WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 200440
CAS#: 195533-98-3 (sodium)
Description: Batabulin, also known as T138067, is a synthetic pentafluorophenylsulfonamide with potential antineoplastic activity. T138067 covalently binds to and selectively modifies the beta 1, beta 2, beta 3, and beta 4 isotypes of beta tubulin at a conserved cysteine residue, resulting in disruption of microtubule polymerization, collapse of the cytoskeleton, an increase in chromosomal ploidy, cell cycle arrest, and tumor cell apoptosis.
MedKoo Cat#: 200440
Name: Batabulin sodium
CAS#: 195533-98-3 (sodium)
Chemical Formula: C13H6F6NNaO3S
Exact Mass:
Molecular Weight: 393.2352
Elemental Analysis: C, 39.71; H, 1.54; F, 28.99; N, 3.56; Na, 5.85; O, 12.21; S, 8.15
Related CAS #: 195533-98-3 (sodium) 195533-53-0 (free)
Synonym: Batabulin sodium; Batabulin; T138067; T-138067; T 138067;
IUPAC/Chemical Name: sodium (3-fluoro-4-methoxyphenyl)-(2,3,4,5,6-pentafluorophenyl)sulfonylazanide
InChi Key: UWPXRVDIKGZQQW-UHFFFAOYSA-N
InChi Code: InChI=1S/C13H6F6NO3S.Na/c1-23-7-3-2-5(4-6(7)14)20-24(21,22)13-11(18)9(16)8(15)10(17)12(13)19;/h2-4H,1H3;/q-1;+1
SMILES Code: O=S([N-]C1=CC=C(OC)C(F)=C1)(C2=C(F)C(F)=C(F)C(F)=C2F)=O.[Na+]
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >5 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
| Biological target: | Batabulin sodium (T138067 sodium) is an antitumor agent which binds covalently and selectively to a subset of the β-tubulin isotypes, thereby disrupting microtubule polymerization. |
| In vitro activity: | To measure the effects of T138067 on microtubule formation, two types of in vitro tubulin polymerization assays were used. In a sedimentation assay, the polymerization reaction was performed in the absence or presence of T138067 (Fig. 3A). The reaction products were size-fractionated by spinning the mixture through a glycerol cushion. Heterodimeric tubulin remains primarily in the cushion, whereas larger molecules (microtubules) sediment through the cushion and form a pellet at the bottom of the tube. In the absence of any agent, a substantial reduction in the amount of tubulin in the cushion fraction was observed in a polymerization reaction that was incubated at 37°C, in comparison to one that was kept at 0°C, indicating the formation of microtubules (Fig. 3A, compare lanes 1 and 2). However, increasing concentrations of T138067 at 37°C increased the amount of tubulin in the cushion fraction to levels comparable to those derived from the control reaction at 0°C (Fig. 3A, compare lanes 1 and 3 to 5). When the pellet fractions were analyzed, a strong reduction of tubulin was observed in reactions containing T138067 in comparison to reactions that were incubated in the absence of the drug. In summary, these results indicate that T138067 prevents microtubule formation. Reference: Proc Natl Acad Sci U S A. 1999 May 11;96(10):5686-91. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC21921/ |
| In vivo activity: | The antitumor efficacies of T138067, paclitaxel, and vinblastine were evaluated in mouse xenograft models. Drug-sensitive, human T cell leukemia CCRF-CEM cells, and their vinblastine/paclitaxel-resistant subline (CCRF-CEM/VBL100) were grafted separately into athymic nude mice. Animals were dosed i.p. at the maximally tolerated doses of paclitaxel (30 mg/kg), vinblastine (1 mg/kg), and T138067 (40 mg/kg) once per week. After a single i.p. dose, all three drugs impaired the growth of the drug-sensitive CCRF-CEM tumors (Fig. 5A). Two additional weekly doses of each drug further impeded tumor growth, resulting in similar antitumor efficacies for all three drugs. T138067 showed the same degree of efficacy when tested against the MDR subline (Fig. 5B). In contrast, paclitaxel and vinblastine showed approximately 50% reduced efficacy against the MDR tumors (Fig. 5B). Thus, T138067 may be clinically useful for the treatment of human cancers that have developed resistance to standard chemotherapeutic agents. Reference: Proc Natl Acad Sci U S A. 1999 May 11;96(10):5686-91. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC21921/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMF | 30.0 | 76.29 | |
| DMSO | 30.0 | 76.29 | |
| Ethanol | 30.0 | 76.29 | |
| Ethanol:PBS (pH 7.2) (1:3) | 0.25 | 0.64 |
The following data is based on the product molecular weight 393.2352 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Shan B, Medina JC, Santha E, Frankmoelle WP, Chou TC, Learned RM, Narbut MR, Stott D, Wu P, Jaen JC, Rosen T, Timmermans PB, Beckmann H. Selective, covalent modification of beta-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc Natl Acad Sci U S A. 1999 May 11;96(10):5686-91. doi: 10.1073/pnas.96.10.5686. PMID: 10318945; PMCID: PMC21921. |
| In vitro protocol: | 1. Shan B, Medina JC, Santha E, Frankmoelle WP, Chou TC, Learned RM, Narbut MR, Stott D, Wu P, Jaen JC, Rosen T, Timmermans PB, Beckmann H. Selective, covalent modification of beta-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc Natl Acad Sci U S A. 1999 May 11;96(10):5686-91. doi: 10.1073/pnas.96.10.5686. PMID: 10318945; PMCID: PMC21921. |
| In vivo protocol: | 1. Shan B, Medina JC, Santha E, Frankmoelle WP, Chou TC, Learned RM, Narbut MR, Stott D, Wu P, Jaen JC, Rosen T, Timmermans PB, Beckmann H. Selective, covalent modification of beta-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc Natl Acad Sci U S A. 1999 May 11;96(10):5686-91. doi: 10.1073/pnas.96.10.5686. PMID: 10318945; PMCID: PMC21921. |
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2: Ling X, He X, Apontes P, Cao F, Azrak RG, Li F. Enhancing effectiveness of the MDR-sensitive compound T138067 using advanced treatment with negative modulators of the drug-resistant protein survivin. Am J Transl Res. 2009 Jul 15;1(4):393-405. PMID: 19956451; PMCID: PMC2780039.
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