(S)-柚皮素 | 480-41-1

• 物质功能分类: 生物化工 - 天然产物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: (S)-柚皮素
• 中文别名: 柚皮素；柑橘素；柚皮苷元；4",5,7-三羟基黄酮；柚皮素(4',5,7-三羟基黄酮)
• 英文名称: naringenin
• 英文别名: (2S)-naringenin；4′,5,7-trihydroxy flavanone；4',5,7-trihydroxyflavanone；5,7,4'-trihydroxyflavanone；(S)-naringenin；(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one；5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one；naringenine；narigenin；NAR；(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 480-41-1
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: FTVWIRXFELQLPI-ZDUSSCGKSA-N

物化性质

• 熔点：
  247-250 °C(lit.)
• 沸点：
  335.31°C (rough estimate)
• 密度：
  1.2066 (rough estimate)
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）
• LogP：
  2.520
• 物理描述：
  Solid
• 碰撞截面：
  166.8 Ų [M-H]-; 166.9 Ų [M+H]+
• 稳定性/保质期：

  避免与不相容材料接触，尤其是强氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn,Xi
• 安全说明：
  S26,S36,S37/39
• 危险类别码：
  R22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2932999099
• 危险品运输编号：
  OTH
• RTECS号：
  DJ2981530
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封保存，宜存放在阴凉干燥的仓库中。

SDS

Name:	4 5 7- Trihydroxyflavanone 97+%(tlc) Material Safety Data Sheet
Synonym:	Naringenin
CAS:	480-41-1

Section 1 - Chemical Product MSDS Name:4 5 7- Trihydroxyflavanone 97+%(tlc) Material Safety Data Sheet
Synonym:Naringenin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
480-41-1	4',5,7-Trihydroxyflavanone	97+%	207-550-2

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 480-41-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: beige - brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 247 - 250 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula:
Molecular Weight: 272.26

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 480-41-1: DJ2981530 LD50/LC50:
Not available.
Carcinogenicity:
4',5,7-Trihydroxyflavanone - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 480-41-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 480-41-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 480-41-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

柚皮素是柚皮甙的甙元，属于二氢黄酮类化合物。常温下为白色针状结晶（溶于甲醇），能溶于乙醇、乙醚和苯，几乎不溶于水。盐酸镁粉反应呈樱红色，四氢硼钠反应呈红紫色，Molish反应阴性。自然界中主要来源于蔷薇科植物樱花的花蕾及漆树科植物梗树的果实核壳。

黄酮类化合物的母核结构相似，多数成分脂溶性和水溶性不理想，生物利用度低。通过对其结构进行修饰，引入脂溶性或水溶性强的基团，可以提高其脂溶性或水溶性，从而提升生物利用度。结构修饰主要包括羟基的烷基化、酰化、磺化、苷化及形成金属配合物等。

应用

柚皮素具有抗菌、抗炎、抗氧化、止咳祛痰、降血脂、抗癌、解痉、清除自由基、预防和治疗肝病、抑制血小板凝结及抗粥样动脉硬化等多种作用，广泛应用于医药和食品领域。其具体效果如下：

1. 抗菌：对金黄色葡萄球菌、大肠杆菌、痢疾杆菌和伤寒杆菌等均有较强的抗菌作用。对真菌也有作用，可降低稻瘟菌感染率40-90%，且对人体和家畜无毒。

2. 抗炎：每天注射20 mg/kg于大鼠腹腔内，能明显抑制羊毛球引起的炎症反应。

3. 抗癌：对大鼠白血病L1210和肉瘤具有活性。

4. 解痉及利胆：为黄酮类化合物中作用较强的品种之一。柚皮素能够显著增加实验动物的胆汁分泌量。

生物活性

Naringenin (NSC 34875, S-Dihydrogenistein, NSC 11855, Salipurol) 是一种来源于食用植物的主要黄酮类化合物，对人体健康有益，具有生物活性。它是一种抗氧化剂、自由基清除剂，并能启动碳水化合物代谢和调节免疫系统。

靶点

• CYP1A2

体外研究

Naringenin 是一种黄酮类化合物，对人体健康有诸多益处。作为一种抗氧化剂、自由基清除剂、抗炎药、糖代谢促进剂及免疫系统的调节剂，Naringenin 在葡萄柚中广泛存在。在体外实验中，这种物质能够减少对DNA的氧化性损伤，并证明了其对人类细胞色素P450同种型CYP1A2具有抑制作用，从而改变某些药物的人类药代动力学。

体内研究

在血糖正常的和非胰岛素依赖型糖尿病大鼠模型中，灌胃给予Naringenin (50 毫克/千克) 后，显著降低了血浆葡萄糖浓度。Naringenin 在小鼠中的LD50大于5克/千克，在大鼠中的LD50同样大于5克/千克。

化学性质

• 溶于：乙醇、乙醚和苯
• 几乎不溶于：水

用途

Naringenin 是一种具有抗菌、抗炎、抗癌及解痉利胆作用的天然黄酮类化合物。它还是一种抗氧化剂，自由基清除剂，抗炎化合物，并能促进碳水化合物代谢和调节免疫系统。研究表明，在体外实验中，Naringenin 可减少DNA氧化性损伤，并抑制病毒通过PPAR介导的机制进行长期装配。

反应信息

• 作为反应物：
  描述：

  (S)-柚皮素 在 FLAVONOL SYNTHASE 、 FLAVANONE 3-HYDROXYLASE 、 TrxA-His-AtF₃H 、 TrxA-His-AtFLS₁ 作用下， 以 aq. buffer 为溶剂， 反应 3.5h， 生成 山奈酚
  参考文献：
  名称：

  柚皮素生产山emp酚的体外多酶合成系统的开发和优化

  摘要：

  开发并优化了体外多酶合成系统，以在单个反应管中高效生产山ka酚。将山fer酚生物合成途径中的两个关键基因Atf3h和Atfls1克隆到原核表达载体中，并在大肠杆菌中过表达。。通过亲和层析纯化重组蛋白，并分别显示出黄烷酮3-羟化酶和黄酮醇合酶的活性，随后开发了用于生产山ka酚的体外合成系统。该系统在100 mM Tris-HCl（pH 7.2）中包含8.2 mMα-酮戊二酸，0.01 mM亚铁离子，0.4％抗坏血酸钠，25μg/ mL的每种重组酶和10％甘油。当反应在40°C下进行40-50分钟时，山ka酚的收率为37.55±1.62 mg / L，从NRN到KMF的转化率为55.89％±2.74％。总体而言，该系统提供了一种经济有效地生产山efficient酚的有前途和高效的方法。

  DOI：

  10.1021/acs.jafc.8b01299
• 作为产物：
  描述：

  柚皮苷 在 硫酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (S)-柚皮素
  参考文献：
  名称：

  铜（II）柚皮素复合物的合成，结构解析和抗自由基活性。

  摘要：

  从环境和经济的角度来看，将类黄酮的提取和衍生化与柑橘加工工业相结合是有吸引力的。在目前的工作中，将水解后的葡萄柚工业中的水：乙醇混合物通过“绿色”提取获得的类黄酮柚皮苷被水解以获得柚皮苷。该类黄酮用于合成复杂的反式-二（水）双（7-羟基-2-（4-羟基苯基）-4-氧代-5-苯并五氢吡喃并）铜（II）。通过光谱技术（UV / Vis，IR，拉曼，NMR和EPR）和热分析（TG和DSC）对这种化合物进行表征。然后，通过单晶X射线衍射分析通过在DMF中溶解和重结晶获得的络合物的单晶。这是柑橘类黄酮复合物晶体结构的首次报道。此外，测定了其对2,2-二苯基-1-吡啶并肼基（DPPH）的抗自由基活性，并将其与柚皮苷进行了比较，表明与铜的配位作用增强了柚皮苷的抗自由基活性。根据进行的Mulliken人口分析，铜有利于所产生自由基的离域和稳定化，因为它充当电子密度受体。

  DOI：

  10.1007/s10534-019-00187-3
• 作为试剂：
  描述：

  肌苷 在 human purine nucleoside phosphorylase 、 (S)-柚皮素 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.05h， 生成 次黄嘌呤
  参考文献：
  名称：

  柑橘类黄酮柚皮苷和橙皮苷对嘌呤核苷磷酸化酶的抑制作用：光谱，原子力显微镜和分子模型研究

  摘要：

  在这项工作中，评估了两种柑橘类黄酮柚皮素和橙皮素对人嘌呤核苷磷酸化酶（hPNP）的抑制作用及其结合机理。酶动力学结果表明，柚皮苷和橙皮苷通过混合型可逆地抑制hPNP，IC 50值为4.83×10 -4  M和5.32×10 -4 M分别。分子模型分析表明，柚皮素和橙皮素都通过产生多种力而直接结合到活性位点，这些力包括氢键，与hPNP的His64，Glu201，Ser220，His257，Phe200和Val217残基的π-π和π-烷基相互作用。抑制hPNP活性。此外，通过三维荧光，圆二色性和原子力显微镜的构象分析表明，柚皮苷和橙皮素与hPNP的结合诱导了hPNP的微环境，二级结构和形态的变化。这些结果表明，占据柚皮素和橙皮素诱导的活性位点和酶构象扰动是减少hPNP活性抑制的主要原因，

  DOI：

  10.1016/j.molliq.2020.112954

文献信息

• [EN] SYNTHETIC ANALOGUES OF XANTHOHUMOL<br/>[FR] ANALOGUES SYNTHÉTIQUES DU XANTHOHUMOL
  申请人：UNIV PISA

  公开号：WO2014167481A1

  公开（公告）日：2014-10-16

  The present invention relates to novel synthetic analogues of xanthohumol and the use thereof.

  本发明涉及新型黄葛素合成类似物及其用途。
• Nitrogen-containing naringenin derivatives for reversing multidrug resistance in cancer
  作者：Ricardo J. Ferreira、Márió Gajdács、Annamária Kincses、Gabriella Spengler、Daniel J.V.A. dos Santos、Maria-José U. Ferreira

  DOI：10.1016/j.bmc.2020.115798

  日期：2020.12

  the flavanone core towards better multidrug resistance (MDR) reversal agents, alkylation reactions and chemical modification of the carbonyl moiety was performed (15–39). Compounds structures were assigned mainly by 1D and 2D NMR experiments. Compounds 1–39 were assessed as MDR reversers, in human ABCB1-transfected mouse T-lymphoma cells, overexpressing P-glycoprotein (P-gp). The results revealed that

  柚皮素（1），分离自大戟pedroi，先前衍生得到的化合物2 - 13。在这项研究中，针对扩展朝向更好多药耐药性（MDR）逆转剂，烷基化反应和化学修饰的，进行羰基部分（黄烷酮芯的类似物的池15 - 39）。化合物结构主要通过1D和2D NMR实验确定。化合物1 - 39被评估为MDR反向，在人ABCB1转染的小鼠Ť -lymphoma细胞，过表达P-糖蛋白（P-gp）的。结果表明，OC-7处的甲基化，以及在C-4或C-4'处引入氮原子和芳族部分，显着提高了活性，是化合物27和37最强的P-gp调节剂，比维拉帕米活性更高。在组合测定中，所选化合物与阿霉素的协同相互作用证实了结果。虽然分子对接表明黄烷酮衍生物起竞争性调节剂的作用，但分子动力学表明二甲基化促进了与调节剂结合位点的结合。此外，黄烷酮还可能在两个核苷酸结合域中都与邻近的ATP结合位点相互作用，从而推测了变构作用模式。
• Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches
  作者：Baojian Wu、Xiaoqiang Wang、Shuxing Zhang、Ming Hu

  DOI：10.1007/s11095-012-0666-z

  日期：2012.6

  Catalytic selectivity of human UGT1A9, an important membrane-bound enzyme catalyzing glucuronidation of xenobiotics, was determined experimentally using 145 phenolics and analyzed by 3D-QSAR methods. Catalytic efficiency of UGT1A9 was determined by kinetic profiling. Quantitative structure activity relationships were analyzed using CoMFA and CoMSIA techniques. Molecular alignment of substrate structures was made by superimposing the glucuronidation site and its adjacent aromatic ring to achieve maximal steric overlap. For a substrate with multiple active glucuronidation sites, each site was considered a separate substrate. 3D-QSAR analyses produced statistically reliable models with good predictive power (CoMFA: q2 = 0.548, r2 = 0.949, r pred 2  = 0.775; CoMSIA: q2 = 0.579, r2 = 0.876, r pred 2  = 0.700). Contour coefficient maps were applied to elucidate structural features among substrates that are responsible for selectivity differences. Contour coefficient maps were overlaid in the catalytic pocket of a homology model of UGT1A9, enabling identification of the UGT1A9 catalytic pocket with a high degree of confidence. CoMFA/CoMSIA models can predict substrate selectivity and in vitro clearance of UGT1A9. Our findings also provide a possible molecular basis for understanding UGT1A9 functions and substrate selectivity.

  通过实验使用145种酚类化合物，并通过3D-QSAR方法分析，确定了人UGT1A9的催化选择性。UGT1A9是一种重要的膜结合酶，催化外源性物质的葡糖醛酸化反应。通过动力学分析确定了UGT1A9的催化效率。使用CoMFA和CoMSIA技术分析了定量结构活性关系。通过将葡糖醛酸化位点及其相邻的芳香环重叠，实现了底物结构的最大立体重叠。对于具有多个活性葡糖醛酸化位点的底物，每个位点被视为单独的底物。3D-QSAR分析产生了统计上可靠的模型，具有良好的预测能力（CoMFA：q2=0.548，r2=0.949，r pred 2=0.775；CoMSIA：q2=0.579，r2=0.876，r pred 2=0.700）。通过轮廓系数图阐明了底物中负责选择性差异的结构特征。将轮廓系数图叠加在UGT1A9的同源模型的催化口袋中，能够高度自信地识别UGT1A9的催化口袋。CoMFA/CoMSIA模型可以预测底物的选择性和UGT1A9的体外清除率。我们的发现还提供了理解UGT1A9功能和底物选择性的可能分子基础。
• SELF-ASSEMBLY OF THERAPEUTIC AGENT-PEPTIDE NANOSTRUCTURES
  申请人：Ohio State Innovation Foundation

  公开号：US20140155577A1

  公开（公告）日：2014-06-05

  Disclosed are conjugates of hydrophobic drugs linked to protected or unprotected amino acids or peptides. The disclosed conjugates are amphiphilic and can self assemble into nanotubes. Nanotubes comprising the conjugates are also described and can have high loading of the drug and protect it from degradation or elimination. The nanotubes are well suited to deliver hydrophobic and unstable drugs to individuals.

  揭示了与受保护或未受保护的氨基酸或肽连接的疏水药物的共轭物。所述的共轭物是两性的，可以自组装成纳米管。还描述了包含这些共轭物的纳米管，可以具有高药物载荷并保护药物免受降解或排泄。这些纳米管非常适合向个体输送疏水和不稳定的药物。
• [EN] ALKYNE-, AZIDE- AND TRIAZOLE-CONTAINING FLAVONOIDS AS MODULATORS FOR MULTIDRUG RESISTANCE IN CANCERS<br/>[FR] FLAVONOÏDES CONTENANT DE L'ALCYNE, DE L'AZIDE ET DU TRIAZOLE UTILISÉS COMME MODULATEURS DE RÉSISTANCE MULTIPLE AUX MÉDICAMENTS DANS LES CANCERS
  申请人：UNIV HONG KONG POLYTECHNIC

  公开号：WO2013127361A1

  公开（公告）日：2013-09-06

  A triazole bridged flavonoid dimer compound library was efficiently constructed via the cycloaddition reaction of a series of flavonoid-containing azides (Az 1-15) and alkynes (Ac 1-17). These triazole bridged flavonoid dimers and their precursor alkyne- and azide-continaing flavonoids were screened for their ability to modulate multidrug resistance (MDR) in P-gp-overexpressed cell line (LCC6MDR), MRPl-overexpressed cell line (2008/MRPl) and BCRP-overexpressed cell line (HEK293/R2 and MCF7-MX100). Generally, they displayed very promising MDR reversal activity against P-gp-, MRPl- and BCRP-mediated drug resistance. Moreover, they showed different levels of selectivity for various transporters. Overall, they can be divided into mono-selective, dual-selective and multi-selective modulators for the P-gp, MRPl and BCRP transporters. The EC50 values for reversing paclitaxel resistance (141 - 340 nM) of LCC6MDR cells, DOX (78 - 590 nM) and vincristine (82 - 550 nM) resistance of 2008/MRPl cells and topotecan resistance (0.9 - 135 nM) of HEK293/R2 and MCF7-MX100 cells were at nanomolar range. Importantly, a number of compounds displayed EC50 at or below 10 nM in BCRP-overexpressed cell lines, indicating that these bivalent triazoles more selectively inhibit BCRP transporter than the P-gp and MRPl transporters. Most of the dimers are notably safe MDR chemosensitizers as indicated by their high therapeutic index values.

  通过对一系列含有三唑基的黄酮类化合物（Az 1-15）和炔烃（Ac 1-17）进行环加成反应，高效构建了一个三唑桥联的黄酮二聚体化合物库。对这些三唑桥联的黄酮二聚体及其前体炔烃和三唑基的黄酮类化合物进行了筛选，以评估它们对P-gp过表达细胞系（LCC6MDR）、MRP1过表达细胞系（2008/MRP1）和BCRP过表达细胞系（HEK293/R2和MCF7-MX100）调节多药耐药性（MDR）的能力。总体而言，它们显示出对P-gp、MRP1和BCRP介导的药物耐药性具有非常有前景的MDR逆转活性。此外，它们对各种转运蛋白显示出不同程度的选择性。总体而言，它们可以分为对P-gp、MRP1和BCRP转运蛋白具有单选择性、双选择性和多选择性调节剂。逆转LCC6MDR细胞对紫杉醇耐药性（141-340 nM）、2008/MRP1细胞对阿霉素（78-590 nM）和长春碱（82-550 nM）耐药性以及HEK293/R2和MCF7-MX100细胞对托泊替康耐药性（0.9-135 nM）的EC50值在纳摩尔范围内。重要的是，许多化合物在BCRP过表达的细胞系中显示出EC50在或低于10 nM，表明这些双价三唑更具选择性地抑制BCRP转运蛋白而不是P-gp和MRP1转运蛋白。大多数二聚体根据其高治疗指数值显示出明显安全的MDR化疗敏感化剂特性。