 |
| WO2018124970A1 (en) * | 2016-12-30 | 2018-07-05 | Agency For Science, Technology And Research | A nanocomplex |
| US11890292B2 (en) | 2017-02-27 | 2024-02-06 | Research Cancer Institute Of America | Compositions, methods, systems and/or kits for preventing and/or treating neoplasms |
| WO2018170457A1 (en) | 2017-03-17 | 2018-09-20 | 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 |
| EP4525922A1 (en) * | 2022-05-16 | 2025-03-26 | 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 |
| WO2006124000A1 (en) * | 2005-05-20 | 2006-11-23 | Agency For Science, Technology And Research | Aldehyde conjugated flavonoid preparations |
| US7858080B2 (en) * | 2005-05-20 | 2010-12-28 | Agency For Science, Technology And Research | Aldehyde conjugated flavonoid preparations |
| JP2009534309A (ja) * | 2006-03-31 | 2009-09-24 | マサチューセッツ インスティテュート オブ テクノロジー | 治療剤の標的化送達のためのシステム |
| JP5612475B2 (ja) * | 2007-10-23 | 2014-10-22 | 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 | 細胞に抗ガン物質を送達する方法 |
| JP5843758B2 (ja) * | 2009-05-29 | 2016-01-13 | 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 | フラボノイドハイドロゲル |
| EP2464388B1 (en) | 2009-08-11 | 2017-05-10 | Agency for Science, Technology and Research | Particulate hyaluronic acid formulations for cellular delivery of bioactive agents |
-
2011
- 2011-03-11 EP EP11753700.1A patent/EP2544768A4/en not_active Withdrawn
- 2011-03-11 US US13/634,036 patent/US9687464B2/en not_active Expired - Fee Related
- 2011-03-11 SG SG2012067575A patent/SG184027A1/en unknown
- 2011-03-11 JP JP2012557010A patent/JP5954877B2/ja active Active
- 2011-03-11 WO PCT/SG2011/000100 patent/WO2011112156A1/en not_active Ceased
- 2011-03-11 SG SG10201501829YA patent/SG10201501829YA/en unknown
-
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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