306305-07-7|4'-乙炔基-2'-脱氧腺苷|4'-Ethynyl-2'-deoxyadenosine|-范德生物科技公司

4'-乙炔基-2'-脱氧腺苷

NMR下载 COA and HPLC MSDS下载
names：
4'-Ethynyl-2'-deoxyadenosine
CAS号：
306305-07-7
MDL Number：
MF(分子式)： C12H13N5O3 MW(分子量)： 275.26
EINECS: Reaxys Number:
Pubchem ID:481527 Brand:BIOFOUNT

4'-乙炔基-2'-脱氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)是一种有效的核苷逆转录酶 (RT)的抑制剂,是一种有效的抗病毒药物,对耐药HIV变异型具有较强的抑制作用，在MT-4细胞中，EC50值是 98 nM.

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中文别名	4'-乙炔基-2'-脱氧腺苷(306305-07-7);4'-E-dA;（2R，3S，5R）-5-（6-氨基嘌呤-9-基）-2-乙炔基-2-（羟甲基）四氢呋喃-3-醇；
英文别名	4'-Ethynyl-2'-deoxyadenosine(306305-07-7);Adenosine, 2'-deoxy-4'-C-ethynyl-;4'-Ethynyl-2'-deoxyadenosine;4'-ETHYNYL-2'-DEOXYADENOSINE;
CAS号	306305-07-7
SMILES	OC[C@]1(C#C)[C@H](C[C@H](N2C=NC3=C(N=CN=C32)N)O1)O
Inchi	InChI = 1S / C12H13N5O3 / c1-2-12（4-18）7（19）3-8（20-12）17-6-16-9-10（13）14-5-15-11（9） 17 / h1,5-8,18-19H，3-4H2，（H2,13,14,15）/ t7-，8 +，12 + / m0 / s1
InchiKey	HMIGVKANVVLEOA-JOAULVNJSA-N
分子式 Formula	C12H13N5O3
分子量 Molecular Weight	275.26
闪点 FP	No data available
熔点 Melting point	No data available
沸点 Boiling point	608.8±65.0 °C(Predicted)
Polarizability极化度
密度 Density	1+-.0.1 g/cm3(Predicted)
蒸汽压 Vapor Pressure
溶解度Solubility
性状	固体粉末Solid
储藏条件 Storage conditions	请根据产品建议的存储条件进行存储,Please store the product under the recommended condition sin the description.

4'-乙炔基-2'-脱氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)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:4'-E-dA试剂,4'-E-dA杂质,4'-E-dA中间体,4'-E-dA密度,4'-E-dA溶解度,4'-E-dA旋光度,4'-E-dA闪点,4'-E-dA熔点,4'-E-dA购买，4'-E-dA结构式，4'-E-dA熔点，

产品说明	4'-乙炔基-2'-脱氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)是一种有效的核苷逆转录酶 (RT)的抑制剂,是一种有效的抗病毒药物
Introduction	4'-乙炔基-2'-脱氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)a nucleosidereverse transcriptase (RT)inhibitor, is an antiretroviral agent which is potent against drugesistant HIV variants,
Application1	(306305-07-7)4'-Ethynyl-2'-deoxyadenosine (4'-E-dA)是一种有效的核苷逆转录酶 (RT)的抑制剂,是一种有效的抗病毒药物,对耐药HIV变异型具有较强的抑制作用，在MT-4细胞中，EC50值是 98 nM
Application2	4'-乙炔基-2'-脱氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)with anEC50of 98 nM in MT cells for antiIV activity.
Application3

4'-乙炔基-2'-脱氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)药理学：

4'-乙炔基-2'-脱氧腺苷（4'-E-dA），一种核苷逆转录酶（RT）抑制剂，是一种抗逆转录病毒药物，对耐药性HIV变异体有效，在MT-中的EC50为98 nM。 4个细胞具有抗HIV-1活性。

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

Mechanism of inhibition of HIV-1 reverse transcriptase by 4'-Ethynyl-2-fluoro-2'-deoxyadenosine triphosphate, a translocation-defective reverse transcriptase inhibitor The Journal of biological chemis

2'-deoxy-4'-C-ethynyl-2-halo-adenosines active against drug-resistant human immunodeficiency virus type 1 variants The international journal of biochemistry & cell biology

2'-deoxy-4'-C-ethynyl-2-fluoroadenosine, a nucleoside reverse transcriptase inhibitor, is highly potent against all human immunodeficiency viruses type 1 and has low toxicity Chemical record (New York

Design, efficient synthesis, and anti-HIV activity of 4'-C-cyano- and 4'-C-ethynyl-2'-deoxy purine nucleosides Nucleosides, nucleotides & nucleic acids

Synthesis of 4'-C-ethynyl and 4'-C-cyano purine nucleosides from natural nucleosides and their anti-HIV activity Nucleosides, nucleotides & nucleic acids

4'-乙炔基-2'-脱氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)参考文献：

1、4'-C-substituted-2'-deoxynucleosides: a family of antiretroviral agents which are potent against drug-resistant HIV variants H Ohrui 1, H Mitsuya
H Ohrui 1, H Mitsuya

Abstract In the past years, a variety of 4'-C-substituted-2'-deoxynucleosides (4'SdNs) were designed, synthesized, and examined as potential therapeutics against human immunodeficiency virus (HIV) infection and certain such analogues proved to exert potent activity against HIV-1 in vitro. Unlike currently available nucleoside reverse transcriptase (RT) inhibitors such as 3'-azido-3'-deoxythymidine (AZT), which have the 2',3'-dideoxy configuration and thereby cause DNA chain termination in the elongating proviral DNA, 4'SdNs do retain the 3'-alpha-OH moiety but also appear to work against retrovirus as proviral DNA chain terminators. Several 4'SdNs have been shown to be active against various laboratory and clinical HIV-1 strains including known drug-resistant HIV-1 variants. Among such 4'SdNs is 4'-azido-2'-deoxythymidine (4'-AZT) which exerts potent antiviral activity against wild type and AZT-resistant clinical HIV strains. More anti-HIV 4'SdNs have recently been reported including 4'-ethynylthymidine, 4'-ethynyl-2'-deoxy-D-ribofuranosyl-2,6-diaminopurine (4'-E-dDAP), 4'-ethynyl-2'-deoxyguanosine (4'-E-dG) and 4'-ethynyl-2'-deoxyadenosine (4'-E-dA). The latter three analogues are highly potent against HIV-1 and HIV-2 with EC50 values ranging from 0.0003 to 0.01 microM and have favorable cytotoxicity profiles with selective index (SI) values ranging from 975 to 2600. These 4'-ethynyl-2'-deoxynucleosides also exert potent activity against all known drug-resistant HIV-1 variants including the multi-dideoxynucleoside-resistant HIV and the variants with the 6-base pair inserts. Some of these compounds have favorable pharmacological properties and further development as potential therapeutics against HIV-1 infection is warranted.

2、Synthesis of nucleotide analogues, EFdA, EdA and EdAP, and the effect of EdAP on hepatitis B virus replication
Mai Kamata 1, Toshifumi Takeuchi 1, Ei Hayashi 1, Kazane Nishioka 1 2, Mizuki Oshima 1 2, Masashi Iwamoto 1 2, Kota Nishiuchi 1, Shogo Kamo 1, Shusuke Tomoshige 1, Koichi Watashi 1 2, Shinji Kamisuki 3, Hiroshi Ohrui 4, Fumio Sugawara 1, Kouji Kuramochi

Abstract 4'-Ethynyl-2-fluoro-2'-deoxyadenosine (EFdA) and 4'-ethynyl-2'-deoxyadenosine (EdA) are nucleoside analogues which inhibit human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. EdAP, a cyclosaligenyl (cycloSal) phosphate derivative of EdA, inhibits the replication of the influenza A virus. The common structural feature of these compounds is the ethynyl group at the 4'-position. In this study, these nucleoside analogues were prepared by a common synthetic strategy starting from the known 1,2-di-O-acetyl-D-ribofuranose. Biological evaluation of EdAP revealed that this compound reduced hepatitis B virus (HBV) replication dose-dependently without cytotoxicity against host cells tested in this study.

3、Effects of substitutions at the 4' and 2 positions on the bioactivity of 4'-ethynyl-2-fluoro-2'-deoxyadenosine
Karen A Kirby 1, Eleftherios Michailidis, Tracy L Fetterly, Musetta A Steinbach, Kamalendra Singh, Bruno Marchand, Maxwell D Leslie, Ariel N Hagedorn, Eiichi N Kodama, Victor E Marquez, Stephen H Hughes, Hiroaki Mitsuya, Michael A Parniak, Stefan G Sarafianos

Abstract Nucleos(t)ide reverse transcriptase inhibitors (NRTIs) form the backbone of most anti-HIV therapies. We have shown that 4'-ethynyl-2-fluoro-2'-deoxyadenosine (EFdA) is a highly effective NRTI; however, the reasons for the potent antiviral activity of EFdA are not well understood. Here, we use a combination of structural, computational, and biochemical approaches to examine how substitutions in the sugar or adenine rings affect the incorporation of dA-based NRTIs like EFdA into DNA by HIV RT and their susceptibility to deamination by adenosine deaminase (ADA). Nuclear magnetic resonance (NMR) spectroscopy studies of 4'-substituted NRTIs show that ethynyl or cyano groups stabilize the sugar ring in the C-2'-exo/C-3'-endo (north) conformation. Steady-state kinetic analysis of the incorporation of 4'-substituted NRTIs by RT reveals a correlation between the north conformation of the NRTI sugar ring and efficiency of incorporation into the nascent DNA strand. Structural analysis and the kinetics of deamination by ADA demonstrate that 4'-ethynyl and cyano substitutions decrease the susceptibility of adenosine-based compounds to ADA through steric interactions at the active site. However, the major determinant for decreased susceptibility to ADA is the 2-halo substitution, which alters the pKa of N1 on the adenine base. These results provide insight into how NRTI structural attributes affect their antiviral activities through their interactions with the RT and ADA active sites.

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