Paclitaxel

Manufactured by AK Scientific

Sourced in United States

Paclitaxel is a natural product extracted from the bark of the Pacific yew tree. It is a complex organic compound with a molecular formula of C₄₇H₅₁NO₁₄. Paclitaxel is a microtubule-stabilizing agent, which means it binds to and stabilizes microtubules, preventing their disassembly. This property makes it useful in various research and pharmaceutical applications.

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Lab products found in correlation

Fetal bovine serum (fbs), by Thermo Fisher Scientific (5 mentions) Trypsin edta solution, by Merck Group (5 mentions) Penicillin streptomycin solution, by Thermo Fisher Scientific (4 mentions) 3 4 5 dimethylthiazol 2 yl 2 5 diphenyltetrazolium bromide mtt, by Merck Group (4 mentions) Dulbecco s modified eagle s medium dmem, by Merck Group (4 mentions) Dicyclohexylcarbodiimide, by Thermo Fisher Scientific (2 mentions) Succinate anhydride, by Merck Group (2 mentions) N hydroxysuccinimide, by Thermo Fisher Scientific (2 mentions) Dimethyl sulfoxide (dmso), by Merck Group (2 mentions) Diethanolamine, by Merck Group (2 mentions) Vinylbenzyl chloride, by Merck Group (2 mentions) Doxorubicin hydrochloride salt dox hcl, by LC Laboratories (2 mentions) Cholic acid, by Merck Group (2 mentions) Verapamil hcl, by Merck Group (1 mentions) Cisplatin, by Merck Group (1 mentions) Carboplatin, by Merck Group (1 mentions) Fmoc lys boc oh, by AnaSpec (1 mentions) Fmoc lys fmoc oh, by AnaSpec (1 mentions) Celltiter 96 aqueous mts reagent powder, by Promega (1 mentions) D α tocopherol succinate, by Merck Group (1 mentions)

11 protocols using paclitaxel

Evaluating Combination Therapy Protocols

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Clinical vial solutions of vintafolide (formally EC145) and EC1456 were used in all experiments (Endocyte Inc.). Carboplatin, cisplatin and verapamil HCl were purchased from Sigma, St. Louis, MO; docetaxel and bevacizumab were obtained from the Purdue University Pharmacy, West Lafayette, IN; paclitaxel and topotecan were purchased from A.K. Scientific, Mountain View, CA. NCI-ADR cells were a kind gift from Dr. Alberto Gabizon, Shaare Zedek Medical Center, Israel. All other common reagents were purchased from Sigma or other major suppliers.

Reddy J.A., Dorton R., Bloomfield A., Nelson M., Dircksen C., Vetzel M., Kleindl P., Santhapuram H., Vlahov I.R, & Leamon C.P. (2018). Pre-clinical evaluation of EC1456, a folate-tubulysin anti-cancer therapeutic. Scientific Reports, 8, 8943.

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Multifunctional Nanoparticle Formulation

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Gambogic acid (GA) and etoposide (VP16) were purchased from AvaChem Scientific. Oridonin (ORD) was obtained from Xi’an Xuhuang Bio-tech Co., Ltd. Triptolide (TPL) was purchased from A Chemtek Inc. Paclitaxel (PTX) was purchased from AK Scientific Inc. Ltd. Monomethoxyl terminated polyethylene glycol monoamine (MeO-PEG-NH₂, M_W: 5000 Da) was purchased from JenKem. (Fmoc)lys(Boc)-OH, (Boc)Lys(Boc)-OH, (Fmoc)Lys(Fmoc)-OH and (Fmoc)Ebes-COOH were purchased from AnaSpec Inc. A hydrophobic cyanine dye of DiI, and a hydrophobic near infrared fluorescence dye of 1,1’-dioctadecyl-3,3,3’,3’-tetramethylindodicarbocyanine perchlorate (DiD) were purchased from AAT Bioquest, Inc. CellTiter 96® AQ_ueous MTS reagent powder was purchased from Promega. Cholic acid (CA), D-α-Tocopherol polyethylene glycol 1000 succinate (TPGS, PEG^1kVE), D-α-tocopherol succinate, diisopropyl carbodimide (DIC), N-hydroxybenzotriazole (HOBt), and all other chemical reagents were purchased from Sigma-Aldrich. Dialysis membrane with 3500 M_W cut off was purchased from Spectrum Laboratories, Inc.

Huang W., Wang X., Shi C., Guo D., Xu G., Wang L., Bodman A, & Luo J. (2015). Fine-Tuning Vitamin E-Containing Telodendrimers for Efficient Delivery of Gambogic Acid in Colon Cancer Treatment. Molecular pharmaceutics, 12(4), 1216-1229.

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Paclitaxel-FTS Conjugate Synthesis and Cytotoxicity

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Paclitaxel (98%) was purchased from AK Scientific
Inc. (CA, U. S. A.). FTS was synthesized and purified following a
published literature.^{27 (link)} Dulbecco’s
phosphate buffered saline (DPBS) was purchased from Lonza (MD, U.
S. A.). Poly(ethylene glycol) methyl ether (MeO–PEG–OH, M_W = 2000, 5000 kDa), dimethyl sulfoxide (DMSO),
succinate anhydride, diethanolamine, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl
tetrazolium bromide (MTT), trypsin-EDTA solution, Triton X-100, and
Dulbecco’s Modified Eagle’s Medium (DMEM) were all purchased
from Sigma-Aldrich (MO, U. S. A.). Fetal bovine serum (FBS) and penicillin–streptomycin
solution were purchased from Invitrogen (NY, U. S. A.). N-hydroxysuccinimide (NHS) and dicyclohexylcarbodiimide (DCC) were
purchased from Alfa Aesar (MA, U. S. A.). 4-(dimethylamino) pyridine
(DMAP) was purchased from Calbiochem-Novabiochem Corporation (CA,
U. S. A.). All solvents used in this study were HPLC grade.

Zhang X., Huang Y., Zhao W., Chen Y., Zhang P., Li J., Venkataramanan R, & Li S. (2014). PEG-Farnesyl Thiosalicylic Acid Telodendrimer Micelles as an Improved Formulation for Targeted Delivery of Paclitaxel. Molecular Pharmaceutics, 11(8), 2807-2814.

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Synthesis and Characterization of Polymeric Nanoparticles

Cited 1 time

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FTS was synthesized and purified following a published literature [18 (link)]. Vinylbenzyl chloride, 4-Cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic acid, oligo(ethylene glycol) methacrylate OEGMA (average Mn=500), 2, 2-Azobis(isobutyronitrile) (AIBN), trypsin-EDTA solution, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) and Dulbecco’s Modified Eagle’s Medium (DMEM) were all bought from Sigma-Aldrich (MO, U. S. A.). AIBN was purified by recrystallization in anhydrous ethanol. Paclitaxel was purchased from AK Scientific Inc. (CA, U. S. A.). DOX·HCl was purchased from LC Laboratories (MA, USA). Fetal bovine serum (FBS) and penicillin-streptomycin solution were purchased from Invitrogen (NY, U. S. A.). Cell culture and animals were similarly handled as described before [32 (link)].

Sun J., Chen Y., Li K., Huang Y., Fu X., Zhang X., Zhao W., Wei Y., Xu L., Zhang P., Venkataramanan R, & Li S. (2016). A Prodrug Micellar Carrier Assembled from Polymers with Pendant Farnesyl Thiosalicylic Acid Moieties for Improved Delivery of Paclitaxel. Acta biomaterialia, 43, 282-291.

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Synthesis and Characterization of Dye-Labeled Compounds

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Paclitaxel (98%) was purchased
from AK Scientific Inc. (CA, USA). Doxorubicin (>99%) was purchased
from LC Laboratories (MA, USA). 1,1′-dioctadecyl-3,3,3′,3′-tetramethylindodicarbocyanine
perchlorate (DiD) was purchased from Invitrogen (NY, USA). N-hydroxysuccinimide (NHS) and dicyclohexylcarbodiimide
(DCC) were purchased from Alfa Aesar (MA, USA). 4-(Dimethylamino)
pridine (DMAP) was purchased from Calbiochem–Novabiochem Corporation
(CA, USA). FTS was synthesized and purified following a published
literature.^{33 (link)}

Zhang X., Huang Y., Zhao W., Liu H., Marquez R., Lu J., Zhang P., Zhang Y., Li J., Gao X., Venkataramanan R., Xu L, & Li S. (2014). Targeted Delivery of Anticancer Agents via a Dual Function Nanocarrier with an Interfacial Drug-Interactive Motif. Biomacromolecules, 15(11), 4326-4335.

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Multifunctional Polymer-based Theranostics

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Vinylbenzyl chloride, 4,4'-Dithiodibutyric acid, oligo(ethylene glycol) methacrylate (OEG950 monomer, average M_n=950), 4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid, 2, 2-Azobis(isobutyronitrile) (AIBN), trypsin-EDTA solution, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) and Dulbecco's Modified Eagle's Medium (DMEM) were all bought from Sigma-Aldrich (MO, U. S. A.). AIBN was purified by recrystallization in anhydrous ethanol. 1-hydroxybenzotriazole (HOBT) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCl (EDC) were purchased from GL Biochem (Shanghai, China). Diisopropylethylamine (DIPEA) was purchased from Acros Organics. Paclitaxel was purchased from AK Scientific Inc. (CA, U. S. A.). Doxorubicin hydrochloride salt (DOX·HCl) and gemcitabine (GEM) were purchased from LC Laboratories (MA, USA). Fetal bovine serum (FBS) and penicillin-streptomycin solution were purchased from Invitrogen (NY, U. S. A.). The animal-related experiments were performed in full compliance with institutional guidelines and approved by the Animal Use and Care Administrative Advisory Committee at the University of Pittsburgh. Informed consent was obtained for experimentation with patient-derived xenograft (PDX) model. And the PDX-related experiments were carried out in accordance with The Code of Ethics of the World Medical Association.

Sun J., Chen Y., Xu J., Song X., Wan Z., Du Y., Ma W., Li X., Zhang L, & Li S. (2020). High Loading of Hydrophobic and Hydrophilic Agents via Small Immunostimulatory Carrier for Enhanced Tumor Penetration and Combinational Therapy. Theranostics, 10(3), 1136-1150.

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Paclitaxel-Conjugate Synthesis and Evaluation

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Paclitaxel (98%) was purchased
from AK Scientific
Inc. (CA, USA). FTS and PEG_5K-FTS₂ conjugate
were synthesized according to published literature.^{6 ,7 (link)} Poly(ethylene
glycol) methyl ether (MeO-PEG-OH, MW = 5000 kDa), dimethyl sulfoxide
(DMSO), succinate anhydride, diethanolamine, trypsin-EDTA solution,
Dulbecco’s Modified Eagle’s Medium (DMEM), and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl
tetrazolium bromide (MTT) were all purchased from Sigma-Aldrich (MO,
USA). Di-Boc-lysine, triethylamine (TEA), and trifluoroacetic acid
(TFA) were obtained from Acros Organic (NJ, USA). Bis(2-hydroxyethyl)
disulfide, dicyclohexylcarbodiimide (DCC), and N-hydroxysuccinimide
(NHS) were purchased from Alfa Aesar (MA, USA). 4-(Dimethylamino)pyridine
(DMAP) was purchased from Calbiochem-Novabiochem Corporation (CA,
USA). All solvents used in this study were HPLC grade.

Zhang X., Liu K., Huang Y., Xu J., Li J., Ma X, & Li S. (2014). Reduction-Sensitive Dual Functional Nanomicelles for Improved Delivery of Paclitaxel. Bioconjugate Chemistry, 25(9), 1689-1696.

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Synthesis and Characterization of Functional Monomers

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4-vinylbenzyl azide (VBA-monomer) was synthesized by reaction of sodium azide with 4-vinylbenzylchloride according to the literature [38 , 39 ]. FTS-monomer and POEG macroCTA were synthesized as previously reported [31 (link)]. 2, 2’-Azobis (2-methylpropionitrile) (AIBN) was recrystallized in anhydrous ethanol before use. Paclitaxel was purchased from AK Scientific Inc. (CA, U. S. A.). Trypsin-EDTA solution, 3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyl tetrazolium bromide (MTT) and Dulbecco’s Modified Eagle’s Medium (DMEM) were all bought from Sigma-Aldrich (MO, U. S.A.). Fetal bovine serum (FBS) was purchased from Invitrogen (NY, U. S. A.). Copper-64 was obtained from Washington University (St. Louis, MO) and University of Wisconsin (Madison, WI). Zirconium-89 was obtained from Washington University (St. Louis, MO). Luna C-18 HPLC columns were from Phenomenex (Torrance, CA, USA).

Sun J., Sun L., Li J., Xu J., Wan Z., Ouyang Z., Liang L., Li S, & Zeng D. (2018). A Multi-Functional Polymeric Carrier for Simultaneous Positron Emission Tomography Imaging and Combination Therapy. Acta biomaterialia, 75, 312-322.

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Synthesis and Characterization of POEG-co-PVD and PGEM Polymers

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POEG-co-PVD and PGEM polymers was synthesized as previously reported [29 (link)]. Paclitaxel was purchased from AK Scientific Inc. (CA, U. S. A.). Doxorubicin hydrochloride salt (DOX·HCl) were purchased from LC Laboratories (MA, USA). Pacific Blue (PB)-conjugated anti-mouse CD8 antibody (#558106) and PE-CF594-conjugated FoxP3 antibody (#9129564) were purchased from BD Company. BV785-conjugated CD4 was purchased from SIRIGEN (#100453). PerCP-conjugated CD45 was purchased from BIOLEGEND (#103130). Penicillin-streptomycin solution and fetal bovine serum (FBS) were purchased from Invitrogen (NY, U. S. A.). All other agents were purchased from Sigma-Aldrich (MO, U. S. A.).
All animal-related experiments were performed in full compliance with institutional guidelines and approved by the Animal Use and Care Administrative Advisory Committee at the University of Pittsburgh.

Sun J., Wan Z., Chen Y., Xu J., Luo Z., Parise R.A., Diao D., Ren P., Beumer J.H., Lu B, & Li S. (2020). Triple Drugs Co-Delivered by a Small Gemcitabine-Based Carrier for Pancreatic Cancer Immunochemotherapy. Acta biomaterialia, 106, 289-300.

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Acquisition of Chemotherapeutic Agents

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The following chemotherapeutics were purchased from AK Scientific Inc. (San Francisco, CA, USA): paclitaxel (99%; A648), carboplatin (99%; H876), and gemcitabine HCl (98%; F287). cis-Diammineplatinum(II) dichloride (cisplatin, 99.99% P4394) and gemcitabine hydrochloride European Pharmacopeia (EP) Reference Standard were purchased from Sigma-Aldrich (St. Louis, MO, USA). Doxorubicin HCl (99%; DOX042) was purchased from BioSchop Canada Inc. (Burlington, ON, Canada).

Bednarska-Szczepaniak K., Przelazły E., Kania K.D., Szwed M., Litecká M., Grűner B, & Leśnikowski Z.J. (2021). Interaction of Adenosine, Modified Using Carborane Clusters, with Ovarian Cancer Cells: A New Anticancer Approach against Chemoresistance. Cancers, 13(15), 3855.

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