VCP-Eribulin - CAS 2130869-17-7

VCP-Eribulin - CAS 2130869-17-7 Catalog number: BADC-00660

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VCP-Eribulin consists the ADCs linker (VCP) and Eribulin. Eribulin is a mechanistically unique microtubule inhibitor for cancer. VCP-Eribulin is an Eribulin-based drug for antibody conjugates.

Category
ADCs Cytotoxin with Linkers
Product Name
VCP-Eribulin
CAS
2130869-17-7
Catalog Number
BADC-00660
Molecular Formula
C59H86N6O16
Molecular Weight
1135.34
VCP-Eribulin

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BADC-00660 -- $--
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Description
VCP-Eribulin consists the ADCs linker (VCP) and Eribulin. Eribulin is a mechanistically unique microtubule inhibitor for cancer. VCP-Eribulin is an Eribulin-based drug for antibody conjugates.
IUPAC Name
[4-[[(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-5-(carbamoylamino)pentanoyl]amino]phenyl]methyl N-[(2S)-2-hydroxy-3-[(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-21-methoxy-14-methyl-8,15-dimethylidene-24-oxo-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-20-yl]propyl]carbamate
Canonical SMILES
C=C1C[C@@]2([H])O[C@@]1([H])CC[C@]3([H])O[C@](C([C@H](C)C3)=C)([H])C[C@@]4([H])[C@]([C@@H](OC)[C@@H](C[C@H](O)CNC(OCC5=CC=C(NC([C@H](CCCNC(N)=O)NC([C@H](C(C)C)N)=O)=O)C=C5)=O)O4)([H])CC(C[C@]6([H])O[C@]7([H])[C@]8([H])O[C@@]9(O[C@@]%10([H])[C@@](O[C@]8([H])[C@@]%10([H])O[C@@]7([H])CC6)([H])C9)CC2)=O
InChI
InChI=1S/C59H86N6O16/c1-29(2)48(60)56(69)65-41(8-7-19-62-57(61)70)55(68)64-34-11-9-33(10-12-34)28-73-58(71)63-27-36(67)24-46-49(72-6)40-23-35(66)22-38-14-16-43-50(76-38)54-53-52(78-43)51-47(79-53)26-59(80-51,81-54)18-17-39-21-31(4)42(74-39)15-13-37-20-30(3)32(5)44(75-37)25-45(40)77-46/h9-12,29-30,36-54,67H,4-5,7-8,13-28,60H2,1-3,6H3,(H,63,71)(H,64,68)(H,65,69)(H3,61,62,70)/t30-,36+,37+,38-,39+,40+,41+,42+,43+,44-,45+,46-,47-,48+,49-,50+,51+,52+,53-,54+,59+/m1/s1
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1.Eribulin induces irreversible mitotic blockade: implications of cell-based pharmacodynamics for in vivo efficacy under intermittent dosing conditions
Towle MJ, Salvato KA, Wels BF, Aalfs KK, Zheng W, Seletsky BM, Zhu X, Lewis BM, Kishi Y, Yu MJ, Littlefield BA
Eribulin (E7389), a mechanistically unique microtubule inhibitor in phase III clinical trials for cancer, exhibits superior efficacy in vivo relative to the more potent compound ER-076349, a fact not explained by different pharmacokinetic properties. A cell-based pharmacodynamic explanation was suggested by observations that mitotic blockade induced by eribulin, but not ER-076349, is irreversible as measured by a flow cytometric mitotic block reversibility assay employing full dose/response treatment. Cell viability 5 days after drug washout established relationships between mitotic block reversibility and long-term cell survival. Similar results occurred in U937, Jurkat, HL-60, and HeLa cells, ruling out cell type-specific effects. Studies with other tubulin agents suggest that mitotic block reversibility is a quantifiable, compound-specific characteristic of antimitotic agents in general. Bcl-2 phosphorylation patterns parallel eribulin and ER-076349 mitotic block reversibility patterns, suggesting persistent Bcl-2 phosphorylation contributes to long-term cell-viability loss after eribulin's irreversible blockade. Drug uptake and washout/retention studies show that [3H]eribulin accumulates to lower intracellular levels than [3H]ER-076349, yet is retained longer and at higher levels. Similar findings occurred with irreversible vincristine and reversible vinblastine, pointing to persistent cellular retention as a component of irreversibility. Our results suggest that eribulin's in vivo superiority derives from its ability to induce irreversible mitotic blockade, which appears related to persistent drug retention and sustained Bcl-2 phosphorylation. More broadly, our results suggest that compound-specific reversibility characteristics of antimitotic agents contribute to interactions between cell-based pharmacodynamics and in vivo pharmacokinetics that define antitumor efficacy under intermittent dosing conditions.
2.Eribulin-based antibody-drug conjugates and methods of use
Earl F Albone, et al.
Linker toxins and antibody-drug conjugates that bind to human oncology antigen targets such as folate receptor alpha and/or provide anti-tubulin drug activity are disclosed. The linker toxins and antibody-drug conjugates comprise an eribulin drug moiety and can be internalized into target antigen-expressing cells. The disclosure further relates to methods and compositions for use in the treatment of cancer by administering the antibody-drug conjugates provided herein.
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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