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[ CAS No. 151038-96-9 ] {[proInfo.proName]}

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Chemical Structure| 151038-96-9
Chemical Structure| 151038-96-9
Structure of 151038-96-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 151038-96-9 ]

CAS No. :151038-96-9 MDL No. :
Formula : C37H42N4O13 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 750.75 Pubchem ID :-
Synonyms :
(E/Z)-Aldoxorubicin;Doxorubicin(6-maleimidocaproyl)hydrazone

Safety of [ 151038-96-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 151038-96-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 151038-96-9 ]

[ 151038-96-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 23214-92-8 ]
  • [ 81186-33-6 ]
  • [ 151038-96-9 ]
YieldReaction ConditionsOperation in experiment
at 30℃; for 12h; 9 For conjugation via the carbonyl group doxorubicin is stirred for 12 h at 30 °C with molar excess of (6-maleimidocaproyl)hydrazide. The primary amino group of 428-ε- Lys-α-NH2 is converted to a thiol by reaction with dithioglycolic acid activated by EDC / NHS and subsequent reduction with TCEP. The doxorubicin-hydrazone-caproyl- maleimide is coupled to the thiol-derivative of 428-ε-Lys-α-NH2 by stirring with 10-fold excess of thiol derivative for 12 h at 30 °C.
  • 2
  • [ 151038-94-7 ]
  • [ 25316-40-9 ]
  • [ 151038-96-9 ]
YieldReaction ConditionsOperation in experiment
58% With pyridine; In methanol; at 20℃; The synthesis of DOXO-EMCH was accomplished using the procedure reported by Willner et al, with several changes to improve the yield (Willner, D., et al.,Bioconjugate Chem., 4:521-27, 1993). DOX'HCl (20 mg, 34 muiotaetaomicron) was dissolved in 6 mL of methanol. Pyridine (12.53 mu) was added to the solution, followed by 35.4 mgEMCH'TFA. The reaction was stirred at room temperature overnight. By HPLC, the reaction was 90% complete. The solvent was evaporated to dryness by rotary evaporation. A minimal amount of methanol was used to dissolve the solid, and six volumes of acetonitrile at 4 C were added to the solution. The resulting solution was allowed to sit undisturbed at 4 C for 48 h for crystallization. The precipitate was collected, and the crystallization method was repeated 4 times. The resulting solids were combined and washed three times with 1 : 10 methanokacetonitrile. The final yield of DOXO-EMCH was 11.59 mg, 58%. HPLC Method 1.1 was used. NMR spectra corresponded to those previously given by Willner (Bioconjugate Chem. 4:521-27. 1993).
  • 3
  • [ 151038-94-7 ]
  • [ 23214-92-8 ]
  • [ 151038-96-9 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; In methanol; at 20℃; for 24.0h;Darkness; 1 mmol of doxorubicin, 3 mmol of 6-maleimidocaproyl hydrazide trifluoroacetate, mix 20mL of methanol and 0.01mL of trifluoroacetic acid, in the dark,The nucleophilic addition reaction was carried out at 20 C for 24 h; the obtained system was mixed with ethanol, and then subjected to precipitation and ultrafiltration centrifugation, and the obtained concentrated material was lyophilized. Obtaining maleimide functionalized doxorubicin; 1 mmol of KLAK peptide with a cysteine at the N-terminus, 15 mmol of tris(2-carbonylethyl)phosphoric acid hydrochloride and 10 mL of phosphate buffer solution (concentration: 20 mmol/L, pH 7.4) were mixed, and stirred at 25 C for 1 h; Then add 3 mmol of maleimide functionalized doxorubicin, adding reaction under stirring at 25 C for 2 h; the obtained system was allowed to stand at 4 C for 22 h, and then subjected to ultrafiltration centrifugation. The resulting concentrated material is lyophilized, an anti-tumor peptide-doxorubicin derivative is obtained.
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