Search
This Journal
This Journal
Anywhere
Quick Search in Journals
Enter words / phrases / DOI / ISBN / keywords / authors / etc
Access type:Only show content I have full access toOnly show Open Access
Advanced Search
0 My Cart
Sign in
Institutional Access

System Upgrade on Tue, May 28th, 2024 at 2am (EDT)

Existing users will be able to log into the site and access content. However, E-commerce and registration of new users may not be available for up to 12 hours.
For online purchase, please visit us again. Contact us at customercare@wspc.com for any enquiries.

ArticlesNo Access

Synthesis and photodynamic properties of maltohexaose-conjugated porphyrins

KYOUSEI Science Center, Nara Women's University, Nara 630-8506, Japan

Corresponding author, tel/fax: +81 742-20-3095.

Search for more papers by this author

,

Graduate School of Engineering, Division of Biotechnology and Macromolecular Chemistry, Hokkaido University, Sapporo 060-8628, Japan

Search for more papers by this author

,

Graduate School of Engineering, Division of Biotechnology and Macromolecular Chemistry, Hokkaido University, Sapporo 060-8628, Japan

Search for more papers by this author

,

Graduate School of Engineering, Division of Biotechnology and Macromolecular Chemistry, Hokkaido University, Sapporo 060-8628, Japan

Corresponding author.

Search for more papers by this author

,

Materials and Bioengineering, Kansai University, Osaka 564-8680, Japan

SPP full member in good standing.

Search for more papers by this author

, and

Graduate School of Material Science, Nara Institute of Science and Technology, 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan

Office of Society-Academia Collaboration for Innovation, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto-daigaku Katsura, Kyoto 615-8520, Japan

Corresponding author.

Search for more papers by this author

https://doi.org/10.1142/S1088424612501155Cited by:8 (Source: Crossref)

Abstract

A series of porphyrin derivatives with one to four maltohexaose moieties in their meso positions have been synthesized. Zinc or free-base m-THPP (5,10,15,20-tetrakis(m-hydroxyphenyl)-porphyrin) was used as the porphyrin platform. The reaction of m-THPP with 3-iodopropyl nonadecaacetylmaltohexaoside afforded a mixture of all possible combinations of glycoconjugated porphyrins having one to four maltohexaose moieties; monoglycosylated (Ac-1), bisglycosylated (Ac-cis-2 and Ac-trans-2), triglycosylated (Ac-3), and tetraglycosylated (Ac-4) porphyrins were obtained in 11–26% yield. Removal of acetyl groups at maltohexaose moiety afforded highly water-soluble glycoconjugated porphyrins 1–4. Zinc derivatives were synthesized in a similar manner. These maltohexaose-linked porphyrins exhibit remarkable water-solublity (530 mg/mL for 4). The singlet oxygen production ability upon visible light irradiation is not affected by the maltohexaose substitution. Photo- and dark cytotoxicities of the maltohexaose-conjugated porphyrins 1–4 and Zn-1–4 were examined against a HeLa cell line, which showed that the mono-maltohexaosylated derivative (1 and Zn-1) was the most effective photosensitizer for PDT.

Keywords:

Most comprehensive & up-to-date research on PORPHYRINS
Handbook of Porphyrin Science now available in 46 volumes

References

S. Achelleet al., Eur. J. Org. Chem. 1271 (2011), DOI: 10.1002/ejoc.201001209. Google Scholar
F. Hammereret al., J. Phys. Chem. A 115, 6503 (2011), DOI: 10.1021/jp202436x. Web of Science, Google Scholar
Y. Zorluet al., Tetrahedron Lett. 51, 6615 (2010), DOI: 10.1016/j.tetlet.2010.10.044. Web of Science, Google Scholar
Y. Mikataet al., Eur. J. Org. Chem. 663 (2010), DOI: 10.1002/ejoc.200900940. Google Scholar
C.-F. Choiet al., Org. Biomol. Chem. 6, 2173 (2008), DOI: 10.1039/b802212g. Web of Science, Google Scholar
M. Obataet al., Biochem. Biophys. Acta 1770, 1204 (2007). Web of Science, Google Scholar
V. Solet al., J. Carbohydr. Chem. 25, 345 (2006), DOI: 10.1080/07328300600770527. Web of Science, Google Scholar
V. Solet al., Bioorg. Med. Chem. 14, 7745 (2006), DOI: 10.1016/j.bmc.2006.08.004. Web of Science, Google Scholar
I. Lavilleet al., J. Med. Chem. 49, 2558 (2006), DOI: 10.1021/jm0580151. Web of Science, Google Scholar
S. Hiroharaet al., J. Photochem. Photobiol. B 84, 56 (2006), DOI: 10.1016/j.jphotobiol.2006.01.011. Web of Science, Google Scholar
M.-C. Desrocheset al., J. Photochem. Photobiol. B 85, 56 (2006), DOI: 10.1016/j.jphotobiol.2006.03.008. Web of Science, Google Scholar
J. P. C. Toméet al., Bioorg. Med. Chem. 13, 3878 (2005). Web of Science, Google Scholar
I. Voszkaet al., J. Photochem. Photobiol. B 79, 83 (2005), DOI: 10.1016/j.jphotobiol.2004.12.003. Web of Science, Google Scholar
S. Hiroharaet al., J. Photochem. Photobiol. B 78, 7 (2005), DOI: 10.1016/j.jphotobiol.2004.09.003. Web of Science, Google Scholar
B. Di Stasioet al., Eur. J. Med. Chem. 40, 1111 (2005), DOI: 10.1016/j.ejmech.2005.04.007. Web of Science, Google Scholar
F. Cañada-Cañadaet al., J. Chromatogr. B 821, 166 (2005). Web of Science, Google Scholar
A. Bautista-Sanchezet al., J. Photochem. Photobiol. B 81, 154 (2005), DOI: 10.1016/j.jphotobiol.2005.05.013. Web of Science, Google Scholar
G. Liet al., J. Org. Chem. 69, 158 (2004), DOI: 10.1021/jo030280b. Web of Science, Google Scholar
S. Hiroharaet al., J. Porphyrins Phthalocyanines 8, 1289 (2004), DOI: 10.1142/S1088424604000659. Link, Web of Science, Google Scholar
S. Hiroharaet al., Photochem. Photobiol,!. 80, 301 (2004), DOI: 10.1562/2004-03-07-RA-103.1. Web of Science, Google Scholar
S. Ahmedet al., Tetrahedron Lett. 45, 6045 (2004), DOI: 10.1016/j.tetlet.2004.06.021. Web of Science, Google Scholar
Y. Arimaet al., Chem. Phys. Lett. 361, 152 (2002), DOI: 10.1016/S0009-2614(02)00916-8. Web of Science, Google Scholar
A. Hamazawaet al., Chem. Lett. 388 (2002), DOI: 10.1246/cl.2002.388. Google Scholar
J. Ali and J. E. van Lier, Chem. Rev. 99, 2379 (1999), DOI: 10.1021/cr980439y. Web of Science, Google Scholar
E. Sternberg and D. Dolphin, Tetrahedron 54, 4151 (1998), DOI: 10.1016/S0040-4020(98)00015-5. Web of Science, Google Scholar
S. Yanoet al., J. Photochem. Photobiol. C 12, 46 (2011), DOI: 10.1016/j.jphotochemrev.2011.06.001. Web of Science, Google Scholar
D. Mitton and R. Ackroyd, Photodiagn. Photodyn. Ther. 5, 103 (2008), DOI: 10.1016/j.pdpdt.2008.04.004. Web of Science, Google Scholar
E. S. Nyman and P. H. Hynninen, J. Photochem. Photobiol. B 73, 1 (2004), DOI: 10.1016/j.jphotobiol.2003.10.002. Web of Science, Google Scholar
K. Ichikawaet al., Biol. Pharm. Bull. 27, 443 (2004), DOI: 10.1248/bpb.27.443. Web of Science, Google Scholar
A. Roby, S. Erdogan and V. P. Torchilin, Eur. J. Pham. Biopharm. 62, 235 (2006), DOI: 10.1016/j.ejpb.2005.09.010. Web of Science, Google Scholar
M. Sibrian-Vazquez, T. J. Jensen and M. G. Vicente, J. Photochem. Photobiol. B 86, 9 (2007), DOI: 10.1016/j.jphotobiol.2006.08.004. Web of Science, Google Scholar
Y. Mikataet al., Tetrahedron Lett. 39, 4505 (1998), DOI: 10.1016/S0040-4039(98)00801-6. Web of Science, Google Scholar
Y. Mikataet al., Bioorg. Med. Chem. Lett. 8, 3543 (1998), DOI: 10.1016/S0960-894X(98)00645-3. Web of Science, Google Scholar
G. Zhenget al., J. Org. Chem. 66, 8709 (2001), DOI: 10.1021/jo0105080. Web of Science, Google Scholar
I. Sylvainet al., Bioorg. Med. Chem. 10, 57 (2002), DOI: 10.1016/S0968-0896(01)00255-3. Web of Science, Google Scholar
E. Davoust, R. Granet and P. Krausz, Tetrahedron Lett. 40, 2513 (1999), DOI: 10.1016/S0040-4039(99)00259-2. Web of Science, Google Scholar
V. Solet al., J. Org. Chem. 64, 4431 (1999), DOI: 10.1021/jo982499+. Web of Science, Google Scholar
D. Oulmiet al., Photochem. Photobiol. 67, 511 (1998), DOI: 10.1111/j.1751-1097.1998.tb09447.x. Web of Science, Google Scholar
R. Bonnettet al., J. Chem. Soc., Perkin Trans. 2, 325 (1999). Google Scholar
R. Bonnetet al., Biochem. J. 277 (1989). Google Scholar
M. Gottschaldt and U. S. Schubert, Chem. Eur. J. 15, 1548 (2009), DOI: 10.1002/chem.200802013. Web of Science, Google Scholar
A. Salas-Burgoset al., Biophys. J. 87, 2990 (2004), DOI: 10.1529/biophysj.104.047886. Web of Science, Google Scholar
R. R. Schmidt, Angew. Chem., Int. Ed. Engl. 25, 212 (1986), DOI: 10.1002/anie.198602121. Web of Science, Google Scholar
N. Sakairi, L.-X. Wang and H. Kuzuhara, J. Chem. Soc., Perkin Trans. 1, 437 (1995). Google Scholar
M. Momenteauet al., SPIE, Photodynamic Therapy of Cancer II 2325, 13 (1994). Google Scholar
D. Kessel, Biochemistry 16, 3443 (1977), DOI: 10.1021/bi00634a023. Web of Science, Google Scholar
E. Gandin, Y. Lyon and A. van de Vorst, Photochem. Photobiol. 37, 271 (1983), DOI: 10.1111/j.1751-1097.1983.tb04472.x. Web of Science, Google Scholar

Journal cover image

Vol. 16, No. 11

Metrics

Downloaded 140 times

History

Received 26 April 2012

Accepted 17 June 2012

Keywords