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Tubulysin M

  CAS No.: 936691-46-2   Cat No.: BADC-00360   Purity: ≥95% 4.5  

Tubulysin M is a Tubulysin D analog with potential anti-cancer properties, used as the cytotoxic component in antibody-drug conjugates.

Tubulysin M

Structure of 936691-46-2

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Category
ADC Cytotoxin
Molecular Formula
C38H57N5O7S
Molecular Weight
727.39
Shipping
Room temperature

* For research and manufacturing use only. We do not sell to patients.

Size Price Stock Quantity
0.1 mg $1099 In stock

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Popular Publications Citing BOC Sciences Products
Synonyms
(2S,4R)-4-{[(2-{(1R,3R)-1-Acetoxy-4-methyl-3-[methyl(N-{[(2R)-1-methyl-2-piperidinyl]carbonyl}-L-isoleucyl)amino]pentyl}-1,3-thiazol-4-yl)carbonyl]amino}-2-methyl-5-phenylpentanoic acid;
IUPAC Name
(2S,4R)-4-[[2-[(1R,3R)-1-acetyloxy-4-methyl-3-[methyl-[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]amino]pentyl]-1,3-thiazole-4-carbonyl]amino]-2-methyl-5-phenylpentanoic acid
Canonical SMILES
CC[C@H](C)[C@@H](C(=O)N(C)[C@H](C[C@H](c1nc(cs1)C(=O)N[C@@H](Cc2ccccc2)C[C@H](C)C(=O)O)OC(=O)C)C(C)C)NC(=O)[C@H]3CCCCN3C
InChI
InChI=1S/C38H57N5O7S/c1-9-24(4)33(41-35(46)30-17-13-14-18-42(30)7)37(47)43(8)31(23(2)3)21-32(50-26(6)44)36-40-29(22-51-36)34(45)39-28(19-25(5)38(48)49)20-27-15-11-10-12-16-27/h10-12,15-16,22-25,28,30-33H,9,13-14,17-21H2,1-8H3,(H,39,45)(H,41,46)(H,48,49)/t24-,25-,28+,30+,31+,32+,33-/m0/s1
InChIKey
POBZYODNVHQLFG-ZRBKHQLFSA-N
Appearance
Soild powder
Shipping
Room temperature
1. Improving Antibody-Tubulysin Conjugates through Linker Chemistry and Site-Specific Conjugation
Ivan J Stone, Martha E Anderson, Julia H Cochran, Margo Zaval, Andrew B Waight, Robert P Lyon, Steven Jin, Thomas A Pires, Patrick J Burke, Joseph Z Hamilton, Scott C Jeffrey, Jamie A Mitchell, Peter D Senter, Kim K Emmerton ChemMedChem . 2021 Apr 8;16(7):1077-1081. doi: 10.1002/cmdc.202000889.
Tubulysins have emerged in recent years as a compelling drug class for delivery to tumor cells via antibodies. The ability of this drug class to exert bystander activity while retaining potency against multidrug-resistant cell lines differentiates them from other microtubule-disrupting agents. Tubulysin M, a synthetic analogue, has proven to be active and well tolerated as an antibody-drug conjugate (ADC) payload, but has the liability of being susceptible to acetate hydrolysis at the C11 position, leading to attenuated potency. In this work, we examine the ability of the drug-linker and conjugation site to preserve acetate stability. Our findings show that, in contrast to a more conventional protease-cleavable dipeptide linker, the β-glucuronidase-cleavable glucuronide linker protects against acetate hydrolysis and improves ADC activity in vivo. In addition, site-specific conjugation can positively impact both acetate stability and in vivo activity. Together, these findings provide the basis for a highly optimized delivery strategy for tubulysin M.
2. Design, Synthesis, and Biological Evaluation of Tubulysin Analogues, Linker-Drugs, and Antibody-Drug Conjugates, Insights into Structure-Activity Relationships, and Tubulysin-Tubulin Binding Derived from X-ray Crystallographic Analysis
Joseph Lyssikatos, Qiuji Ye, Jose Trinidad, Nicole Taylor, Bogusław P Nocek, Monette Aujay, Christine Gu, Amanda Valdiosera, Dionisios Vourloumis, Stephan Rigol, Joseph Sandoval, Stefan Munneke, Hetal Sarvaiaya, Rohan D Erande, K C Nicolaou, Baiwei Lin, James W Purcell, Julia Gavrilyuk, Kiran K Pulukuri, Marybeth Pysz, Christina Lee, Mikhail Hammond, Saiyong Pan J Org Chem . 2021 Feb 19;86(4):3377-3421. doi: 10.1021/acs.joc.0c02755.
Molecular design, synthesis, and biological evaluation of tubulysin analogues, linker-drugs, and antibody-drug conjugates are described. Among the new discoveries reported is the identification of new potent analogues within the tubulysin family that carry a C11 alkyl ether substituent, rather than the usual ester structural motif at that position, a fact that endows the former with higher plasma stability than that of the latter. Also described herein are X-ray crystallographic analysis studies of two tubulin-tubulysin complexes formed within the α/β interface between two tubulin heterodimers and two highly potent tubulysin analogues, one of which exhibited a different binding mode to the one previously reported for tubulysin M. The X-ray crystallographic analysis-derived new insights into the binding modes of these tubulysin analogues explain their potencies and provide inspiration for further design, synthesis, and biological investigations within this class of antitumor agents. A number of these analogues were conjugated as payloads with appropriate linkers at different sites allowing their attachment onto targeting antibodies for cancer therapies. A number of such antibody-drug conjugates were constructed and tested, both in vivo and in vitro, leading to the identification of at least one promising ADC (Herceptin-LD3), warranting further investigations.
3. The X-ray structure of tubulysin analogue TGL in complex with tubulin and three possible routes for the development of next-generation tubulysin analogues
Qiuqi Xia, Yanyan Wang, Dongsheng Lei, Yuyan Li, Shaoxue Zeng, Xiutian Sima, Lun Tan, Ting Zhang, Zhixiong Zhang, Wenting Li Biochem Biophys Res Commun . 2021 Aug 6;565:29-35. doi: 10.1016/j.bbrc.2021.05.086.
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.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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