DHA-paclitaxel
WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#:206077
CAS#:199796-52-6
Description:DHA-paclitaxel, also know as Taxoprexin, is prodrug comprised of the naturally occurring omega-3 fatty acid docosahexaenoic acid (DHA) covalently conjugated to the anti-microtubule agent paclitaxel. Because tumor cells take up DHA, DHA-paclitaxel is delivered directly to tumor tissue, where the paclitaxel moiety binds to tubulin and inhibits the disassembly of microtubules, thereby resulting in the inhibition of cell division. Paclitaxel also induces apoptosis by binding to and blocking the function of the apoptosis inhibitor protein Bcl-2 (B-cell Leukemia 2). DHA-paclitaxel exhibits improved pharmacokinetic and toxicity profiles when compared to conventional paclitaxel and has demonstrated antineoplastic activity in animal models of cancer.
Price and Availability
DHA-paclitaxel is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.
Chemical Structure
Theoretical Analysis
MedKoo Cat#: 206077Name: DHA-paclitaxelCAS#: 199796-52-6Chemical Formula: C69H81NO15Exact Mass: 1163.56062Molecular Weight: 1164.38Elemental Analysis: C, 71.17; H, 7.01; N, 1.20; O, 20.61
Synonym:DHA-paclitaxel; DHA-Taxol; DHA-Tax; Docosahexaenoic Acid-Paclitaxel conjugate; US brand name: Taxoprexin.
IUPAC/Chemical Name:(2aR,4S,4aS,6R,9S,11S,12S,12bS)-9-(((2R,3S)-3-benzamido-2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy)-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b-diyl diacetate.
InChi Key:LRCZQSDQZJBHAF-PUBGEWHCSA-N
InChi Code:InChI=1S/C69H81NO15/c1-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-35-42-55(74)83-59(57(49-36-29-26-30-37-49)70-63(76)50-38-31-27-32-39-50)65(78)82-52-44-69(79)62(84-64(77)51-40-33-28-34-41-51)60-67(7,53(73)43-54-68(60,45-80-54)85-48(4)72)61(75)58(81-47(3)71)56(46(52)2)66(69,5)6/h9-10,12-13,15-16,18-19,21-22,24-34,36-41,52-54,57-60,62,73,79H,8,11,14,17,20,23,35,42-45H2,1-7H3,(H,70,76)/b10-9-,13-12-,16-15-,19-18-,22-21-,25-24-/t52-,53-,54+,57-,58+,59+,60-,62-,67+,68-,69+/m0/s1
SMILES Code:O=C1[C@H](OC(C)=O)C(C2(C)C)=C(C)[C@@H](OC([C@@H]([C@H](C3=CC=CC=C3)NC(C4=CC=CC=C4)=O)OC(CC/C=CC/C=CC/C=CC/C=CC/C=CC/C=CCC)=O)=O)C[C@@]2(O)[C@@H](OC(C5=CC=CC=C5)=O)[C@@]6([H])[C@@]1(C)[C@@H](O)C[C@@H]7[C@@]6(OC(C)=O)CO7
Technical Data
Additional Information
DHA-paclitaxel (or Taxoprexin) is an investigational drug (from Protarga Inc) made by linking paclitaxel to docosahexaenoic acid (DHA), a fatty acid that is easily taken up by tumor cells; the DHA-paclitaxel “appears not to be cytotoxic until the bond with DHA is cleaved within the cell.” The advantage of DHA-paclitaxel over paclitaxel is DHA-paclitaxel’s ability to carry much higher concentrations of paclitaxel to the cells, which are maintained for longer periods in the tumor cells, thus increasing their action. With increased activity, DHA-paclitaxel, also known as Taxoprexin, may have a more successful response in cancer patients than Taxol, and it may be able to treat more types of cancer than Taxol has been able to treat. In 2007, a phase II clinical trial reported "modest activity in patients with oesophago-gastric cancer". (source: http://en.wikipedia.org/wiki/DHA-paclitaxel).
References
1: Homsi J, Bedikian AY, Papadopoulos NE, Kim KB, HwuWJ, Mahoney SL, Hwu P. Phase 2 open-label study of weeklydocosahexaenoic acid-paclitaxel in patients with metastatic uvealmelanoma. Melanoma Res. 2010 Dec;20(6):507-10. doi:10.1097/CMR.0b013e3283403ce9. PubMed PMID: 20881508.
2: Bedikian AY, DeConti RC, Conry R, Agarwala S, Papadopoulos N, Kim KB,Ernstoff M. Phase 3 study of docosahexaenoic acid-paclitaxel versusdacarbazine in patients with metastatic malignant melanoma. Ann Oncol.2011 Apr;22(4):787-93. doi: 10.1093/annonc/mdq438. Epub 2010 Sep 20.PubMed PMID: 20855467.
3: Homsi J, Bedikian AY, Kim KB, Papadopoulos NE, Hwu WJ, Mahoney SL,Hwu P. Phase 2 open-label study of weekly docosahexaenoic acid-paclitaxelin cutaneous and mucosal metastatic melanoma patients. Melanoma Res.2009 Aug;19(4):238-42. doi: 10.1097/CMR.0b013e32832a1e2f. PubMed PMID:19521262.
4: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find ExpClin Pharmacol. 2008 May;30(4):313-31. PubMed PMID: 18773127.
5: Fracasso PM, Picus J, Wildi JD, Goodner SA, Creekmore AN, Gao F,Govindan R, Ellis MJ, Tan BR, Linette GP, Fu CJ, Pentikis HS, ZumbrunSC, Egorin MJ, Bellet RE. Phase 1 and pharmacokinetic study of weeklydocosahexaenoic acid-paclitaxel, Taxoprexin, in resistant solid tumormalignancies. Cancer Chemother Pharmacol. 2009 Feb;63(3):451-8. doi:10.1007/s00280-008-0756-0. Epub 2008 Apr 15. PubMed PMID: 18414864.
6: Jones RJ, Hawkins RE, Eatock MM, Ferry DR, Eskens FA, Wilke H, EvansTR. A phase II open-label study of DHA-paclitaxel (Taxoprexin) by 2-hintravenous infusion in previously untreated patients with locallyadvanced or metastatic gastric or oesophageal adenocarcinoma. CancerChemother Pharmacol. 2008 Mar;61(3):435-41. Epub 2007 Apr 18. PubMedPMID: 17440725.
7: Payne M, Ellis P, Dunlop D, Ranson M, Danson S, Schacter L, Talbot D.DHA-paclitaxel (Taxoprexin) as first-line treatment in patients withstage IIIB or IV non-small cell lung cancer: report of a phase IIopen-label multicenter trial. J Thorac Oncol. 2006 Nov;1(9):984-90.PubMed PMID: 17409983.
8: Harries M, O"Donnell A, Scurr M, Reade S, Cole C, Judson I, GreystokeA, Twelves C, Kaye S. Phase I/II study of DHA-paclitaxel in combinationwith carboplatin in patients with advanced malignant solid tumours. Br JCancer. 2004 Nov 1;91(9):1651-5. PubMed PMID: 15494716; PubMed CentralPMCID: PMC2410023.
9: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. MethodsFind Exp Clin Pharmacol. 2004 Apr;26(3):211-44. PubMed PMID: 15148527.
10: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. MethodsFind Exp Clin Pharmacol. 2004 Mar;26(2):129-61. PubMed PMID: 15071612.
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MedKoo是世界领先的供应商之一的抗癌化学试剂和激酶抑制剂。我们制造、销售和分发高质量的抗癌小分子肿瘤学研究试剂。我们的使命是建立世界上最全面的抗癌小分子的集合。我们也为医药行业提供高质量的研究服务、医学研究机构和学术机构。我们致力于提供优质的服务。 MedKoo是世界领先的供应商之一的抗癌化学试剂和激酶抑制剂。我们制造、销售和分发高质量的抗癌小分子肿瘤学研究试剂。我们的使命是建立世界上最全面的抗癌小分子的集合。我们也为医药行业提供高质量的研究服务、医学研究机构和学术机构。我们致力于提供优质的服务和分子有竞争力的价格。MedKoo是您可靠的合作伙伴采购药物发现和药物分子。 MedKoo是世界的抗癌化学试剂和激酶抑制剂供应商之一。我们制造,销售和分销用于肿瘤学研究的高质量抗癌小分子试剂。我们的使命是建立世界上全面的抗癌小分子集合。我们还为制药行业,医学研究组织和学术机构提供高质量的研究服务。我们致力于以具有竞争力的价格提供服务和分子。MedKoo是您可靠的药物发现和药物分子采购合作伙伴。 CRISPR-Cas9是近年兴起的用于靶向基因组特定位置,进行DNA修饰的重要工具。研究发现CRISPR是细菌为了应对病毒的攻击而演化而来的获得性免疫防御机制。具体来说,在CRISPR和Cas9的作用下,经由小RNA分子的引导,靶向并沉默入侵者遗传物质核酸的关键部分。在该系统中,crRNA(CRISPR-derivedRNA)与tracrRNA(trans-activatingRNA)结合形成的复合物能特异性识别靶基因序列,并引导Cas9核酸内切酶在靶定位点剪切双链DNA,随后,细胞的非同源末端连接修复机制(NHEJ)重新连接断裂处的基因组DNA,并引入插入或缺失突变。另外也可以提供一个外源双链供体DNA(Donor)通过同源重组(HR)整合进断裂处的基因组,从而达到对基因组DNA进行修饰的目的。
目前,CRISPR-Cas9系统的高效基因组编辑功能已被应用于多种生物,包括小鼠、大鼠、斑马鱼、秀丽隐杆线虫,也包含多种细菌和植物,甚至在人体上也有应用。
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