Dolastatin 10 - CAS 110417-88-4
Catalog number:
110417-88-4
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C42H68N6O6S
Molecular Weight:
785.09
COA:
Inquire
Targets:
ADCs Cytotoxin | Microtubule/Tubulin
Description:
Dolastatin 10 is an inhibitior of microtubule disassembly (IC50= 1.2μM) and potently inhibits vincristine binding to tubulin in a noncompetitive manner ( Ki= 1.4μM).
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Brife Description:
An inhibitior of microtubule disassembly (IC50= 1.2μM)
Appearance:
White to off-white solid
Synonyms:
(2S)-2-[[(2S)-2-(dimethylamino)-3-methylbutanoyl]amino]-N-[(3R,4S,5S)-3-methoxy-1-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-N,3-dimethylbutanamide; Dolastatin 10; UNII-EI946JT51X; CCRIS 7310; EI946JT51X; NSC 376128; L-Valinamide, N,N-dimethyl-L-valyl-N-(2-methoxy-4-(2-(1-methoxy-2-methyl-3-oxo-3-((2-phenyl-1-(2-thiazolyl)ethyl)amino)propyl)-1-pyrrolidinyl)-1-(1-methylpropyl)-4-oxobutyl)-N-methyl-,(2S-(1(1R*(R*),2S*),2R*(1S*,2S*,3(R*))))-; isodolastatin 10; 110417-88-4; deo-dolastatin 10; SCHEMBL6423272; C42H68N6O6S; CHEBI:67357; ZINC95803508; CS-1825; HY-15580; LS-161286
Solubility:
Soluble to 10 mM in DMSO
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -57℃ for long term (months to years).
MSDS:
Inquire
Boiling Point:
903.6ºC at 760 mmHg
Density:
1.116 g/cm3
InChIKey:
OFDNQWIFNXBECV-VFSYNPLYSA-N
InChI:
1S/C42H68N6O6S/c1-13-28(6)37(47(10)42(52)35(26(2)3)45-40(51)36(27(4)5)46(8)9)33(53-11)25-34(49)48-22-17-20-32(48)38(54-12)29(7)39(50)44-31(41-43-21-23-55-41)24-30-18-15-14-16-19-30/h14-16,18-19,21,23,26-29,31-33,35-38H,13,17,20,22,24-25H2,1-12H3,(H,44,50)(H,45,51)/t28-,29+,31-,32-,33+,35-,36-,37-,38+/m0/s1
Canonical SMILES:
CCC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NC(CC2=CC=CC=C2)C3=NC=CS3)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)N(C)C
1.A synthetic dolastatin 10 analogue suppresses microtubule dynamics, inhibits cell proliferation, and induces apoptotic cell death.
Gajula PK1, Asthana J, Panda D, Chakraborty TK. J Med Chem. 2013 Mar 28;56(6):2235-45. doi: 10.1021/jm3009629. Epub 2013 Mar 19.
We have synthesized eight analogues (D1-D8) of dolastatin 10 containing several unique amino acid subunits. Of these agents, D5 was found to be most effective in inhibiting both HeLa cell proliferation and microtubule assembly in vitro. At low nanomolar concentrations, D5 inhibited the proliferation of several types of cancer cells in culture. D5 bound to tubulin with a dissociation constant of 29.4 ± 6 μM. D5 depolymerized microtubules in cultured cells and produced mulitpolar spindles. At its half-maximal inhibitory concentration (15 nM), D5 strongly suppressed the dynamics of individual microtubules in live MCF-7 cells. D5 increased the accumulation of checkpoint proteins BubR1 and Mad2 at the kinetochoric region and caused G2/M block in these cells. The blocked cells underwent apoptosis with the activation of Jun N-terminal kinase. The results suggested that D5 exerts its antiproliferative action by dampening microtubule dynamics.
2.Discovery of cytotoxic dolastatin 10 analogues with N-terminal modifications.
Maderna A1, Doroski M, Subramanyam C, Porte A, Leverett CA, Vetelino BC, Chen Z, Risley H, Parris K, Pandit J, Varghese AH, Shanker S, Song C, Sukuru SC, Farley KA, Wagenaar MM, Shapiro MJ, Musto S, Lam MH, Loganzo F, O'Donnell CJ. J Med Chem. 2014 Dec 26;57(24):10527-43. doi: 10.1021/jm501649k. Epub 2014 Dec 9.
Auristatins, synthetic analogues of the antineoplastic natural product Dolastatin 10, are ultrapotent cytotoxic microtubule inhibitors that are clinically used as payloads in antibody-drug conjugates (ADCs). The design and synthesis of several new auristatin analogues with N-terminal modifications that include amino acids with α,α-disubstituted carbon atoms are described, including the discovery of our lead auristatin, PF-06380101. This modification of the peptide structure is unprecedented and led to analogues with excellent potencies in tumor cell proliferation assays and differential ADME properties when compared to other synthetic auristatin analogues that are used in the preparation of ADCs. In addition, auristatin cocrystal structures with tubulin are being presented that allow for the detailed examination of their binding modes. A surprising finding is that all analyzed analogues have a cis-configuration at the Val-Dil amide bond in their functionally relevant tubulin bound state, whereas in solution this bond is exclusively in the trans-configuration.
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CAS 110417-88-4 Dolastatin 10

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