A4393-500mg | Paclitaxel (Taxol) [33069-62-4] Clinisciences

Paclitaxel is a novel antineoplastic agent, which was discovered in a screen of extracts of thousands of plants and natural products for antineoplastic activity by a National Cancer Institute program. Alought it functions as a mitotic inhibitor like vinca alkaloids, paclitaxel promotes the polymerization of tubulin instead of inducing the disassembly of microtubules, which inhibits the microtubules disassembly and promotes the formation of excessively stable, dysfunctional microtubules. Paclitaxel has exhibited antitumor activity against a broad spectrum of human cancers, including ovarian, breast, head and neck, and lung cancer, in a large number of studies.

Reference

Ross C. Donehower. The clinical development of paclitaxel: a successful collaboration of academia, industry and the National cancer Institute. STEM CELLS 1996;14:25-28

1. Schwartz, Hannah, et al. "In vitro Methods to Better Evaluate Drug Responses in Cancer." UMass Chan Medical School. September 8, 2022.
2. Darya A. Stepanova, Vladislava A. Pigareva, et al. "Ultrasonic Film Rehydration Synthesis of Mixed Polylactide Micelles for Enzyme-Resistant Drug Delivery Nanovehicles." Polymers (Basel). 2022 Sep 25;14(19):4013. PMID: 36235958
3. Shengli Dong, Hassan Yousefi, et al. "Ceritinib is a novel triple negative breast cancer therapeutic agent." Mol Cancer. 2022 Jun 29;21(1):138. PMID: 35768871
4. Prateek Bhardwaj, Vikram Gota, et al. "Loco-regional radiosensitizing nanoparticles-in-gel augments head and neck cancer chemoradiotherapy." J Control Release. 2022 Mar;343:288-302. PMID: 35101477
5. Mikhail S. Chesnokov, Marianna Halasi, et al. "Novel FOXM1 inhibitor identified via gene network analysis induces autophagic FOXM1 degradation to overcome chemoresistance of human cancer cells." Cell Death Dis. 2021 Jul 14;12(7):704. PMID: 34262016
6. Anirban Roychowdhury, Mayur Jondhale, et al. "Landscape of toll-like receptors expression in tumor microenvironment of triple negative breast cancer (TNBC): Distinct roles of TLR4 and TLR8." Gene. 2021 Aug 5;792:145728. PMID: 34022297
7. Catherine Suzanne Snyder. "Polymer Nanoparticle Design for Ovarian Cancer Therapies." University of Michigan 2021.
8. Juanwen Lian, Tao Hua, et al. "Interleukin-1β weakens paclitaxel sensitivity through regulating autophagy in the non-small cell lung cancer cell line A549." Exp Ther Med. 2021 Apr;21(4):293. PMID: 33717236
9. Chu xue, Si-Xue Liu, et al. "Corydalis Saxicola Bunting Total Alkaloids Inhibits Paclitaxel-Induced Peripheral Neuropathy By Regulating PKCε-TRPV1 and p38 MAPK-TRPV1 Signaling Pathways." Research Square. doi.org/10.21203/rs.3.rs-332970/v1.
10. Yongman Liu, Jianye Wang, et al. "Quantifying 3D cell–matrix interactions during mitosis and the effect of anticancer drugs on the interactions." Nano Research. ISSN 1998-0124 CN 11-5974/O4.
11. Shahbandi A, Rao SG, et al. "BH3 mimetics selectively eliminate chemotherapy-induced senescent cells and improve response in TP53 wild-type breast cancer." Cell Death Differ. 2020;10.1038/s41418-020-0564-6. PMID: 32457483
12. Gamache JE, Kemper L, et al. "Developmental pathogenicity of 4-repeat human tau is lost with the P301L mutation in genetically matched tau-transgenic mice." J Neurosci. 2019 Nov 4. pii: 1256-19. PMID: 31685653
13. Tonnessen-Murray CA, Frey WD, et al. "Chemotherapy-induced senescent cancer cells engulf other cells to enhance their survival." J Cell Biol. 2019 Sep 17. pii: jcb.201904051. PMID: 31530580
14. Chung HK, Zou X, et al. "A compact synthetic pathway rewires cancer signaling to therapeutic effector release." Science. 2019 May 3;364(6439). PMID: 31048459
15. Zhang Y, Xia F, et al. "miR-135b-5p enhances doxorubicin-sensitivity of breast cancer cells through targeting anterior gradient 2." J Exp Clin Cancer Res. 2019 Jan 21;38(1):26. PMID: 30665445
16. Deng Y, Li F, et al. "Triptolide sensitizes breast cancer cells to Doxorubicin through the DNA damage response inhibition." Mol Carcinog. 2018 Jun;57(6):807-814. PMID: 29500880
17. Zina Hamoudi , Thang Manh Khuong, et al. "A fruit fly model for studying paclitaxel-induced pain [version 1;referees: awaiting peer review]" F1000Research 23 Jan 2018, 7:99.
18. Yu Wang，Zhenxin Zhu, et al. "The effect of phenotypic conditioned medium on the proliferation of BGC823 in human gastric cancer cell line." Academic Journal of Second Military Medical University,Dec.2017,Vol.38,No.12.

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Physical Appearance	A solid
Storage	Store at -20°C
M.Wt	853.91
Cas No.	33069-62-4
Formula	C₄₇H₅₁NO₁₄
Synonyms	Taxol
Solubility	≥85.6 mg/mL in DMSO; insoluble in H2O; ≥31.6 mg/mL in EtOH with ultrasonic
SDF	Download SDF
Canonical SMILES	O=C(N[C@H]([C@H](C(O[C@H]1C[C@]2(O)C(C)(C)C([C@@H](OC(C)=O)C([C@@]3(C)[C@]([C@@](CO4)(OC(C)=O)[C@H]4C[C@@H]3O)(14)[C@@H]2OC(C5=CC=CC=C5)=O)=O)=C1C)=O)O)C6=CC=CC=C6)C7=CC=CC=C7
Shipping Condition	Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips	We do not recommend long-term storage for the solution, please use it up soon.

Cell experiment: [1]
Cell lines	Human arterial endothelial (haEC) cells
Preparation method	The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while.Stock solution can be stored below -20°C for several months.
Reaction Conditions	1 μM, 24 hours
Applications	Nonstop and single-dose (24-hour) applications were performed and cell proliferation was determined after 6 days by use of cell counting, BrdU-ELISA and MTT tests. A dose-dependent, significant growth inhibition occurred at high concentrations (0.01 to 1.0 μmol/L), whereas lower paclitaxel doses (0.1 to 1.0 nmol/L) did not inhibit haEC growth significantly. Furthermore, no unspecific cytotoxic effects were observed within this concentration range.
Animal experiment: [2]
Animal models	Female CB17 SCID mice
Dosage form	Intravenous injection, 12.5 mg per kg body weight
Applications	In mice treated with paclitaxel, the interface between tumor and dermal graft was ill defined, and small groups of tumor cells were seen within the human dermis and were surrounded by dilated vessels. Quantification of vessel cross-sections confirmed the histologic impression: numbers of vessels per high power field were significantly less in LP-treated mice compared with paclitaxel- and liposome-treated mice, respectively.
Other notes	Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.
References: [1] Axel D I, Kunert W, Göggelmann C, et al. Paclitaxel inhibits arterial smooth muscle cell proliferation and migration in vitro and in vivo using local drug delivery. Circulation, 1997, 96(2): 636-645. [2] Kunstfeld R, Wickenhauser G, Michaelis U, et al. Paclitaxel encapsulated in cationic liposomes diminishes tumor angiogenesis and melanoma growth in a “humanized” SCID mouse model. Journal of investigative dermatology, 2003, 120(3): 476-482.

Description	Paclitaxel is a microtubule polymer stabilizer with IC50 of 0.1 pM in human endothelial cells.
Targets	Microtubule (human endothelial cells)
IC50	0.1 pM