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MBC-11

CAT: 0931-T11956L-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0931-T11956L-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
332863-86-2
Target
Others, Apoptosis
Related Pathways
Apoptosis, Others
Purity
>99.99%
Bioactivity
MBC-11 is a first-in-class conjugate of the bone-targeting bisphosphonate etidronate covalently linked to the antimetabolite cytarabine (araC), with potential to treat tumor-induced bone disease (TIBD) .
Smiles
O[C@@H]1[C@@H](O[C@H](COP(OP(C(P(=O)(O)O)(C)O)(=O)O)(=O)O)[C@H]1O)N2C(=O)N=C(N)C=C2
Molecular Formula
C11H20N3O14P3
Molecular Weight
511.21
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Mbc-11

Etidronate-Cytarabine Conjugate MBC-11 is a synthetic conjugate composed of the bisphosphonate etidronate linked to the cytostatic agent and antimetabolite cytarabine, with potential antineoplastic and antiresorptive activities. Upon intravenous administration of the etidronate-cytarabine conjugate MBC-11, the etidronate moiety targets bone and the two moieties are released upon hydrolysis. Etidronate binds to hydroxyapatite crystals in bone tissues and prevents its resorption. This prevents bone destruction and induces bone cell mineralization. In addition, the bone-targeting nature of this agent allows for the accumulation of cytarabine in bone tissue, where it is able to exert its antitumor effect locally by competing with cytidine for incorporation into DNA, thereby inhibiting DNA synthesis, while reducing systemic exposure. This leads to a destruction of bone-associated tumor cells, an inhibition of tumor cell proliferation and bone metastasis, and prevents tumor-mediated bone destruction.

CAS Number332863-86-2
PubChem CID44463769
IUPAC Name[1-[[[(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]-1-hydroxyethyl]phosphonic acid
Molecular FormulaC11H20N3O14P3
Molecular Weight511.21
XLogP-6.1
Topological Polar Surface Area279
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count14
Rotatable Bond Count8
Heavy Atom Count31
Formal Charge0
Complexity934
SMILES
CC(O)(P(=O)(O)O)P(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@@H]([C@@H](O1)N2C=CC(=NC2=O)N)O)O
InChI
InChI=1S/C11H20N3O14P3/c1-11(18,29(19,20)21)30(22,23)28-31(24,25)26-4-5-7(15)8(16)9(27-5)14-3-2-6(12)13-10(14)17/h2-3,5,7-9,15-16,18H,4H2,1H3,(H,22,23)(H,24,25)(H2,12,13,17)(H2,19,20,21)/t5-,7-,8+,9-,11?/m1/s1
InChIKey
HUIKCRXUQCSUJS-ZLRZYOKSSA-N
Chemical Structure
2D Structure
2D structure of Mbc-11
CAS: 332863-86-2
CID: 44463769
Formula: C11H20N3O14P3
MW: 511.21
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight511.21
XLogP3-6.1
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count14
Rotatable Bond Count8
Exact Mass511.01581331
Monoisotopic Mass511.01581331
Topological Polar Surface Area279 Ų
Heavy Atom Count31
Formal Charge0
Complexity934
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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