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4'-乙炔基-2'-脫氧腺苷

NMR下載 COA and HPLC MSDS下載
names：
4'-Ethynyl-2'-deoxyadenosine
CAS號(hào)：
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'-脫氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)是一種有效的核苷逆轉(zhuǎn)錄酶 (RT)的抑制劑,是一種有效的抗病毒藥物,對(duì)耐藥HIV變異型具有較強(qiáng)的抑制作用，在MT-4細(xì)胞中，EC50值是 98 nM.

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中文別名	4'-乙炔基-2'-脫氧腺苷(306305-07-7);4'-E-dA;（2R，3S，5R）-5-（6-氨基嘌呤-9-基）-2-乙炔基-2-（羥甲基）四氫呋喃-3-醇；
英文別名	4'-Ethynyl-2'-deoxyadenosine(306305-07-7);Adenosine, 2'-deoxy-4'-C-ethynyl-;4'-Ethynyl-2'-deoxyadenosine;4'-ETHYNYL-2'-DEOXYADENOSINE;
CAS號(hào)	306305-07-7
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
溶解度Solubility
性狀	固體粉末Solid
儲(chǔ)藏條件 Storage conditions	請(qǐng)根據(jù)產(chǎn)品建議的存儲(chǔ)條件進(jìn)行存儲(chǔ),Please store the product under the recommended condition sin the description.

4'-乙炔基-2'-脫氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)實(shí)驗(yàn)注意事項(xiàng)：
1.實(shí)驗(yàn)前需戴好防護(hù)眼鏡，穿戴防護(hù)服和口罩，佩戴手套，避免與皮膚接觸。
2.實(shí)驗(yàn)過(guò)程中如遇到有毒或者刺激性物質(zhì)及有害物質(zhì)產(chǎn)生，必要時(shí)實(shí)驗(yàn)操作需要手套箱內(nèi)完成以免對(duì)實(shí)驗(yàn)人員造成傷害
3.實(shí)驗(yàn)后產(chǎn)生的廢棄物需分類(lèi)存儲(chǔ)，并交于專(zhuān)業(yè)生物廢氣物處理公司處理，以免造成環(huán)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.

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產(chǎn)品說(shuō)明	4'-乙炔基-2'-脫氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)是一種有效的核苷逆轉(zhuǎn)錄酶 (RT)的抑制劑,是一種有效的抗病毒藥物
Introduction	4'-乙炔基-2'-脫氧腺苷(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)是一種有效的核苷逆轉(zhuǎn)錄酶 (RT)的抑制劑,是一種有效的抗病毒藥物,對(duì)耐藥HIV變異型具有較強(qiáng)的抑制作用，在MT-4細(xì)胞中，EC50值是 98 nM
Application2	4'-乙炔基-2'-脫氧腺苷(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'-脫氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)藥理學(xué)：

4'-乙炔基-2'-脫氧腺苷（4'-E-dA），一種核苷逆轉(zhuǎn)錄酶（RT）抑制劑，是一種抗逆轉(zhuǎn)錄病毒藥物，對(duì)耐藥性HIV變異體有效，在MT-中的EC50為98 nM。 4個(gè)細(xì)胞具有抗HIV-1活性。

警示圖
危險(xiǎn)性	warning
危險(xiǎn)性警示	Not available
安全聲明	H303吞入可能有害+H313皮膚接觸可能有害+H2413吸入可能對(duì)身體有害
安全防護(hù)	P264處理后徹底清洗+P280戴防護(hù)手套/穿防護(hù)服/戴防護(hù)眼罩/戴防護(hù)面具+P305如果進(jìn)入眼睛+P351用水小心沖洗幾分鐘+P338取出隱形眼鏡（如果有）并且易于操作,繼續(xù)沖洗+P337如果眼睛刺激持續(xù)+P2393獲得醫(yī)療建議/護(hù)理
備注	實(shí)驗(yàn)過(guò)程中防止吸入、食入，做好安全防護(hù)

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'-脫氧腺苷(306305-07-7,4'-Ethynyl-2'-deoxyadenosine,4'-E-dA)參考文獻(xiàn)：

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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