Tubulysin C
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| Category | Antibiotics |
| Catalog number | BBF-02727 |
| CAS | 205304-88-7 |
| Molecular Weight | 816.02 |
| Molecular Formula | C41H61N5O10S |
| Purity | 98% |
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Description
Tubulysin C is a highly cytotoxic peptide isolated from the myxobacterial species Archangium geophyra and Angiococcus disciformis. Tubulysin C is a cytotoxic activity tubulysin which inhibits tubulin polymerization and leads to cell cycle arrest and apoptosis.
Specification
| Synonyms | Tubulysin C; 205304-88-7; 072P54KU0L; UNII-072P54KU0L; (2S,4R)-4-[[2-[(1R,3R)-1-acetyloxy-4-methyl-3-[[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]-(propanoyloxymethyl)amino]pentyl]-1,3-thiazole-4-carbonyl]amino]-5-(4-hydroxyphenyl)-2-methylpentanoic acid; Benzenepentanoic acid, gamma-(((2-((1R,3R)-1-(acetyloxy)-4-methyl-3-(((2S,3S)-3-methyl-2-((((2R)-1-methyl-2-piperidinyl)carbonyl)amino)-1-oxopentyl)((1-oxopropoxy)methyl)amino)pentyl)-4-thiazolyl)carbonyl)amino)-4-hydroxy-alpha-methyl-, (alphaS,.ga; SCHEMBL24218753; EX-A5466C; HY-N2347; AKOS040740942; CS-0021784; BENZENEPENTANOIC ACID, .GAMMA.-(((2-((1R,3R)-1-(ACETYLOXY)-4-METHYL-3-(((2S,3S)-3-METHYL-2-((((2R)-1-METHYL-2-PIPERIDINYL)CARBONYL)AMINO)-1-OXOPENTYL)((1-OXOPROPOXY)METHYL)AMINO)PENTYL)-4-THIAZOLYL)CARBONYL)AMINO)-4-HYDROXY-.ALPHA.-METHYL-, (.ALPHA.S,.GAMMA.R)- |
| Storage | Store at -20°C |
| IUPAC Name | (2S,4R)-4-[[2-[(1R,3R)-1-acetyloxy-4-methyl-3-[[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]-(propanoyloxymethyl)amino]pentyl]-1,3-thiazole-4-carbonyl]amino]-5-(4-hydroxyphenyl)-2-methylpentanoic acid |
| Canonical SMILES | CCC(C)C(C(=O)N(COC(=O)CC)C(CC(C1=NC(=CS1)C(=O)NC(CC2=CC=C(C=C2)O)CC(C)C(=O)O)OC(=O)C)C(C)C)NC(=O)C3CCCCN3C |
| InChI | InChI=1S/C41H61N5O10S/c1-9-25(5)36(44-38(51)32-13-11-12-18-45(32)8)40(52)46(23-55-35(49)10-2)33(24(3)4)21-34(56-27(7)47)39-43-31(22-57-39)37(50)42-29(19-26(6)41(53)54)20-28-14-16-30(48)17-15-28/h14-17,22,24-26,29,32-34,36,48H,9-13,18-21,23H2,1-8H3,(H,42,50)(H,44,51)(H,53,54)/t25-,26-,29+,32+,33+,34+,36-/m0/s1 |
| InChI Key | NZCNGJHOIKMMCG-UZRVFEFTSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
Reference Reading
1. The X-ray structure of tubulysin analogue TGL in complex with tubulin and three possible routes for the development of next-generation tubulysin analogues
Wenting Li, Lun Tan, Zhixiong Zhang, Qiuqi Xia, Dongsheng Lei, Yuyan Li, Ting Zhang, Shaoxue Zeng, Xiutian Sima, Yanyan Wang Biochem Biophys Res Commun. 2021 Aug 6;565:29-35. doi: 10.1016/j.bbrc.2021.05.086. Epub 2021 Jun 2.
Microtubule-targeting agents (MTAs) are the most commonly used anti-cancer drugs. At least fourteen microtubule inhibitors and ten antibody drug conjugates (ADCs) linking MTAs are approved by FDA for clinical use in cancer therapy. In current research, we determined the crystal structure of tubulysin analogue TGL in complex with tubulin at a high resolution (2.65 Å). In addition, we summarized all of the previously published high-resolution crystal structures of ligands in the vinca site to provide structural insights for the rational design of the new vinca-site ligands. Moreover, based on the aligned results of the vinca site ligands, we provided three possible routes for designing new tubulysin analogues, namely macrocyclization between the N-14 side chain and the N-9 side chain, the hybird of tubulysin M and phomopsin A, and growing new aryl group at C-21. These designed structures will inspire the development of new MTAs or payloads in cancer therapy.
2. Structure-activity relationships of tubulysin analogues
Joel R Courter, Joseph Z Hamilton, Nathaniel R Hendrick, Margo Zaval, Andrew B Waight, Robert P Lyon, Peter D Senter, Scott C Jeffrey, Patrick J Burke Bioorg Med Chem Lett. 2020 Jul 15;30(14):127241. doi: 10.1016/j.bmcl.2020.127241. Epub 2020 May 5.
The tubulysins are an emerging antibody-drug conjugate (ADC) payload that maintain potent anti-proliferative activity against cells that exhibit the multi-drug resistant (MDR) phenotype. These drugs possess a C-11 acetate known to be hydrolytically unstable in plasma, and loss of the acetate significantly attenuates cytotoxicity. Structure-activity relationship studies were undertaken to identify stable C-11 tubulysin analogues that maintain affinity for tubulin and potent cytotoxicity. After identifying several C-11 alkoxy analogues that possess comparable biological activity to tubulysin M with significantly improved plasma stability, additional analogues of both the Ile residue and N-terminal position were synthesized. These studies revealed that minor changes within the tubulin binding site of tubulysin can profoundly alter the activity of this chemotype, particularly against MDR-positive cell types.
3. Synthetic Approaches Towards the Total synthesis of tubulysin and its fragments: A review
Nosheen Iqbal, Ameer Fawad Zahoor, Nasir Rasool, Samreen Gul Khan, Rabia Akhtar, Raheel Ahmad Curr Org Synth. 2021 Dec 22. doi: 10.2174/1570179419666211222163417. Online ahead of print.
Background: Tubulysins, linear tetrapeptides show extraordinary cytotoxicity against various cancer cells, with IC50 values in nano or picomolar range. Due to their extremely vigorous anti-proliferative and antiangiogenic characteristics, tubulysins exhibit captivating prospects in the development of anticancer drugs. This review focuses on diverse routes for the total synthesis of natural and synthetic tubulysins as well as their fragments. Objective: The purpose of this review is to present the synthetic strategies for the development of antitumor agents, tubulysins. Conclusion: A range of synthetic pathways adopted for the total synthesis of tubulysins and their fragments have been described in this review. Synthesis of fragments, Tuv, Tup, and Tut can be accomplished by adopting appropriate strategies such as Manganese-mediated synthesis, Ireland-Claisen rearrangement, Mukaiyama aldol reaction, and Mannich process etc. Tubulysin B, D, U, V, and N14-desacetoxytubulysin H have been prepared through Mitsunobu reaction, tert-butanesulfinamide method, Tandem reaction, aza-Barbier reaction, Evans aldol reaction, and C-H activation strategies etc. The remarkable anticancer potential of tubulysins toward a substantiate target make them prominent leads for developing novel drugs against multidrug-resistant cancers.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
