WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 201955
CAS#: 827031-83-4
Description: Thymectacin, also known as NB-1011, is a small molecule phosphoramidate derivative of (E)-5-(2-bromovinyl)-2'-deoxyuridine with potential antineoplastic activity. Selectively active against tumor cells expressing high levels of thymidylate synthase (TS), BVdU pronucleotide analogue NB1011 is converted intracellularly by TS to bromovinyldeoxyuridine monophosphate (BVdUMP) which competes with the natural substrate, deoxyuridine monophosphate, for binding to TS. Unlike TS inhibitors, this agent is a reversible substrate for TS catalysis.
MedKoo Cat#: 201955
Name: Thymectacin
CAS#: 827031-83-4
Chemical Formula: C21H25BrN3O9P
Exact Mass: 573.05118
Molecular Weight: 574.3
Elemental Analysis: C, 43.92; H, 4.39; Br, 13.91; N, 7.32; O, 25.07; P, 5.39
Synonym: NB1011; NB-1011; NB 1011; NB101; Thymectacin.
IUPAC/Chemical Name: (2S)-methyl 2-(((((2R,3S,5R)-5-(5-((E)-2-bromovinyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
InChi Key: CFBLUORPOFELCE-BACVZHSASA-N
InChi Code: InChI=1S/C21H25BrN3O9P/c1-13(20(28)31-2)24-35(30,34-15-6-4-3-5-7-15)32-12-17-16(26)10-18(33-17)25-11-14(8-9-22)19(27)23-21(25)29/h3-9,11,13,16-18,26H,10,12H2,1-2H3,(H,24,30)(H,23,27,29)/b9-8+/t13-,16-,17+,18+,35?/m0/s1
SMILES Code: C[C@H](NP(OC1=CC=CC=C1)(OC[C@H]2O[C@@H](N(C(N3)=O)C=C(/C=C/Br)C3=O)C[C@@H]2O)=O)C(OC)=O
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: >2 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
The following data is based on the product molecular weight 574.3 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 |
1. Congiatu, C.; McGuigan, C.; Jiang, W. G.; Davies, G.; Mason, M. D. Naphthyl phosphoramidate derivatives of BVdU as potential anticancer agents: Design, synthesis and biological evaluation. Nucleosides, Nucleotides & Nucleic Acids (2005), 24(5-7), 485-489. CODEN: NNNAFY ISSN:1525-7770. CAN 145:271969 AN 2005:1151332
2. Nakata, Rieko. Development of novel anticancer agent targeting thymidylate synthase. Kagaku to Kogyo (Tokyo, Japan) (2003), 56(11), 1260. CODEN: KAKTAF ISSN:0022-7684. CAN 140:35079 AN 2003:927328
3. Dellinger, Ryan W.; Karjian, Patricia L.; Neuteboom, Saskia T. C. NB1011 induces Ser15 phosphorylation of p53 and activates the G2/M checkpoint. Anti-Cancer Drugs (2003), 14(6), 449-455. CODEN: ANTDEV ISSN:0959-4973. CAN 140:35438 AN 2003:543256
4. Natarajan, Gita; John, Elizabeth; Maniar, Manoj. Formulation development of a nucleotide phosphoramidate. Pharmaceutical Technology (2003), 27(6), 66,68,70. CODEN: PTHEC9 ISSN:1543-2521. CAN 140:64854 AN 2003:515896
5. Sergeeva, Maria V.; Cathers, Brian E. Cellular transformation of the investigational new anticancer drug NB1011, a phosphoramidate of 5-(2-bromovinyl)-2'-deoxyuridine, results in modification of cellular proteins not DNA. Biochemical Pharmacology (2003), 65(5), 823-831. CODEN: BCPCA6 ISSN:0006-2952. CAN 139:190589 AN 2003:164629
6. Boyer, Christopher R.; Karjian, Paticia L.; Wahl, Geoffrey M.; Pegram, Mark; Neuteboom, Saskia T. C. Nucleoside transport inhibitors, dipyridamole and p-nitrobenzylthioinosine, selectively potentiate the antitumor activity of NB1011. [Erratum to document cited in CA138:248065]. Anti-Cancer Drugs (2002), 13(10), 1077. CODEN: ANTDEV ISSN:0959-4973. CAN 139:316719 AN 2003:54370
7. Boyer, Christopher R.; Karjian, Patricia L.; Wahl, Geoffrey M.; Pegram, Mark; Neuteboom, Saskia T. C. Nucleoside transport inhibitors, dipyridamole and p-nitrobenzylthioinosine, selectively potentiate the antitumor activity of NB1011. Anti-Cancer Drugs (2002), 13(1), 29-36. CODEN: ANTDEV ISSN:0959-4973. CAN 138:248065 AN 2002:694508
8. Neuteboom, Saskia T. C.; Karjian, Patricia L.; Boyer, Christopher R.; Beryt, Malgorzhata; Pegram, Mark; Wahl, Geoffrey M.; Shepard, H. Michael. Inhibition of cell growth by NB1011 requires high thymidylate synthase levels and correlates with p53, p21, Bax, and GADD45 induction. Molecular Cancer Therapeutics (2002), 1(6), 377-384. CODEN: MCTOCF ISSN:1535-7163. CAN 137:272912 AN 2002:328912
9. Li, Qing; Boyer, Christopher; Lee, Jean Y.; Shepard, H. Michael. A novel approach to thymidylate synthase as a target for cancer chemotherapy. Molecular Pharmacology (2001), 59(3), 446-452. CODEN: MOPMA3 ISSN:0026-895X. CAN 134:361084 AN 2001:167005
10. Lackey, D. B.; Groziak, M. P.; Sergeeva, M.; Beryt, M.; Boyer, C.; Stroud, R. M.; Sayre, P.; Park, J. W.; Johnston, P.; Slamon, D.; Shepard, H. M.; Pegram, M. Enzyme-catalyzed therapeutic agent (ECTA) design: activation of the antitumor ECTA compound NB1011 by thymidylate synthase. Biochemical Pharmacology (2001), 61(2), 179-189. CODEN: BCPCA6 ISSN:0006-2952. CAN 134:290064 AN 2001:24117
11. Sergeeva Oksana A; Khambatta H Godrej; Cathers Brian E; Sergeeva Maria V Kinetic properties of human thymidylate synthase, an anticancer drug target. Biochemical and biophysical research communications (2003), 307(2), 297-300. Journal code: 0372516. ISSN:0006-291X. PubMed ID 12859954 AN 2003330291
