# US 9,040,687 B2 · Process for the preparaton of novel porphyrin derivatives and their use as PDT agents and fluorescence probes

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- Number: US 9,040,687 B2
- Document ID: US9040687B2
- Status: Granted
- Kind: B2
- Application number: 13/574,512
- Filed: 2011-01-21
- Published: 2012-12-06
- Granted: 2015-05-26
- Earliest claimed: 2010-01-22
- Assignees: Council of Scientific and Idustrial Research
- Applicants: Danaboyina Ramaiah; Suneesh C. Karunakaran; Jisha S. Vadakkancheril; Chandrashekar K. Tavarekere; Srinivasan Alagar; Madhavan Radhakrishna Pillai; Sivakumari Asha Nair; Saneesh Babu P. Saras; Mohan Chintalagiri Rao; Kunchala Sridhar Rao
- Inventors: Danaboyina Ramaiah; Suneesh C. Karunakaran; Jisha S. Vadakkancheril; Chandrashekar K. Tavarekere; Srinivasan Alagar; Madhavan Radhakrishna Pillai; Sivakumari Asha Nair; Saneesh Babu P. Saras; Mohan Chintalagiri Rao; Kunchala Sridhar Rao
- Web page: https://patentgrep.com/patent/US9040687B2

## CPC

- C07D 487/22: in which the condensed system contains four or more hetero rings
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides novel porphyrin derivatives represented by the general formula 1 and/or pharmaceutically acceptable derivatives thereof as NIR sensitizers for photodynamic therapeutic and diagnostic, biological and industrial applications. These porphyrin derivatives possess absorption (400-700 nm) and emission (600-750 nm) in the regions where biological chromophores do not absorb and hence are ideal candidates for application as NIR PDT agents and fluorescence sensors for medicinal applications in biology. The substituents like hydroxyl and glycolic units on these dyes render them amphiphilicity thereby improving their solubility in the aqueous media and cellular uptake and localization. These dyes show no toxicity in the dark and are highly selective towards tumor cells and stain nucleus very rapidly. Accordingly, these porphyrin derivatives are extremely useful as NIR PDT fluorescence sensors in photodynamic therapeutic and diagnostic, biological and industrial applications.

## Claims

### Claim 1

Porphyrin derivatives of the general formula 1,
wherein, R1, R3, R5=OH; R2, R4=H; M=2H;
wherein, R1, R3, R5=OH; R2, R4=H; M=Zn,Co, Cu, Fe, Au;
wherein, R1, R3, R5=OH; R2, R4=I; M=2H;
wherein, R1, R3, R5=OH; R2, R4=I; M=Zn,Co, Cu, Fe, Au;
wherein, R1, R2, R4, R5=H; R3=(OCH2CH2)nOH (where n=3-7); M=2H;
wherein, R1, R2, R4, R5=H; R3=(OCH2CH2)nOH (where n=3-7); M=Zn,Co, Cu, Fe, Au.

### Claim 2 (depends on 1)

The porphyrin derivative of claim 1, wherein R1, R3, R5=OH; R2, R4=H; M=2H.

### Claim 3 (depends on 1)

The porphyrin derivative of claim 1, wherein R1, R3, R5=OH; R2, R4=H; M−Zn.

### Claim 4 (depends on 1)

The porphyrin derivative of claim 1, wherein R1, R2, R4, R5=H; R3=(OCH2CH2)nOH (where n=3); M=2H.

### Claim 5 (depends on 1)

The porphyrin derivative of claim 1, wherein R1, R2, R4, R5=H; R3=(OCH2CH2)nOH (where n=3); M=Zn.