37571-12-3Relevant academic research and scientific papers
Practical Peptide Synthesis Mediated by a Recyclable Hypervalent Iodine Reagent and Tris(4-methoxyphenyl)phosphine
Zhang, Chi,Liu, Shan-Shan,Sun, Bo,Tian, Jun
supporting information, p. 4106 - 4109 (2015/09/01)
6-(3,5-Bis(trifluoromethyl)phenyl)-1H,4H-2aλ3-ioda-2,3-dioxacyclopenta[hi]indene-1,4-dione (p-BTFP-iodosodilactone, 1a) was synthesized and demonstrated to be an efficient hypervalent iodine(III) reagent for the synthesis of dipeptides from various standard amino acids, including sterically hindered amino acids, in good to high yields within 30 min in the presence of tris(4-methoxyphenyl)phosphine. In addition, the combined system of 1a/(4-MeOC6H4)3P was used to synthesize the pentapeptide leu-enkephalin in protected form. It is worth noting that 1a can be regenerated readily after reaction.
Design and synthesis of Hsp90 inhibitors: Exploring the SAR of Sansalvamide A derivatives
Sellers, Robert P.,Alexander, Leslie D.,Johnson, Victoria A.,Lin, Chun-Chieh,Savage, Jeremiah,Corral, Ricardo,Moss, Jason,Slugocki, Tim S.,Singh, Erinprit K.,Davis, Melinda R.,Ravula, Suchitra,Spicer, Jamie E.,Oelrich, Jenna L.,Thornquist, Andrea,Pan, Chung-Mao,McAlpine, Shelli R.
experimental part, p. 6822 - 6856 (2010/10/18)
Utilizing the structure-activity relationship we have developed during the synthesis of the first two generations and mechanism of action studies that point to the interaction of these molecules with the key oncogenic protein Hsp90, we report here the design of 32 new Sansalvamide A derivatives and their synthesis. Our new structures, designed from previously reported potent compounds, were tested for cytotoxicity on the HCT116 colon cancer cell line, and their binding to the biological target was analyzed using computational studies involving blind docking of derivatives using Autodock. Further, we show new evidence that our molecules bind directly to Hsp90 and modulate Hsp90's binding with client proteins. Finally, we demonstrate that we have integrated good ADME properties into a new derivative.
Biodegradation of poly(2-hydroxyethyl methacrylate) (PHEMA) and poly{(2-hydroxyethyl methacrylate)-co-[poly(ethylene glycol) methyl ether methacrylate]} hydrogels containing peptide-based cross-linking agents
Casadio, Ylenia S.,Brown, David H.,Chirila, Traian V.,Kraatz, Heinz-Bernhard,Baker, Murray V.
scheme or table, p. 2949 - 2959 (2011/10/08)
PHEMA-peptide and P[HEMA-co-(MeO-PEGMA)]-peptide conjugate hydrogels [where PHEMA ) poly(2- hydroxyethyl methacrylate; PEGMA ) poly(ethylene glycol) methacrylate] were readily prepared via photoinitiated free-radical polymerization in water. The PHEMA-peptide hydrogels were opaque and had a heterogeneous morphology of interconnected polymer droplets, characteristic of polymers that separate from the aqueous phase during the polymerization experiment. The P[HEMA-co-(MeO-PEGMA)]-peptide conjugates were transparent gels with a homogeneous morphology when formed in water, but when formed in aqueous NaCl solutions the P[HEMA-co-(MeO-PEGMA)]-peptide conjugates were also opaque and exhibited the heterogeneous morphology of interconnected polymer droplets. When incubated in solutions containing activated papain, P[HEMA-co-(MeOPEGMA)]- peptide conjugates underwent degradation that was characterized by macroscopic changes to sample shape and size, sample weight, and microscopic structure. PHEMA-peptide conjugates did not undergo any significant degradation when incubated with papain, although ninhydrin-staining experiments suggested that some peptide cross-linker groups were cleaved during the incubation. The difference in degradation behavior of PHEMA-peptide and P[HEMA-co-(MeO-PEGMA)]- peptide conjugates is attributed to differences in aqueous solubility of PHEMA and P[HEMA-co-(MeO-PEGMA)].
A comprehensive study of Sansalvamide A derivatives: The structure-activity relationships of 78 derivatives in two pancreatic cancer cell lines
Pan, Po-Shen,Vasko, Robert C.,Lapera, Stephanie A.,Johnson, Victoria A.,Sellers, Robert P.,Lin, Chun-Chieh,Pan, Chung-Mao,Davis, Melinda R.,Ardi, Veronica C.,McAlpine, Shelli R.
experimental part, p. 5806 - 5825 (2009/12/24)
We report an extensive structure-activity relationship (SAR) of 78 compounds active against two pancreatic cancer cell lines. Our comprehensive evaluation of these compounds utilizes SAR that allow us to evaluate which features of potent compounds play a
Comprehensive study of sansalvamide A derivatives and their structure-activity relationships against drug-resistant colon cancer cell lines
Otrubova, Katerina,Lushington, Gerald,Vander Velde, David,McGuire, Kathleen L.,McAlpine, Shelli R.
, p. 530 - 544 (2008/09/18)
We report an extensive structure-activity relationship (SAR) of 62 compounds active against two drug-resistant colon cancer cell lines. Our comprehensive evaluation of two generations of compounds utilizes SAR, NMR, and molecular modeling to evaluate the
Synthesis of second-generation Sansalvamide A derivatives: Novel templates as potential antitumor agents
Rodriguez, Rodrigo A.,Pan, Po-Shen,Pan, Chung-Mao,Ravula, Suchitra,Lapera, Stephanie,Singh, Erinprit K.,Styers, Thomas J.,Brown, Joseph D.,Cajica, Julia,Parry, Emily,Otrubova, Katerina,McAlpine, Shelli R.
, p. 1980 - 2002 (2007/10/03)
We report the synthesis of 34 second-generation Sansalvamide A derivatives. San A derivatives have unique anticancer properties and target multiple cancers, including colon, pancreatic, breast, prostate, and melanoma. As novel templates, the derivatives d
Novel antimicrobial peptides based on tripeptide repeats
-
Page/Page column 10, (2008/06/13)
The invention described herein relates to compositions of novel antimicrobial peptides that comprise hydrophobic and cationic residues, based on monomeric tri-peptide units. The peptides of the present invention exhibit high antibacterial activity and low
A single point chiral inversion that selforganizes a randomcoil peptide. Apolar solvent conformation of Boc-(L/D)-Glu-Ala-Leu-LysNHMe
Bobde,Beri,Rawale,Satyanarayana,Durani
, p. 3077 - 3086 (2007/10/02)
The tetrapeptide Boc-L-Glu-Ala-Leu-LysNHMe (1) reveals a random coil conformation, based on its Glu(γ) and Lys(ε) methylene proton aniosotropic shift, GluNH chemical shift, NOEs in the chloroform-DMSO (6:1), and its amide proton temperature coefficients in DMSO, while on similar considerations, the diastereomer Boc-D-Glu-Ala-Leu-LysNHMe (2) is characterized as a highly ordered 3/10 type distorted protohelix with a remarkably stable intramolecular salt bridge under these solvent conditions.
MIXED ANHYDRIDES IN PEPTIDE SYNTHESIS. A STUDY URETHANE FORMATION WITH A CONTRIBUTION ON MINIMIZATION OF RACEMIZATION
Chen, Francis M. F.,Lee, Young,Steinauer, Rene,Benoiton, N. Leo
, p. 613 - 618 (2007/10/02)
A study of the factors contributing to urethane formation during the coupling of N-alkoxycarbonylamino acids with an amino acid ester by the mixed carboxylic-carbonic acid anhydride method has been carried out, using nuclear magnetic resonance spectroscop
Mixed Anhydrides in Peptide Synthesis. Reduction of Urethane Formation and Racemization Using N-Methylpiperidine as the Tertiary Amine Base
Chen, Francis M. F.,Steinauer, Rene,Benoiton, N. Leo
, p. 2939 - 2941 (2007/10/02)
The side reactions of urethane formation and racemization accompanying couplings by the mixed anhydride method are reduced when N-methylpiperidine is used as base, the best results being achieved in dichloromethane.
