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MedKoo product information:
Thymectacin
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MedKoo Code#: 201955
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Name:
Thymectacin
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CAS#:
827031-83-4
Synonym: Thymectacin,
NB-1011, NB-101; N-[[5-[(E)-2-Bromovinyl]-2'-deoxyuridin-5'-O-yl](phenoxy)phosphoryl]-L-alanine
methyl ester. (E)-5-(2-Bromovinyl)-2'-deoxy-5'-uridyl phenyl L-methoxyalaninylphosphoramidate;
L-Alanine, N-[5-[(1E)-2-bromoethenyl]-2'-deoxy-P-phenyl-5'-uridylyl]-,
methyl ester
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
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Chemical structure: |
Theoretical analysis
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Chemical Formula: C21H25BrN3O9P
Exact Mass: 573.05118
Molecular Weight: 574.3
m/z: 573.05118 (100.0%), 575.04913 (97.3%),
574.05453 (22.7%), 576.05249 (22.1%), 575.05789 (2.5%),
577.05584 (2.4%), 575.05542 (1.8%), 577.05338 (1.8%), 574.04821
(1.1%), 576.04617 (1.1%)
Elemental Analysis: C, 43.92; H, 4.39; Br,
13.91; N, 7.32; O, 25.07; P, 5.39
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Availability and price:
This agent is not in stock, which may be available through custom synthesis. To inquire quotation and lead time or to ask questions, please send email to
sales@medkoo.com to describe your needs. A representative
will respond your email shortly. We offer big discount for orders of bulk quantities.
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Quality control
data:
Product will be shipped with
supporting analytical data.
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Information about this agent
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Thymectacin 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.
Thus, TS retains activity and converts BVdUMP into cytotoxic
metabolites. As key enzyme in the de novo synthesis of dTMP, TS is an
enzyme critical to DNA biosynthesis and is overexpressed in many solid
tumors. (from
NCI's webpage)
Current developer: NewBiotics/Elan/Kiadis
Pharma Inc
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
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