155589-16-5

Basic information

• Product Name: rapamycin 42-hemisuccinate
• Synonyms: rapamycin 42-hemisuccinate
• CAS NO: 155589-16-5
• Molecular Weight: 1014.26
• Mol File: 155589-16-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: rapamycin 42-hemisuccinate(CAS DataBase Reference)
• NIST Chemistry Reference: rapamycin 42-hemisuccinate(155589-16-5)
• EPA Substance Registry System: rapamycin 42-hemisuccinate(155589-16-5)

Safety Data

• Hazardous Substances Data: 155589-16-5(Hazardous Substances Data)

Upstream product

• 108-30-5 succinic acid anhydride 
• 53123-88-9 sirolimus 
• 143136-12-3 rapamycin 42-hemisuccinate benzyl ester 
• 155589-15-4 rapamycin 42-hemisuccinate methyl ester 

Relevant articles and documents

Lipase-catalyzed regioselective esterification of rapamycin: Synthesis of temsirolimus (CCI-779)

(Chemical Equation Presented) A lipase-catalyzed acylation of the immunosuppressant rapamycin with complete regioselectivity is described. The method was successfully applied to the synthesis of 42-hemiesters and temsirolimus (CCI-779), an investigational oncology drug.

Enhanced Cytotoxicity to Cancer Cells by Codelivery and Controlled Release of Paclitaxel-loaded Sirolimus-conjugated Albumin Nanoparticles

Recently, it is suggested that mTOR signaling pathway is an important mediator in many cancers especially breast cancer. Therefore, effects of sirolimus as a mTOR inhibitor in breast cancer have been studied in combination with paclitaxel with or without controlled release effect. In this work, we prepared a water-soluble formulation of sirolimus-conjugated albumin nanoparticles loaded with paclitaxel, to study the effects of sirolimus concentration when it releases more later than paclitaxel in comparison with sirolimus–paclitaxel-loaded albumin nanoparticles. Also effects of paclitaxel loading on cytotoxic properties of nanoparticles were studied. Sirolimus was succinylated at 42-OH with enzymatic reaction of Candida antarctica lipase B, and then its carboxylic group was activated with EDC/NHS and conjugated to the lysine residues of albumin. Paclitaxel was loaded on albumin surface by nab technique in concentration range of 0–10 μg/mL. Sirolimus-conjugated nanoparticles with 0.01 μg/mL paclitaxel showed lowest cell viability of 44% while it was 53% for non-conjugated nanoparticles in MDA-MB-468 cell lines after 48 h (p-value = 0.003). In MCF-7 cell lines, sirolimus-conjugated nanoparticles with 0.1 μg/mL paclitaxel showed lowest cell viability of 35.69% while it was 48% for non-conjugated nanoparticles after 48 h (p-value = 0.03). We guess that when cancer cell lines arrest in G2-M by anticancer drugs like paclitaxel, Akt activates mTOR to make cells continue living, then inhibiting mTOR can enhance anticancer effects.

PROCESS FOR PREPARING RAPAMYCIN 42-ESTERS AND FK-506 32-ESTERS WITH DICARBOXYLIC ACID, PRECURSORS FOR RAPAMYCIN CONJUGATES AND ANTIBODIES

Methods for the synthesis of regiospecific rapamycin 42-hemiesters and regiospecific FK506 32-esters with dicarboxylic acids is described. The methods involve catalyzing the reaction between a rapamycin or a FK-506 and a dicarboxylic anhydride or a bifunc