186256-68-8

Upstream product

• 208581-45-7 (E)-5-(4-methoxyphenylmethyloxy)-2-methyl-2-pentenol 
• 208581-53-7 (E)-ethyl 5-(4-methoxyphenylmethyloxy)-2-methyl-2-pentenoate 
• 162465-33-0 allyl (2S)-2-Hydroxy-4-methylpentanoate 
• 13748-90-8 (S)-2-hydroxyl-3,3-dimethylbutyric acid 
• 162465-45-4 (R)-2-((tet-butoxycarbonyl)amino)-3-(3-chloro-4-methoxyphenyl)propanoic acid 
• 478183-57-2 (2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-hydroxyphenyl)propanoic acid 
• 556-02-5 tyrosine 
• 162599-95-3 (R)-3-(3-Chloro-4-methoxy-phenyl)-2-((2E,7E)-(5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2,7-dienoylamino)-propionic acid 2,2,2-trichloro-ethyl ester 

Downstream Products

• 186256-69-9 cryptophycin 55 
• 186256-67-7 cryptophycin 52 
• 204397-66-0 C₃₆H₄₇ClN₂O₉ 
• 270901-32-1 (E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 
• 204398-47-0 pentanoic acid, 3-chloro-N-[(2E,6S,7R,8S)-8-chloro-8-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]-5,7-dihydroxy-6-methyl-1-oxo-2-octenyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->1⁵)-lactone, (2S)- 
• 204397-83-1 3-tert-Butoxycarbonylamino-2,2-dimethyl-propionic acid 4-{(1S,2R,3R)-1-chloro-3-[(E)-(3S,10R,16S)-10-(3-chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-2-hydroxy-butyl}-benzyl ester 
• 204397-96-6 3-tert-Butoxycarbonylamino-2,2-dimethyl-propionic acid 4-{(1S,2R,3R)-1-chloro-3-[(E)-(3S,10R,16S)-10-(3-chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-2-hydroxy-butyl}-phenyl ester 
• 204398-06-1 pentanoic acid, N-[(1,1-dimethylethoxy)carbonyl]-N-methylglycyl-(2E,5S,6S,7R,8S)-8-[4-(aminomethyl)phenyl]-8-chloro-5,7-dihydroxy-6-methyl-2-octenoyl-3-chloro-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (5->2⁵)-lactone, (2S)- 
• 204398-46-9 cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6S)-6-[(2R,3R)-3-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]oxiranyl]-5-hydroxy-2-heptenoyl-3-chloro-O-methyl-D-tyrosyl] 
• 204397-74-0 tert-Butoxycarbonylamino-acetic acid 4-{(1S,2R,3R)-1-chloro-3-[(E)-(3S,10R,16S)-10-(3-chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-2-hydroxy-butyl}-benzyl ester 

Relevant academic research and scientific papers

Cryptophycin-55/52 based antibody-drug conjugates: Synthesis, efficacy, and mode of action studies

Cryptophycin-52 (CR52), a tubulin inhibitor, exhibits promising antitumor activity in vitro (picomolar level) and in mouse xenograft models. However, the narrow therapeutic window in clinical trials limits its further development. Antibody-drug conjugate (ADC), formed by coupling cytotoxic compound (payload) to an antibody via a linker, can deliver drug to tumor locations in a targeted manner by antibody, enhancing the therapeutic effects and reducing toxic and side effects. In this study, we aim to explore the possibility of CR52-based ADC for tumor targeted therapy. Due to the lack of a coupling site in CR52, its prodrug cryptophycin-55 (CR55) containing a free hydroxyl was synthesized and conjugated to the model antibody trastuzumab (anti-HER2 antibody drug approved by FDA for breast cancer therapy) via the linkers based on Mc-NHS and Mc-Val-Cit-PAB-PNP. The average drug-to-antibody ratios (DARs) of trastuzumab-CR55 conjugates (named T-L1-CR55, T-L2-CR55, and T-L3-CR55) were 3.50, 3.29, and 3.35, respectively. These conjugates exhibited potent cytotoxicity in HER2-positive tumor cell lines with IC50 values at low nanomolar levels (0.58–1.19 nM). Further, they displayed significant antitumor activities at the doses of 10 mg/kg in established ovarian cancer (SKOV3) and gastric cancer (NCI–N87) xenograft models without overt toxicities. Finally, the drug releases were analyzed and the results indicated that T-L3-CR55 was able to effectively release CR55 and further epoxidized to CR52, which may be responsible for its best performance in antitumor activities. In conclusion, our results demonstrated that these conjugates have the potential for tumor targeted therapy, which provides insights to further research the CR55/CR52-based ADC for tumor therapy.

Enantioselective Synthesis of (+)-Cryptophycin 52 (LY355703), a Potent Antimitotic Antitumor Agent

A highly enantioselective and convergent synthesis of cryptophycin 52 (2), an exceedingly potent cytotoxic agent, is described. Cryptophycin 52, a synthetic variant of the cryptophycin family, is currently undergoing clinical trials. The synthesis is conv

A convergent approach to cryptophycin 52 analogues: Synthesis and biological evaluation of a novel series of fragment A epoxides and chlorohydrins

Cryptophycin 52 is a synthetic derivative of Cryptophycin 1, a potent antimicrotubule agent isolated from cyanobacteria. In an effort to increase the potency and water solubility of the molecule, a structure-activity relationship study (SAR) was initiated

Synthesis of cryptophycin 52 using the shi epoxidation

Matrix presented A synthesis of cryptophycin 52 is reported using a Shi epoxidation strategy to install the epoxide moiety in a diastereoselective fashion. Several epoxidation results for cryptophycin substrates are disclosed followed by a discussion of t