333994-00-6|TAK-220|TAK-220|MFCD28502079-范德生物科技公司

TAK-220

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names：
TAK-220
CAS号：
333994-00-6
MDL Number： MFCD28502079
MF(分子式)： C31H41ClN4O3 MW(分子量)： 553.14
EINECS: Reaxys Number:
Pubchem ID: Brand:BIOFOUNT

TAK-220(333994-00-6)是口服可生物利用的小分子CCR5拮抗剂。目标：CCR； TAK-220是新型趋化因子受体拮抗剂的成员，对CCR5具有高度特异性。TAK-220抑制RANTES与表达CCR5的细胞结合，IC50为3.5 nM，而它抑制膜融合和病毒复制，EC50分别为0.42 nM和0.60至0.68 nM。TAK-220抑制R5 HIV-1（JR-FL）包膜介导的膜融合，IC50值为0.42 nM，但不影响X4 HIV-1（HXB2）包膜介导的膜融合，即使在浓度为1,000 nM。

货品编码	规格	纯度	价格 (¥)	现价(¥)	特价(¥)	库存描述	数量	总计 (¥)
YZM000650-5mg	5mg	99.95%	¥ 3543.00	¥ 3543.00		2-3天	- +	¥ 0.00
YZM000650-1mg	1mg	99.95%	¥ 1462.50	¥ 1462.50		2-3天	- +	¥ 0.00

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中文别名	TAK-220(333994-00-6), TAK-220，TAK 220，TAK220; 1-乙酰基-N- [3- [4-[（4-氨基甲酰基苯基）甲基]哌啶-1-基]丙基] -N-（3-氯-4-甲基苯基）哌啶-4-羧酰胺;
英文别名	TAK-220(333994-00-6), TAK-220, TAK 220, TAK220; 1-acetyl-N-[3-[4-[(4-carbamoylphenyl)methyl]piperidin-1-yl]propyl]-N-(3-chloro-4-methylphenyl)piperidine-4-carboxamide;
CAS号	333994-00-6
SMILES	O=C(C1CCN(C(C)=O)CC1)N(CCCN2CCC(CC3=CC=C(C(N)=O)C=C3)CC2)C4=CC=C(C)C(Cl)=C4
Inchi	InChI=1S/C31H41ClN4O3/c1-22-4-9-28(21-29(22)32)36(31(39)27-12-18-35(19-13-27)23(2)37)15-3-14-34-16-10-25(11-17-34)20-24-5-7-26(8-6-24)30(33)38/h4-9,21,25,27H,3,10-20H2,1-2H3,(H2,33,38)
InchiKey	ASSJTMUEFHUKMJ-UHFFFAOYSA-N
分子式 Formula	C31H41ClN4O3
分子量 Molecular Weight	553.14
闪点 FP	412.1±32.9 °C
熔点 Melting point	No data available
沸点 Boiling point	757.8±60.0 °C at 760 mmHg
Polarizability极化度	61.8±0.5 10-24cm3
密度 Density	1.2±0.1 g/cm3
蒸汽压 Vapor Pressure	0.0±2.6 mmHg at 25°C
溶解度Solubility	生物体外In Vitro:DMSO溶解度≥ 50 mg/mL(90.39 mM)*"≥" means soluble可溶, but saturation unknown溶解度未知.
性状	固体粉末,Power
储藏条件 Storage conditions	-20°C 3 years年 4°C 2 years年 / In solvent溶液中:-80°C 6 months月 -20°C 1 month月

TAK-220(333994-00-6)实验注意事项：
1.实验前需戴好防护眼镜，穿戴防护服和口罩，佩戴手套，避免与皮肤接触。
2.实验过程中如遇到有毒或者刺激性物质及有害物质产生，必要时实验操作需要手套箱内完成以免对实验人员造成伤害
3.实验后产生的废弃物需分类存储，并交于专业生物废气物处理公司处理，以免造成环境污染Experimental considerations:
1. Wear protective glasses, protective clothing and masks, gloves, and avoid contact with the skin during the experiment.
2. The waste generated after the experiment needs to be stored separately, and handed over to a professional biological waste gas treatment company to avoid environmental pollution.

Tags:TAK-220试剂,TAK-220杂质,TAK-220中间体,TAK-220密度,TAK-220溶解度,TAK-220旋光度,TAK-220闪点,TAK-220结构式,TAK-220购买,TAK-220MSDS,

产品说明	TAK-220(333994-00-6)是口服生物利用小分子CCR5拮抗剂。
Introduction	TAK20is a selective and orally bioavailableCCR5antagonist, withIC50s of 3.5nM and1.4nM for inhibition on the binding of RANTES and MIPα to CCR5, respectively, but shows no effect on the binding to CCR1, CCR2b, CCR3, CCR4, or CCR7; TAK20 also selectively inhibitsHIV, withEC50s of 1.2nM (HIVKK)0.72nM(HIVCTV)1.7nM(HIVHKW)1.7nM(HIVHNK)0.93nM(HIV HTN)and0.55nM(HIV HHA)andEC90s of 12 nM(HIV KK)5nM(HIV CTV)12nM(HIV HKW)28nM(HIV HNK)15nM(HIV HTN)and4nM(HIV HHA)in PBMCs.
Application1	TAK-220(333994-00-6)是口服生物利用小分子CCR5拮抗剂。TAK-220是GPCR / G蛋白；可用于免疫学的炎症。
Application2	(333994-00-6)TAK-220 是一种有效的选择性的可口服的CCR5拮抗剂够抑制 RANTES，MIP-1α 与 CCR5 结合，IC50值分别是 3.5 nM 和 1.4 nM，但是对 CCR1，CCR2b，CCR3，CCR4 或者 CCR7 无作用; TAK-220 也可选择性地抑制HIV-1，在外周单核细胞中，EC50值分别是 1.2 nM (HIV-1 KK)，0.72 nM (
Application3	0.72 nM (HIV-1 CTV)，1.7 nM (HIV-1 HKW)，1.7 nM (HIV-1 HNK)，0.93 nM (HIV-1 HTN) 和 0.55 nM (HIV-1 HHA)，EC90值分别是 12 nM (HIV-1 KK)，5 nM (HIV-1 CTV)，12 nM (HIV-1 HKW)，28 nM (HIV-1 HNK)，15 nM (HIV-1 HTN) 及 4

TAK-220(333994-00-6)药理学：

※TAK-220是GPCR / G蛋白；可用于免疫学的炎症。

※TAK-220是口服可生物利用的小分子CCR5拮抗剂。目标：CCR； TAK-220是新型趋化因子受体拮抗剂的成员，对CCR5具有高度特异性。TAK-220抑制RANTES与表达CCR5的细胞结合，IC50为3.5 nM，而它抑制膜融合和病毒复制，EC50分别为0.42 nM和0.60至0.68 nM。TAK-220抑制R5 HIV-1（JR-FL）包膜介导的膜融合，IC50值为0.42 nM，但不影响X4 HIV-1（HXB2）包膜介导的膜融合，即使在浓度为1,000 nM。

※TAK-220是一种选择性CCR5拮抗剂，具有IC₅₀3.5 nM和1.4 nM分别抑制CHO细胞中RANTES和MIP-1α与CCR5的结合，但对CCR1，CCR2b，CCR3，CCR4或CCR7的结合没有影响。TAK-220（0-1000 nM）与CCR5相互作用，但与RANTES不相互作用，并抑制CCR5介导的Casup> 2+信号传导。TAK-220通过IC抑制R5 HIV-1（JR-FL）包膜介导的膜融合₅₀值为0.42 nM，但不会改变X4 HIV-1（HXB2）包膜介导的膜融合。TAK-220还可以通过EC选择性抑制HIV-1₅₀分别为1.2 nM（HIV-1 KK），0.72 nM（HIV-1 CTV），1.7 nM（HIV-1 HKW），1.7 nM（HIV-1 HNK），0.93 nM（HIV-1 HTN）和0.55 nM （HIV-1 HHA）和EC₉₀12 nM（HIV-1 KK），5 nM（HIV-1 CTV），12 nM（HIV-1 HKW），28 nM（HIV-1 HNK），15 nM（HIV-1 HTN）和4 nM PBMC中的（HIV-1 HHA）。TAK-220对R5分离物具有强抑制活性，具有IC₅₀抗HIV-1 R5-08的浓度为3.12 nM，抗HIV-1 R5-06的浓度为13.47 nM，抗HIV-1 R5-18的浓度为2.26 nM。TAK-220（> 100 nM）对未感染的PBMC无毒性。

警示图
危险性	warning
危险性警示	Not available
安全声明	H303吞入可能有害+H313皮肤接触可能有害+H2413吸入可能对身体有害
安全防护	P264处理后彻底清洗+P280戴防护手套/穿防护服/戴防护眼罩/戴防护面具+P305如果进入眼睛+P351用水小心冲洗几分钟+P338取出隐形眼镜（如果有）并且易于操作,继续冲洗+P337如果眼睛刺激持续+P2393获得医疗建议/护理
备注	实验过程中防止吸入、食入，做好安全防护

Takashima K, et al. Highly potent inhibition of human immunodeficiency virus type 1 replication by TAK-220, an orally bioavailable small-molecule CCR5 antagonist. Antimicrob Agents Chemother. 2005 Aug

Tremblay CL, et al. TAK-220, a novel small-molecule CCR5 antagonist, has favorable anti-human immunodeficiency virus interactions with other antiretrovirals in vitro. Antimicrob Agents Chemother. 2005

Binding site exploration of CCR5 using in silico methodologies: a 3D-QSAR approach Archives of Pharmacal Research 2013 23325486

Selective and Dual Targeting of CCR2 and CCR5 Receptors: A Current Overview Chemokines 2014

What’s New in HIV/AIDS? Chemokine Receptor Antagonists: A New Era of HIV Therapy? Infection 2005 16258879

TAK-220(333994-00-6)参考文献：

1.New advances in HIV entry inhibitors development.
Rusconi S;Scozzafava A;Mastrolorenzo A;Supuran CT Curr Drug Targets Infect Disord. 2004 Dec;4(4):339-55.

Considerable advances have been made in the last years in the design of derivatives acting as inhibitors of HIV entry and fusion. The discovery of chemokines focused the attention on cellular coreceptors used by the virus for entering within cells, and consequently the various steps of such processes have been characterized in detail. Intense research led to a wide range of effective compounds that are able to inhibit the initial steps of HIV life cycle. All steps in the process of HIV entry into the cell may be targeted by specific compounds that may be developed as novel types of antiretrovirals. Thus, several inhibitors of the gp120-CD4 interaction have been detected so far (zintevir, FP-21399 and BMS-378806 in clinical trials). Small molecule chemokine receptor antagonists acting as HIV entry inhibitors also were described in the last period, which interact both with the CXCR4 coreceptor (such as AMD3100; AMD3465; ALX40-4C; T22, T134 and T140), or which are antagonist of the CCR5 coreceptor (TAK-779, TAK-220, SCH-C, SCH-D, E913, AK-602, UK-427857 and NSC 651016 in clinical trials), together with new types of fusion inhibitors possessing the same mechanism of action as enfuvirtide (such as T1249).

2.Analysis of binding sites for the new small-molecule CCR5 antagonist TAK-220 on human CCR5.
Nishikawa M;Takashima K;Nishi T;Furuta RA;Kanzaki N;Yamamoto Y;Fujisawa J Antimicrob Agents Chemother. 2005 Nov;49(11):4708-15.

G protein-coupled receptor CCR5 is the main coreceptor for macrophage-tropic human immunodeficiency virus type 1 (HIV-1), and various small-molecule CCR5 antagonists are being developed to treat HIV-1 infection. It has been reported that such CCR5 antagonists, including TAK-779, bind to a putative binding pocket formed by transmembrane domains (TMs) 1, 2, 3 and 7 of CCR5, indicating the importance of the conformational changes of the TMs during virus entry. In this report, using a single-round infection assay with human CCR5 and its substitution mutants, we demonstrated that a new CCR5 antagonist, TAK-220, shares the putative interacting amino acid residues Asn252 and Leu255 in TM6 with TAK-779 but also requires the distinct residues Gly163 and Ile198 in TMs 4 and 5, respectively, for its inhibitory effect. We suggested that, together with molecular models of the interactions between the drugs and CCR5, the inhibitory activity of TAK-220 could involve direct interactions with amino acid residues in TMs 4, 5, and 6 in addition to those in the previously postulated binding pocket. The possible interaction of drugs with additional regions of the CCR5 molecule would help to develop a new small-molecule CCR5 antagonist.

3.Discovery of a piperidine-4-carboxamide CCR5 antagonist (TAK-220) with highly potent Anti-HIV-1 activity.
Imamura S;Ichikawa T;Nishikawa Y;Kanzaki N;Takashima K;Niwa S;Iizawa Y;Baba M;Sugihara Y J Med Chem. 2006 May 4;49(9):2784-93.

We incorporated various polar groups into previously described piperidine-4-carboxamide CCR5 antagonists to improve their metabolic stability in human hepatic microsomes. Introducing a carbamoyl group into the phenyl ring of the 4-benzylpiperidine moiety afforded the less lipophilic compound 5f, which possessed both high metabolic stability and good inhibitory activity of HIV-1 envelope-mediated membrane fusion (IC(50) = 5.8 nM). Further optimization to increase potency led to the discovery of 1-acetyl-N-{3-[4-(4-carbamoylbenzyl)piperidin-1-yl]propyl}-N-(3-chloro-4-methylphenyl)piperidine-4-carboxamide (5m, TAK-220), which showed high CCR5 binding affinity (IC(50) = 3.5 nM) and potent inhibition of membrane fusion (IC(50) = 0.42 nM), as well as good metabolic stability. Compound 5m strongly inhibited the replication of CCR5-using HIV-1 clinical isolates in human peripheral blood mononuclear cells (mean EC(50) = 1.1 nM, EC(90) = 13 nM) and exhibited a good pharmacokinetic profile in monkeys (BA = 29%). This compound has been chosen as a clinical candidate for further development.

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